When I founded my first company Connected back in 2011, I was really surprised by the intensity of the emotional rollercoaster. By then I’d already worked everywhere from large corporate Microsoft to tiny new startup and felt prepared. I was dead wrong. I remember describing it to a friend as, “After I started a company, everything became 10x more intense. The highs and lows filled with terror, sometimes all in the same hour. Everything else I’d done in my professional career fades in comparison.”

In retrospect, I may have made every mistake in the book. I made the company the core of my identity and self-worth. Churned customers and even chance negative remarks were crushing and the metrics controlled the oscillation of my mood. When Connected launched on TechCrunch, the post was flooded with negative comments because we’d done something unthinkable at the time — we’d launched with a 14-day paid trial and weren’t giving the product away. The self-doubt was agonizing and we debated pricing long into the night. In hindsight, this turned out to be one of the best decisions we’d made because it focused us on the users which mattered.

I had impostor syndrome before I had a name for it. We were just some kids working out of a one-bedroom apartment, and that feeling made it difficult to go out to events and pitch the company on stage. I worked intensely, considered weekends nonexistent, and dropped almost all my outside relationships, rarely having one-on-one conversations with anyone that wasn’t work related.

And all of this happened with a pretty successful story as we raised funding and ultimately sold the company to LinkedIn!

Looking back now, I realize how unprepared I was for the emotional toll of being a founder. There’s something uniquely difficult about being a startup founder that I didn’t know to expect.

The challenges of being a founder

I’m writing this as a way to share some of the unique insanity that pervades the founder experience. My hope is that others will be a little more prepared and to offer a little relief if you’re struggling with these feelings now because you aren’t the only one. In no particular order, here are some of the challenges that I’ve struggled with myself or noticed others have faced too. It’s a hard job, and this is a pretty long list!

1. The lack of structured days. What should I do today? What is the right way to focus my time and energy? When you’re starting a company, it starts with sitting at your desk and deciding what you want to do. The early startup experience removes the comfort of a boss, clear objectives, scheduled meetings, and the rhythms of operating within a team. The need to build a plan from scratch AND execute on it is a unique challenge.
2. The lack of feedback. Am I doing the right things? Did any of the work I did today matter if the business isn’t moving? In an academic world, there are grades and GPAs to provide regular feedback on progress. In the corporate world, there are titles, compensation, performance reviews, and peer feedback. In society, there’s status from your employer and profession. Startups are like a black hole for feedback. No one tells you you’re doing a good job, and most of the world is demanding more. The clear milestones for achievement aren’t availableand replaced with highly ambiguous ones.
3. The lack of data to make decisions. Is this the right decision? Will this work? Starting a company is like charging down a path without a map and hoping that you’ll burst into clarity later. There are reasons to second guess every decision you’ve made, like my earlier story about launching Connected with a paid trial. I call this high ambiguity environment “the fog of war,” where it’s unclear whether or not things will work and quick decisions must be made based on conviction rather than data.
4. Completely justified Impostor Syndrome. Am I cut out for this? Do I have what it takes? Founders are often critically unqualified for their roles. Objectively, they would not have passed an interview process for their role or level of responsibility. As their businesses scale, they find themselves in positions of leadership, management, and cross-functional responsibility which they have to rapidly to grow into. This is everything from how to actually operate a business to critical soft skills like how to hold others accountable. When your whole team is counting on you, the pressure is intense.
5. Intense highs and lows. There are certain milestones of running a company that take up large blocks of time and emotional energy: fundraising, hiring, firing, restructuring, churning key customers, etc., all happening at the same time. It was thrilling to have the first investment check hit the bank account and feel the validation that someone believes. But a quick follow-up was mapping out our runway and contemplating certain death if we don’t figure it out.
6. Your identity is your startup. It is really difficult not to deeply tie your identity and self-worth to your startup. I think we all know we shouldn’t, but it’s very common to feel so much ownership that moods fluctuate with ARR and churn, self-worth is in lockstep with fundraising, and every comment feels personal. Successful companies are a combination of skill and blind luck, and it is possible to do everything right and still fail. It’s really hard to keep this fact top of mind.
7. It’s a sales job. Sales is an integral part of the job. Founders are always selling their idea and painting visions of what it will become. From fundraising to hiring to management to closing sales, it’s a relentless sales process to try to eke some yes’s out of a sea of no’s. This can be intensely demoralizing and stressful. It’s a rare subset of the population that is cut out to be in sales, and it’s a surprise to many that this is a core part of the job.

An additional insight into a lot of these challenges: it’s incredibly difficult for founders to get support. There’s is a “We are crushing it! Up and to the right!” bravado and highlighting of winners within startup culture which pushes relentless optimism without room for conversation about hardship. It feels like everyone is winning except you.

Also, there is a clear downside for talking about problems — who do you talk about them with? If you talk to your investors, you could impact your next round. If you talk to your cofounders and employees, you could demoralize them. If you talk to your partner or friends in your network, maybe it’ll bite you later? Would they even get it? Not to say that this is true, but the paranoia isn’t uncommon.

Dealing with the problems

A lot of entrepreneurs struggle when they hit these challenges, and are constantly tested at certain decision points such as heading into another cycle of fundraising, evaluating their exits, or pouring more years of their life into their startup. So what do you do to manage this? As you hold everything together and grow your team and business, here are some strategies that might be helpful to you.

• Expect it and normalize it. One of the reasons why I’m writing this post is to shed some light on the challenges of being a founder. Invariably you’ll hit bumps. Finding ways to manage your expectations can reduce the intensity of the highs and lows, and normalizing it as part of what founders go through can make it easier to bear.
• Build your support before you need it. I don’t mean joining a founder community and humblebragging. Form real relationships where you can have Real Talk and have trusting and vulnerable conversations. Maybe this is with family, friends, or making an effort with other founders you meet. This will be useful and helpful to you in those crucial moments.
• Diversify your portfolio. It’s tempting to devote 100% of your time and mental energy to your startup. This is a mistake. It is not sustainable in the long-run because you’re shelving everything else in your life, and the challenges get magnified to epic proportions without anything to offset them. Invest in finding other outlets and take care of yourself. This can be exercise, relationships with friends and family, hobbies, and personal passions. There is nothing wrong with this and it is a healthy and good investment for you.
• Focus on yourself, today. Not your legacy, not the story others will tell, not the way others will perceive you. It is a rabbit hole to always think about the big picture and the hypotheticals of where this will go and what might happen. What is the one big thing you want to accomplish today to move forward? Focus on impressing yourself and your needs now, and see what comes.
• Celebrate wins. There is scientific evidence that practicing gratitude can change your brain. There are many approaches to this that aren’t just gratitude journals, from thanking others to counting your blessings to mindfulness practices. It’s worth looking into.

There is no magical panacea for the founder’s journey, but with time and some hard-earned wisdom I’ve found that it does get easier. I could write a lot more about this, but I’ll save thoughts for next time. :)

Ada Chen Rekhi is co-founder & COO of Notejoy, a collaborative notes app for individuals and teams. She’s also an executive coach who works with founders and executives looking to scale themselves as they scale their teams. If you enjoyed this essay, subscribe to her newsletter or follow her on @adachen.

7 Things No One Tells You About Being a Startup Founder was originally published in Ada Chen Rekhi on Medium, where people are continuing the conversation by highlighting and responding to this story.

What we investigated

In evaluating the decision to have a child, we tried to consider as much as possible. We approached it as an active choice rather than a default conclusion and had many spirited debates in the decade of marriage before we brought our daughter Zoe into the world. Not only did we interview our friends who had made choices either way, but we also explored forums like r/childfree and op-eds from people who had made the choice against.

Financial impact

The most obvious challenge to having a child is the financial one. How much does it cost to raise a child in the best and worst case? I built a spreadsheet taking a well-padded estimate of the total cost of raising our child to the age of 21. We compared that against our finances to discuss what the impact to our lifestyle was. Unsurprisingly, the biggest drivers of cost in this model are childcare and education.

Lifestyle impact

We talked about the changes and constraints to our lifestyle once we had a family. It’s difficult different to travel with a child, the schedule of childcare especially in the early years is demanding, and it erects more barriers to some dreams that I’ve had like spending a year abroad. Was I open to accepting this tradeoff?

Emotional impact

We spent a lot of time discussing how the emotional weight of parenthood would affect us. One of the primary concerns (which proved out) is the worry and focus tax. One of our friends sent us this Paul Graham essay that while isn’t about parenting captures the issue. How much does this prevent us from being effective at our other goals?

The surprises about parenthood

Reflecting on the last two and a half years, here are the biggest surprises.

Surprise 1: The sheer amount of planning to execute childcare and enrichment

• What I Thought: Childcare is a well-understood process that costs money and some effort.
• Actual: There is hunger games level of planning and logistics due to local market economics.

I am still a little shocked by the difficulty to identify, evaluate and secure childcare. Maybe this is a symptom of the Bay Area, pandemic times, and my optimizer brain, but the effort is huge. Childcare is a hyper-local services marketplace and it’s hard to evaluate quality. The first challenge was even finding providers. Like most parents, I don’t want to drive more than 10–15 minutes out of their way because with traffic that’s an additional hour of commute. Finding and mapping all centers and trying to understand their unique characteristics was not as easy as I thought.

Let’s say that I’m not even trying to optimize for a great childcare solution. As a working parent, having a childcare solution is not optional. Finding any spot in any daycare center requires research and pre-planning because openings are so rare. So what if in addition I’m trying to find an optimal solution for Zoe? The waiting lists are outrageous, sometimes years long. We started signing Zoe up for daycare waiting lists when we were pregnant, and there are several places where we haven’t heard back. There is a well-known preschool that many consider one of “the best” and I know of examples where people have enacted elaborate strategies of donations and extreme networking to get their child in. This applies not only to schools, but enrichment programs like finding dance or swim classes.

Surprise 2: Parenthood unlocked a whole new level of relating to others

• What I Thought: I know my close friends and colleagues with kids well.
• Actual: I was experiencing a filtered version of themselves that didn’t include one of the most important aspects of their life.

After we shared the child news, a very old friend exclaimed, ‘I’m so excited you’re going to be parents! I’m going to be able to be closer friends with you!’ He shared that kids are one of his most top of mind topics but he consciously filters himself to not bore the non-parents, so he would have a more authentic relationship with us. In addition to this, kids introduce friction in social gatherings where parents often have to step out to take care of the child. While parents implicitly understand that, non-parents don’t.

I’ve understood since then how different parent-life truly is. And the positive corollary to this is that it’s opened up a whole new way of relating to other parent friends. The way their eyes light up as they talk about the small successes and challenges of their family life is incredible. Sometimes it comes as a shock to realize how little of their lives they shared before.

Surprise 3: The Chaos Bomb that is a child

• What I Thought: The time impact for children was just additional tasks and schedules.
• Actual: Children are inflexible chaos bombs that make schedules very difficult.

I have not slept in past 7am for past two and a half years. I can count the number of late evening dinners out on a single hand. Pre-child, the practice of staying up to late to socialize, introspect, work, or otherwise chase my flow was really a core part of how I worked. I would just sleep in the next day to make up for a late night. I didn’t truly internalize that going on a long run, late night dinners, taking trips, sleeping in was going to get massively more complicated. As much as I try to stick to a routine, my schedule gets blown on on a regular basis.

Obviously your mileage will vary. Lots of people manage to sleep in and go out, but the difficulty of this was surprising to me.

Surprise 4: “Your world goes from black and white to technicolor”

• What I Thought: We had a reasonable understanding of the social and emotional impact of parenthood.
• Actual: There is an experience to parenthood that isn’t possible to know before you experience it.

When we did our social learning interviews with friends, one of them said, “your world goes from black and white to technicolor and you never realized what you’d missed out on until it was there.” It is so spot on. While we had a good sense of the financial and social impact, the ability to truly understood the experience of parenthood is hard to understand without experiencing.

What I could not accurately value is the depths of highs and lows, and the intensity of emotions it unlocked. It’s just a surprise. I know it is different to everyone, but as far as life experiences go, it’s a really unique one for me that was described several times but never fully internalized.

Embracing the journey

I am squarely in the camp that kids are not for everyone. Not everyone should have or needs to have this experience. However, I’ve been embracing this journey now that we are on it. Zoe is growing up so fast that I’m being pulled along to adapt and grow alongside her. I’m sure in a few more years, I’m going to be surprised all over again by a whole different set of things.

What’s Surprised Me About Parenthood was originally published in Ada Chen Rekhi on Medium, where people are continuing the conversation by highlighting and responding to this story.

With all of the talk of The Great Resignation, it doesn’t come as a surprise that many people are asking the question, what do I really want to do?

Many people follow a guiding star throughout their early career. Their career transitions are based on what their parents or peers expected, what their peers did, where there was the highest status, or even taking what they were good at to its natural extreme. Later on, what they begin to question is whether that work is meaningful or significant to them.

In their book, “Designing Your Life”, Burnett and Evans define this as your “encore career,” or finding work that combines personal meaning, continued income, and social impact. Rather than follow the default path laid out by your previous achievements, maybe there is a way to have it all — meaningfulness AND feeding your family. In Designing Your Life, they address this search head-on by providing a framework to apply design thinking to life and career decisions. It’s based on their popular Life Design course taught at Stanford, which uses design principles and philosophies to create a program for assessing your life and moving forward.

Here are a few of the concepts I found most interesting and actionable from the book.

Where you are

My favorite takeaway from this book, and the one that I will regularly revisit for myself, is their intitial exercise challenging you to start by mapping out where you are.

They present a simple health / work / play / love dashboard as a way to take stock of your current situation. The dashboard is a chart with gauges at 25%, 50%, 75%, and 100%. The directions are simple: make a list of your activities in each category and fill in the gauge based on how satisfied you are with it.

Each category is carefully defined:

Health — not just physical health, but an engaged mind and satisfied spirit.

Work — not just what you’re paid to do, but also include other duties such as second jobs, consulting, advising, volunteering, home-making, houseworking.

Play — any activity that brings joy just for the sake of doing it, which can include organized activities or productive endeavors so long as they’re done for fun and not merit.

Love — the health of your primary relationship, children, pets, community, or anything else tied to affection. Where is the love flowing in your life, from you or from others?

What I like about this framework is how thoughtful and inclusive the categories are. By explicitly calling out Play as anything that brings joy that is not Work, there’s a distinction made between activities you want to do and activities you have to do. They’ve redefined the category labels in a way that focuses on the impact and effect to you. After completing the exercise for myself, asking the question ‘What would I change here?’ was a powerful follow-up.

When I did this exercise, I definitely noticed how many items I had to list in Health and Work, and how relatively few I had in the category of Joy. It was a powerful moment of realization to compare the lists in each of these categories and notice where they were off from my ideal. I have a strong history of letting work take over my life, and it was an important check for me to think about how to prune my work commitments and set clearer boundaries on my time.

The power of the reframe

The application of design thinking is all about reframing how you define the problem and as a result the potential solution. It removes the filters and boxes you tend to put in place with problem-solving, by challenging us to view problems through a different lens. The argument overall is that this process helps us think more creatively about what to do with ourselves.

Instead of thinking about your work as a list of what you want from or out of work, Burnett and Evans ask you to think about it as what work is and what it means to you. Why work? What’s work for? What does work for? What defines good or worthwhile work? What does money, experience, fulfillment have to do with it?

Likewise, instead of thinking of your life as a list of activities and affiliations, they ask you to think about what values and perspectives define your understanding of life. Why are we here? What’s the point of family, country, and the rest of the world? What is the role of joy, work, justice, conflict in life?

What they’re getting at with their exercises is cultivating an environment of curiosity as to what the possibilities are. What if we were open to letting go of our limitations to explore other options open to us?

In my opinion, the most powerful reframe they had in the book is this idea of prototyping with your career. Instead of entering the next step of your career with an air of finality, they encourage the reader to think about prototyping conversations and prototyping experiences. What are the smaller more incremental steps that we can take to validate our interest and passion for bigger moves? If you’re interested in leaving your career as a software engineer to be a restauranteur, can you talk to people who are doing it? Can you host a few dinners and cook for friends? Can you set up a catering business? There are so many other paths to get there that don’t involve the wholesale leap that will still build confidence in the path forward.

Overall, I thoroughly enjoyed Designing Your Life and would recommend it as a thought-provoking read to anyone who’s exploring what next. Unlike many of the common structured frameworks out there, the questions and exercises throughout the book are well-designed to be open-ended and nurture creativity and curiosity.

Finding Meaningful Work with “Designing Your Life” was originally published in Ada Chen Rekhi on Medium, where people are continuing the conversation by highlighting and responding to this story.

When I coach founders and execs, I often encounter them in a point of transition. Reaching the point in your career where you transition from individual contributor to a people leader is often a story of struggle. Here’s why it’s so difficult to rise to the new challenge: The Leadership Chasm.

The leadership chasm represents the gap in skills, competencies and realities that now stand in the way for you to be successful.

The skills that got you here won’t get you there

For many first time managers, you achieve your promotion to people management by being stellar as an individual contributor. By executing well, you’ve shown that you understand what good output looks like. Naturally, the logic follows, if you’re elevated to a people leader you’ll be able to drive the same output through others.

Here’s the problem with this logic:

• The skills and competencies to drive results through others isn’t the same as doing the work yourself. The work of the individual contributor is to actually do the work, while your work is actually to help your team achieve great outcomes. That means your core work are actually more around behaviors like motivation, feedback, and process/resource management.
• The new work associated with your role isn’t as easy to measure, and may not be immediately obvious. It’s not as simple as helping your team deliver more of the work you’ve been delivering well to date. It’s about hiring, growing and retaining talent. It’s about unblocking team members and building better processes. It’s about inspiring them to deliver results. All of this is part of a leader’s job.
• Accepting that not everyone works the way you do requires a mindset change. There are multiple ways to launch a campaign, ship a product, makes a sale, or otherwise execute great work. It’s not important that they do it in the way you’d do it, but it’s hard not to get hung up in details especially if you’re very familiar with them yourself.

This last piece is really important. A common mistake that new leaders make is they focus on delivering output through their team by intensely managing the execution process of others. How about you just teach everyone to do it the way you do it? Not everyone works the same way, and often this is the slippery path into micromanagement. Instead, your role is to help that person become their best self by providing them with resources, clear goals, and constructive feedback.

Facing your new reality

I remember telling my team, you’re the ones that are actually doing the work. Instead, I would be spending my days mired in budget planning, project reviews, team meetings and 1:1s, and recruiting. Outside of seeing bullet points on progress, I often felt distanced from the actual work of improving the company metrics. I deeply missed the execution work.

A friend helped me by asking, “What’s the most valuable thing you can do for the team that no one else can do?” It helped me see it in a new light. I was uniquely situated to helping the team procure resources (budgets), gather and disseminate information (reviews), give feedback (team meetings), and recruit teammates. And this was actually the most impactful activity for my time spent.

The sooner I came to accept that as my new reality, the sooner it enabled me to embrace these activities as productive and integral to my role. And by focusing on this, the sooner I came to realize that being great at these activities requires mastering a completely different set of skills and competencies.

Conclusion

This story about the leadership chasm isn’t about not focusing on the execution and deliverables that got you to where you are. I’m certainly not saying that, they do help. But I do think you need to develop a self-awareness about how different the skills and competencies are to operate as an effective leader. Recognizing where you have the most leverage to add value is important. And when you get too bogged down in managing execution over tactics, that’s when you’re stuck in the canyon.

Ada Chen Rekhi is co-founder & COO of Notejoy, a collaborative notes app for individuals and teams. She’s also an executive coach who works with founders and executives looking to scale themselves as they scale their teams. If you enjoyed this essay, follow her on @adachen and subscribe to her newsletter.

The Leadership Chasm was originally published in Ada Chen Rekhi on Medium, where people are continuing the conversation by highlighting and responding to this story.

How did I get here?

For many years now, I’ve been working with founders as a growth and marketing advisor. In addition to those topics, I was always fascinated by the conversations on leadership style, work/life balance, and personal development. As we scale our businesses, how can we ourselves scale as leaders? Figuring out how we can operate at our best is often the linchpin to unlocking the potential of the teams we’re building. This spurred my initial impetus to start coaching, and as I started working with founders I’ve found I love the work! It’s incredibly energizing and meaningful for me to help.

Why is this stuff important?

As a founder myself, I can empathize with the challenges of trying to scale yourself while building the best for your team. Here are a few themes that you may find relatable.

Leadership can be incredibly lonely. Sometimes it feels like everyone is looking at you to project confidence and set a vision when you don’t feel it.

Your role is changing under your feet. The skills that got you here aren’t what you need to get you there, particularly in areas like communication, navigating conflict, and people management.

It’s a struggle to balance personal with professional. The pull of your business and team can pull the balance of time spent on personal priorities out of whack. All of us are wearing multiple hats, not only as leaders but as partners, parents, community members and more.

It’s a rollercoaster to tie your identity and emotions to your business. Finding a way to build your resilience and stamina to the shocks of business building is a huge factor in staying the course.

I wish I had had someone helping me in my early career as a founder and executive. Not to tell me how or what to do, but to help me figure out my own unique leadership style and navigate these roadblocks when I hit them the first time. There are many successful models of leadership, but finding one that is authentic and aligned with my values was critical in helping me grow into my new role.

Who do I work with?

I work with leaders who are scaling themselves to the next level and want a partner in their personal and professional journey. My coaching is informed by my experiences as a founder and executive in Silicon Valley. I’m a 2x founder (Notejoy, ConnectedHQ acquired by LinkedIn), former SVP at SurveyMonkey, and have worked everywhere from tiny startups to large companies. I’m also an avid hiker, hit-or-miss experimental chef, and wife and mom.

My approach to coaching is personalized and pragmatic. I don’t believe in there being one right answer, but I do believe in finding the personalized answer for you through curiosity and reflection. On the pragmatic side, leaders seek coaching because they want to make a change but they’re getting stuck. My role is to provide the accountability and support to move them forward.

Get in touch

Let’s chat if you’d like to learn more! Contact me

✨I’m an executive coach✨ was originally published in Ada Chen Rekhi on Medium, where people are continuing the conversation by highlighting and responding to this story.

Inspired by a recent conversation that reminded me of Ben Horowitz’s Good Product Manager/Bad Product Manager post, I wanted to share a cleaned up version of a similar talk I prepped for a subset of my team at SurveyMonkey on what a world class marketer looks like.

Sometimes people ask me how marketers can get a seat at the table, and this is a summary of some of the areas where I believe marketing delivers differentiated value within an organization. Not every marketer is going to be able to hit these areas out of the gate, but I wanted to talk about what world class marketers look like. If you can deliver compelling value in these areas, you won’t have to fight for a seat at the table, the meeting won’t be able to start until you are there.

Good marketers are experts at the customer. Not only are they up-to-speed on the overview and description of historical insights, they have the real-time pulse of what’s going on. They are constantly searching for additional data: user research studies, customer support inquiries, Twitter threads, lurking on forums, chatting with customers, watching the news about the market and competition. They are the go-to resource for people internally in the organization and are often collating real-time updates on what they are hearing and seeing. Over time they develop strong opinions about where the company should be going backed by the data they see. Internal teams consider good marketers an invaluable resource to get the pulse on customers. Bad marketers are stuck in the weeds of execution and production and rarely examine the market and industry.

Good marketers are experts at the product. They are intimately familiar with how the product works, and have in-depth knowledge about how customers use it and what they’re frustrated with or love about it. Bad marketers parrot the bullet points on the website or marketing materials without deep knowledge of what the features are. If needed, a good marketer’s knowledge is deep enough to spend a day at a conference expo table and pitching customers and answering basic questions about what the product does or doesn’t do. If you can’t do this, then spend a day playing with your product and asking a lot of questions. Good marketers need this depth of product knowledge in order to be effective and add value to the organization. Internal teams trust marketers to package and market their work, and lean on good marketers as a channel for product ideas and feedback. Good marketers are in the weeds of the details and know what product launches are upcoming and spend time getting to know the product and engineering planning process to channel feedback in. Bad marketers are surprised by product launches and have an abstract and hazy knowledge of the product.

Good marketers are the internal experts and leaders to execute and coordinate external launches and campaigns. This is their domain and an area where they should be lead. They align the teams on shared goals such as user growth or education, and apply their knowledge to make informed recommendations on how to get there from both the qualitative aspects such as messaging and positioning to the quantitative goals and tactics to get there. They have studied prior launches inside and outside of the company and have dissected what messages resonated and what did not, what channels worked and did not work, and are hungry for more learning and feedback. For example, faced with a team that wants SEM and SEO campaigns for a launch, they should have the knowledge and expertise to assess whether or not this is a successful strategy, and in the process teach those teams something along the way. Internal teams value good marketers as experts on go-to-market tactics and messaging, and respect them when they push back. Bad marketers take a punch list of inputs from all parties and blindly execute without an opinion of whether or not the work makes sense. They get bogged down in administrative work and take the path of least resistance without holding a quality bar on the work that gets out the door.

Ada Chen Rekhi is co-founder & COO of Notejoy, a collaborative notes app for individuals and teams. She’s also an executive coach who works with founders and executives looking to scale themselves as they scale their teams. If you enjoyed this essay, follow her on @adachen and subscribe to her newsletter.

Good Marketer / Bad Marketer was originally published in Ada Chen Rekhi on Medium, where people are continuing the conversation by highlighting and responding to this story.

Inquiring minds want to know… What is the average free to paid conversion rate from a free trial or freemium? What is a “good” conversion rate from free trial to paid?

Without an industry survey out there and in the process of defining the growth plan for my own company Notejoy, I was curious to see whether benchmarks could be compiled from companies and experts who have shared data points of what they have typically seen. My summary compiled below.

There are three primary models for free-to-paid in SaaS

Most SaaS companies primarily follow three primary business models when offering free to paid products.

• Freemium — the product is offered free of charge, but money is charged for advanced features or functionality
• Free trial (without credit card) — the product is offered on a “try before you buy” basis without credit card information
• Free trial (with credit card) — the product is offered on a “try before you buy” basis with credit card details collected up-front

It’s important to recognize the differences between these models because they result in starkly different conversion funnels and quality of downstream user. For instance, a free trial with credit card is naturally going to result in a more qualified but smaller number of signups, resulting in a higher trial-to-paid conversion rate downstream than a similar flow that doesn’t demand credit card details up-front. When the specifics of with/without credit card were unavailable, I’ve omitted them from this dataset rather than attempt to draw conclusions from them — a good example of this being Groove’s 2013 survey of 1,500 companies, which is worth checking out but omitted from the list due to this issue.

While many consumer products are freemium (e.g., Skype, Spotify, Dropbox), most B2B products tend to skew toward free trial. The 2015 Pacific Crest SaaS survey suggests that 30% of companies are deriving some ACV from “freemium” while 60% derive revenue from free trial “Try Before You Buy”.

Freemium to Paid Conversion Benchmarks

Freemium conversion rates are generally in the low single-digits.

Sources

• 1–10% Insight Venture Partners article on companies like 37signals, Dropbox, Evernote, GitHub, HootSuite, New Relic, SurveyMonkey, Weebly, Zendesk (2012)
• 3% for SaaS or B2B Web Apps — Lincoln Murphy from Sixteen Ventures (2010)
• 4% — Dropbox’s % paid of total userbase (2012)
• 30% — Slack (2014)
• 6% after 2 years; 4.9% of MAUs — Evernote (2010) & TC article (2009)

Free Trial to Paid (without credit card) Conversion Benchmarks

Free trial conversion to paid conversion rates vary considerably from low single digits to upwards of 25% depending on product category and target customer.

Sources

• 6–10% — Customer.io (2014)
• 10% with peaks as high as 18% — Justuno (2016)
• 15% — Totango study of ~100 SaaS companies (2012)
• 25% — Recapture.io (2016)
• 2–3% — 3 Minute Optimizer (2015)
• 2–4% — GoToMyPC / GoToMeeting (2011)
• 3.75% — Salesforce (2006)
• 15% — Chargebee (2016)
• 10% — Gutensite (2013)

Free Trial to Paid (with credit card) Conversion Benchmarks

When credit card details are collected up-front, trial-to-paid conversion rates are significantly higher and range from 30–50%.

Sources

• 50% — Totango study of ~100 SaaS companies (2012)
• 30–40% — 3 Minute Optimizer (2015)
• 40–45% — GoToMyPC / GoToMeeting (2011)
• 40–50% — Callwave (2011)
• 56% — Moz (2012)

Did I miss any data points? Leave me a comment and I will post an update. Also, get the full presentation here.

Ada Chen Rekhi is co-founder & COO of Notejoy, a collaborative notes app for individuals and teams. She’s also an executive coach who works with founders and executives looking to scale themselves as they scale their teams. If you enjoyed this essay, subscribe to her newsletter or follow her on @adachen.

Freemium and Free Trial Conversion Benchmarks was originally published in Ada Chen Rekhi on Medium, where people are continuing the conversation by highlighting and responding to this story.

Just about every startup has to cross this bridge at some point: making their first marketing hire. I often get asked about this topic and after several conversations, I was inspired to put together a guide on how to scope, evaluate and hire a strong first marketer for your team.

Defining the scope of your marketing role

The challenge for many teams of hiring a marketer is that often they aren’t entirely sure what they want. Hiring a marketer can mean a lot of things depending on what your business needs, and it’s not always a specific or quantifiable set of activities. This results in marketing searches that are centered on a set of marketing activities and traditional areas of ownership, rather than how marketing is expected to help the business grow. With that said, I do think there are useful frameworks to approach how to define and structure your marketer’s role.

The first step is to take a step back and consider what’s prompting you to make this hire. Start with the top 1 or 2 outcomes that you’re hoping to achieve. Imagine that you’ve brought on a marketer and it’s now six months after they joined the team. You’re reflecting on what a rockstar they are and how you can’t imagine in such a short time what an impact they’ve made to the business because they’ve really moved the needle on … what outcomes?

Here are some example outcomes I’ve heard in response to this question:

• establishing my brand so when press writes about my product category, I’m one of the companies listed
• taking over the prioritization and execution of testing new top-of-funnel growth channels to get more customers for my business
• getting the whole team on the same page on how we talk about my business, and updating our website and marketing materials to better improve our lead and conversion rates
• partnering with my sales team and help them more efficiently close the leads they have
• taking my fledgling SEM tests that have seen positive results and scale it
• figuring out how we can get more developers to start using our product
• figuring out the market that our product is resonating with and achieve product-market fit
• building out our blog and social media channels to create sales leads
• taking our existing product which is generating a lot of press and buzz already, and amplify and focus it on generating business leads

During this process of defining the top outcomes for your business, it’s a good idea to ask this question of your team as well to gauge what they consider success for your new marketing hire. Often what I find is that there are often multiple desired outcomes within a team, and it’s a valuable discussion to determine which of those are most important or where they overlap. This enables you to clearly communicate what success looks like to your team as well as the marketer you bring on board.

After you’ve identified the one or two items on this list, think about what they need to do in order to achieve these outcomes. What challenges do they need to overcome in order to move the business forward? Are there specific skills, experience or knowledge that would be critical to getting them there? Map these against your outcomes.

Appending to the earlier examples in italics:

• establishing my brand so when press writes about my product category, I’m one of the companies listed
   — experience in public relations
   — skill in messaging and positioning my product relative to others
• taking over the prioritization and execution of testing new top-of-funnel growth channels to get more customers for my business
   — experience working with product and engineering teams
   — knowledge of growth metrics, A/B testing, statistical significance
   — skill in critically evaluating and prioritizing tradeoffs
• getting the whole team on the same page on how we talk about my business, and updating our website and marketing materials to better improve our lead and conversion rates
   — experience copywriting and working with design teams
   — skill with customer segmentation, messaging and positioning
   — skill with leading initiatives across cross-functional teams
• partnering with my sales team and help them more efficiently close the leads they have
   — knowledge of b2b marketing levers and funnel measurement
   — experience working with sales teams
   — skill with measuring and optimizing funnels
• taking my fledgling SEM tests that have seen positive results and scale it
   — skill and experience managing SEM campaigns
   — experience working with product and engineering teams for tracking
• figuring out how we can get more developers to start using our product
   — skill in customer research or experience in developer community
   — knowledge of potential marketing and growth levers
   — skill in primary and secondary customer research and problem solving
• figuring out the market that our product is resonating with and achieve product-market fit
   — skill in primary and secondary customer research and problem solving
   — knowledge of potential marketing and growth levers
• building out our blog and social media channels to create sales leads
   — experience in blogging and social media
   — knowledge of your company’s space or skill in customer research
   — knowledge of quantitative metrics for lead generation
• taking our existing product which is generating a lot of press and buzz already, and amplify and focus it on generating business leads
   — experience in public relations
   — knowledge of quantitative metrics for lead generation

Ultimately, your objectives and the key experiences and skills will become the basis of your job description for the marketer you’re hiring. It should clearly spell out the top business objective you’re hoping they will help with, and the key experiences and skills they would ideally have for the position. By starting with the business outcomes, you’re able to create a much more precise and targeted job description than just a list of responsibilities or activities.

This also becomes a valuable tool to begin your search for the right candidate. This list of skills and attributes is a useful way to describe your ideal candidates.

For example, the desired outcome of “working with my sales team and help them more efficiently close the leads they have” closely maps to the field marketing or demand generation function. It’s much more specific to say “I’m looking for a marketing leader to help my sales team close leads, ideally they have a background in field marketing or demand generation.”

I’ll often look at the top objectives of a company and map it to the function or job title their target candidate likely has passed through or has. As a guide to figuring out what function that might be, I refer you to my ‘Anatomy of a Marketing Organization’ post where I cover the different functions within a larger marketing organization. Having the vocabulary to describe what you’re looking for makes the search much easier when guiding a recruiter, searching LinkedIn or asking for referrals from other people.

Evaluating a marketing candidate

A common challenge that startups face when they’re hiring their first marketer is that they don’t know how to evaluate them. If you have no marketing expertise, how can you evaluate if they’re the right marketer for you?

Establish a strong hiring process

The hiring process that I’ve found effective is loosely modeled off the Microsoft interview process. For a given marketing position, I’ll select a group of people for the interview loop who will be closely working with the candidate if they are hired for that position. This small group is committing to meet with every candidate for this position, and I assign each of them a specific area of focus to interview every candidate against. This focus area is based on the interviewer’s strengths as well as one of the desired skills for the candidate. Assigning a focus is helpful because it ensures that one person on the team is going to go in-depth on that area, and it avoids the issue where too many interviews get bogged down in general ‘walk me through your resume’ discussion. One key note to this process is that I also ask every person to focus on asking the same questions to every single candidate.

Even if no one on the team is an expert in a specific area, they should be able to assess some of the hard skills or ask the candidate to teach them about that area. Here are some examples of responsibilities I might assign:

• Product manager — Focus: knowledge of growth metrics, A/B testing, statistical significance. Assess the candidate’s quantitative understanding of typical growth metrics and levers, as well as if they understand the concept of how to structure an A/B test.
• Designer — Focus: experience copywriting and working with design teams. Assess the candidate’s prior experience working with marketing design and product designs teams. Show them the current homepage design and assess how well they can evaluate and suggest improvements on messaging and design.
• Sales — Focus: experience working with sales teams. Assess the candidate’s prior experience working with sales teams and understanding of sales process and funnels. Ask them to walk you through how they’ve worked with sales in the past and how they’d want to work with you.
• Anyone — Focus: communication and cross-group collaboration. Assess the candidate’s ability to lead cross-functional initiatives. Ask them to walk through the biggest project they’ve ever done, communicate the rationale, and walk through how they resolved conflict and got people to agree.
• Anyone — Focus: experience with public relations. Assess the candidate’s prior experience with public relations. Ask the candidate to explain a previous PR effort they’ve done, and explain/teach you the best practices on how they would go about structuring an outreach campaign for our company.

By keeping the interview loop and the questions the same, each interviewer on the loop should have the ability to meet multiple candidates and gauge for how well they’re answering the questions in their specific area of focus. The group convenes as soon as possible after each candidate’s loop and provides their yes/no vote and feedback to the group based on their focus area. After asking several candidates the same question, in my experience the difference between an excellent and good answer becomes very clear.

Establishing a strong interview process is a huge asset to anyone who is hiring whether it’s at scale or a single hire. For your team, developing a shared internal process centered on transparency and candor can go a long way to establishing the expectation of what type of talent you want in your company. When members of my team see me hold the bar high on filling a position and waiting it out, it sets a powerful example that we aren’t going to hire quickly just to fill a seat. Document and take notes as much as possible, because you never know if you’re going to need to look back at prior candidates or refresh your memory if a search is running long. I like to capture the hiring pipeline in a spreadsheet for the hiring group to see who is in phone screen, first round, second round, and whether we’ve made a decision to keep the process organized and moving quickly.

In the competitive hiring market, making sure candidates have a great experience is key as well. When you’re interviewing a lot of people at once, it’s easy for it to devolve into a funnel and numbers game. Make candidates feel great with personal touches, like asking interviewers to review their resume in advance and offering them refreshments or tours while they’re visiting. Leverage the interview process as a way to ensure they are having a high-quality experience. Use the feedback from the interviewers to send timely feedback and get back to them quickly. While large companies struggle with the speed of feedback, startups can have a unique advantage in showing that they are delivering a personalized and fast-moving recruiting experience.

When the perfect candidate isn’t available, interview for potential

It’s not uncommon to see situations where the ideal candidate just isn’t available or doesn’t exist. Many startups are focused in new markets or product categories where people with relevant experience simply don’t exist. In situations like this, it’s a priority to find people with the potential and curiosity to rise to the challenge. Often these are the marketers who need to be capable of (and excited about) wearing multiple hats and adaptable to meet the needs of a rapidly evolving business.

To interview against potential, I primarily look for the the traits of curiosity and problem-solving. For curiosity, I try to ask them questions to get at an aptitude for learning. For example, I might ask a marketer what they know about the technology of the company they are currently or previously worked at. Or, what happens to a lead after they fill out a lead form at their company? If they know the answer, how did they learn that? Curious people have a tendency to pick up details about how the world works around them. They are the folks that are constantly asking questions and trying to understand the system beyond the world they think in which creates great starting points for creative thinking.

For problem solving, I like case questions as a great way to evaluate this, either as prepared interview homework or a live case interview in the office. The goal is to have the candidate address a unique marketing challenge and walk me through their thought process on how they would investigate and solve this problem. Here is an example of a case study might look like:

For this exercise, we’re going to take a complete fictional example. There are no right answers but I would like you to walk me through your thought process as you consider this situation. Imagine we are launching a product for school nurses in K-12 schools. Can you walk me through how you’d figure out how to reach these nurses and promote to them?

In the candidate’s response to this example, I’m looking for several things:

• Customer research — are they reaching out to the nurses to find out if there are events they attend, articles they read, associations they are part of? Often I will probe for how they would go about locating and contacting the nurses.
• Hustle — are they extrapolating from their previous work or experiences ideas that might apply to this situation? A candidate might share that they would reach out to the parents of school-age kids and work through them to get ideas.
• Creativity — are they willing to brainstorm some crazy ideas?

Hire based on the strengths of your current team

I am strong believer that it’s important to focus on hiring people who are A+ on an area that your team needs help in over hiring someone who is a solid B+ all around. Well rounded doesn’t always make sense for a first marketing hire. Instead, it’s important to aspire for the T-shaped person who has depth in key areas you need help with, paired with the capacity to collaborate and learn across disciplines. Rather than searching for the full stack, hire based on the strengths of your existing team and how collectively this team can address the needs of your business. If you have strong expertise on the team in quantitative marketing but need help in brand, it’s more important to get a rockstar brand marketer in the door rather than someone who has done both fairly well.

I often see companies passing on candidates who are extremely strong in a functional area because they lack substantial management experience. However if the candidate has willingness to learn and there are strong managers on the team that can coach them in this area, it may be worthwhile to weigh the risks and give them a chance. This is a unique opportunity to get a high-quality hire who is going to immediately add value and attract and retain them with a substantial learning opportunity.

Your first marketing hire doesn’t have to be hard

In conclusion, hiring your first marketer at your company doesn’t actually have to be hard, but it should be a thoughtful process to ensure that you and your hire are set up for success. Start by defining a clear scope for your marketing role, reinforce it by running a strong hiring process, and ensure you are laser focused on the skills and experiences you need to move your business forward.

Ada Chen Rekhi is co-founder & COO of Notejoy, a collaborative notes app for individuals and teams. She’s also an executive coach who works with founders and executives looking to scale themselves as they scale their teams. If you enjoyed this essay, subscribe to her newsletter or follow her on @adachen.

How to Make Your First Marketing Hire was originally published in Ada Chen Rekhi on Medium, where people are continuing the conversation by highlighting and responding to this story.

Shoe Dog is the memoir of Phil Knight, founder and CEO of Nike and details the company from its early start through their 1980 IPO. There are several good reviews of the overall book (here, here, and here), but it surprises me that so few have discussed the ethical quandaries that Knight faces as he builds Nike.

There are three key moments where Knight flat-out lies or steals information to build the fledgling Nike. I puzzled over these as an entrepreneur and leader myself and wondered if I would sleep well at night doing something like that.

When is it ok to lie about your business? When is it ok to steal information?

Example #1. Lying about having a company he doesn’t have yet

In his very first meeting with Onitsuka, the Japanese company manufacturing the Tiger shoes which Knight goes on to distribute, he lies about having a company. Having walked in with no more than the information he prepared for a Stanford GSB class project, Knight delivers his presentation and makes up a company name on the spot which he doesn’t have.

“Blue Ribbon,” I blurted. “Gentlemen, I represent Blue Ribbon Sports of Portland, Oregon.”

This was a moment of existential crisis for the early company, and Knight pulls through with a lie. If he had admitted that he didn’t have a company, he wouldn’t have a deal. So he faked it. Despite admiration for his gutsiness, consider for a moment the other side. How would you feel if you were Onitsuka and a business partner lied in this way?

Example #2. Lying about an office he doesn’t have yet

When a competing distributor of Tiger shoes, who Knight dubs ‘The Marlboro Man’ begins to compete against them with national ads, Knight flies out to Japan to meet with Onitsuka again. Faced with the concern that the Japanese company wants a larger U.S. Distributor, he lies again.

Onitsuka wanted for its U.S. distributor someone bigger, more established, a firm that could handle the workload. A firm with offices on the East Coast. “But, but,” I spluttered, “Blue Ribbon does have offices on the East Coast.”

The lie is so successful that he wins the deal:

I tried to be nonchalant as I signed the papers and placed an order for five thousand more shoes, which would cost twenty thousand dollars I didn’t have. Kitami said he’d ship them to my East Coast office, which I also didn’t have.

Example #3. Stealing information from his opponent

Over time, the relationship with Onitsuka begins to sour and Knight suspects that Kitami, the export manager, is talking to his competition. In order to verify this he steals valuable information during a visit to his offices.

The moment he was out of sight I jumped from behind my desk. I opened his briefcase and rummaged through and took out what looked like the folder he’d been referring to. I slid it under my desk blotter, then jumped behind my desk and put my elbows on the blotter.

Clearly, inviting someone over to your office and stealing information from them is wrong! However, it enables Knight to glean valuable information to plan for the preservation of his company. This is the most egregious sin he commits against the company in the book, but also the climax of several other missteps.

An effective leadership strategy, justified by winning

As an entrepreneur, I have great admiration for Knight, Nike and what he’s been able to accomplish. We can only aspire to build such a successful and enduring company. While so many leadership books present overly simplistic, black and white aphorisms, this is the real deal, complete with all of the warts, complex unsolvable problems and unexpected news that entrepreneurs face. While I’m not sure about my own personal comfort level with Knight’s actions, it’s undeniable that this along with everything else was a winning strategy. Today Nike’s market cap is worth over $87 billion dollars and they are an iconic global brand.

It is easy to talk about integrity, but what happens when the entirety of your business and life savings hangs on a thread, and one lie can save you? Where is the line between committing an ethically wrong act and “fake it til you make it”? These are worthwhile and important questions to ask ourselves because every day is a test of our own values and integrity. Through his narrative, Knight is able to build a connection with the reader to the point where I found myself sympathetic, or even understanding, as he toes and transgresses beyond the ethical line of what is right and wrong.

Recently Fortune’s Erin Griffith published a piece, The Ugly Ethical Underside of Silicon Valley, highlighting a long and growing string of startups committing fraud: Hampton Creek, Theranos, Lending Club, Skully, Zenefits. There are examples from outside of tech startups, too, like Volkswagen’s emissions scandal. What if they all began as one white lie? Shoedog highlights the fragility of our own integrity and how easily, when pushed to the brink, entrepreneurs can walk a darker path.

The honesty and openness of Phil Knight’s memoir was refreshing and delightful. Definitely recommend Shoe Dog as a read for anyone.

Ada Chen Rekhi is co-founder & COO of Notejoy, a collaborative notes app for individuals and teams. She’s also an executive coach who works with founders and executives looking to scale themselves as they scale their teams. If you enjoyed this essay, subscribe to her newsletter or follow her on @adachen.

Phil Knight’s Shoe Dog and the slippery slope of founder ethics was originally published in Ada Chen Rekhi on Medium, where people are continuing the conversation by highlighting and responding to this story.

One of the areas I often advise startups on are questions around how to structure a marketing organization or make their initial marketing hires. I noticed there isn’t a lot of information out there about the different types of marketers, so I wanted to share some of the key functions that make up a marketing organization and thoughts on how to build and structure your team.

Eight Key Marketing Functions and Roles

As with most industries, there are many specialties in the marketing role. Some marketers may be strong at creating a crisp narrative to tell the story of your brand while others may be excellent at devising and executing quantitative online growth strategies. In a larger organization, the marketing department often looks like a group of specialists with distinct skill sets and responsibilities. Below I highlight eight of the key marketing functions that you will often find in a larger organization — with the caveat that this list is by no means comprehensive.

Creative & Content

Members of the Creative team drive the development of high-quality collateral based on the target audience, positioning, and channels where the content appears. Sometimes this looks like creative team members who directly create the content, and other times it can look like defining guidelines and identifying agencies to get this work done at high quality. At scale, a content marketing team can include many roles such as designers, copywriters, technical writers, editors, researchers, web developers, and content strategists. Effective Creative teams are focused on creating marketing materials that intersect high-quality content with high-performing content, and are hungry for data to understand how their output contributed to the organization’s objectives.

Example outputs: ad creatives, blog posts, website, landing pages, videos, e-books, podcasts, list of agency vendors, creative guidelines

Key metrics: team and project hours (estimated vs. actual), unique visits from content, conversions from content, impact from executed campaigns

Demand Generation (B2B specific)

Demand generation marketers are the B2B-specific version of online marketing, focused on driving leads with sales through both online and offline channels. These channels can include paid search & display, list buying, webinars, content marketing, events and more. In addition to this, they are often responsible for lead nurture programs to qualify customers over time as well as working closely with the sales team to improve lead capture and scoring. While their duties may appear very similar to online marketers, I chose to define them as a separate group because their skill sets are not interchangeable. This is due to key differences in common channels and tools, but also a vast divide in working with an online vs. sales conversion funnel. High-functioning demand generation teams are not only focused on getting lead form fills, but follow the lead all the way through to the closed-won sale to gather insights on how they can improve close rate over time.

Example outputs: lead generation forecast, media buying plan, channel test plan, list buying, landing page optimization, lead nurture programs

Key metrics: MQLs (marketing qualified leads), sales bookings influenced by marketing (# and $ deals won)

Field Marketing (B2B specific)

Field marketers drive sales revenue by driving sales pipeline and accelerating sales close rates through marketing programs. Often field marketing organizations are a crucial part of providing localized support for geographically dispersed sales teams through in-market events, webinars and outreach. Strong field marketing organizations are deeply involved with and share accountability with the sales organization on meeting their revenue targets. They should be developing marketing plans that build into how they will drive the sales revenue number, taking into account product mix, account quotas, geographic distributions, average deal size, and sales cycles.

Example outputs: lead generation forecast, events calendar, webinar schedule, collateral plan, case studies

Key metrics: MQLs (marketing qualified leads), sales bookings influenced by marketing (# and $ deals won)

Marketing Communications

Communications marketers drive brand strategy and corporate messaging, playing a key role in ensuring a consistent look, feel and message across all media. Depending on your business’s objectives, this can include social media, conference speakers, employee relations, public relations, publicity, analyst relations, influencers and more. They are tuned in to the industry and trends, helping to define the overall narrative of the company to ensure that your organization’s story is relevant, timely and furthers your goals.

Example outputs: media plans, press mentions, speaking tours, product placements

Key metrics: brand awareness, press mentions, earned media (often measured in traffic, conversions)

Marketing Operations

The marketing operations team provides the critical technical expertise and execution skill to execute on marketing programs and optimize their effectiveness. The advent of robust marketing technologies has enabled deep levels of personalization and targeting to prospects and customers, and there is huge demand for data-driven marketing campaigns. However, the need for personalized marketing has created an explosion in tool complexity. Marketing teams now have to manage everything from database size to building and running clean A/B tests to establishing automated drip email campaigns to customers which change based on their product engagement state. In addition to this, they need to ensure clean processes exist for analyzing and optimizing campaigns for ROI as well as centrally owning CRM systems which multiple teams leverage. This is where an excellent marketing operations team comes in. Having an excellent marketing operations team can make the difference between a campaign’s success or failure based on their ability to effectively execute the campaign strategy. Often roles within marketing operations teams include email marketers, data analysts, and web developers and can also leverage external consultants and vendors.

Example outputs: newsletter, landing pages, email A/B tests, triggered messaging, drip series, winback campaigns, referral campaigns

Key metrics: email volume, email deliverability, impact from executed campaigns

Marketing Research

Marketing researchers provide the key insights to the organization to make smarter, data-informed decisions. They leverage data from primary sources (e.g., user interviews, sales data, surveys) and secondary sources (e.g., industry reports, benchmarks) to provide quantitative and qualitative insight to their partner teams. Marketing research teams can provide a distinct competitive advantage for your company, because they enable you to listen effective to your customers and market and react to make adjustments quickly. The research team can also provide leading indicators through data of market shifts or changes in customer sentiment.

Example outputs: customer satisfaction and driver analysis, competitive intelligence, usability tests, vertical-specific research

Key metrics: project throughput, impact of research

Online Marketing

Online marketers drive customer acquisition through online channels such as SEO, social media, paid search & display. Often, they are highly quantitative and technical, working to maximize the number of customers acquired at the lowest cost through campaigns and continuous optimization. Sometimes this looks like marketers leveraging an external agency, or hands-on work done by an individual within the organization. Excellent online marketers keep a close eye on changing market dynamics, such as competitive environment, search algorithm updates, or new ad products. While their duties may appear very similar to demand generation marketers, I chose to define them as a separate group because their skill sets are not interchangeable. This is due to key differences in common channels and tools, but also a vast divide in working with an online vs. sales conversion funnel.

Example outputs: media buying plan, channel test plan, landing page optimization, SEO content plan

Key metrics: conversions, CPA (cost per acquisition), CPA/LTV (cost per acquisition relative to customer lifetime value)

Product Marketing

Product marketers accelerate product growth by championing the customer, communicating product value, and driving distribution. Often they are working closely with product and other cross-functional teams to launch products as well as drive product engagement initiatives across multiple channels. Excellent product marketers are successful at driving results through close partnership and communication with other team members who provide the expertise and execution. Often this role looks similar to that of a product manager, where they need to deliver results through influence without authority. For more detail, check out my earlier post ‘What is Product Marketing?’.

Example outputs: go-to-market plan, pricing, product messaging & positioning, customer segmentation, customer satisfaction dashboard

Key metrics: product adoption metrics, product engagement metrics, customer net promoter score

Growing your marketing organization

If you’re an early technology company thinking through initial marketing organization, this may seem like a formidable list. However, keep in mind that not all organizations require all functions. Depending on the needs of your business, you may choose not to have anyone fulfilling some of these marketing functions until you need them or have a single individual who is fulfilling multiple roles at one time. For example a startup will often choose to hire one generalist marketer who has experience in one or two functional areas but is versatile enough to cover additional areas as well.

As your business grows, it’s natural that the marketing organization should evolve to reflect its current needs. As organizations grow and mature, they should be continuously adapting their structure to whatever needs come about. One resource I have found helpful is HubSpot’s CMO’s Guide to Marketing Organization Structure which shows great examples of how companies have chosen to structure their teams and why.

Marketing organization structure

One of the key factors worth considering early is how to align your organizational structure. Often this looks like a decision on whether to create a single centralized marketing organization or a decentralized marketing organization where marketers are dedicated in multiple parts of the organization. Centralized marketing organizations are structured as a marketing leader with senior marketing leaders reporting to them who execute across all audiences and product lines. Decentralized marketing organizations are structured as multiple marketing teams aligned to execute against dedicated product lines or business units.

There are benefits to both structures. Centralized marketing organizations can build functional marketing teams that drive consistency and shared learnings across the entire company. If the online marketer of a product is seeing strong results from a new online media channel being tested, it’s far more likely that those learnings will get expanded and leveraged to other product lines in the business. Customers are more likely to see a consistent message in the market with a central marketing organization because all creatives and messages are more tightly coordinated.

However, marketers in centralized organizations have to balance competing priorities across the organization, and this can create inefficiency and slow execution. In particular these conflicting priorities can make it very challenging for upstart products within a mature organization to get the marketing support they need. Centralized organizations are also incentivized to drive up gains for the overall organization, so they tend to be more inflexible to the needs of individual product lines. For example customizing emails for a specific product line may seem like a no-brainer for the business, but fall to the bottom of the priority list because the marketing organization is focused on larger optimizations that impact everyone.

Decentralized marketing organizations can enable organizations to make decisions and act more quickly. They can hire marketers with deep expertise in a product or audience, and commit dedicated resources to ensuring a product or business unit is successful. The success of the marketing organization is more tightly coupled with the success of the product, with clear priorities and alignment on what it means to create success for the product line they support.

There are downsides to decentralized organization structure as well. If each product or business unit has to hire their own marketers, it can often be inefficient for managing cost or leveraging senior expertise. An example of this I’ve seen is a team trying to improve its efficiency in leveraging customer data to target sales outreach. Despite the fact there were senior leaders within the company with deep expertise in this area, this smaller team struggled both to make substantial gains in this area and also sent duplicate messages to the same customer. Decentralized teams often lack close coordination and communication between product lines, and this can result in inconsistent marketing messages.

Neither structure is inherently better or worse, rather which you should choose depends on where you are as an organization. Choose to have a centralized marketing organization that does a better job at coordinating across units and get the benefit of shared services? Or one that decentralizes marketing activities to business units where marketers are far more aligned to customers and the business unit priorities they support?

The key here is to progressively build out your marketing organization based on key functional expertise you need, and find versatile talent along the way. As you prove out repeatable channels that drive growth, this enables deeper investment with specialized roles. It’s not uncommon (and completely fine) to find very asymmetrical marketing organizations, such as performance-driven companies that have virtually no marketers other than online marketers.

I hope this gives you a look into some of the common functions and roles within a marketing organization. While this is certainly not the comprehensive list, thinking through and articulating where your business can benefit from marketing can improve your hiring effectiveness. And hopefully help you build and scale a high-functioning marketing organization!

Ada Chen Rekhi is co-founder & COO of Notejoy, a collaborative notes app for individuals and teams. She’s also an executive coach who works with founders and executives looking to scale themselves as they scale their teams. If you enjoyed this essay, subscribe to her newsletter or follow her on @adachen.

Anatomy of a Marketing Organization was originally published in Ada Chen Rekhi on Medium, where people are continuing the conversation by highlighting and responding to this story.