Sales Techniques for Young Entrepreneurs

The less I sounded like a salesperson, the more I sold. The more I admitted we were held together with duct tape, the faster people bought. Everything I learned closing deals from cafe wifi in San Francisco while my co-founder fixed bugs in real-time: 1. You're not selling a product, you're selling belief: Early customers aren't buying features, they're buying your conviction. They want to see fire in your eyes when you talk about the problem. The demo matters less than whether they believe you'll still be around in 6 months to support them. 2. Every "no" is actually "not yet" (until it's not): You'll hear no 47 times before someone says yes. Then that same person who said no will circle back in 3 months when their pain gets worse. Your job is less about closing fast, and more about staying memorable until the timing aligns. 3. Your first 10 deals will come from places you'd never expect: You'll obsess over landing that dream logo. Then your college roommate's cousin becomes customer number 1. That random LinkedIn comment turns into a $50K deal. Serendipity beats strategy in the early days. 4. Discovery calls are therapy sessions where you happen to sell: Prospects don't want a pitch, they want someone who understands their pain better than they do. Shut up. Ask questions. Let them vent. The sale happens when they realize you've lived their nightmare. 5. Your close rate means nothing until deal 50: 3 deals closed out of 5 conversations? Cool, your sample size is meaningless. One founder gets lucky with timing. Real patterns don't emerge until you've had 50+ real sales conversations. 6. Discounting is admitting you don't believe in your price: The moment you drop your price without them asking, you've told them it wasn't worth it. Hold the line. If they can't afford it, they're not your customer yet. Come back when the pain is expensive enough. 7. The demo is where deals go to die: You'll build the perfect demo flow. Polish every click. Then realize prospects zone out after 4 minutes. Show one thing that makes them say "oh sh*t, I need this." Everything else is noise. 8. Your competition isn't another startup, it's doing nothing: You'll obsess over competitor features. Meanwhile your prospect's real alternative is a Google Sheet and hoping the problem goes away. You're not fighting other vendors, you're fighting inertia. 9. Following up is the entire game: 80% of deals close after the 5th touchpoint. Most founders give up after 2. The money is in the patient, non-desperate follow-up that adds value each time, not "just checking in." 10. You can't scale what you haven't done 100 times yourself: Every founder wants to hire a VP Sales after deal 10. You don't know what good looks like yet. You don't know the real objections. Do 100 deals yourself or you'll hire someone to fail expensively.

In 27 months, we grew Retention.com from $1M-$13M ARR with only 1 salesperson (me) doing 1,000's of sales calls. Here are my 10 biggest pieces of advice for any startup who wants to book and close more sales calls: 1. Ask for 15 mins, but book 30 When booking a meeting outbound, you have a better shot at getting a meeting by asking for 15 mins than 30. You may have piqued their interest but with a busy schedule, they are going to weigh learning about your business vs their time. Ask for 15 but send a meeting invite for 30.  If they can’t do the full 30, they will let you know, but from my experience, this rarely happens. 2. Tell your story People remember a story more than a product  Figure out your short story that you can tell prior to getting into the product pitch. How does your story connect to your business / product? 3. 5X5 Pitch Keep your product deck for your initial call to 5 slides / 5 minutes and make sure you answer any of the common questions you get from prospects. You can always book a follow up call to share more detail once you hook their interest. 4. Always Be Pitching Take control of the call and the sales cycle. You will only learn what does and doesn’t work by actually pitching.  5. Tell a customer story Again, people remember stories more than they do stats. Tell a story of a customer before implementing your product and the business outcome after implementing it. Don’t just talk numbers. Talk about how people felt, what they said, etc. 6. Create Urgency Attach an incentive if the deal is done by the end of the week or month.  (Example: 20% more credits or a 15% discount)  This also sets you up well for follow up as it now makes them feel like you are on their team to try and help them get the deal in for their benefit. 7. Land and expand We all want to close the big ACV deals, but the truth is most buyers don’t want to make a big commitment without seeing how your product works. Find a way to get them on for a small $ amount, with the plan to expand if the product meets their expectations. 8. Opt-Out Period Reduce buyer friction by offering a 90 day opt out period if you are trying to close 12 month agreements. It shows confidence that your product will drive the results you say it will. 9. Deck Recap Create a 1-2 pager highlighting the most important parts of your sales deck that you can send via email after every call (even if they don’t ask for it). The prospect won’t remember all details from the call, so this gives them something to look back on and will help sell internally if other stakeholders are involved. 10. Video for FAQs Create short form talking head video answering all FAQs. This will add value in your follow up, show you listened to the questions they had and that you care about making sure they understand the answers. It also helps internally as others will likely have the same questions as the person on the phone. Have questions about how to book/close more calls? AMA anything 👇

I was ready to quit.  My startup was flatlining.  Sales were a rollercoaster—one month we were celebrating, the next we were scrambling to make payroll.  Then, everything changed.  We discovered a systematic sales approach that transformed our struggling venture into a thriving powerhouse.  𝗛𝗲𝗿𝗲’𝘀 𝘁𝗵𝗲 𝘁𝗵𝗶𝗻𝗴:   ↳ It wasn’t flashy.   ↳ It wasn’t revolutionary.   ↳ It was just consistent, measurable, and repeatable.  𝗛𝗲𝗿𝗲’𝘀 𝗵𝗼𝘄 𝘄𝗲 𝗱𝗶𝗱 𝗶𝘁:  1️⃣ 𝗟𝗲𝗮𝗱 𝗚𝗲𝗻𝗲𝗿𝗮𝘁𝗶𝗼𝗻 We defined our ideal customer profile and launched targeted campaigns.  2️⃣ 𝗤𝘂𝗮𝗹𝗶𝗳𝗶𝗰𝗮𝘁𝗶𝗼𝗻 We built a scoring system to prioritize high-value leads.  3️⃣ 𝗢𝘂𝘁𝗿𝗲𝗮𝗰𝗵 We created templates for every touchpoint—cold emails, follow-ups, you name it.  4️⃣ 𝗗𝗶𝘀𝗰𝗼𝘃𝗲𝗿𝘆 We developed a framework to uncover customer pain points.  5️⃣ 𝗣𝗿𝗲𝘀𝗲𝗻𝘁𝗮𝘁𝗶𝗼𝗻 We standardized our pitch decks and demo scripts.  6️⃣ 𝗡𝗲𝗴𝗼𝘁𝗶𝗮𝘁𝗶𝗼𝗻 We set clear guidelines for discounts and terms.  7️⃣ 𝗖𝗹𝗼𝘀𝗶𝗻𝗴 We implemented a smooth handoff process to customer success.  𝗧𝗵𝗲 𝗿𝗲𝘀𝘂𝗹𝘁𝘀? ↳ 37% shorter sales cycles   ↳ 52% higher conversion rates   ↳ 215% revenue growth YoY   ↳ 28% lower customer acquisition costs But the real win?  Predictability.  We could forecast with accuracy, scale efficiently, and sleep at night knowing we had a repeatable path to success.  𝗛𝗲𝗿𝗲’𝘀 𝘄𝗵𝗮𝘁 𝗜 𝗹𝗲𝗮𝗿𝗻𝗲𝗱: Consistency > Charisma   Data > Gut Feelings   Process > Luck This systematic approach didn’t just save our startup—it became our competitive advantage.  👉 Want to transform your sales?  Stay tuned for the launch of “The B2B Sales Playbook”—a step-by-step guide to building a scalable, predictable revenue engine.  P.S. What’s your biggest sales challenge? Drop it in the comments, and let’s brainstorm how a systematic approach could help.  #SalesTransformation #StartupGrowth #B2BSales

I sucked at sales when we started Outset. My background? Product and research. My co-founder Michael Hess? Engineering through and through. Yet, we had to master sales to will our startup into existence. Here's what I wish someone had told me earlier: ↳ Confidence isn't optional, it's everything. You need to believe in your solution completely. Customers can smell uncertainty from a mile away. Every win feeds this confidence like rocket fuel. You can't fake it, you have to build it. ↳ Listening reveals what customers actually need. In early calls, I spoke 75% of the time. Big mistake. I was missing crucial signals. Understanding team dynamics matters more than pain points. Their organizational structure tells you what they'll actually buy. ↳ Rejection is the tuition you pay for success. The best salespeople get rejected constantly. Each "no" teaches you something your "yes" never will. Your ability to absorb rejection determines your ceiling. The sting fades, but the lessons compound. ↳ Bonus: Follow-ups matter way more than you think. That simple "bump" email might feel desperate to you (it did for me). But your prospect is drowning in their own chaos. Your solution isn't their priority – until suddenly it is. The right follow-up often lands at exactly the right moment. What sales lesson hit you hardest when starting out?

In the early days of a startup, the founder needs to be the de-facto salesperson. Why? Usually only they have the unique confluence of context, vision, and passion to sell their product effectively. And while sales is more art than science, I do think there’s some method to all of the madness. Having personally made every selling mistake you can make as an early-stage founder, here are FOUR simple tactics I’ve picked up over the years to accelerate velocity and conversion during sales calls: #1: Do your research While it's easier now than ever to find detailed intel on your prospect, it’s alarming how many founders don’t do basic research on prospects before a call. To address this hurdle, I block 15 minutes before each meeting to do a high-level prospect research. This helps personalize my pitch, demo, or approach based on their industry and hypothesized needs. #2: Listen more Sales demos/calls are meant to be a two-way conversation - so start with questions about their goals, priorities, and problems. Genuinely synthesize their responses without interjecting or thinking of what to say next. Easier said then done! #3: Context framing As you pitch, tie EVERYTHING back to the problem your prospect is trying to solve (which you should now know via #1 and #2). Articulate how your product uniquely solves their challenges better than the status quo. Resist the urge to regurgitate a pre-configured script (prospects can tell) #4: Leverage pre and post-demo collateral I might be biased, but I always try to “show, not tell” through collateral like Supademo, Paage.io 😈 , Flowla 🌊, or Journey before and after the sales call. Interactive demos can serve as critical ammunition for your champions, who can now loop in decision makers or sell your product internally, without being an expert in how to promote your product. Ultimately, by doing a small bit of homework, understanding your audience, and by context framing, you'll turn potential customers into loyal clients. Happy selling!

Too many people chasing AI trends and automation to help them sell better. You are better off doing the stuff that has worked for the last 50 years. They will still work 50 years from now. Here are a few of my favorites: 1. People don’t read They can read, but they don’t. Keep your message short and make it interesting enough to earn their attention. 2. Bring value to every interaction. The fastest/easiest way is to educate. If you can teach someone something about their business they didn’t already know, you’re halfway to earning them as a customer. 3. Don’t negotiate against yourself. You probably don’t need to drop your price. If a prospect is pushing back, it’s usually a sign you haven’t built enough value. Add more things to the package before you take money off the table. 4. Use discounts to speed deals, not win them. A discount won’t convince someone to buy, but it can make them buy faster. Time-based incentives have worked for hundreds of years for a reason. 5. Follow up like it’s your job. Because it is. Most people are just busy, not uninterested. Persistence is what separates the top 10% of salespeople from the rest. _____ At Levelset, we scaled from $0 to $30M ARR by building our sales culture on fundamentals like these. I've helped over 100 companies do the same over the last few years. These habits work. They are not gimmicks or shortcuts. If you’re in sales today, focus on mastering these before you start chasing the next shiny tool.

Early in my career I constantly was told that I wasn’t ready to do sales even though I wanted to… Coincidentally, it was all men older than me telling me that I wasn’t ready. Sure, there is truth to having the gravitas to command a room, comfort to field questions and general acumen to have a dialogue with people more senior to you. But I’ve since learned watching women younger than me become power houses in sales, that age is really just a number. If you have the skills… it really doesn’t matter. So this is for the women in their 20s and 30s… a few tips and tricks of the trade to get you further in that sale. 1. “Would you be completely opposed to…” — People default to “no” because it feels safe, so framing a request this way gets you a “no, I wouldn’t be opposed,” which is really a yes. 2. Use their name more than feels natural — Almost nobody uses names anymore, so dropping someone’s name (“Hey Scott, what are we thinking?”) instantly makes them feel important. 3. Offer two options instead of an open question — Instead of “where do you want to eat?”, ask “do you want here or here?” Both work for you, but it gives the other person a sense of control. Works on clients, partners, toddlers, indecisive friends. 4. Label people into the behavior you want — Praise the behavior every time it happens (“you’re so thoughtful, nobody does this”) and people rise to the label. 5. Just ask for the thing — Directly asking, even for something bold (like cutting a security line), often works. No ask, no get. 6. Talk with periods, not commas — Rushing words together makes you easy to dismiss. Downward inflection and real pauses make people listen. 7. Mirror the last 3 words someone says — Repeating someone’s final few words back (e.g., they say “work has been really stressful lately,” you echo “really stressful lately”) to build rapport and keep them talking. What did I miss?