Key Criteria for Choosing a New Role

I’ve turned down CEO and COO offers. Here’s why: I wasn’t confident I could deliver the outcomes the investors wanted — and I didn’t believe anyone else could either. I’ll take calculated risks, but there has to be some reasonable or foreseeable path to success. And, the challenge has to match the title. A C-suite position that’s really a Director or VP role in disguise doesn’t teach you much if you’ve led in similar environments at those levels before. That big title might open future doors, but will include a lot of false positives. The opportunity itself — and the company it’s at — matters most. Here are six things I look for when thinking about new job opportunities (and yes, this list has been refined by good and not so good career choices): 📈 Business fundamentals: product-market fit, financial sustainability (e.g., path to profitability or likelihood to be able to successfully raise a round), runway, churn rate, growth rate. 🌎 Macroenvironment context: Is the sector expanding or contracting? Is the company well positioned competitively? 🧑💼Employee signals: Glassdoor reviews, attrition rates, internal promotion rates, strength of backchannel references (as available). 💬 Customer signals: Public customer reviews (G2, Capterra), NPS scores, strength of word of mouth, ability to do a free trial of the product (Did I understand the onboarding flow? Was it performant? Easy to use?). 🎯 Leadership: Strength of the founder and executive team (track record, vision, honesty — can I validate what they’re saying in any provable way), values and culture alignment, competence and caring (aka are these humans I’d trust to make hard decisions that impact real people’s lives). 🧩Personal fit: Does the role advance my 5-10 year career goals? Does it make sense from a total rewards perspective (e.g., compensation compared to workload)? Is the environment (e.g., size, funding model) where I do my best work? What job opportunities have you turned down? And, how do you identify the right ones? __ 👋 I'm Melissa Theiss, 4x Head of People and Business Operations and advisor for bootstrapped and VC-backed SaaS companies. 🗞️ In my newsletter, “The Business of People,” I share tips and tricks that help People leaders think like business leaders.

For the job seekers in my network Here are 12 considerations to keep in mind if you’re looking for **longevity** in a tech sales role. 1. Industry Work for a company that sells into an industry that resonates with you. e.g. If you work for a SaaS company that sells into the legal industry, but you aren’t that interested in what lawyers are interested in… well, that’s not ideal. Your company is not going to randomly pivot from legal and start selling into restaurants, or financial services, or construction. 2. Buyer persona Work for a company where you’ll be having conversations with customers you are open to talking with, to see if you can help. Similar to #1. Examples: If you sell cybersecurity, you will be talking to IT personas all day every day. If you sell ATS, you will talk with HR personas all day every day. 3. Product Work for a company where you **aren’t unexcited** about the product. And of course, it’s much better if you’re actually genuinely excited about the product you sell. Cause you’ll be talking about the product a LOT. 4. Career path How long does it usually take to promote? WHAT does it take? What is measured? What does a day in the life look like after that first promotion? 5. Sales enablement What resources are available internally at this company that will help you do your job more effectively? 6. Professional development What resources are available internally at this company that will help you grow as a person? 7. Financials Does the company have three months of runway left before it goes belly up? Did they do 2 rounds of layoffs over the past 4 months? 8. Category leadership Is this company’s product widely considered to rank eighth in a product category that has seven other products that rank ahead of theirs? If so, you might be in for some rather rough competitive sales cycles. For a lot of buyers, perception is reality. 9. Marketing air cover Your life as a seller will be a lot easier if the company you work for actually cares about marketing. Not all do. And customers will generally be happier too, if marketing and sales are working together in unison. 10. Tech stack You will use this company’s internal tech all day every day. Find out what it is and if you can live with it. For example, can you live with a CRM that’s NOT HubSpot? 11. W2 Find out, what does a rep average on a W2? OTE is one thing. How much you can expect to actually make in Year 1 and Year 2 is another. Beware of FauxTE. Money is important. 12. Realistic quotas Find out how attainable the quota actually is. No org ever has 100% of reps hit quota. But 55% of reps hitting quota is a big difference from 30%. Low performance cultures aren’t healthy cultures. Avoid unhealthy sales cultures and say no to FauxTE: https://lnkd.in/gSA8sSqx What would you put in the list as number 13? . .

“I don’t want people to micro-manage me” Defining our next role is often about what we 𝙙𝙤𝙣'𝙩 want 🙅♀️. But how can we figure out what we actually DO want? My coaching clients have found this approach effective: 🔍 𝗦𝘁𝗲𝗽 𝟭 Reflect on your most and least satisfying jobs. Focus on your personal experience, not what ‘should’ make a job satisfying. 📋 𝗦𝘁𝗲𝗽 𝟮 Identify what specifically made those roles satisfying or not. Make a list. 🔎 𝗦𝘁𝗲𝗽 𝟯 Compare your list with the 7 factors that research supports as leading to job satisfaction (see below). 💡 𝗖𝗼𝗺𝗯𝗶𝗻𝗲 𝘆𝗼𝘂𝗿 𝗹𝗶𝘀𝘁 𝗼𝗳 𝗽𝗮𝘀𝘁 𝘀𝗮𝘁𝗶𝘀𝗳𝘆𝗶𝗻𝗴 𝗲𝘅𝗽𝗲𝗿𝗶𝗲𝗻𝗰𝗲𝘀 𝘄𝗶𝘁𝗵 𝘁𝗵𝗲 𝗯𝗲𝗹𝗼𝘄 𝘁𝗼 𝗰𝗿𝗲𝗮𝘁𝗲 𝗮 𝘁𝗮𝗶𝗹𝗼𝗿𝗲𝗱 “𝗰𝗵𝗲𝗰𝗸𝗹𝗶𝘀𝘁” 𝗳𝗼𝗿 𝘆𝗼𝘂𝗿 𝗻𝗲𝘅𝘁 𝗿𝗼𝗹𝗲 𝘀𝗲𝗮𝗿𝗰𝗵. 📚 The 7 factors that tend to lead to higher job satisfaction: ✅ 𝙋𝙚𝙧𝙨𝙤𝙣-𝙅𝙤𝙗 𝙁𝙞𝙩: roles that match your strengths, values, and where you can be yourself. ✅ 𝘼𝙪𝙩𝙤𝙣𝙤𝙢𝙮: meaningful control over your work, like flexible scheduling or choice in projects. ✅ 𝘾𝙤𝙡𝙡𝙚𝙖𝙜𝙪𝙚𝙨: a team that shares your values and goals. ✅ 𝘿𝙚𝙫𝙚𝙡𝙤𝙥𝙢𝙚𝙣𝙩 𝙊𝙥𝙥𝙤𝙧𝙩𝙪𝙣𝙞𝙩𝙞𝙚𝙨: growth opportunities aligned with your interests. ✅ 𝙏𝙖𝙨𝙠 𝙑𝙖𝙧𝙞𝙚𝙩𝙮: What keeps you engaged? Identify the level of variety that suits you. ✅ 𝙒𝙤𝙧𝙠𝙞𝙣𝙜 𝘾𝙤𝙣𝙙𝙞𝙩𝙞𝙤𝙣𝙨: both the physical workspace and the company's culture. Does it foster creativity, trust, etc.? ✅ 𝙒𝙤𝙧𝙠𝙡𝙤𝙖𝙙: a balance – not overwhelming but enough to keep you engaged. 🤔 What qualities will you look out for in the next role? Reach out if you're looking for guidance on this path.

Making Career Decisions with Confidence If you have been interviewing, the odds are good that you'll have the opportunity to consider multiple jobs. These decisions can feel overwhelming. How do you ensure you're making the right choice for the right reasons? 📌 Use this Decision-Making Framework to evaluate your options objectively: 1️⃣ List Your Job Options (e.g., Job 1, Job 2, Job 3) 2️⃣ Identify Your Criteria/Priorities – What truly matters to you in your next role? (e.g., career growth, flexibility, salary, impact) 3️⃣ List Criteria in order of importance 4️⃣ Score Each Job (1-5) based on how well it meets each of your criteria 🔎 Example criteria to consider: ✔ Career advancement ✔ Work-life balance ✔ Creativity & innovation ✔ Job security & stability ✔ Compensation & benefits ✔ Autonomy & decision-making ✔ Impact & purpose Once you've scored each option, the decision becomes clearer—based on facts, not just emotions. 💬 Will this help you evaluate jobs both pre and post interview?