Deciding to change jobs can be an exhausting and overwhelming process, especially if you’re someone who puts their heart and soul into their work. Emotions, relationships with coworkers, comfort in your role, and our own career goals typically factor into these decisions much more than objective components like compensation or PTO policies.

The following is a framework I’ve used successfully in the past to help me decide whether or not an opportunity is worth taking. It consists of 6 dimensions, all starting with T so it’s easy to remember - TAM, Team, Trends, Traction, Technology, and Timing.

• TAM (Total Addressable Market): Is this a venture backable business? Startups come in all shapes and sizes, and the ones which have been most interesting to me are those which are VC backed. Contrast this with privately owned lifestyle businesses. Those opportunities may be rewarding, but aren’t likely going to experience the kind of exponential growth needed to unlock life changing ROI on your stock options. The larger the Total Addressable Market, the more likely you’ll see disproportionate returns on your time invested in the company. Startups competing in small markets have a hard time raising money and making the kinds of big bets which create massive success.
• Team: Is this the team capable of executing on the vision? Liking the folks you work with is one thing, but the chances of a startup succeeding depends on a lot more than that. Realistically, the best predictor of success is past success. I personally look for teams who’ve worked together before, because that usually points to a dynamic leader and shared bonds. Ideally, those bonds come from at least one previously successful exit in a related space.
  • Don’t despair if not all / none of these things are true. Successful businesses can be built by first time founders, although this is more true in some industries vs. others (e.g. common in consumer tech, not as common in B2B or B2E companies). One thing I would never compromise on is domain knowledge. The founding team needs to have deep knowledge about the problem space, market, and a foundational insight (ideally a technical innovation which translates into a business model innovation) which all success is predicated on.
• Trends: Will the wind be towards your back? Great businesses aren’t built around amazing products alone. Something else needs to be working in your favor. Startups are hard enough already. Avoid joining a company where a significant amount of your energy will be fighting against trends happening across an entire market.
  • Ideally the startup is capitalizing on some secular (i.e. completely outside of it’s control) trend like HR departments taking on IT responsibilities in SMBs, cloud infrastructure utilization, or mobile phone adoption. With the wind to your back, doors you wouldn’t imagine existing will just open for you.
• Traction: What has the team done already? Unless you’re joining at day 1, you’ll have the opportunity to evaluate the work the team has done so far. Their output should be wildly disproportional to their size and stage. Use the product and ask yourself, “Does this work? And am I impressed?”.
  • You can also judge this by looking at the company’s org chart. Early stage (pre-product, pre-revenue, pre-product-market-fit) startups with a many “directors”, “VPs”, or “chief” roles should scare you. Typically that’s a sign that people on the team are more incentivized to build their careers v.s. an amazing business.
• Technology: Is it cool? This is a big one for me personally. What the company is building has to just be cool and technically interesting in order for me to be fully engaged with what I’m doing. You know you’ve hit a bullseye on this one if you’d pay for your own ticket to a conference where someone from the company was presenting.
  • At the end of the day, when I’m talking with engineers building the product, I need to feel like I’m back on my FIRST Robotics team in High School - a bunch of nerds who eat, breath, and sleep whatever it is they’re working on at the moment.
• Timing: Does it make sense for you now? All other aspects of the opportunity may score high, but if the timing isn’t right for you then it ultimately isn’t a good fit. Good timing is when the startup has the perfect role for you today. Less good timing means they have a role for you, but not a perfect role yet. What “perfect” means varies quite a bit between individuals, stages in your career, and your personal goals. Factors include compensation, work-life-balance, and scope of role.
  • This dimension can also mean timing the market, if you zoom out a bit. When did the company raise? At what valuation? Is the macro landscape in the company’s favor for when they raise again? Will it take a lot for them to grow into their valuation, therefore potentially limiting your upside? You need to answer all of these questions, and more, when figuring out if it’s the right time for you to take another opportunity.

Hopefully this helps you decide what to do next. Feel free to ping me on LinkedIn if you have any thoughts or comments.