Which startup should I join?

Evaluating early-stage opportunities

“How do I pick the right startup to work for?” is by far the more popular question I get from my network.

At the early stages, you can’t be certain that you’re picking something destined for an exceptional financial outcome. But you can evaluate whether a given startup will provide an environment where you can be successful. Here are the elements I look for in an early-stage opportunity:

1. Team

You spend a lot of time with your founders and fellow early employees. Are these people you want to see for hours every day? Do you want to have tough conversations with them about pivots, underperformance, or interpersonal issues? Do you sense the empathy, humbleness, and mutual respect that will allow you to move through these moments and still want to work together? Do they have talents that complement yours?

There’s no silver bullet for feeling this out in a 30 minute Zoom call— but here are a few examples of red and green flags I encountered on a recent job search:

• Green flags: calm and thoughtful responses to challenges to the business model, target buyer, competitive landscape; shows a genuine curiosity about me and what I can bring to the team (e.g. they ask thoughtful follow-up questions about my experience, not just reading from an interview script); clear idea of why they’re hiring this role, and what skill gap on the team they need to fill
• Red flags: over-indexing on credentials instead of accomplishments — e.g. bringing up their elite business school degree in every conversation; deriding “people who have done this before,” not interested in hiring any people with experience in the industry or space

2. Real market insight

This one is difficult to evaluate, especially when you’re switching industries or problem spaces. Here are a few things I try to suss out, even when I don’t know the space:

• Can the founders clearly articulate why their approach is different?
• Can the founders clearly articulate why they are well-positioned to win, even if their approach is similar to others in the space? Do they have an ‘unfair’ advantage that will enable them to get a head start (capital, customers, prior knowledge of the space, IP, talent)?
• Have the founders done work with customers, past or present, to validate their approach and position?
• Can the founders explain broad trends in the space to you, and why this business opportunity arose?
• When I spend 30 minutes googling around, looking at competitors in the space, reading industry articles from other founders or investors — do the founders’ answers hold water? When I see potential conflicts with their answers, can the founders directly address those concerns without handwaving? When they really don’t know the answer, are they willing to acknowledge it? Do they have a reasonable intuition for how they would eventually find the answer?
• If I summarize the founders’ approach and pitch it to a trusted colleague who invests or works in the space, do they see the same opportunity?

3. Problem I’m excited about

I’ve been asked a lot about why I moved from finance, to healthcare, to education — many people hesitate to switch industries and worry about the transferability of their skills and experience.

There is work to do in each transition. But I’ve found that industry is less important to me than solving a problem I find exciting and worthwhile. Industry is a big bucket — within education tech, building classroom tools for K-12 teachers is a completely different endeavor than building enterprise adult learning programs. If I’m excited about the problem we’re trying to solve and the people we’re trying to solve it for, then I’m also willing to put in the work to learn the market and the customer.

4. The company needs my skills and job function

When the founders say they’re hiring someone within a given job function… are you all on the same page about what skills this person needs? What are some representative examples of problems they would need to solve, or projects they would need to own?

Digging deeper, I have often found that founders who say they want to hire a product manager are actually looking for what I would consider a technical project manager, or an engineering manager. Or they’re working within a constrained budget, and hoping that they can find someone who can cover multiple different roles. It’s important to know what you’re signing up for, and what the plans are to close skill gaps on the team when they arise.

5. I’ll have space to do my role

In the early stages, founders are often leading multiple functions. Even if they are formally a CXO, they’re leaning on skillsets from previous jobs. They need to feel comfortable backing away, and giving you the opportunity to fill those gaps instead. A few questions I like to ask:

• Why did the founders want to start this company, from a personal career opportunity perspective? Do they have a vision for what they want to learn or how they want to spend their time outside of their previous roles?
• What do they love about their day-to-day? What are they eager to give away?
• Do they have experience managing people, especially in my function? Can they give specific examples to illustrate when they would lean in vs. support my autonomy?
• Are the founders committed to receiving and acting on feedback from people that work for them? Do they have ready examples of influential feedback they have received and given?

6. We’re aligned on the opportunity

Last but not least — is there philosophical alignment between you and the founders about what you’re there to do? Are you looking to head a function? Multiple functions? At what stage of company maturity? What kind of performance would we have to see to expand the team, and where would those hiring priorities be? How long would you be expected to be an individual contributor, or to work alone? How are those current and future expectations reflected in the offer package? Overall, do you feel confident that they value you, so that you can focus on the work instead of trying to close that gap?

If I look back across these dimensions of an early-stage evaluation, we’re really answering 3 questions — Can they do it? (team and insight), Can I do it? (interest and skills), and Can we do it together? (autonomy and opportunity). With intention in early conversations, it is possible to find a mutual fit.

The biggest mistake that I see most people make is that they don’t evaluate opportunities at all — they accept an offer from the first startup that enters their inbox on a week when they felt ready for change. Or they evaluate opportunities narrowly on one dimension — I want this title! — without considering whether the company overall will support their goals. Consider a broader framework — it will put you on a faster path to happiness at work.