How to Think Like a VC When Evaluating a Startup Role
A venture capitalist inspired checklist for choosing your next startup role. The questions to ask before you invest your time and energy.
Today’s article is coauthored with my friend
, an ML engineer turned venture capitalist, who splits her time between backing bold founders, writing her own Substack on AI, design, and venture, and building community for women in tech.If you’re weighing a new role, chasing an idea that only you can bring to life, or simply curious about where tech is headed, she’s someone worth knowing. Find her here.
Thank you, Oana, for graciously sharing your insights in this article!
Picture this: you get a message from a recruiter:
We’re growing fast and building something you don’t want to miss. We’ve got strong momentum and exciting opportunities for engineers and managers. When is a good time to chat?
So you take a look. The space seems interesting. Their website looks polished. They seem to be doing well. Then you talk to the recruiter, meet the hiring manager, or the founding team. Everyone’s sharp, enthusiastic, and easy to talk to. You go through the interviews. Eventually, you get an offer.
If the project feels promising and the people seem great, it’s tempting to say yes.
But joining a startup is a bet. You’re not writing a check. Instead, you're putting in something harder to get back: your time, focus, energy, and reputation. Once those are spent, there’s no refund.
That’s why you have to think like an investor.
Venture capitalists do exhaustive due diligence before signing a check. They spend weeks, sometimes months, evaluating a company, questioning the market, the team, the business model, and the timing. They stress-test their assumptions. They don’t just ask, “Is this exciting?” They ask, “Is this going to be at least a 500m exit or an IPO? Is the upside worth the risk?”
If choosing a company is such a big deal for a VC, why wouldn’t you approach finding a job with the same level of scrutiny?
Of course, you won’t have weeks to evaluate every opportunity. You probably won’t get full access until you have an offer in hand. But you can still sharpen how you think. You can still ask better questions: earlier, faster, and more deliberately. This article will help you do that, so keep reading.
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1. Is this a market worth betting on?
Don Valentine, the late founder of Sequoia, always started by looking at the market: its size, its dynamics, and the nature of the competition. Some early-stage VCs are more into the founder’s story, but most VCs Series A and beyond are market-first.
Why? Because the market sets the ceiling. A brilliant team in a shrinking or crowded space won’t get far. But even a mediocre product can survive in a fast-growing market with real demand.
As someone considering joining a startup, you should be asking similar questions. Here’s how to think about it:
Is this market growing, or just trendy? A lot of startups pitch themselves as riding some inevitable wave (AI, climate, fintech, whatever’s hot). But the real question is: what’s changing now that didn’t exist five years ago? Are there real tailwinds pushing this market forward?
How big could this get if they win? This is where most people get stuck because “market size” feels abstract. You don’t need to get it perfectly right, but you do need a sense of scale. Are we talking thousands of customers or millions? Is this a niche product or a category-defining company? Does this feel like a $50M business or a $5B one?
Pro tip: Use AI to sanity check your assumptions
“What is the total addressable market for [X] in [industry]?”
“What would it take for a company in this space to reach $100M in annual revenue?”How many customers would they need to hit $100M ARR? If they sell a $5,000/year SaaS tool, they need 20,000 customers. Is that realistic in this market? How hard is customer acquisition? Is the pricing sustainable?
Is this a market you believe in? Deciding the market potential is about conviction as much as it is about scale. If this space grows, will you be proud to say you spent your time here? Will it open doors for you in the future, or box you in?
If the market looks promising, there will be competition, so the next question is whether this company has what it takes.
2. Can this team actually win?
VCs often say they invest in teams, not just ideas, and for good reason. The team that learns fastest, hires well, sells well, and actually delivers is the one that wins.
As a candidate, you won’t get the full cap table, but you can still try to understand who’s building this thing, how they think, and whether they can actually pull it off.
Who is the founding team, and how do they complement each other? Do they bring different strengths (tech, product, domain)? Or is it two engineers with a deck and no traction? Look them up. See what they’ve shipped, what companies they’ve worked at, and what ideas they’ve explored in public.
How big is the team now, and who are the early hires? A 5-person company looks different from a 25-person one. Early hires set the tone and culture. Are there strong engineers on board? Any respected operators or advisors? Ask who you’ll be working with directly (actual collaborators, not just reporting lines).
Can you get a sense of what leadership values? A company’s culture is a mirror of its leaders; it shows in what gets rewarded, ignored, and how people act under pressure. Is that aligned with your values? Ask:
“What kinds of decisions have been the hardest so far?”
“How does the team handle conflict?”
“What happens when something goes wrong?”
Are strong people sticking around? Ask how long early hires have stayed. Ask what roles they’ve grown into. Some turnover is normal and desired, but if all early hires left, that’s a red flag. “Hire fast, fire faster” is just an excuse for not knowing how to hire well.
Are they moving fast and learning in public? Check their changelog, blog, GitHub, product releases, anything that gives a sense of how fast they move. Are they shipping? Are they listening to feedback? Or are they quietly building in a vacuum?
Do they have founder–market fit? How did they become interested in this space? How well do they know the industry? Do they understand the problem firsthand?
3. Is there a business behind the product?
It’s easy to get excited about a product that looks cool or feels new. But VCs are trained to look past the surface and ask: Is this a real business?
As a candidate, you don’t need a financial model. But you do need to understand whether there’s a path to real revenue, sustainable growth, and customer pull.
Is this a vitamin or a painkiller? In tough markets, people pay for painkillers, not vitamins.
Is there a clear business model? Ask how they plan to make money. Who’s the buyer? What budget is this coming from?
Is anyone paying or committed to paying? If not, are there active pilots, contracts in the pipeline, or users who’ve tried to pay?
What’s the quality of revenue? Retention matters as much as growth. Are customers renewing? Ask about usage, customer feedback, or churn.
If things go well, what does this business look like in 2–3 years?
How much money do they have in the bank, and when do they have to raise again? What milestone do they need to hit for a successful raise?
4. What’s the actual $$$ deal you’re getting?
If you’ve made it this far, the market looks good, the team seems capable, and the business is real. Now it’s time to look at the actual offer.
In venture, this would be the part where investors obsess over one thing: entry price. Because no matter how promising the company is, the question becomes: Is it still a good deal at this price?
You should be asking the same thing:
What’s the current valuation? You don’t need an exact number, but ballpark matters. This impacts how much your equity could be worth, and how much risk is already priced in. Ask directly or estimate based on the last funding round and stage.
How much equity are you being offered, and what does it translate to in ownership? A big-sounding equity number (e.g. “you’ll get 50,000 shares”) is meaningless without knowing the total shares outstanding. Try to get your actual percentage. If they won’t tell you, that’s a signal in itself.
Are they planning to raise soon, and what happens to your stake if they do? Raising another round can help the business, but it also dilutes your equity. Ask how much they’ve raised already, how much runway they have, and what the next raise might look like.
What are the financial outcomes that could make this meaningful for you? If this company exits at $500M, what would your stake be worth? Is that outcome plausible, or are you hoping for a unicorn to break even?
What are you giving up by taking this deal? Lower salary? Less stability? Fewer benefits? Be clear about the tradeoffs you’re making, advocate for yourself, and negotiate (yes, you can!).
5. Is this the right move for you?
This is the part VCs don’t ask, because it doesn’t affect them. They’re not joining the company. This is where you shift from evaluating the company to evaluating your fit with the company.
Why are you considering this opportunity? Is it money? Experience? Ownership? Impact? Or just an escape from something else? Be honest with yourself.
Does the stage match where you are in your career and life? Pre-seed & Series A might sound exciting, but do you actually want the constant uncertainty? Series B and beyond might be more stable, but the financial upside will be smaller.
Will this role grow your skills, or stall them? Who will you be learning from? Will you be building momentum for your next step?
Are you excited to work with these people, every day, in hard moments? Does this group seem like the kind of people you can trust to navigate the chaos?
Conclusion
Treat picking a job with the rigour and scrutiny it deserves. Aim to answer these 5 key questions:
Is this a market worth betting on?
Can this team actually win?
Is there a business behind the product?
What’s the actual deal you’re getting?
Is this the right move for you?
Remember: You’re making one of the biggest investments you can make: your time, focus, and energy. Treat it like a VC treats millions of dollars.
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 | A guest post by
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Love that money is #4 on your list. But in the gambling calculus, most nerds I know start there because it’s a gamble with long odds. “Will I be OK with my deal while the game is being played? Will I be OK if we lose this round?” Most people I’ve talked to in my startup era and since consider the win to be frosting as long as both answers are yes. The other parts of the analysis only matter if you’re trying to or need to guarantee the win.
I think there’s so much company culture hiding in the last bullet of number four that it really deserves its own section. Recent offers to abandoned members of the company formerly known as Windsurf include an expectation of 80-hour weeks, for example. There are crazy startup hours and then there’s grind for the sake of pretending you can do good work for that many hours in a row.