In September 2021, Amplitude went public at a $7B valuation and I shared some observations on Twitter on how it felt to build a high-growth startup and what I hope will be a generational company without any hype surrounding it. My primary motivation was to offer a contrast to 2021, where pre-revenue unicorns, pre-emptive offers for $100M+ rounds and back-to-back funding rounds for oversubscribed startups feel like daily news.  

I got a lot of great questions from readers about my experience at Amplitude. These three came up the most often: 

1. How should I pick a great early-stage startup and role to grow in my career? 
2. How does one succeed at a high-growth startup as an early non-technical hire?
3. As an early-stage founder, how do I add high-potential hires to my team? 

It’s hard to do justice to all three at once, so I’ll address one question in each post and make this a three-part series! In this first post, I share my thoughts on the first question holistically, generalizing not just from my own experience but that of many others in my circle of acquaintances. I am also specifically going to address this question for non-technical roles (i.e. not engineering) because the considerations are different. 

How should I pick a great early-stage startup and role?

There’s no one right answer because we all have different values, strengths, and long-term potential. You have a better chance of making the right choice if you know yourself well and can be authentic in both your search and your decision-making process. 

In 2016, I was running a small emerging market venture fund at Khosla Ventures. I had previous founder experience before joining the VC industry but had never scaled a business past million in revenue. I felt strongly that I shouldn’t continue further in my early-stage VC role without scaling a software company. As the companies I was investing in progressed past the $1M in revenue/ARR mark and started to find product-market fit, my ability to continue helping them scale declined. I could see how much more effective VCs with operating experience were at supporting the founders they invested in. The difference could be orders of magnitude. 

Once our fund was fully invested, I stepped away from venture capital to join Amplitude full time as a PM. At the time, Amplitude’s FMV (fair market valuation, more relevant than the last round’s valuation for an employee) was less than $30M and today it’s a public company worth more than $10B. So how did I pick this role and ride the 300x (to-date) growth? 

Phase 1: Preparing to get lucky

There is a lot of luck involved in the eventual outcome for any startup — you can’t wish that away. Having “tier 1” VC brands is absolutely not a guarantee — most startups fail. Even “unicorns” can have a high failure rate, especially if they were minted ahead of their revenue traction by competitive market forces. 

So how do you set yourself up to get lucky? You look for startups where the fundamental odds are in their favor — they have unfair advantages that will help them get to some level of success easily. The following three questions are critical: 

1. Is the addressable market big and growing? 

Look for problems that are deeply meaningful to solve. Look for tailwinds and trends that make it obvious the problem this startup solves is only going to get bigger over time. A big market also means that the startup has more options to pivot and more room for mistakes in execution. 

2. Does the startup have a strong set of founders and engineering team? 

Even if you’re not reporting them, pick founders that you want to work with. I will address this further in the reverse interview phase below. As a non-technical hire, especially in PM roles, the lack of quality engineering resources can be the bottleneck for any idea you have that moves the needle. A high quality engineering team also means the company is a more attractive acquisition candidate in case the IPO dreams don’t pan out. 

3. Do early adopters LOVE the product? 

Looking for customers who rave about the company’s product (and weren’t angel investors in it) was a key part of my process. I also picked products and problem areas that I resonated with because the primary quality needed in a great non-technical hire at a startup is customer empathy. 

What if there’s no product yet, you ask? Then you should most likely not join the company in a non-technical role. There are happy exceptions but the risk-return math doesn’t work.  

Sidebar: The incredible option value of a junior VC role i.e. why you should consider a 2 year stint in venture capital

What you might not have noticed if you haven’t worked in venture capital is that the three questions above are an exact subset of the diligence most early stage investors do when they invest. To me, this is one of the best things about an investment associate role in a good fund. Even if you decide an investing job isn’t for you in the short term, you now have the skills and exposure to land a great role at a great startup. You know how to evaluate not just products but also markets and founders. 

For instance, if you’re thinking about the next 30 years, how should you compare careers in crypto and climate change to enterprise software? This kind of market evaluation is hard to do from inside a single company and is the best thing about being in venture. You get the 30,000-foot view of rapidly changing markets and can speak to some of the smartest founders at the bleeding edge of them to develop a vision for the future. 

That brings us to picking founders. Working in venture helps you understand what founders’ true priorities are, what they are looking for in early hires, and how to serve them best — making you a great partner for the right founder. A couple years in venture can help you skip forward 5–10 years in operating roles by helping you become more strategic — both in how you choose startups and how founders see your ability to help. I’ll share more on this in my second post — how to succeed in a high-growth startup. 

Phase 2: The reverse interview 

Don’t forget that interviews are for the company and for you to both get to know each other. Before choosing Amplitude, I interviewed with dozens of startups that all fit my phase 1 criteria — big growing markets, solid teams, and happy customers. Indeed, a majority of the startups I seriously considered have done incredibly well. However, not all of them knew how to interview me — which was also a helpful signal that I might not succeed there. 

These the four questions I would ask myself over the course of an interview with any startup:  

• Do they know what they need from me in the next 6-12 months? Can they frame it in the form of results rather than activities? 
• Did the panel coordinate beforehand on what questions would be asked in each interview and why? Are they taking my unique background into account?
• Are they intentional about the culture they are creating and does it feel like I would authentically be a good fit? 
• And this one was a critical question for me wherever the founders were young and relatively inexperienced: Are they trying to learn something from me even during the interview process? Are they demonstrating a strong growth mindset? 

If I felt good about these, I would then reach out to customers and investors in the company to see how responsive they were to chatting with me or just responding to my questions over email. With a great company, the entire ecosystem around them responds quickly and passionately, encouraging you to join while offering pros and cons. For a problem company, you will often get radio silence or very late response because most people don’t want to be disingenuous but would also rather avoid sharing direct negative feedback with a stranger. 

Phase 3: The culture test 

Every person I have ever interviewed for a job says they’re looking for a great culture. Every company says they have a great culture while trying to hire candidates. 

But the reality is that culture is an extremely challenging aspect of any company to nail down. The founders’ personality and values are really your best indicator of the company’s desired culture in which people will succeed. I could see my own priorities and attitudes reflected in Amplitude’s founding team, which gave me a lot of confidence. 

Founders have to be tremendously intentional about defining their company culture, reinforcing it with actions (not just posters on walls), as well as finding daily avenues for dialogue about how certain decisions align with their stated culture. In my experience, when it comes to culture, there is no such thing as overkill. If you don’t talk about culture on an exhausting daily basis, you don’t have an intentionally defined culture. The best way to understand a company’s culture is to talk to employees who have joined recently and ask them for examples of how the culture shapes daily work. 

You also need to know yourself well to understand if you will thrive with a particular culture. Are you a jerk sometimes? Do you avoid conflict? Do you like talking about politics and what’s happening outside the building with your colleagues? Do you like solving problems-first principles vs. leaning on past experience? The more you know yourself, the better you can choose a company where you will thrive. More on this in our second post in the series.

Phase 4: The right offer 

You will likely have come across this advice already but it bears repeating. The title does not matter. The only two things that truly matter for your early stage startup offer are as follows:

• Your boss 
• % Equity

Picking the right boss 

In an early stage startup, you either want to report to a founder or to someone the founders find mindblowingly smart and valuable. You want to admire and respect your manager so much, you would pay to get to work with them. This is important because startup “work-life” is going to be hard. High growth startups are all consuming. There is never enough time to get to everything urgent that needs your attention. Hiring more people doesn’t necessarily solve the issue because it takes more time than anyone budgets to hire and onboard people well. 

So, find a manager (and peers) you love to work with. If you are not inspired by what you are learning from them, you are going to feel burnt out in a few months no matter what else is happening around you.   

Understanding Equity

There are 5 questions you want to ask as a part of negotiating your equity offer: 

1. What % of the company does your option grant represent? 

The current valuation and strike price don’t matter as much in an early stage company. What you need to decide is - can this be a $1B/$5B/$10B+ company? And how much of that could you own?

2. Will the company let you do an “early exercise” of unvested options when you join? 

If you are a senior, cash rich professional, you want this option to be a part of your offer to optimize for lower tax payments by taking on more risk. 

3. What’s the exercise window of vested options, in particular after you leave the company? 

Good companies offer 10 years so that employees who are risk averse can exercise options after the stock is liquid. 

4. Has the company issued additional grants to high performing employees for going above and beyond? Would the founders consider this and under what circumstances? 
5. If the company is > 3 years old, do they have a policy for refresher grants? 

In a competitive hiring market the first 3 (high %, early exercise option, long window) are must-haves in a good offer. The other two are (very) nice to have. 

Together, a great boss and lots of equity in the right company will benefit your career orders of magnitude more than a particular title that might look good on LinkedIn. Choose future growth over current status. 

Parting thoughts

If you take away one thing from this post, it is the importance of perspective and diligence. Picking how you spend 40–80 hours/week for the next few years is the most important decision you’re making right now for your entire work life, which could be decades. Invest in gaining perspective about different markets, especially ones that are changing fast. Invest time and effort in your due diligence of companies you are evaluating. Last, but not the least, invest in understanding yourself and where you will thrive.