Your First Startup Job Offer - Part 1: Clarity

Learn the playbook and pragmatic tactics for early-stage fundraising from Mike Wilner, a startup founder, advisor, and author of Oversubscribed, a book on seed fundraising.

 min read
Last Updated: 
July 5,2021
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A Tactical Guide to Seed Fundraising

Learn the playbook and pragmatic tactics for early-stage fundraising from Mike Wilner, a startup founder, advisor, and author of Oversubscribed, a book on seed fundraising.

 min read
Last Updated: 
July 5,2021
Sachin Maini
Editorial and Content Lead
Sachin Maini
Editorial and Content Lead
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This is the first in a three-part series on startup job offers for early-career professionals.

Alright, here's the scene— you're young, fresh enough out of school to remember what it's like to spend a hungover Sunday in the library before a Monday exam, and hungry to do something meaningful with your career, whatever that means.

I'm Rishi, and I work as On Deck's Chief of Staff. This is my first job out of college, and four months in, I can say it's without a doubt the best career decision I've made to turn down a return offer to join Google as an APM to come work with this team at On Deck. In addition to being a fan of this company in particular, I've learned so much about the startup scene, careers, personal values, and teamwork recently, and I'm writing this guide to help people figure out which of their available options is best for them.

In the past year, I've had over 100 real-time conversations with college students and young professionals about how to approach the next part of their careers, and also recently became a
manager to three amazing interns; I'm energized by helping people realize their potential.

If you're reading this post about startup job offers, you're might be lucky / privileged enough to be in the closing stages of a hiring process with a small, early-stage, relatively unproven company, and you're simultaneously incredibly stoked and petrified about the opportunity to take a huge risk this early on.

Or you're just dreaming about the possibility, which is just as valid :)

If you're coming from a university setting, all paths to this point have been previously blazed and proven. Here you're making a bet on something that is statistically likely to fail. Everything up until this point has been designed to put you in a position where you have as many career options as possible at your fingertips. What do you do now, faced with an option? This post is here to help you decide whether you should take the leap.

This guide will cover the "Three C's" of startup job offers, aimed at junior-level young professionals (0-3 years of experience) thinking about joining an early-stage startup. (pre-Series B // less than 25 employees) :

  • Clarity: How to decide whether working at a startup is the right move for you right now
  • Conviction: What it means to have conviction in a company and figure out whether it's worth taking this leap for your career, including questions to ask
  • Compensation: How to evaluate an offer, and what compensation and equity might be fair given what you can bring to an early-stage company.

This is not a guide about how to get a job or break into startups; there's plenty of great advice on that out there already.

Today's post will cover the first section - Clarity. Hopefully this is helpful in answering the question "Should I work at an extremely early-stage startup?"

Over the next few weeks, I'll follow up with additional sections on Conviction ("Should I work at this particular startup?") and Compensation ("Should I sign this offer at this startup?"). Let's dive in!

Part 1: Clarity

The first big step to making a decision is to brutally, honestly, check in with yourself to see if you're ready to work at a startup — especially an early-stage one — at this point in your life.

A lot of the commentary around startups, especially on the tech-focused parts of Twitter, tends to gloss over the turbulence and pace of change within these companies. It's an understandable oversight; ostensibly, most of the people who have developed significant platforms in those forums are people who love and thrive on those aspects of startup life, and have been successful in doing so.

There's a huge selection bias in the public narrative to celebrate the good news and cover up the common reality of overwhelming stress that comes with the journey of creating something from scratch. Startups sound sexy, but they're a slog, and the earlier you join, the more true that's likely to be.

Early-stage startups aren't for everyone. Here are some of the key questions to consider when debating the shift, especially if you're coming from somewhere very far away from startups:

How do you feel when faced with uncertainty?

Startups frequently place their stakeholders into highly ambiguous situations, which is a roundabout way of saying that there's not always a right answer to the problems you face. Consider how you react when you have to answer questions to which no one can give you a correct answer (because one doesn't exist). It's going to happen a lot — a healthy balance of excitement and nerves in these situations might be a sign that you'd like a startup environment.

If you perform best being able to see, with crystal clarity, where you will be in a year (e.g. in consulting, promoted to Senior Associate), a startup will not give you this sense of satisfaction. Instead, the voyage may leave you nauseous, as you're unable to clearly see the shoreline of what personal success looks like 9-12 months in the future. You’ll likely fare better at sea if you can derive satisfaction from improving your response to each successive storm you sail into, taking solace when one settles to celebrate your learnings, even if it means drifting off your charted course. Just as quickly, you’ll be expected to recalibrate your compass and brace for the next storm, reinvigorated and energized by your growth.

Is it exciting to you to have to create your own clarity? Fast-growing startups are almost always goal-oriented as opposed to process-oriented. It's likely that the team will have a destination in mind and have to build the plane as it's flying. This means the steps will likely be defined and documented (by you) as they occur, not in advance.

Are you comfortable with highly unstructured mentorship and learning through osmosis?

More experienced folks and leaders at startups are spending their time on building the things that need to be built for the company to succeed, and not as much time giving structured mentorship to junior employees. Developing a robust mentorship program is just not a high-leverage or worthwhile effort for a company fighting for its survival.

The ability to learn and grow by doing and observing, as opposed to by being told how to do something, is crucial to your own professional development in this sort of environment: Tacit knowledge is the currency of learning at high-growth startups. Additionally, responsibility will be put on your platter faster than you can make sense of it, and likely before you feel you're prepared for it.

One thing that differentiates working at a startup from other sorts of jobs (especially at big tech companies) is that your learning is highly network-driven, where you learn not only from the people you work with, but all the people that they know (at other companies, from past jobs, past investors, etc) as well. The ecosystem feels relatively small once you're on the inside, and people are readily willing to help and share their knowledge and experiences with other startup employees. This comes from a shared identity as members of a band of underdogs (as opposed to incumbents), and creates an incredibly powerful effect that helps build deep ties remarkably quickly. Additionally, if you join a startup, the early employees can become your tribe and serve as a strong support system for the rest of your career.

Personally, I struggle as to whether I should be embracing osmotic learning in stride, or taking time out of my day to record and collect small moments / observations / learnings from my colleagues, which are never explicitly framed as "advice" or "mentorship". I love learning by doing, though. Feeling myself palpably, tangibly, develop new capabilities by doing is profoundly fulfilling and one of my favorite parts of working at a startup where I'm pushed from my comfort zone into the growth zone each day.

Does the risk profile of joining an early-stage venture match your lifestyle right now?

Taking a job at an early-stage startup is, in some sense, risky — your employer may not exist in a year, in which case you depart with no notable brand name on your resume, but potentially with lots of hard-earned experience and secrets. Startups themselves are a series of risks, and no matter what, you're going to fail a lot and have to learn from those failures to keep growing. Risk, in this context, is perhaps a less scary concept than a gamble — one way of thinking about risk is the degree to which your circumstances and temperament enable you to accept and be resilient in the face of the consequences of your actions and (sometimes) circumstances out of your control.

That said, the right opportunity, even at an incredibly early-stage venture, may not be nearly as risky as it seems, and there is a lot that you can do to de-risk a specific decision. Much of the "conventional" wisdom around why and how startups are risky is sorely misguided — I thought I knew a lot about startups from my involvement in entrepreneurial clubs/programs in college, but now I realize that my thinking was WAY off base until just a few months ago, in terms of how to evaluate risk. In part two of this series, where we'll cover how to build conviction around a role, I'll present a framework for evaluating the risk of a given opportunity, taking into account role, company, team, and more.

Holistically, understanding the texture and flavor of the risk you're taking from a financial, social, and emotional perspective is what's important. It's okay if you're not in a position to dive into a particular risk-laden opportunity right now; our risk tolerances, like our taste buds, evolve over time, and I don't think startups as a whole are going anywhere anytime soon. If you feel the need to figure out a personal situation, or pay off student loans to feel comfortable taking the leap, and an alternative seems more attractive than joining a startup, seriously consider taking care of that business first — be clear with yourself as to what your priorities are.

Do you like startups?

"What a stupid question.", you think. "I'm literally 70% through a post on startup job offers on a startup's blog. Of course I like startups."

Let's take a step back to figure out whether your values and desires are compatible with how the startup ecosystem operates. These questions aren't meant to be a strong filter, but rather a gut check - if your answer to one of these is no, you'll know it quickly.

  • Do you believe that responsible economic growth is good, and support the role that startups play in creating wealth and mobility for their stakeholders when they succeed (but also acknowledge that they usually fail)?
  • Are you at peace with, or even excited by, the fact that you'll be stretched beyond your comfort zone to grow and scale the business you work for at a pace and intensity you've likely never experienced?
  • Do you believe in technology as a lever for change, and in people's responsibility for how that lever is created as the most important part of the equation?

Did you answer no to any of those questions? Fantastic, you've likely saved yourself at least a year of misery.

  • Bonus point to chew on: Will you pay it forward to help others in your shoes 1-3 years from now by sharing your wisdom, experiences, network, and potentially capital (social and financial)?

It's really hard to simultaneously 1) work at a startup, 2) be anti-startup, and 3) feel fulfilled.

Startup Roles

The range and volatility of a role at a startup can be either a blessing or a curse depending on how you want to grow. Your title is fluid; while it needs to be understood by your teammates, it is subject to evolving into what the organization needs. It can be helpful to be willing to step into open spaces even if it doesn't seem like your dream job if it is something that helps the team. Make sure you're okay with that.

If you join an early-stage company, especially when there are anything at this kind of company, so if you are enthusiastic and capable, you can likely take on additional responsibilities and choose which ones. This is part of the "wearing multiple hats" refrain that is commonly echoed around the early-employee ethos.

Regardless of when you join an early stage company, your role will definitely bridge multiple disciplines and be stretched beyond its initial scope.

Some of the common roles that I see young folks take at startups, and my quick 2¢ on each, with an example job description:


Relatively similar most places. If you are working on a team with more senior engineers, you'll learn a lot about how to build "production systems" from scratch. Lots of growth opportunity and ability to influence product decisions. Note the difference between "product" and "infrastructure" engineers.

Job Description: Stir (Photo)


Junior designers will likely work to drive product vision by crafting UI/UX decisions. You can add tremendous value if you can also implement frontend code.

Job Description: Notion (around 20 employees when this was posted) (Photo)


I'd be wary of junior product roles at startups. I'm saying this despite the fact that I took one, but my role was more of a generalist role with a product title slapped on top. I haven't seen many high-quality junior PM roles at startups - let me know if you know of one. Usually, product/eng teams don't need PMs, let alone junior ones, at such an early stage. If you do take a product role, you'll likely be working with/against the founders in driving product direction.

Jason Evanish on the Second First PM

Lenny Rachitsky on the First PM

Customer Success / Community

I think CS is a severely underrated role, given its direct exposure to the problems your company is solving. This is the most relevant role that exercises 'product skills' at most startups, in my opinion. You work directly with customer to understand their needs and how they use the product, and bring the customer voice into every internal meeting to shape the future vision. That said, it often doesn't carry the same clout as other roles - my sense is that that's changing. This role is more common in B2B startups; the parallel in a consumer company is likely a Community role.

Job Descriptions:
WorkOS (~10 employees) (Photo)

Notion (~30 employees) (Photo)


Your job will be to get stuff done. Ops is part process-building, part elbow grease, and all about high-velocity, goal oriented execution. It's also incredibly high variance and very dependent on what your team needs. This role will be difficult to execute well on if you have low intrinsic motivation, poor discipline, or don't resonate with the mission you are executing.

Job Description: On Deck (~15 employees) (Photo)

Sales / Marketing / BD

All of these roles can be described as "funnel building / management" - your role is to bring in revenue, either from crafting messages to attract people broadly (marketing), to doing direct outreach + selling explicitly (sales), to building and growing relationships with new and existing customers and partners (BD). It's important to know who you'll be learning the ropes from, if anyone, in this role. Can be really fun to understand how money actually comes in to a business.

Job Description: Mercury (~20 employees) (Photo)

Chief of Staff

I'm still figuring this one out myself — it's an interesting role if you have a broad range of experience / skills / expertise / curiosity, but this role runs somewhere on the spectrum of "executive assistant" to "strategic leader".

Job Description: MainStreet

First Round Review piece on the CoS Role

Julia Dewahl on the Silicon Valley Chief of Staff


If you made it this far, congrats! You've now explored a good toolkit for figuring out whether working at a startup is your next step. Next week, we'll discuss conviction, and frameworks for figuring out whether the startup that's on your mind is really the one.

Looking to join an early-stage company? Check out the First 50 Fellowship! Want to join us? Check out our Careers Page.

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