I’ve been working in the startup ecosystem for more than a decade as both an investor and operator. Given my somewhat unique experience, I am asked reasonably frequently for advice about finding the right startup to join and how to negotiate the right startup job offer. Startup negotiation is different than at a big company, so below is a consolidated set of advice, tips, and resources for people wondering how and what they should negotiate for.
Let’s start with the obvious - finding a job is stressful. Like with any job search, finding a job at a startup is a time-consuming and exhausting process that can include research, networking, multiple phone screens, assignments, and Zoom interviews (and hopefully one day soon, on-site interviews). Startup job searches also have an added layer of complexity since you need to figure out whether the company has what it takes to last. What's the team background? What traction has the product seen in the market? How early in the product-market fit life cycle is the business? How much funding have they raised? I'll get into the startup search process another time. What I want to focus on for now is what to do after you get a job offer.
There is a strong temptation to accept the first offer presented, especially if it feels reasonable. It makes sense! After all the work to this point, getting an offer feels like a weight has been lifted, the hard work has been done. And after all, you don't want to seem greedy or petulant, rub your new colleagues the wrong way, and walk in to work on the first day as "that person". Why not take it? Because you'd be selling yourself short.
Getting an offer is the most definitive signal that the company wants you. They have spent time, money, and effort trying to fill a spot on their team. Your signing an offer is the end of a journey, both for you and the company. The faster you sign, the faster someone on the other side can move on to the rest of their to-do list (and, if an external recruiter referred you, the quicker they get paid). What does that mean when it comes to negotiating your offer? You’ve got leverage, and it's time to use it.
When it comes to negotiating your offer, there are generally a few areas to focus on:
Base pay: Have a floor for the cash compensation you want that you will not go below. It will make it easier to determine whether or not the company is a fit. Startups are generally more cash constrained than large, public companies, but a company that has raised money from outside investors has funds to put to work. If you're leaving a large organization to join a startup, you'll likely be taking a pay cut, but if the final number makes you wonder how you'll pay your bills, it's probably not going to be worth it to switch. Look at some of the tools available like AngelList, Front, Glassdoor, and PayScale to assess what is typical for the role you're considering and in which city you'll be working. Also, if you haven't yet asked and the numbers aren't available on Crunchbase or CB Insights, ask the hiring manager or recruiter how much money the company has raised to date, and what plans are for future capital raises. Assuming the company plans on raising more money, as part of your salary negotiation, it is reasonable to ask for written confirmation that your base will go up once more funding is raised.
Equity (aka stock): Equity is your upside. If the company does well, the stock will **hopefully** be worth something. It is important to note that startup equity grants are usually presented as a fixed number of shares (for example “50,000 shares”) NOT as a % ownership of the company. It is reasonable to ask for a fully diluted number of shares, as well as the most recent post-money valuation of the company so you can calculate how much of the company you own and how much the grant is worth today. It's also worth remembering that this grant is usually going to be the biggest one you get. One way to try and increase the number of shares in this grant is to trade off base pay. Salaries go up over time and, if you join an early-stage company (Seed or Series A), will typically get reset to 'market' after the next funding round. If that cash trade-off makes sense for you, it's worth considering. Wealthfront and Holloway both have some great resources to look at.
Performance Bonus: In some cases, performance bonus components are offered by the company, usually as a % of cash compensation. If you have a total cash compensation number in mind and performance bonuses are something offered at the company, you can use this as a way to make up the difference.
Signing bonus: The cash component of the offer in the first year can be often be supplemented with a signing bonus, particularly at a larger startup. While not as good as a performance bonus (signing bonus will only apply to the first year on the job), negotiating for a signing bonus to make up the difference between the offered base salary and your target cash compensation is a good way to go.
Title: Unless you're joining a leadership or externally facing role, startups usually have generic titles for employees. In my experience, asking for a higher title and being willing to compromise on it to get something in return (like an increase in salary, more equity, or a signing bonus) can be an effective strategy to get other things.
Exercise window: Typically startups offer employees 90 days to exercise their options after they leave. There are a whole host of reasons why this can be challenging. Asking for an extended exercise window will offer you more flexibility when you leave, and avoid potentially significant cash or tax consequences. Check out the Holloway guide to Taxes on Equity Compensation for more information.
Other: There are myriad other things to look out for in an offer and will differ from company to company. These include benefits like health and medical, 401k plans, PTO, flexible work hours, remote workdays, and more. Try your best to understand them all and figure out what matters to you.
Photo by Freshh Connection on Unsplash
A few things other things to remember:
Make decisions asynchronously ("I'll get back to you")
Whether the offer you get exceeds your wildest dreams or is so far apart it's not worth the time, remember to thank the person and say you'll get back to them after you've had time to think. Processing information while not on the spot will give you more time to read the fine print, and help you operate from rational thinking rather than emotional thinking. Even after you're done negotiating and agreed on terms, accept after the fact. It will ensure you're making the best decision for you.
You're negotiating with a company, not a person
It's important to remember when negotiating an offer that you're not negotiating with an individual. You might be interacting most with a recruiter or your hiring manager, but you're negotiating with a company. Companies have budgets, funding, and roles to fill. Asking for more of anything - cash compensation, equity, title - isn't “making life hard” for the person you are talking to. You're not taking anything away from them. Don't compromise, feel bad, or think you're unreasonable when asking for changes. Don't negotiate against yourself. A 10% increase in base salary might make a big difference to you, but it certainly won’t bankrupt the business. So ask for it. The worst thing a company can say is no. Guess what? You’d be exactly where you started anyway!
Understand the person you’ll be working for
While you’re negotiating with a company, you’ll eventually be working for a person. Make sure you get to know your manager and the team you will be joining. What is their management style? How do they deal with conflict? Are they hands-off or do they micromanage? How do they support members of their team to help them thrive? Figuring out whether your personality fits with your future manager’s is critical, as it will likely be one of the most important contributors to your fulfillment in the new role. Don’t be afraid to ask your prospective manager for references from people that have reported to them before. Better still, see if you can do some LinkedIn sleuthing and find people who have worked with the person in the past to reach out to for feedback.Understand how you will be measured
As with any job, understanding what success means in the role is critical. It is especially important at a startup where, if things go well, it will undergo a lot of change very quickly! Aligning early around the expectations and objectives of the role, how you fit in the broader context of the company, and how success will be measured is essential.Get your company questions answered
You've been on the receiving end of a lot of questions through this point in the journey. Hopefully, you've been able to get some of your questions answered as well, but if not, now's a good time to ask! Get to know the company’s culture, values, how the business has been doing, and more. If a feeling is nagging at you about the work-life harmony at the company or your spidey sense is activated about whether the product works the way it’s supposed to, ask! It's up to you to get as much information as possible to make an informed decision - no one is going to do it for you. The reality of startups is there is an incredible asymmetry of information. Unlike a public company or one with thousands of employees, it's hard to get an objective sense of what's happening internally. Use this time to learn as much as possible and shift the balance back in your favor.
Receiving an offer is an exciting time, the culmination of a lot of hard work and preparation. There are a lot of variables to factor in, and I know it can seem overwhelming. Make sure you take a step back, breathe, and remember that everyone has a different process and approach to negotiation. It's also important to remember that the right offer for you will look different than other people. Like a piano, different keys will result in different songs. You might be looking for more equity, less cash compensation, and the ability to work from home a few days a week. Others might be looking for more cash, less equity, a signing bonus, and a Manager title. The right offer will on your specific needs. Take the time to figure out what's not negotiable for you, what you're optimizing for, and where you're willing to compromise and negotiate in a way that’s is comfortable to you. You might end up surprising yourself with where you end up!
Useful guides and resources
Salary and Equity
Startup Salary and Equity from AngelList
Compensation and Equity Calculator from Front
Salary Calculator from Glassdoor
Salary Comparison from PayScale
Wealthfront’s Guide by Equity and IPOs from Wealthfront
9 Terms You’ll See In your Equity Offer and What They Actually Mean from AngelList
The Holloway Guide to Equity from Holloway
Taxes and Exercising Equity
The Taxes on Equity Compensation from Holloway
F*** Your 90 Day Exercise Window from Zach Holman
Company research
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