Spend a little time scrolling through "Tech Twitter" and chances are, you'll come across someone giving their hot-take on the latest rocket ship to take off. In this case, "rocket ship" is referring to a high-growth startup.
This term was supposedly coined by Sheryl Sandberg during her 2012 commencement speech at Harvard Business School. Since then, the de facto advice for ambitious people early in their career has been to find a seat and jump aboard.
“If you’re offered a seat on a rocket ship, don’t ask what seat. Just get on.” — Sheryl Sandberg
Recently, I decided to take this advice and join Hugo, a fast-growing startup creating a smarter interface for meeting notes. I've wanted to work at an early-stage startup for a while now, but it's hard to believe that it's actually happening.
It shouldn't feel this way though. This certainly didn't happen overnight. It took nearly 4 months of grinding through applications and interviews before I found the right fit for me. This post exists to share what I learned throughout the process, in the hopes of helping you find your rocket ship.
Before I go into my experience searching for roles, should you even join a startup? Among others, Justin Kan of Atrium has talked about the pros and cons of startups at great length. I have some thoughts here as well.
Where bigger companies win:
- Financial stability
- Building a network
- Supporting infrastructure
Where startups win:
- Individual learning rate
- Ability to move the needle
- Potential upside
The right choice for you depends on what stage of your journey you are at. It's also possible that neither of these are the right fit and you're better suited at a medium-sized company or making it as a freelancer. It's your path to choose.
Finding a Rocket Ship
If startups still seem like the right fit for you, let's break down the three main ways that I sourced opportunities: networking, job boards, and cold emails.
Finding jobs through your network is the ideal scenario. If you have been working in tech for a while then you have probably built a decently-sized network. Don't be afraid to use it!
If someone that you used to work with has gone off and joined a new startup, then that's an opportunity for you to reach out and connect. If you worked together in the past and you left a good impression, they might even open up a role for you that previously didn't exist.
Elad Gil has an excellent post on career decisions that touches on the benefits of connecting with other talented people throughout your career:
In Silicon Valley networks of people work together repeatedly. If you fall in with the right crowd, you will have outsized opportunities over time. Being part of the original PayPal network exposed you to companies like LinkedIn, Yelp, Tesla, SpaceX, and Facebook.
You might not have been a part of PayPal mafia, but you can still use your network for your benefit. Schedule calls to catch up with former-colleagues and see what they're doing. Who knows where it might take you.
Job boards are a useful asset to consider in your search as well. I stuck with AngelList pretty exclusively here. You can find some startups on LinkedIn's job board, but there are also larger companies there. This makes it difficult to cut through all the noise.
The search preferences on AngelList are pretty good. The biggest thing here is the "Company size" setting. Startups are very different experiences at different points in their evolution. Joining a team as the 10th employee is very different than joining as the 50th employee.
This advice is echoed by Hiroshi Mikitani, CEO of Rakuten. He says that everything changes at roughly every third and tenth steps:
When you go from one person to three people it’s different. When it’s just you, you know what you are doing and then you have three people and you have to rethink how you are doing everything.
But when there are 10 people it’s all going to change again. And when there are 30 people it will change again. Same when you reach 100 people. At every one of those steps everything kind of breaks. Everything.
Another useful tip on AngelList is to set "Last active" to 7 days. This is the minimum and means that only employers that have been active on the site within the last week will appear.
The most difficult part about AngelList is that there is very little barrier to entry. Just about anyone can put up a posting, so it's difficult to evaluate only the real options. If a company is actively looking, then they most likely mean business.
Last but not least, cold emails can be a powerful tool. If you have an idea of which startups you want to pursue, this is a great place to start. You can find vetted companies by browsing through prominent investor portfolios like Y Combinator. Once you have the name of a recruiter or founder, you're off and running.
Through some pretty straightforward research you can find their email domain name — chances are it's somewhere on their website. Using Gmail's browser client, open up a new draft and start plugging in potential combinations of their first and last name. If you're emailing the founder, it's probably going to be their first name. If you hover over the correct email, you'll see a picture and name pop up. Just like that.
Once you have the right email address, you need to figure out what to say. I'm not a cold email expert by any means, but I have more experience than most. Through lots of trial and error, I was able to iterate on my approach and come up with this:
My name is Conor Dewey. I'm a Data Scientist currently on the Growth team at Squarespace. I’m looking for a new role in data/growth and I’m super interested in what you’re doing with [Product].
[Thoughts on a recent feature or list of ideas for the product].
I’d love to jump on a call and connect if you think there’s a possible fit. You can find my resume attached to this email and check out my website if you're interested.
This isn't the best template in the world, but it's not a bad place to start. It's concise, offers value, and is straight to the point.
What makes this work is the middle section with product ideas or thoughts. This is where you should do a little research and say something intelligent enough to peak the interest of the person on the other end. If they think they might get some valuable insight from you, it won't be hard to get them on the phone. People like people with ideas.
Depending on the role and the stage of the company, interviews are a mixed bag. Video calls, coffee meetups, take-home assignments, and reference checks are all on the table. The process could take 2 weeks or 2 months. I don't have any killer advice here but to roll with the punches and be resilient. Control what you can control and let the chips fall where they may.
One of the few constants in startup interviews is the opportunity to ask questions. I leaned heavily on Harrison Harnisch's playbook through this process, and add a few questions of my own:
- What is the base yearly salary?
- What are the details of the health, eye, and dental insurance plans?
- Does the company offer relocation? (If you need it)
- How many total options are offered?
- What is the total number of issued shares?
- What is the vesting schedule?
- What is the exercise window of vested options?
- What is the strike price? (You might not get an answer to this one)
- What is the total amount of funding raised?
- How much cash is on hand?
- What is the burn rate? Current runway?
- What round of funding has the company raised?
- What are your future funding plans?
- What is the companies exit strategy?
- Who has invested in the company?
- In the last year, has the company failed to make payroll?
- Who is on the board and how many seats does each member have?
- How did the idea for the product come to be?
- How does the business model work exactly?
- What's the long-term vision for the product?
- Who is your customer right now? In 5 years?
- What's a major win the team has recently celebrated?
- What big things has the team been focused on lately?
- What could the team improve on?
- What's the biggest challenge to overcome?
- What do the next 6 months look like for the product?
- What's been the most surprising thing so far?
- How does the company collect feedback from customers?
- Has the company found product market fit? How do you know?
- How do you anticipate growing the team over time?
- What are some principles that the team leans on?
- What makes your culture difference from other startups?
- What does an average week look like in terms of process? Meetings?
- Why is now the right time to hire for this role?
- What projects do you picture I'd work on?
- Who would I be working with on these projects?
- What would my first 30, 60, 90 days look like?
It's not easy to find a seat on a rocket ship, but it's certainly not impossible. If you're reading this now, then you're at least thinking about startups. Based on my extremely limited experience, it seems like it's something that everyone should do at some point in their career. Everyone should try and build something great, at least once.
Some people want to work for a successful company; others want to make a company successful
This is idealistic, but attainable. Chances are good that you won't get rich at a startup. In fact, you can almost definitely make more money long-term by working at a FAANG company. That's not why you should do it. You should do it because of the personal and professional growth. Besides, building something new is fun. Remember that, and remember to understand your users, and you'll be just fine. Good luck. 🚀
Before I leave you, I thought it would be helpful to share my favorite resources relevant to joining a startup. Many of these were referenced previously in this post, but all of them are worth your time. In no particular order, enjoy reading!
- Marc Andreessen's Guide to Startups
- The Ideal Startup Career Path
- How to Invest in Startups
- How Startup Options Work
- Startup = Growth
- Big Companies vs. Startups
- Working for a Startup Makes Increasingly Less Sense
- 20 Questions To Ask Before Joining A Startup
- Breakout List Roles and Advice
- A Student's Guide to Startups
- Joining a Startup Fucked Up My Life
- The Most Valuable Startup Compensation
- How to Find the Perfect Startup Job: Start with When
- Read This Before Joining as Employee 1 to 20 at a Startup
- Elad Gil: Career Decisions
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