I spoke with the first engineer at Calendly. During Brett’s 7-years with the company, Calendly went from:
2 Employees to over 500
$97k ARR to over $100M
< $1M valuation to over $3B
7 things I learned from Brett:
1/ Choose your next company based on business model and market
Before Calendly, Brett saw many startups fail for two reasons:
the high cost of acquiring customers: a product might be technically impressive, but companies often run out of money just trying to get users.
the need for critical mass: many products are great but only work if enough people use them. For example, being the only person on a social network is pointless.
Calendly avoided both problems. You can be the only Calendly user in the world and it still works. On top of that, every user helps bring in new users by sharing their Calendly link.
Brett saw this early on and couldn’t ignore it. If optimizing for company success, engineers should focus first on business model and market, not technical complexity or industry. The earlier you recognize this in a company, the better your opportunity and potential upside.
2/ If you want to be successful, think more about the company and less about your career
This was a critical mindset shift for Brett. Once he saw that his equity might be worth something, he decided he was going to do whatever did the most good for the company, regardless of his personal interests or career ambitions.
The startup’s success becomes your measure of success. Tie your success to the success of the company. I feel like interpersonal things get a lot smoother when it's clear to everyone else that you will always do what you think is best for the company. People give you more benefit of the doubt. People trust you more.
This led Brett to take a PM role, something he had previously rejected because it didn’t fit his career ambitions at the time. Calendly needed this, and Brett grew to love it. He realized that if you want to make an outsized impact on the company then you’re likely going to need to be directly involved in product decision-making.
3/ Definitely get equity, but maybe not too much?
Think about early-stage compensation decisions as investment decisions. You’re trading time and expertise for a potential payout later. Like any investment, only risk what you can afford to lose, and be ready for the long haul.
Prioritize a salary that lets you live comfortably before maximizing equity. It’s better to hold a small stake in a successful company you can stick with than a large stake in one destined to fail, whether because of company issues or your inability to work there over years.
Be clear about expectations (hours, workload, and responsibilities) because higher pay or equity usually comes with higher expectations. Brett knew that he needed a fair salary, modest equity, and roughly 40-hour weeks, which gave him the ability to commit long-term and ensure that the quality of his work would be consistently strong.
4/ Know thyself and be realistic about IC vs management roles
As a company like Calendly scales, there are many opportunities for advancement. Brett was interested in the CTO role. In retrospect, there were times when he was qualified to be a CTO at Calendly two or three years prior. Brett was growing really fast, but just not at the rate that Calendly was growing. Had he somehow finagled his way into the CTO role, Brett now sees that he would have likely failed. His time would have been spent on problems he’s not that interested in solving - pay structures, personnel decisions, investor relations.
5/ Make the app do what the user thinks the app will do
Brett dove deep into product at Calendly. One thing he learned was that a good user experience is “when the application does what the user thinks the application will do”. It doesn't matter how beneficial the outcome is. If it was not anticipated, then it's kind of unwelcome. If you grab a fire extinguisher and you pull the handle and $2,000 comes out, that's great - you just got $2,000, but you really wanted the fire extinguisher to extinguish the fire. Not a good user experience.
6/ Start recruiting well before you need to hire
Most processes at Calendly, if they existed, got rebuilt every 3 months. Constant change. That means that what you need now can’t be who you’re hiring for now. Depending on the role, it could take you 6 months to hire the right person. And then it could take another 6 months to fully ramp up.
By the time you finish your hiring process, the requirements for the role have changed. The person you’ve just hired is no longer a fit for the updated demands of their role. This was a constant struggle through much of Calendly’s growth. Whatever hiring philosophy you adopt, start hiring well before you need to make the hire and don’t hire for what you need today.
7/ This is how you know you should work at a startup
If you’re the type who can’t stop thinking about a problem until it’s solved, you’ll feel wasted at a big company. At a startup, your incremental mental energy can compound the value of your equity in the company and step-change the potential outcome.
If your brain can’t turn work off, you’ll likely thrive in an early-stage company. But Brett warns that you should take this as a marathon, not a sprint. What’s often missed is that to realize the full potential of your investment, you’re going to need to stay for years. Even though it’s cool to be hard core and work 996 these days, it’s difficult to sustain years-long impact if you’re pushing too hard all of the time.
Follow Brett on LinkedIn to be in the loop on his new startup journey. Learn more about his time at Calendly on his about page.
Curious what current top startups are a fit for your experience? Reply with your resume or LinkedIn profile and any filter criteria you care about, and I’ll reply with a list of curated roles!
Cheers!
Michael (LinkedIn)
P.s. Let me know if there are other early engineers you think we should feature here 🙂