“What I Wish I’d Known Earlier” Engineering Leadership Lessons with Zapier’s Co-Founder & CTO

Bryan Helmig is the Co-Founder and CTO of Zapier, the no-code breakout company that provides “easy automation for busy people.” Zapier is reported to have eclipsed $140M+ ARR in 2021 and is valued at over $5B.

The fundamental idea for Zapier was born out of a two-day project at a startup weekend in Missouri and ever since the company has been famously efficient in its path to scale. Today, Zapier is a thriving unicorn with 3M+ users and is widely seen as the most pioneering company in the white-hot category of “no-code”.

Yet the journey has not always been a linear one for Bryan, Zapier’s CTO. As a first-time founder, Bryan had to learn multiple critical lessons about what it takes to build the product, team, and culture.

Recently, Bryan sat down with the FirstMark CTO Guild, a private community for engineering leadership from breakout technology businesses, to share his three most important lessons he learned along the way.

Lesson #1: Hire Your Executive Tier Earlier

One of the most common anti-patterns for fast-growing startups is to learn (the hard way) that you have waited too long to build your executive tier.

Bryan believes one of the biggest mistakes he made as a leader was to wait too long to hire an executive team. Zapier didn’t begin building its executive team in earnest until they had reached ~150 employees. In hindsight, he recommends starting this process when you hit the ~50 employee mark.

There are multiple compelling reasons to build an executive tier early. At a foundational level, leaders need sufficient time to get fully ramped, which is a process that requires time in the seat. They need to understand the company’s vision, product, and existing team — all while embodying the company culture, building out their own team, addressing any cross-executive misalignment in terms of leadership vision or strategy, and implementing the systems and processes their organization needs.

While there are a number of important consequences of waiting too long to build an executive tier, there are two that Bryan notes can be particularly tough to correct for later. First, the longer you wait, the more difficult it becomes to mitigate top-down issues such as culture or leadership misalignment. Second, as much as any business hopes that an executive will thrive, it is not always the case. Mid-flight leadership changes are always disruptive, and the more time you’re afforded to identify and address any issues, the better of you will be.

On this latter point, Bryan suggests one preventive measure to take: build your “bench” of potential executive talent. Identify and build relationships with external leaders proactively, particularly those with deep experience at the current or next stage of scale. That way, not only will potential executive hires be in the wings when roles open, but they’ll also be much more familiar with the context of your business.

Lesson #2: Your Coach is Your Secret Weapon

A second common pattern in fast-growing startups is to lose sight of the importance of continuous development for founders and leaders. There is a frequent analogy to sports: simply put, you can’t win a championship without great coaching. So why would startups be any different?

In Bryan’s view, “anyone who’s managing managers should have a coach.” Bryan himself got a coach when Zapier had 300 employees but wishes he had found one sooner. He suggests starting the coach search process early because you should give each coach you work with a 1 to 2 month trial period. Even once you choose one you like, it takes time to build rapport and trust.

Coaches aren’t a silver bullet, Bryan emphasized, but they allow you to talk through problems and brainstorm solutions without having to maintain the composed image often demanded of a startup leader. Every executive at Zapier takes advantage of coaching, and now the company offers coaching support for its Director-level leadership as well. As for a recommended vendor in that space, Bryan recommends Reboot.io, led by longtime friend of FirstMark and “Yoda of Silicon Valley,” Jerry Colonna.

Lesson #3: “The CTO Wears No Clothes” & Evolving Your Focus

During the early days of Zapier, Bryan talked to a lot of different CTOs to learn how he could succeed in the role and avoid common pitfalls. He quickly learned that nobody had the same job description — there really didn’t seem to be just one CTO archetype. Once he came to that conclusion, he leaned into the aspects of the CTO role that he enjoyed the most and was actually good at, rather than trying to divide his time between what he excelled at, and what he perceived the CTO role “should” be.

Bryan categorized his responsibilities at Zapier into three groups:

1. People management
2. Technical product architecture
3. Core product work

The efforts that resonated most with Bryan were related to core product work, pushing projects forward — in some ways, more like an individual contributor than what a CTO was “supposed” to do. Once he embraced this belief, Bryan set out to scope his own work more strategically, ultimately settling on a “barbell” strategy: he focused on core, hands-on product work and the highest-level strategy. “Everything in between is someone else’s job.”

A few key hires provided Bryan with the most leverage and allowed him to focus on the work he cared most about. His first hire was a VP of Engineering who could keep technical teams moving along on the day-to-day. Zapier also introduced the concept of embedding a People Ops person in every function — not just in Engineering, but throughout the company. These individuals became key players because of their high connectivity to the day-to-day work of their respective organizations. This enabled them to home in on each department’s unique organizational issues.

While delegating day-to-day work has improved Bryan’s own productivity and impact as a CTO, it eventually gave him a sense of being disconnected from the rest of the organization. This matters a lot because, as founder and CTO, Bryan is responsible for communicating strategy and culture, which becomes harder as an org grows–and doubly so if a leader is disconnected.

One of the tactical approaches Bryan took to reconcile this was to focus on building deep, one-to-one relationships with leaders and Principal Engineers. During these 1:1 sessions, Bryan and teammates dig deep into whatever problems (systems, process, culture) engineers are experiencing. Bryan also uses that time to bring company strategy and the “why” behind what they’re doing into the conversation. Through these 1:1s, Bryan can push high-level strategy concepts into his teams.

For more on an effective and scalable 1:1 strategy, see A CTO’s Toolkit: 3 Tactics to Scale Yourself and Your Team with the former CTO of One Medical.

This piece was originally published on FirstMark’s Medium here. Stay up to date: click here to get the latest insights, news, and events from across the FirstMark community.