Tales from the tech trenches: leadership tips for CTOs

What do Hootsuite, InVision, MailChimp and Peloton have in common? In addition to being unicorn (or soonicorn!) companies, they were all speakers at this year’s FirstMark CTO Summit, which brings together the brightest minds in the tech industry — hailing from some of the most successful startups and enterprises in the world — for a day of learning and networking. This year’s line-up included CTOs and VPs of Engineering from Gusto, Greenhouse, Splunk, and more. Here are a few of the best insights from CTO Summit 2017:

Bjorn Freeman-Benson

CTO, Invision

On making the hard things easier

As a fully distributed startup, InVision’s challenges are no different than most companies experiencing rapid growth; they need to make sure everyone is aligned and working in the same direction, that colleagues are communicating effectively, and that important project details aren’t forgotten and left behind in a rush to ship. Bjorn’s solution to these issues? Make everything smaller. By breaking a larger organization up into teams of no more than six people, each group is able to function as efficiently as an early-stage startup. This strategy can be scaled as the team grows, allowing a company of 100 to function with the freedom and agility of 20 five person teams.

Leaving the corporate hierarchy behind

Bjorn takes a bottom-up approach to management; recognizing that the builders — in his team’s case, the engineers — are the ones doing the work. The manager’s role is to make it possible for their builders to do the best work they can, which is why InVision trains employees to lead their teams with the why, not the what. Explaining why a builder is working on a project, rather than telling them specifically what to do gives everyone space to make their own decisions on execution, while still working towards team and company goals. Bjorn says the bottom-up approach breeds creativity and a positive workplace culture, while mitigating some of the issues common to the typical corporate organizational structure, like micromanagement and apathy. The strategy can also be scaled; while previously leading New Relic as SVP of Engineering, Bjorn used it to grow his department from three to 300.

Eric Muntz

VP of Engineering, MailChimp

What’s going to break?

Chances are, at some point technology will fail you. Eric approaches this theory with a different mindset, saying most of the time, it is you failing technology that’s the actual problem. To avoid potentially catastrophic mishaps, he recommends gathering as a team and asking, “What’s going to break?”. MailChimp has applied this mentality to everything from building an offline data recovery system to planning for customers: in thinking ahead about the 2015 holiday season, the company was able to calculate that they didn’t have enough bandwidth in place for the impending rush of outbound email. A painful, costly situation was easily avoided with a simple capacity upgrade.

Keeping up with change…

The debate over whether or not you should rewrite your product is a hot one, but Eric couldn’t recommend it more. Rewriting MailChimp’s product in 2008 to suit their customers’ changing needs was the one of the best decisions the company has ever made, he says, and the “single biggest inflection point in MailChimp history”. Without a new, mature tech stack, the next 9 years of astronomical growth the company experienced would not have been possible.

…and embracing boredom

Making changes to your tech stack for the benefit of your users and end product is one thing — but Eric cautions against doing so just for the sake of engineering. Referencing a blog post by programmer Dan McKinley on embracing boring technology, Eric says the point is not to pick boring tech, but rather, to consider the unknowns. MailChimp’s web stack may not be the most exciting, but for a company delivering a billion emails a day, tried-and-true technology is a much safer bet than the shiny new tech that’s bound to deliver surprise outcomes.

Geordie Henderson

VP Engineering, Hootsuite

On working out loud

From day one HootSuite has worked by well-known Shopify credo, “Do Things, Tell People”. Years later, Geordie says the simple action of keeping coworkers informed of his team’s actions has been critical to scaling the company. By getting his message about progress out quickly and often, Geordie created a mechanism for continuous improvement to the engineering department’s processes.

Taking visibility to the next level

In late 2013, Hootsuite faced a challenge: the company needed to update its software system to handle rapid growth, but doing so would require 75% of the development team’s effort and capacity. In order to appease coworkers and leadership anxious over this dramatic resource allocation, Geordie needed to come up with a method for communicating what his team was working on, what the customer value of that work was, and how much effort was being spent. Taking the company credo one step further, his team launched a strategy that provided, “weekly visibility into allocation of effort against all work — at a macro-level, to the entire company”. Equal parts quantitative (defining epics in progress and attributing a percentage of individual effort to each epic) and qualitative (presenting the reports in a format that could be meaningful to non-technical employees), Hootsuite was able to automate the process, building a lightweight web app to aggregate weekly data and generate reports.

Yony Feng

Founder and CTO, Peloton

Build vs. buy?

The decision of whether to build custom software or purchase an off-the-shelf solution is a dilemma many companies face, and is always going to be hard. It’s also a choice that’s going to be influenced by the current stage of your company, Yony says. Early stage companies should optimize for the experience level of individual engineers on the team. If an engineer has a lot of experience with a more extensible, advanced database like PostgreSQL, for example, it makes sense to commit. As the company grows however, evaluation of the tech landscape and team’s core competencies will be necessary to inform how much you’ll have to invest upfront in educating on new solutions.

Lather, rinse, repeat

Constant analysis of their ecosystem’s value chain guided Peloton’s decision to invest in the product’s leaderboard technology early on: by looking at the space, they were able to determine this would be the core differentiator for the company. Since then, Yony’s perfected an iterative loop that allows for constant technology improvement — assessing the ecosystem, strategizing which pieces of tech have evolved the most and are highest on Peloton’s value chain, executing on evolving the current infrastructure accordingly, and collecting feedback to begin the process all over again. This cycle motivates his team to spend energy on the areas that matter most for the product.

We’re grateful to all of this year’s speakers. If you’re interested in learning more from senior leaders across the tech industry, click here to join our upcoming events and watch past talks.

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