Meet Will Kessler, Head of Product at Sydecar:
Meet Will Kessler, Head of Product at Sydecar, with a decade-spanning career that began at Minted, a startup where he learned the importance of prioritizing team building over simultaneous product development. Will’s journey includes stints at Crunchbase, Power Reviews, and Cloud Labs, showcasing his expertise in team management, talent retention, and resolving team dysfunction.
Listen Up: Will Kessler, Head of Product at Sydecar — Full Podcast Episode on Spotify
Watch Now: Vit’s In-Depth Talk with Will Kessler
Quick Read: Will Kessler, Head of Product at Sydecar, Interview Highlights
Building and Managing Global Engineering Teams: A Conversation with Will Kessler
In the recent episode of Default Global, I had the chance to engage in an insightful conversation with Will Kessler, former product and engineering leader at Sydecar. We delved into his vast experience in building and managing engineering teams across various companies.
Building Teams and Learning from Mistakes
Will kicked off the discussion by sharing his experiences from various companies, including Minted, Crunchbase, Power Reviews, and Cloud Labs. He emphasized the importance of focusing on building a solid team rather than trying to build the product and the team simultaneously, a mistake he made at Minted.
He noted, “As a leader, you should focus on building the team and get that team going…If you’re open to hiring remotely, you might be able to accelerate this process.”
Moreover, he emphasized the importance of team bonding, communication, and support. At Crunchbase, he used a live demo deadline to motivate the team, while at Power Reviews, he combated poaching by keeping constant communication with his engineers.
Addressing Distributed Teams
When I asked about his approach to integrating distributed teams, Kessler highlighted the importance of social functions, frequent demos, and engaging engineers in design and product discovery. He noted that having engineers from different locales working together during hackathons was a great bonding exercise.
Will also discussed the benefits of having global teams at Udacity, where the global teams’ input was essential in creating courseware and learning environments that work for various cultures.
Hiring Strategy in LATAM
Discussing his time at Sydecar, Will highlighted the value of hiring senior engineers from Latin America due to their availability, reasonable cost, and familiarity with working for US companies.
He mentioned, “The great thing about using engineers in Latin America is that they can take that morning shift without sweating at all. Then the US engineers can come in 9 or 10 a.m. their time, and the South American engineers can go offline.”
Leadership Techniques for International Teams
When asked about his leadership techniques, Will emphasized the importance of bringing engineers together physically at least twice a year to combat isolation. He also mentioned the need to adjust stand up times to accommodate different time zones and to be sensitive to the formation of unified teams within remote locales.
He stated, “It’s pretty important to figure out what’s going to work…Maybe you could do some of the stand up in an asynchronous way with a Slack channel.”
The conversation with Will underscored the importance of strong team building, open communication, and cultural understanding in managing global engineering teams. It offered valuable insights for leaders navigating the challenges and advantages of a distributed workforce.
