Cultural Leadership: 5 Proven Lessons from Dave Kaplan, CTO at Alma

Dave Kaplan, CTO of Alma, brings more than 15 years of experience building software products, navigating the complex world of tech architecture, and using cultural leadership to drive innovation within teams. In the latest Connecting the Americas NYC event, Kaplan shared his key insights on Kaplan shared his key insights on cultural leadership strategies for remote teams, emphasizing the importance of fostering trust and empowering distributed teams.

Dave Kaplan (@davekaplan)

Here are five lessons that every tech leader can implement to boost team efficiency and foster a generative culture:

Strategy 1. Cultivate a Generative Culture for Remote Success

Kaplan highlights the importance of cultivating a generative culture, a concept developed in the 1980s by sociologist Ron Westrowers. He explained that organizations fall into three categories: pathological (fear-based), bureaucratic (rule-based), or generative (empowerment-based). 

Leaders should strive for the latter, where teams are empowered to make real, consequential decisions on the ground, and are critical to developing a sense of ownership among team members.

“In a generative culture, you want your teams to make real, consequential decisions. It’s not enough to just say ‘you’re empowered’—you need to put systems in place where that empowerment is actually lived.” — Dave Kaplan

Transforming a team’s culture to allow them to think critically and act on the ground leads to high performance.

“We always say we want to empower our people, but anyone who’s done that knows it takes a cultural shift and a lot of work,” Kaplan said.

He warned that, without this cultural shift, engineering teams often fall into the trap of becoming mere “ticket takers,” working through task management systems like JIRA or Asana without truly engaging in meaningful problem-solving:

“You’re never going to be a high-performing individual if all you’re doing is taking tickets off a board,” Dave said.

Building high-performing remote teams starts with promoting a sense of ownership and accountability.

Strategy 2. Foster Accountability: The Key to Remote Team Alignment & Performance

Kaplan highlights that accountability is key to remote team performance, helping align distributed teams toward common goals. Incorporating cultural leadership best practices is essential: setting a vision, defining goals, and maintaining a consistent follow-up are all part of ensuring that everyone is working toward the same objectives.

“You have to set the vision for the company,” he explained. “Leaders are shepherds, guiding their teams. But that vision has to trickle down to every member so they’re solving problems that matter.”

To him, accountability is a mix of goal-setting, clear communication, and constant feedback, ensuring that each team member is moving in the same direction. To improve remote team collaboration, leaders must regularly communicate expectations and ensure everyone is clear on their roles and responsibilities.

Leaders must follow through on their commitments and check in with their teams to ensure progress is being made, but without micromanaging. Kaplan advocates for regular retrospectives and check-ins as essential tools for keeping teams on track while giving them enough room to innovate independently.

Strategy 3. Maximize Global Talent Through Multi-Country Strategies

The rise of remote work has changed how companies operate globally. Kaplan reflected on how remote-first strategies enable companies to tap into talent from anywhere in the world. 

He advocates for adopting a multi-country strategy from day 1, since the first hire. 

“I would start off with multi-country from the beginning. There’s great talent everywhere, and we don’t need everyone to be in high-cost areas like San Francisco,” he noted.

This approach not only broadens the talent pool but also helps companies save on operational costs while maintaining high efficiency.

Strategy 4. Embrace Agile Practices for Continuous Remote Improvement

Kaplan’s team implemented agile practices during the pandemic, regularly conducting retrospectives to address work-from-home challenges and improve collaboration. This practice fostered collaboration and kept the team focused on continuous improvement, even in remote settings.

“We started doing weekly retros with the entire engineering and product department. We would work through home life issues and adjust accordingly,” he shared.

This approach to effective virtual team leadership helped maintain a balance between technical work and business-critical tasks.

Now, Kaplan promotes a balance between technical work (like addressing tech debt) and business-critical tasks (like developing new features). He prefers that teams make their own decisions about how much time to dedicate to each, but expects them to explain and justify their choices:

“I expect teams to spend around 20% of their time on tech debt and system improvements, but this varies depending on business priorities. The important thing is for teams to be able to explain why they’re focusing on a specific area.” — Dave Kaplan

By empowering teams to make these decisions, Kaplan builds a culture of trust where teams are free to prioritize the work that matters most without constant oversight from management. To him, this is what makes teams able to stay aligned and productive, despite remote work.

Strategy 5. Boost Team Cohesion with Strategic Off-Sites

While remote work offers flexibility, building trust and accountability becomes more complex. Kaplan emphasizes the need for in-person collaboration through off-site meetings.  

To maintain team cohesion, he has implemented several operational changes, including off-sites and regular meetings.

“Off-sites are critical for team camaraderie and solving problems. You can’t replicate the serendipity of in-person interactions over Zoom,” Dave said.

He believes that in-person collaboration is vital for building remote team trust and fostering creative problem-solving. Gathering teams in person periodically recharges the team’s energy and fosters creative problem-solving that’s difficult to achieve solely through virtual collaboration.

“I’ve attended eight off-sites in six months, and it’s critical for building momentum. It energizes the team like nothing else,” Kaplan explained.

Whether for leadership teams or the entire company, regular in-person meetings help build camaraderie and foster more dynamic decision-making.

(Sidenote: More in Enhancing Team Collaboration with Shared Memories)

How Cultural Leadership Can Transform Team Efficiency

Dave Kaplan’s leadership philosophy revolves around empowering teams through a combination of accountability, clear vision, and operational flexibility. His focus on outcomes over metrics, coupled with a generative culture, ensures that teams remain innovative, effective, and continuously improving.

These leadership lessons offer a roadmap for tech leaders looking to foster high-performing teams, even in fully remote or distributed settings. After all, building high-performing teams requires insight, strategy, and a focus on outcomes. 

Learn More from Industry Leaders Like Dave Kaplan

Evan Korth (NYU) mediated the panel in which Dave Kaplan (Alma), Scheila Farias (Ubiminds), and Randy Shepherd (ex-Giphy) offered invaluable perspectives on team leadership, organizational design, and fostering a collaborative culture. Photo by Thiago Reis.

To dive deeper into these topics and connect with industry experts like Dave, join the Connecting the Americas community. Discover how top leaders are navigating today’s challenges and unlocking team potential.

If you’re looking to boost your team’s performance with talented professionals from across the Americas, reach out to Ubiminds for support in expanding and optimizing your workforce. Together, we can help your teams thrive!

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Thiago Reis

Dad, Marketer, Salesman, Guitar Player. Self-starter, agile learner, and people-oriented, Thiago Reis is passionate about shaping the future of tech. Specialized in the Education Sector, previously excelling in Telecom, ISPs, and Digital Agencies.