5 Team Leadership Lessons From Giphy’s Former CTO, Randy Shepherd

Mastering team leadership is essential for building high-performing teams, especially in remote environments. Learn from industry leaders like Randy Shepherd how to apply effective leadership in remote teams, foster a positive culture, and manage distributed teams to drive success.

As remote work reshapes modern businesses, former Giphy CTO Randy Shepherd shares invaluable insights on leading teams, especially within remote-first environments. Drawing from his experience navigating the unique challenges of managing a fully distributed workforce, here are five key leadership takeaways that can help you build and manage effective teams.

Randy Shepherd

Lesson #1 Champion Shared Values and a People-First Culture

Why must leaders must prioritize fostering team culture to support employee well-being and balance? 

Because in effective team leadership, prioritizing a people-first leadership approach creates stronger high-performing teams, fostering long-term retention and engagement.

At Giphy, the top value was “people before product.” While this may sound unconventional from a business perspective, Randy emphasized that prioritizing employee well-being had significant long-term benefits.

“The number one on our list of company values is people before product which sounds maybe suicidal from a capitalistic standpoint, but it’s worked out pretty well for us,” Randy explains.

This people-first culture resulted in tangible benefits, such as high retention rates. Randy emphasized,

“If you invest in your people and give them the tools they need to succeed and feel fulfilled, they will feed energy back into the company.”

Lesson #2 Connect Work to Meaning and Purpose

Shepherd highlights how crucial it is to give employees meaningful work that aligns with a larger purpose. By helping teams understand how their contributions fit into the company’s bigger goals, leaders can foster engagement and motivation.

Giphy’s product, by its very nature, was fun and resonated with users, which gave employees a sense of purpose.

“People were naturally aligned with the product at Giphy because it brought joy to users,” Randy shared.

In distributed team leadership, connecting individual tasks to larger company goals helps remote employees find meaning and remain engaged. It helps team members see how their contributions impact the product, the users, and the overall business growth.

Lesson #3 Embrace Clear Communication and Repetition

Randy stresses the importance of crystal-clear communication, especially in remote settings. He notes that communication needs to be repeated multiple times to ensure understanding and alignment across teams.

“You’ve got to say something 26 times for people to hear and understand it,” 

he jokes, emphasizing that repeated communication through various channels is key to keeping everyone on the same page.

Randy also highlights the need for a structured system of communication, including regular team meetings, one-on-one check-ins, and clear OKRs.

“You’ve got your company goals, your OKRs, your team charters, and your reviews. You’ve just got to keep hammering those home.”

Lesson #4 Focus on Outcomes, Not Vanity Metrics

Randy advocates for a results-oriented approach. Successful remote team management emphasizes outcomes rather than tracking superficial productivity metrics like lines of code or number of code reviews.

“I find those [productivity metrics] to be infantilizing. As soon as you introduce a system like that, people are incentivized to find ways to manipulate it.”

He cautions against relying solely on software tools that quantify developer productivity, arguing that they can lead to a focus on gaming the system rather than achieving true results. 

“Focusing on outcomes is the way to sidestep all that noise. You understand the business problems that need solving, and from there, you set clear objectives with the team. Then, let them figure out how best to achieve those goals.”

Instead, he advises leaders to avoid getting bogged down by these metrics and instead focus on the true results the team needs to achieve.

Lesson #5 Leverage the Power of a Distributed Workforce

A fully remote workforce offers significant advantages, including access to a broader talent pool and cost savings. Effective team leadership in a remote-first environment can tap into global talent, leading to innovative solutions and diverse perspectives.

“Maybe it seems obvious in hindsight, but suddenly you’re like, oh wait, we can hire from anywhere in the country, and we can open our talent pool or prospective talent pool to many different places which will make it easier to find the skills that we need. We’ll drive down the average cost of the salary, that sounds great. And then you realize from there: oh wait, they don’t even need to be in the United States. This is not actually a prerequisite at all!”

Additionally, Randy highlights the value of diverse perspectives, noting that they lead to more creative problem-solving and a deeper understanding of global audiences.

“Having people from different parts of the world helps us understand what’s trending globally, and allows us to design features that resonate with various markets.”

To him, knowing where to source talent and for what roles is the true secret to success. 

“If I want someone to be up in the middle of the night monitoring real-time production workloads, then I might have some one in the other side of the world. But if I want people checking the code and building features, it might be easier to have them in the same time zones. But I think there’s no reason not to build an international team. 

While there are operational challenges with distributed teams, Randy suggests delegating those tasks to specialized firms to streamline HR, legal, and accounting processes.

“Now that said, if you try to do that yourself, that’s operationally pretty difficult from like an HR, legal accounting standpoint. Just paying people in different states is a headache as I understand it, just from a tax law standpoint and other concerns. So to the extent that you could delegate that to a firm that can handle that stuff for you, it’s what I do.”

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.

So, What Have We Learned?

By focusing on building a positive, people-centric culture and promoting clear communication, purpose-driven work, and a focus on results, Randy Shepherd provides a blueprint for leaders seeking to build and manage high-performing teams.

If you’re inspired by Randy’s insights and want to connect with more industry leaders like him, join the Connecting the Americas community—a space where founders, C-level executives, and tech enthusiasts exchange advice and support one another in navigating the future of work.

Additionally, if you’re looking to grow your team internationally across the Americas, Ubiminds can help you source top-tier talent to support your goals. Feel free to reach out—we’d love to assist you in building a distributed team that drives innovation and success.

High-performing Team Leadership FAQ

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.