How Teams at Pie Insurance ‘Commit to Change’ Through Strong Cross-Functional Collaboration

Two leaders describe how the insurance technology company drives effective teamwork through a combination of strong leadership and powerful practices.

Written by Olivia McClure
Published on Dec. 28, 2023
How Teams at Pie Insurance ‘Commit to Change’ Through Strong Cross-Functional Collaboration
Pie Insurance
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Maintaining cross-functional collaboration is hard enough — so what happens when you add scale into the mix?

Senior Director of Marketing Marin Perez knows how challenging this can be, which is why he and other leaders at Pie Insurance take an intentional, strategic approach to building teamwork across departments. 

For Perez, this approach begins with one simple action: listening. He considers it essential to give team members space to share their unique insights — and this goes beyond exchanging surface-level pleasantries. 

“To better understand colleagues on other teams, you must show genuine interest, curiosity and empathy,” Perez said. 

Once leaders have a better sense of team members’ experiences, they can use this knowledge to create stronger cohesion. But without some semblance of structure, these efforts to pursue action can fall short. 

That’s why Chief of Staff Lisa Donovan and her peers have rolled out a collaboration and decision-making process that’s designed to create greater engagement and alignment among teams. She believes that this process, coupled with other opportunities to foster open communication, fits into an overarching focus on seeking solutions with long-term impact. 

“At Pie, we’re continually questioning assumptions and seeking the root cause of problems,” Donovan said. “By encouraging questions, analyzing underlying data, challenging the status quo and applying creative thinking, we can commit to change.”

As the company continues to grow, its team members rely on each other’s insights to push the company’s vision — to redefine small business insurance — forward. And with the proper level of guidance and right practices, they get to do just that and more. 



Pie is dedicated to making small business insurance simpler, less expensive and more transparent. 


Leading the Way

When Perez joined Pie, he had a lot of questions on his mind. 

“What do they value?” “What are the major challenges they’ve had at the company?” “What do they enjoy doing outside of work?” These are just some of the queries Perez posed during his “listening tour,” where he met with as many employees as possible across various departments. 

While this undertaking helped Perez get to know his colleagues as both people and professionals, it also served a larger purpose; it enabled him to gauge how different teams work together and helped him prioritize what he calls “A+ problems,” or high-impact, difficult-to-solve issues.  

As a result, Perez began to drive cross-departmental progress. “There were some quick wins I helped push through, which built trust across teams,” he said. “From there, it was about consistently listening, communicating and delivering value in ways that help all the teams win.”

Improving communication and delivering value as a leader is critical, especially if you’re chief of staff. Donovan considers it her responsibility to bridge different points of view, which she accomplishes by interacting frequently with different departments. 

“I seek to understand others’ perspectives, communicate often, solicit feedback and bring stakeholders along on the journey through regular touchpoints in order to build engagement and alignment with any change that will be needed,” she said. 

Donovan shared that she encourages teams to share progress updates, their vision and mission, their organizational structure and other key focus areas. By inspiring cross-functional knowledge-sharing, she aims to foster strong teamwork with far-reaching positive effects. 

“The more often our teams can consider others’ points of view, even if contrary to their own, the more comprehensive our solutions tend to be and the more alignment we have across functions. This ultimately has a positive impact on the company overall and encourages greater engagement,” Donovan explained. 


“The more often our teams can consider others’ points of view, even if contrary to their own, the more comprehensive our solutions tend to be and the more alignment we have across functions.”


As Donovan seeks to identify gaps in understanding across the company, she takes the initiative to find solutions along the way. Recognizing the importance of meetings when it comes to facilitating the flow of knowledge, she launched an annual operating calendar that enables teams to plan around business-critical meetings, which can be related to problem-solving, status updates, decision-making or upskilling. 

“Knowing the ‘who,’ ‘what,’ ‘where,’ ‘when,’ ‘why’ and ‘how’ of our key meetings is critical to ongoing alignment and building good working relationships across teams,” Donovan said. 



According to Perez, Pie’s focus on cross-functional collaboration is always evolving, driven in part by the feedback employees give to its leaders. And the company’s executive team doesn’t simply read these insights — they act upon them. “Our co-founders, John Swigart and Dax Craig, actively listen to this feedback and are willing to change things — such as tooling, decision-making frameworks and processes — to make collaboration and alignment better,” Perez said.


The Right Practices

Having a strong leadership vision is critical for successful cross-functional collaboration — but what happens if team members don’t have the right practices in place? 

This need for resources inspired Donovan and her peers to create the company’s new collaboration and decision-making process, which encourages team members to establish stakeholder roles early in project proposals and solution recommendations. 


The company’s new collaboration and decision-making process encourages team members to establish stakeholder roles early in project proposals and solution recommendations.


“With early buy-in to their respective roles, the project leader can then capture needs and seek and consider feedback in accordance with each stakeholder’s agreed level of engagement,” she explained. “These roles can then shift or multiple decision matrices can be established for various work streams, according to project needs.”

To ensure this process is effective, Donovan added, team members must rely on universal terminology across the organization and its foundational tools, which includes project and solution proposal documentation. Having common language also creates clearer communication of the scope, objectives, deliverables and milestones associated with a project, ultimately resulting in a better solution. 

“Since project and program leads have alignment up front on roles, they can focus on gathering the necessary input, soliciting decisions and building awareness and alignment around their initiative with the goal of addressing the most needs possible to maximize the value of their proposed solution,” Donovan said. 

While this new process is undoubtedly a game changer when it comes to communication, there are other opportunities for team members to effectively come together and exchange ideas. Donovan said the company hosts weekly all-hands meetings, open Q&A forums and “culture conversations,” all of which serve as spaces for employees to actively participate in building up the culture through a collaborative lens. 

All of these tools and practices point to the key elements of Pie’s approach to cross-functional collaboration: a supportive work environment and the right resources. With guidance from leaders and access to opportunities that unlock empowerment, employees across the company have the ability to foster teamwork with the potential to transform a growing industry. 

“We want to ensure that all ‘Pie-oneers,’ as per our operating principles, are comfortable being direct, seeking to understand, giving and receiving feedback and challenging the status quo, all of which are critical to achieving effective cross-functional collaboration and alignment,” Donovan said. 



Responses have been edited for length and clarity. Images provided by Pie Insurance.

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