Matthew Cullen – Porch Group

Being the general counsel of a growing public company presents unique challenges that require patience, a willingness to learn, strategic foresight, adaptability, and a strong team of legal experts. Matthew Cullen strives to bring precisely that to the table for Porch Group, where he serves as senior vice president, general counsel and corporate secretary. He joined in 2020 as part of the go-forward executive team that led the company’s initial public offering on Nasdaq.

Matthew Cullen | Porch Group | SVP, General Counsel & Corporate Secretary

Headquartered in Seattle, Porch Group specializes in home services and insurance. The company offers a unique combination of software, data insights, home protection services, and concierge solutions to simplify homeownership. Porch partners with home service providers, leveraging data to provide tailored insurance products and related services. This data-driven approach enables Porch to design innovative solutions that meet homeowners’ needs, from insuring their properties to helping them book movers or connect with trusted service providers.

“We position ourselves as a new kind of insurance company, delivering value through B2B software, unique data insights, advantaged underwriting, and more protection,” Cullen tells Vanguard during an interview in November.

As the company grows, Cullen continues to address diverse issues, from financings and M&A to recruiting and retention of the team, to independent board governance, intellectual property and data security, employment law and litigation, commercial transactions, government relations and risk management, all while aligning with the company’s growth objectives and disruptor-DNA. Cullen sees great teams (legal and otherwise) as proactive thinkers seeking to design business systems that perform at scale and as data-driven problem-solvers when faced with high-stakes challenges—that’s where agility, patience and precision matter. Additionally, fostering a cohesive and empowered legal team in a fast-paced, remote-first environment adds layers of leadership responsibility and learning opportunities for Cullen. He protects the company from legal, reputational and other risks, supports innovation and gets things done.

Cullen, who grew up in Westchester County, north of New York City, thrives when he’s arms-locked with colleagues trying to move the big rocks impeding business success. He and his team seek creative but straightforward solutions to problems as unpredictable as the weather, which often impacts Porch Group’s insurance businesses!

“For my team, the real test is turning obstacles into opportunities, and this approach will serve us well as we launch new products and roll out new insurance legal structures in 2025,” he explains. “At Porch broadly, but certainly within the legal team, we take each day as an opportunity to learn and hopefully improve a little bit.”

Building a foundation

Cullen says his team of roughly 15, which includes attorneys, paralegals, compliance professionals and support staffers, embodies resilience as they navigate the intersection of macroeconomic and microeconomic challenges, growing regulatory compliance expectations, a warming planet that has resulted in more extreme weather, and strategic business shifts.

This philosophy is crucial as Porch prepares for the transformative milestone of its new product launches next year, including in the data vertical (where the product is known as “Home Factors”) as well as using a new legal structure known as a “reciprocal exchange” for the insurance vertical (where the product will be branded “Porch Insurance”). In particular, on the insurance front, Cullen applauds his team for being heavily involved in designing the proper structure to support the best product for consumers, which will uniquely protect the “whole home” more comprehensively than its competitors.

The introduction of this new legal “reciprocal” framework is only the beginning. Cullen’s team will oversee compliance (and contribute to strategy) across product, intellectual property, government relations, marketing, distribution and claims handling—all crucial elements underpinning the offering that provides more protection to homeowners who choose this product. This ambitious project highlights the department’s role in innovation.

As for data, Home Factors products are expected to provide unique data insights to other insurance carriers. The product is built on Porch’s unique data sets about properties, combined with an extensive consumer database including billions of buyer intent signals. Home Factors will provide insurance carriers insights across 90 percent of U.S. homes. The product is expected to deliver value for homeowner consumers (i.e., more fair pricing tied to the actual risk of the property in question) and insurance carriers (both Porch Insurance and third-party carriers) as it presents an opportunity to achieve more accurate pricing and lower underwriting costs.

“Product launches are exciting for any business, especially when innovation is a hallmark of the launch. For the Porch Insurance launch, cultivating and building regulatory relationships has helped set the foundation and get the necessary approvals —now, we must launch in close collaboration with our go-to-market distribution network. And as for Home Factors, we are keenly aware of the importance of building secure systems that protect our proprietary data and reinforce Porch’s position in the market as a data-advantaged company,” Cullen notes.

A leader who cares

Cullen’s role extends beyond legal and risk strategy to influencing Porch’s company culture and team dynamics. He credits his leadership role to his professional commitment to the value of “care deeply.” For Cullen and at Porch, this means being empathetic and finding ways to go above and beyond. With a fully remote-first work model, the legal team is spread across multiple states, with three attorneys and an externship program based in Seattle, where Cullen resides. Cullen credits his prior experience at Expedia Group, where he managed a globally distributed team of professionals, for his ability to manage distributed teams effectively through a playbook of virtual cadences, in-person team off-sites, and (most importantly) hiring caring leaders that foster a strong sense of mission and culture. He emphasizes the value of smaller teams, allowing him to build close connections with his colleagues while promoting autonomy and empowerment. This operating model enables team members to act decisively without constant oversight, fostering a collaborative environment where shared values and mutual respect are paramount.

Cullen takes pride in cultivating talent within his department. His approach involves a high-potential leader program, skill development programs, and succession planning. Under his guidance, the legal department has matured significantly as the business has grown, providing ample opportunities for legal team members to leave their fingerprints and impact across the organization. Cullen actively identifies high-potential individuals through traits like executive presence, analytical capabilities, willingness to learn, and comfort with ambiguity. These qualities, coupled with a supportive environment, have created a team that is effective and deeply connected to Porch’s mission.

“There are benefits to having a team that is our size, like connecting with everybody and working more deliberately and intentionally to develop great leaders,” Cullen says.

Additionally, Porch has a formalized program across the company that identifies people early in their tenures who show an aptitude for their work and display the qualities the company looks for in its leaders. In the legal department, Cullen says the focus is on giving attorneys and other professionals the best opportunities to grow and provide value to the company.

Finding his path

His career path reflects a balance of intentionality and openness to opportunity. With a background in finance, Cullen—who earned a degree in finance and international business from Georgetown University—initially pursued roles in banking and finance before gravitating toward law. After earning a JD from New York Law School, his early focus was on corporate matters and mergers and acquisitions, starting his career at Sullivan & Cromwell LLP in Manhattan. He eventually transitioned to in-house roles, drawn by the opportunity to act more like an owner. Cullen’s approach to leadership is shaped by his belief in understanding the business profoundly and fostering cross-departmental collaboration. For him, true leaders are those who (after careful study) grasp the intricacies of their organization, can guide it through complex situations with poise and are willing to adjust their approach.

His appreciation for teamwork and adaptability also influences Cullen’s leadership style. He thrives in collaborative environments, valuing the camaraderie and diverse perspectives that teams bring. His experiences have taught him that different situations require different types of leadership and communication. This flexibility is crucial in an industry where clear answers and manuals are often absent. Cullen relies on his team, his board—which includes Porch’s CEO and seven independent directors—and mentors outside the company to navigate challenging questions and decisions. These relationships provide him with invaluable insights, he says.

Cullen’s journey from finance to law and eventually to a leadership role at Porch Group is a testament to his adaptability, curiosity, patience and commitment to growth. His ability to navigate ambiguity, foster a culture of collaboration, and align his team’s values with the company’s broader goals has made him an integral part of Porch’s success. As the company continues to evolve, Cullen’s strategic foresight and dedication to his team’s development will undoubtedly play a pivotal role in shaping its future.

“I love coming to work every day mainly because of my team—together, we strive to learn something new at each opportunity and use it to impact our business results. Heading into 2025, we should see many opportunities for legal to be a key part of the successes of Porch Group’s planned product launches and, in turn, many opportunities for the team to learn and grow closer together. As the leader, I am excited to enable and support as many opportunities for team and company success as possible,” Cullen says.