What’s in this article?

Bold Penguin enters 2026 at a critical moment for the future of insurance and technology. With a new Chief of Staff & Head of Strategy who brings firsthand experience, we are sharpening our focus on building a more connected, tech-enabled commercial insurance ecosystem. 

The conversation below unpacks where Bold Penguin is investing, our growth plan, and why organizational alignment matters when scaling a platform built for speed, intelligence, and distribution efficiency.

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A message from Bold Penguin’s Chief of Staff & Head of Strategy

Hear from Jay Patel as he shares a forward-looking perspective on how Bold Penguin will deliver consistent, meaningful value to our network in 2026.

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Question 1: Since joining the Glacier in early 2025 as Chief of Staff and Head of Strategy, what have you outlined as short-term goals for Bold Penguin heading into 2026?

I was fortunate to be part of the Corporate Development team at American Family that acquired Bold Penguin in 2021, so in many ways I had a head start on getting to know the business. That experience gave me a valuable perspective and allowed me to step into this role with a level of familiarity and speed that would not have been possible otherwise.

Bold Penguin’s vision is to be the premier network and leading digital platform for commercial insurance, and that vision continues to guide our short- and long-term priorities as we head into 2026. Our goals are focused on consistently delivering value to our network by expanding our top-of-funnel, improving sales yield both on and off the platform, and thoughtfully curating carrier panels for our top-of-funnel partners.

We are executing on this by continuing to enhance our platform capabilities across the full insurance lifecycle, including submission intake, policy comparison, market intelligence, multi-carrier and multi-product bundling, programmatic bind and cross-sell, and broker- and carrier-led book rolls.

At the same time, we are investing in the buildout of our retail agency and digital wholesale business to ensure we can serve our partners more comprehensively. A recent example of this investment into our digital wholesale capabilities is our acquisition of SquareRisk, which provides Bold Penguin with the ability to quote and write business with more than 40 specialty and E&S (excess & surplus) carriers.

Taken together, these initiatives position us to deliver better outcomes for our partners and continue strengthening Bold Penguin’s leadership position in the market.

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Question 2: As Chief of Staff, you work cross-functionally and can be described as the organizational “glue” between strategic growth, financial performance, and operational excellence. What tips do you have for keeping everyone aligned throughout high-growth times in the insurance and technology business?  

As Chief of Staff, I have the privilege of learning from a wide range of incredibly smart and talented people both inside Bold Penguin and across the insurance and technology industry. My role is to synthesize those perspectives, form my own point of view, and work closely with our leadership team to shape a clear strategic narrative around how we create value for our stakeholders.

We then translate this strategy into a financial plan. The plan becomes our operating model; it helps us understand what resources we have, what we need, and where to deploy them to drive the greatest impact and return on investment. Along with a set of non-financial measures, this becomes our scoreboard for tracking performance towards operational excellence.

During periods of rapid growth in insurance and technology, clarity becomes everything. Alignment happens when everyone understands the strategy, the metrics we’re tracking, and how their individual role contributes to team success. When that foundation is in place, teams can make better decisions independently and confidently, even when not all information flows perfectly, which it never does.

Ultimately, alignment comes from a shared understanding of the “north star” and the priorities that support it. When people know where the company is headed and why, the organization becomes more resilient, more agile, and better equipped to scale successfully.

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Question 3: What does the term “Be Bold” mean to you?

To me, “Be Bold” means having the courage to take risks while owning the responsibility that comes with them. It’s about being both thoughtful and action-oriented, taking the time to assess a situation, but ultimately maintaining a bias toward action.

Being bold often means stepping into the uncomfortable and uncertain, especially when the outcome isn’t guaranteed. It also means accepting that things won’t always go as planned. When that happens, being bold requires accountability, holding yourself to a higher standard, learning from the experience, and making better decisions the next time.

At its core, being bold is about growth. You embrace risk; not recklessly, but intentionally, with the understanding that progress rarely comes without it. As the saying goes: fortune favors the bold—especially in insurance and technology innovation.

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Bonus Question: As a native Midwesterner, with all your most loved sports teams  in Chicago but currently living in the South, what brought you to Nashville, and what do you love about living there?

Chicago will always be “home” to me, and I’ll forever be a loyal Chicago sports fan and supporter of my alma maters. I moved to Nashville four years ago for a career opportunity helping build a strategic finance function at a private equity-backed reinsurance firm. During my nearly three years there, I learned an incredible amount - not just about business, but also about myself.

That experience clarified something important: my true passion is in the venture and entrepreneurial world, where I had spent much of my career before moving to Nashville. So, I took a leap and launched my own consulting firm, partnering with venture-backed companies on strategic planning, corporate development, and financing strategies. Starting my firm gave me both the professional independence I wanted and the ability to continue putting roots down in Nashville.

Today, I live in the Charlotte Park neighborhood on the west side of the city. I love that Nashville has all four seasons, is growing rapidly, and offers the convenience of an expanding airport with direct flights to most major cities. Being close to parks and nature, along with the city’s food scene, music culture, and overall energy, makes it an easy place to build a life.

Ironically, Nashville had almost been part of my life much earlier. I once debated between studying at Vanderbilt University or Indiana University. I ultimately chose IU; but when I relocated to Nashville, I ended up living right off Vanderbilt’s campus. Life came full circle.

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Recap: How is Bold Penguin creating the future of insurance and technology with Jay Patel?

As Bold Penguin advances its focus on the future of insurance and technology, Jay Patel is helping shape that trajectory from the inside out. Drawing on his unique vantage point—from helping American Family acquire Bold Penguin to now serving as Chief of Staff, and Head of Strategy—Jay is steering the company into 2026 with a clear blueprint: expand the top-of-funnel, strengthen digital distribution capabilities, and elevate the platform across the full commercial insurance lifecycle.

His operating philosophy is straightforward: clarity drives alignment; alignment drives performance. Jay’s approach to strategy, financial planning, and organizational cohesion reflects a bias toward action paired with accountability—his own interpretation of “Be Bold.”

That’s how we leverage experience, perspective, and leadership to build a modern, scalable commercial insurance network at the intersection of insurance and technology.

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How is Bold Penguin leading insurance and technology innovation?

Check out other pages and announcements regarding Bold Penguin’s products, team members, and partners:

• Bold Penguin adds parametric insurance coverage through partnership with Adaptive
• Strategic partnerships and driving growth: 3 Questions with Brenda Koenig

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