3 Questions: Jeff Stucke, Chief People Officer

Bold Penguin CPO Talks Insurance, Careers and Insurance Careers


We’re a business built by and FOR insurance’s data age. Nevertheless, the idea of “digital transformation” is a destination and not a “thing.” How does an organization like Bold Penguin staff for this ongoing business transformation?

Our transformation is about taking a concept and building it to maturity. We’re creating “Bold Penguin 2.0” and looking at ways to measure and improve what we do. This approach isn’t exactly revolutionary; all successful transformations eventually become evolutionary.

Our evolutionary phase is anchored to a holistic approach that creates a success-cycle for recruiting, hiring, engaging and empowering: “Hire, inspire and engage…” 

Bold Penguin has pivoted rapidly from being a tech startup to a fully functioning technology organization. Improving our workplace culture at Bold Penguin faced turning points by two important events: COVID-19, and our acquisition by an outside company in early 2021.

Like many organizations, Bold Penguin quickly learned how to adapt to the pandemic. For us, this meant creating meaningful engagement with our 200+ employees who were suddenly doing their jobs remotely. Turns out that this was a great crisis-meets-opportunity moment.

We refocused our employee engagement philosophy to host brief all hands meetings (“Waddles,” in penguin parlance) twice weekly. These Waddles have played a critical role in keeping everybody aligned to our shared vision and goals, while also providing a fun setting for meeting with teammates, participating in philanthropic events and engaging with senior leadership more closely than was possible before.  We divided our engagement planning into company wide as well as the team level where we empowered teams to identify meaningful activities and/or swag items to spend a budget on rather than dictating the entire plan.  

For 2022 we have even bigger dreams: we have an RV wrapped in Bold Penguin branding, and are doing a multi-city cross-country tour to company hubs (aka “Icebergs”) for  team-building gatherings, as well as events with clients and prospective customers. If our team can’t come to The Glacier, then we will bring The Glacier to them.   

You’re not from an insurtech background. What are some best practices from outside the industry that you apply to Bold Penguin Issues: 

The foundations for success are pretty universal. They might be simple but they’re not easy. Building a high-performance organization needs responsive leadership from everybody. People at all levels both want and need support to be efficient, engaged and effective. This is a process that’s equal parts education and action:

  • Listen. Take an active role in hearing what your people need; whether the culture is one that they can be proud of; and whether they are empowered to assume ownership of their part in where the business is headed. 
  • Learn: Engage to make sure you’re making the right conclusions from listening. 
  • Plan: Make plans that go to the core of organization needs–now and in the future. Establish the right practices and tools (HR dashboarding; collaboration and communications platforms) to enable your people team 
  • Execute: Make progress on plans as they’re universally accepted.
  • Evolve: Do, measure, adjust, do.

In part because it’s a remote-first workplace Bold Penguin already is an organically diverse organization. How are your teams working to build Bold Penguin as a leader in diversity, equity and inclusion?  

Over the past 18 months, our company has made progress toward our  DEI goals through hiring or promotion from the C-level on down. In 2021, Bold Penguin tasked our executive leadership team  to build a more diverse and inclusive organization and culture, and in January 2022, we launched our formal Diversity, Equity and Inclusion (DEI) Board, responsible for thought leadership and delivery of vital diversity and inclusion initiatives this year and beyond. 

A key component of this meant placing and empowering a more diverse team of leaders at the decision-making table, which has improved our culture by helping us to become one of the most diverse insurtech companies in the business. 

Bold Penguin is committed to  DEI. We recognize that continuous improvement is the natural path towards building a diverse and inclusive workplace experience for all. 

Recent Articles

The fifth installment in the Bold Penguin series on The Evolving Risks Of Small Businesses addresses the excess and surplus needs and available high-risk insurance coverage for small commercial customers.

Top 100 Corporate Counsel Award recognizes leadership excellence and commitment

Bold Penguin is a great place to work and is now certified as a Most Loved Workplace® backed by the research and analysis of the Best Practice Institute (BPI)

Write More Commercial Insurance

Our newsletter will show you how
Thank you! Your submission has been received!
Oops! Something went wrong while submitting the form.