Culture and Technology Pave a Path Skyward

Describe Skyward’s transformation over the past five years. How does the company look now compared to where it started?

When I joined in 2020, the company did not have anything that truly set it apart. The first thing we did was to identify the parts of the business with real potential and build around them with a strategy we call “rule our niche.” That meant focusing on highly specialized markets where we could deliver unique, defensible solutions that are valuable to clients and partners, while also producing sustainable results. By being selective, we not only reshaped our portfolio but also attracted top talent and developed technical advantages that fueled our momentum.

That approach has paid off. In the past five years, nearly every part of our business has been transformed into something distinctive. In surety, for example, we’ve built innovative solutions across both contract and commercial surety, with products tailored to renewables, and we are about to launch a first-of-its-kind offering for the oil and gas sector, which due to recent large surety losses is finding it difficult to access the market. In professional liability, we have developed solutions for emerging risks like Web3 and cannabis. These are just a few instances of how we have leaned into specialization to deliver real value.

Our goal has never been to be the biggest player, but to become deeply valuable to our trading partners by building a portfolio of targeted, differentiated solutions. For example, we recently entered into an agreement to acquire Apollo Group, a leading Lloyd’s specialty insurer. With Apollo’s proven platform and cutting-edge technology, this is a natural progression of our strategy to “rule our niche,” as it broadens our portfolio to new niches like the sharing economy and enhances our ability to deliver innovative solutions.

How important has culture been to this transformation?

Culture has been the single most important and impactful driver of our success. We say it often— talent wins. We’ve built a team of more than 600 employees, and you can see the caliber of that culture in every measure: our Glassdoor ratings rank among the best in the industry, 96% of our employees say they’re proud to work here, and we’ve been recognized as a top employer by several different outlets.

What makes our culture powerful is that it is both intentional and employee-driven. We cascade objectives clearly from the CEO down to the front-line underwriter, so everyone knows how their work contributes to our strategy. That combination of world-class talent, clarity of purpose, and employee ownership of culture has been the backbone of our success.

How has Skyward used processes or tools to promote innovation?

Culture may be our No. 1 driver, but technology is a close second, and the two together fuel our innovation. We have borrowed practices from the tech world, like using OKRs [objective and key results] to set clear goals and measure progress, and we have embedded that mindset across the company.

When AI and large language models first emerged in 2023, we did not hesitate. We brought one of the pretrained public GPTs behind our firewall and trained it on our proprietary data. We then challenged every employee with experimenting with it, and then to develop a specific use case for how AI could make their role more effective, which has created company-wide familiarity and fluency and some notable examples of success.

We have also built structures that spread innovation. Twice a year, our business leaders present the innovations that they have implemented in combination with our technology team. This not only spreads best practices across our businesses but also sparks healthy competition around who can drive the next big advancement. For us, technology is not a side project. Instead, it is core to how we operate and stay ahead.

What tools does Skyward leverage to enable employees to make truly data-driven decisions?

SkyBI is our key enterprise business intelligence platform, essential to our operations for its advanced data-driven decision capabilities. It tracks data throughout the insurance life cycle, enabling leaders to analyze performance in detail and make real-time strategic adjustments.

Complementing SkyBI, our award-winning underwriting tool, SkyVUE, offers underwriters a unified interface that simplifies back-end complexity and integrates new insights, predictive analytics, and risk signals directly into their workflow.

These systems ensure all decisions are data-driven, from portfolio management to individual underwriting, maintaining agility as new data and models emerge.

What roadblocks did you encounter to Skyward’s transformation? How did you overcome them?

Of course, there were roadblocks along the way, but what was unique about us is how our people turned potential obstacles into accelerants. When I joined, we had about 375 employees. Today we are well over 600, but only about 200 of those original employees remain. Those who stayed were the ones who genuinely wanted to be part of changing the company and making it special. And the people who joined us have had that same belief and orientation. Over time, the organization itself became the driver of change, so the typical challenges of change management were far less significant.

As a high-growth company, we needed access to capital early in our journey, which led to the decision to go public. In order to position us for sustained success, we had to improve our financial strength ratings. When I started, we were rated A- with a negative outlook by AM Best. Today, we are A with a stable outlook and a size 11 company, but getting there required close engagement with AM Best and a clear demonstration of our progress.

So rather than thinking about roadblocks, I would describe these as key accelerants. Those milestones were not just challenges to overcome, but they were turning points that fueled our transformation.