- Key insight: Essential advice from insurtech leaders include building trust.
- Expert quote: "Even the most flashy technology will have a hard time covering up losses or misuse of a carrier's trust and capacity." –Andrew Engler, CEO and co-founder at RockRose Risk
Looking back on their recent successes, insurtech leaders say the most important factors were those that helped them build trust and reputation.
"Insurance is ultimately a business built on trust, capital and underwriting results, so technology should make those fundamentals better, not distract from them. Build something that works in the real insurance market, not just something that looks good in a product demo," Andrew Engler, CEO and co-founder of RockRose Risk, said.
Sean G. Eldridge, CEO of Crosstie, said: "Insurance is a relationship-driven industry. You cannot growth-hack your way around credibility. You earn it by showing up, delivering, learning the details of your customers' workflows and being honest about what your technology can and cannot do."
These insights and more came from Digital Insurance's new Meet the Insurtech Leaders series. Read more below and click the links for each executive's full profile.
What advice would you give to other insurtech leaders, or to yourself five years ago?
Andrew Engler, CEO and co-founder at RockRose Risk
Technology changes rapidly;
Insurance is ultimately a business built on trust, capital and underwriting results, so technology should make those fundamentals better, not distract from them. Build something that works in the real insurance market, not just something that looks good in a product demo.
Sean G. Eldridge, CEO of Crosstie
I would tell myself to be patient.
I would also tell other insurtech leaders not to confuse novelty with value. Insurance buyers do not need more technology for technology's sake. They need solutions that fit into existing operations, respect regulatory and compliance realities, integrate with legacy systems and produce measurable improvements. The best products in this industry are not always the flashiest. They are the ones that actually get adopted, reduce friction and continue creating value after implementation.
Finally, I would emphasize trust. Insurance is a relationship-driven industry. You cannot growth-hack your way around credibility. You earn it by showing up, delivering, learning the details of your customers' workflows and being honest about what your technology can and cannot do.
Paul Templar, co-founder and CEO of VIPR Solutions
Building an entrepreneurial business requires a lot of
It's also important to recognize that not every opportunity is a good opportunity. Especially early on, it's tempting to say "yes" to everything because growth feels urgent. Over time, we have learned that focus is one of the most valuable assets a company can have. VIPR became successful because we stayed deeply specialized rather than trying to become everything to everyone.
Another valuable lesson is understanding that culture scales faster than process. The people you hire early on shape the entire trajectory of the business. Technical expertise matters, but mindset matters more. We built VIPR around people who genuinely care about solving client problems and removing market challenges. That creates trust both internally and externally.
We also underestimated how important operational infrastructure would become. Security, governance, compliance and scalability can feel secondary when you're a smaller company, but if you want to work with major global organizations, those foundations are critical. Achieving our Systems and Organizations Control 2 compliance (SOC 2) and building enterprise-grade operational resilience became essential parts of our growth journey.
Finally, I wish I'd worried less about whether insurance technology sounded exciting enough from the outside. Early on, there's a temptation to compare yourself to more visible tech sectors, but over time, I realized that solving meaningful problems in critical industries is far more valuable than chasing trends.
Ashwin Agarwal, CEO and co-founder at Advocate Technologies
Our industry is not about optimizing workflow. So many tech companies have staked their future on a better way to submit quotes, a better processing option and that is it. Workflow solutions are an optimization for an industry that has much deeper problems. Dream bigger. We have so much more to fix than streamlining submissions.
My advice to other insurtech leaders: there are ways to increase the size of our market in the next 20 years. We all know the world is insured to 20% or less of the total value that could benefit from risk transfer. The path to making this happen is data-driven transparency — when the customer understands what they are buying, they buy more of it.
Pablo Palafox, CEO and co-founder of HappyRobot
I would tell other leaders to find people they truly want to be in the trenches with, and to stay customer-obsessed, not competitor-obsessed. The moment you're tracking what everyone else is building instead of what your customer actually needs, you've already lost the thread. I'd also remind myself that the best companies aren't built by trying to do everything at once. Pick a hard problem, go deep, earn trust and expand from there.









