This article is part of Carrier Management’s Cultural Q&A series featured in the Nov/Dec 2018 print edition.

Q: There is a famous saying, “Culture eats strategy for breakfast.” Do you agree? Do you spend more time on culture or strategy? How does your culture support your strategy and vice versa?

Jason Griswold, Co-Founder and COO, REIN

“Built on data. We create new insurance technology for a dynamic and connected world,” REIN’s LinkedIn page says, providing a brief description of the InsurTech that Jason Griswold and Steve Rabbitt co-founded in 2015.

A longer, more detailed statement says, “REIN is an InsurTech company creating new, custom-made insurance technology products around the emerging risks in mobility, robotics and online ecosystems.”

Responding to a world of “evolving risks, changing customer behavior, and unprecedented demand for speed and simplicity in insurance products,” REIN uses unstructured “data, machine learning and modern tools to help companies bring new insurance products to market faster.”

The company recently launched its first digital product,, offering commercial drone pilots tailored coverage through an intuitive web- and mobile-ready dashboard that replaces paperwork and complexity with data-driven automation and user control.

An online video describes the problem that REIN sought to solve through, noting that data—including weather data, flight data, environmental data, location data and information about the software that the drone operates on—are all factors that needed to be pulled together in a single system. Software then had to be put on top of that to extract information that would allow underwriters to make informed decisions, Griswold says in the video.

The 24/7 ground and usage-based flight coverage for drones, sensors and essential flight equipment is underwritten through Liberty Specialty Markets. The company looks to apply the same type of approach to other parts of the connected world: robotics, mobility and the Internet of Things.

Founded in 2015, REIN has offices in Chapel Hill, N.C.; Maynard, Mass.; and Halifax, Nova Scotia. REIN’s wholly owned subsidiary, Acend Insurance Solutions LLC, is a licensed surplus lines producer nationwide.

In June, REIN announced a $7.3 million funding round from investors including Liberty Mutual Strategic Ventures and Kiplin Capital.

Jason Griswold, Co-Founder and COO, REIN: There is another saying about having “the right people with the right tools in the right place at the right time” that is also popularly used in business. We don’t see this as an either/or proposition. At REIN, success is achieved by having equal measures of both culture and strategy. Our culture from Day 1 has been a key component in how we execute on our strategy. We are big believers that autonomy breeds accountability with the right systems in place.

In our business, most of the problems and opportunities we are tackling have no prerequisite for success or failure. Therefore, we have to hire talented people that can execute in a high-velocity environment and be able to shift roles and jobs based on the challenges along the way.

Q: How would you describe your company’s culture today? Has the culture changed since the early startup days? If so, what prompted the change?

Griswold: My co-founder, Steve [Rabbitt], and I are career entrepreneurs, which basically means we have general business athleticism across a number of functional areas. As such, when we see a problem, intellectual curiosity compels us to find out about everything related to that problem. Then, it’s time to build out a team with the right technology and domain expertise to find solutions to the problem.

This was the situation when we launched REIN, and it is still true today. What has changed is the need to execute on a much larger scale while still maintaining the right mix of culture and strategy. It requires balancing a culture of action, autonomy and increased transparency. It’s easy to pick up the phone or nudge your co-worker when it’s only a few of you, but when you get beyond 40 people, for example, you have to have systems in place to promote communication and to motivate individuals by ensuring their work is tied directly to the company mission and values.

We think about our structure in three main ways:

  1. How do we make REIN a great place to work?
  • Create autonomy.
  • Enable everyone to have a voice.
  • Make sure everyone is engaged.

2. Clear path to success.

  • Have clarity to our objectives.
  • Make it transparent from top to bottom.
  • Be focused.
  1. Hit objectives.
  • All must be striving for constant alignment.
  • Have a structure but not process in place; things always change.
  • Be data-driven.

Q: How does the structure of your organization support the current culture?

Griswold: We are a very flat organization, which means each person is a direct contributor. It also means there are multiple points of view on issues and opportunities. A new person has just as much of an opportunity to exert influence as the founder. High-impact decisions that need debate and rigor involve the core leadership team to finalize. Otherwise, our teams run and make the best decisions they can along the way. The anchor is that each person knows where we need to go, and how we are getting there, and what the required initiatives are for us to get there.

Q: Describe your role in shaping and perpetuating the culture.

Griswold:This is hard. My role demands a lot of flexibility and a visceral understanding of our company’s constantly evolving structure and condition. This means I get to wear a lot of hats. Sometimes I’m the executor, mentor, leader or change agent. As COO, it’s important for me to see where the company needs help scaling and lean in for as long as it takes. This gives me the opportunity to work across all groups and hopefully facilitate culture and strategy.

Q: Does the company have a chief culture officer, or are you considering adding that role to the C-suite? What other leaders help to shape the culture of your company, and how?

Griswold:At REIN, we’ve created a culture team that’s comprised of staff across all our departments. This structure allows us to communicate and collaborate at the highest levels and ensure that everyone has a voice and a seat at the table.

More articles in Carrier Management’s Cultural Q&A series: