The mistake keeping insurance teams siloed

By Jason Contant, | June 1, 2026 | Last updated on June 2, 2026
3 min read
Three grain storage silos
iStock.com/Kim Grosz

Communication issues remain the key mistake organizations make when they try to break down silos between functions such as sales and customer experience (CX) operations, a speaker said Thursday during a Rival Insurance Technology webinar.

One key element of communication breakdown is a “pretty distinct lack of vision that is effectively communicated out to the team,” says Ema Roloff, co-founder and chief growth officer at digital strategy advisory firm Roloff Consulting.

“So, it’s not that leadership doesn’t have an idea of where they’re going — sometimes they don’t and sometimes they’re chasing shiny objects and just doing things for the sake of doing them — but even when a leadership team has a very clear vision of where they want to take the company and why…there is typically a breakdown in communication going back to the team,” Roloff says.

“For there not to be silos in your organization, everybody needs to have a super clear vision of where you’re going and what role they play in it,” she says, “and how those dependencies play off of one another.”

Roloff was responding to a question from Ellen Quinn, Rival’s director of business operations and moderator of the ‘Beyond the Tech’ panel discussion. Quinn noted there’s often a challenge of getting different parts of an organization to work together. She asked Roloff what’s the most common mistake she sees organizations make when they try to break down silos between functions such as sales and CX operations.

Roloff notes the breakdown is not insurance-specific — it’s across industries and companies in general.

Competitive streak

Part of the problem is that within companies, incentive structures or individual goals within departments have co-workers competing with each other rather than moving in the same direction, Roloff says.

“Even yesterday, I had a conversation with someone who works in an insurtech, and she was talking about how, in their upcoming planning meeting, she might have to duke it out with development to figure out who’s going to get the money,” Roloff says. “We shouldn’t be thinking about duking things out within departments to try and figure out how we accomplish a goal.

“There should be conversations about where we’re going as an organization and what are the priorities that we need to put in front of everybody to get us there.”

Far too often it’s the communication between the executive team that’s setting the vision and each department where things fall apart, Roloff says.

So, what can organizations do to bring things back on track?

Roloff points to the 4 Ps of the vision:

  • Purpose — Why you’re making changes; this goes to the organizational level or specific changes being rolled out, such as a new platform
  • People — Focus on who’s going to be impacted and involve them in the conversation
  • Process — How you’re going to accomplish the goal, including setting expectations and demystifying the change or its path
  • Participation — Making leadership participation a reality, “not just setting the vision and throwing it over the fence and saying good luck and walking away,” Roloff says.

People first

Organizations often miss the first P (people) side of the equation, says Paul Harper, president and chief operating officer at Mitch Insurance.

“So, a lot of it is focused heavily on how quickly can we roll out this new platform or get this in place, and trying to make the day after implementation look really different than the day before,” Harper says. “And there are people who are in the middle of all of this, and they’ve been doing work a specific way.”

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What often gets underestimated is the pride and ownership people feel towards the business they’re working in, one they may have helped build, Harper says. Or there may already be a process in place and workers don’t feel it needs to be ‘fixed.’

“People tend to protect what they’ve been working on and they believe works well…,” Harper says. “So, you really have to understand that a successful integration is people first, it’s culture first, and then it’s systems and then it’s processes.

“But if you go in the wrong order, people will not feel heard. They’re not going to feel like they belong in here, and they’re going to feel like something’s making them change what they do.

“And you get a lot better result if you bring people along…”

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Jason Contant

Jason has been an award-winning journalist with Canadian Underwriter for more than a decade, including the past three years as associate editor and, before that, as digital editor for seven years.