WIL 2025: Kari Allen

Kari Allen
Kari Allen

When transforming an agency's sales culture, emotional intelligence can be an invaluable tool – and Insureon's Kari Allen is living proof.

Kari Allen is vice president and head of sales for Insureon, a digital agency exclusively serving small business clients. Allen spearheaded an overhaul of its sales organization, incorporating much-needed structure and engendering an entirely new culture for its salespeople.

When she joined Insureon in January 2021, Allen inherited a sales staff impacted by high turnover. Prior to her arrival, she says, the sales staff "weren't being asked about their professional development, or about their future with the organization."

Allen quickly set about rebuilding the producer team, hiring and developing new, strong performers and implementing a clear leadership framework. She established three director and three assistant director roles, each with defined responsibilities and growth pathways – providing the team new leadership and a vision for career advancement.

In order to inspire maximum performance, Allen also knew she had to learn what incentives would drive her salespeople.

"You have to find out what motivates them, what their passion is," she says. "You have to listen, learn from what they tell you, and then build that into the compensation and reward structure. Different people are motivated by different things. Some will say, 'I want to travel with my family.' So, if we do well in a certain quarter, the team award is a travel gift certificate."Making Insureon's producers feel valued and respected, she says, goes a long way. However, she cautions, "If you're going to ask people what motivates them, you'd better be prepared to act on it."

Recognizing the importance of a consistent onboarding experience and continuous development, Allen created a dedicated learning and development role. This function spearheaded the design and implementation of a robust training program, aligning best practices and daily operating routines into a centralized "sales playbook" utilized by each team member.

"When I came here, there was no true development or training role, and I struggled with that because I came from a place where we did," says Allen. "There always have to be central, go-to solutions for onboarding, for creating training initiatives, for getting new people up and running. The quicker you can get people up to speed, the faster you can get them into production."

 Additionally, she introduced standardized sales operating routines focused on efficiency, accountability and client satisfaction to help the team consistently deliver each customer a high-quality experience. Allen is passionate about Insureon's client set, cognizant of small businesses' uniquely small margin for financial error.

"Four in 10 small business owners say it's more stressful to get insurance than it is to do their taxes, and only 10% of small business owners believe they have the right insurance coverage," she notes. "That's frightening. You don't want to see them lose their most valuable asset. It's their heart and soul."

After more than four years in her role, mentoring remains a key pillar of Allen's leadership approach. One of her first initiatives was the creation of a structured mentorship program that paired team members with both internal colleagues and external partners, based on each individual's development needs and career aspirations.  

Most recently, she launched an initiative called Spark Sessions, a peer-led support model designed to foster openness and collaboration among newer producers. These sessions bring together two key groups: team members who are within their first 90 days, and a "sophomore" class who are just beyond the initial ramp-up phase. Held a few times a week in an informal, leaderless setting, these virtual meetings encourage participants to share challenges, ask questions and offer real-time advice while actively working through live policies.When it comes to sustaining a high-performing sales culture, Allen says, "You have to make sure you're engaging your team, and allowing them to bring fresh ideas to the table. If you don't, they'll find someplace else to go."

Allen applies the same mindful leadership approach to her community, serving as Deputy Mayor and devoting time to multiple civic boards in upstate New York, where she also leads events in support of active-duty service members and veterans. "When I'm not working, I'm working," she laughs. "If not me, then, who? If I'm not going to be involved, I have no business complaining about the state of my community.

"There are only so many hours in the day, but at the end of the day I need to be remembered for something," she adds. "I can't just be somebody who was good at her job." 

Digital Insurance will continue to share individual profiles of the honorees for The Women in Insurance Leadership (WIL) program, the WIL NEXT program and the WIL Lifetime Achievement. Check back in to learn about these leaders.

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