Mentorship, Progress, and Finding a Passion: Sally Borland Reflects on Career Journey After Winning Woman to Watch Award

Sally Borland embodies the difference between “having a job” and a “building a fulfilling career.”

Years before her current role as AssuredPartners’ National VP of Commercial Operations, Sally was working at a staffing firm in the Chicago area. At the time, it wasn’t about pursuing a passion but simply earning a paycheck after relocating for her husband’s career.

“It was just a job,” Sally recalls. “It was just something to get my foot in the door of some other companies.”

During her role, Sally regularly visited local businesses to discuss their staffing needs. One of her visits led her to Esser Hayes Insurance Group, a firm later acquired by AssuredPartners in 2019. When she asked about staffing needs, she was given a business card for the agency’s President, Howard Weiss, currently AP’s VP of Carrier Relationships.

“I wound up emailing Howard my resume, and he responded, ‘I love it, let’s set up an interview.’”

Nearly a decade after that pivotal meeting, Sally is celebrating a thriving career in a field she loves. Sally was recently named a “Woman to Watch” by Business Insurance. The award honors women in the field based on their recent achievements, leadership qualities, and their roles in the advancement of women in commercial insurance. Sally was among just 30 women to receive the honor at the 2024 Women to Watch Awards and Leadership Conference in New York City.

“Being nominated by my leadership team is incredibly meaningfully,” Sally says. “It’s humbling to know my contributions are valued. This award isn’t just personal—it’s a testament to the collaborative culture at AssuredPartners, and it drives me to continue making a difference”

The Value of Mentorship

One of the key qualities highlighted by the “Women to Watch” judges was Sally’s dedication to mentorship, something she credits as instrumental in her own journey.

“When I interviewed with Howard Weiss, I knew nothing about insurance,” Sally explains. “But he recognized my drive and told me, ‘I can teach you insurance.’ He’s been my mentor ever since.”

Sally has continued to grow under the guidance of her mentors, developing new skills and gaining the confidence to take risks. As she progressed into leadership roles—first as a local Small Business Leader, then as National Practice Leader for Small Business—she made it her mission to create opportunities for others within the company to discover their passion for insurance.

“When I see the strategies I’ve worked on not only succeed but also enable others to thrive, it reaffirms my passion for this industry,” Sally says. “I’m focused on ensuring my team feels supported, engaged, and motivated in their work.”

Sally emphasizes the importance of fostering a positive environment where employees can grow without becoming overwhelmed. “If people aren’t enjoying their job, that’s when it becomes ‘just a job’ and not a ‘career.’ If people feel valued and have room to grow, they’ll want to stay and build their careers with us.”

A Spotlight on Women in the Industry

Sally’s recognition as one of the industry’s top women comes at a time of significant progress for women in insurance. A recent Agency Universe study found a 12% increase in firms with women in senior leadership roles since 2018. Sally has witnessed this evolution firsthand at AssuredPartners.

“The rise of strong female leaders in our company has been both inspiring and motivating,” she says. “It’s not just about representation; it’s about leveraging the unique perspectives and strengths women bring to leadership roles.”

As a mentor, Sally takes pride in supporting and guiding female colleagues as they advance their careers. Her advice to young women entering the field? “Take a chance.”

“Leadership can be intimidating, but growth happens when you step out of your comfort zone. Talk to your leaders and learn from their experiences.”