Influential Woman · Expense Reduction, Operational Optimization, and Talent Retention
Tracy Sabol
President & Founder | Solutions Broker, Connect The Dots Solutions
Oconomowoc, WI
Her Story
About Tracy
I’ve always believed that the most valuable opportunities aren’t the ones you’re sold—they’re the ones that are uncovered.
For 14 years, I built my career in the insurance industry, where I was proud to maintain a 98% client retention rate in a field that averages closer to 86%. But that success didn’t come from simply delivering insurance solutions. It came from something deeper—taking the time to truly understand my clients’ needs and connecting them with the right people, strategies, and resources beyond just my own scope of work.
Even then, I wasn’t just working in insurance—I was connecting the dots.
During that time, I also had the opportunity to help develop a private label program that scaled nationwide. It was a defining experience that showed me the power of building something bigger than a single solution—something that could create meaningful impact at scale.
But eventually, I reached a point where I knew I wanted more.
Not more success—but more impact.
So, I made the decision that many wouldn’t expect. I sold my book of business, stepped away from a career I had built and excelled in, and started over.
That decision led me to found Connect The Dots Solutions.
Today, I help school districts and businesses reduce expenses, optimize operations, and uncover financial opportunities that are often hiding in plain sight. My work focuses on identifying solutions that don’t add cost or disrupt operations—but instead strengthen budgets and improve outcomes using what already exists.
One of my primary areas of focus is working with school districts—partnering with superintendents, CFOs, and business officers who are navigating increasing financial pressure. Through a curated portfolio of best-in-class partners, I bring forward strategies that address critical areas like energy spend, payroll tax efficiency, employee financial wellness, and sustainable funding models.
On any given day, you’ll find me prospecting new opportunities, building relationships, running outreach campaigns, and—most importantly—educating. Because at the core of everything I do is a belief that when leaders are equipped with the right information, they make better decisions.
If I had to define my proudest professional achievement, it wouldn’t be a title or a number.
It would be the decision to take a risk on myself.
To walk away from something I was very good at…
To challenge expectations…
And to build something new with the intention of helping more people in a more meaningful way.
Because in the end, success isn’t just about what you build—it’s about the impact you create along the way.
Her Interview
Ten minutes with Tracy
01What do you attribute your success to?
I attribute my success to a mindset I developed early on—never limiting myself to what’s directly in front of me. Whether in insurance or now with Connect The Dots Solutions, I’ve always gone beyond the expected, looking for ways to truly help people by connecting them to the right opportunities. That willingness to go deeper, build strong relationships, and take risks—even when it’s uncomfortable—has shaped everything I’ve achieved.
02What’s the best career advice you’ve ever received?
The best career advice I’ve ever received is to continue stretching yourself every day and to do what you truly love—the rest will follow.
I’ve been fortunate to have incredible mentors throughout my career, and that message always stuck with me. For a long time, I was successful in the insurance industry and genuinely cared about my clients, but I started to feel a sense of burnout. It wasn’t because I didn’t value the work—it was because I knew I had more to give in a different way.
That advice gave me the confidence to pivot.
It reminded me that growth doesn’t happen when you stay comfortable—it happens when you challenge yourself to step into something new. When I made the decision to walk away from a successful career and start Connect The Dots Solutions, it was rooted in that belief.
When you’re aligned with what truly energizes you, the work feels natural, the impact is greater, and the success follows.
03What advice would you give to young women entering your industry?
The first piece of advice I always give is to stretch yourself. Growth doesn’t happen in comfort, so it’s important to consistently push beyond what feels easy or familiar. If you’re not stretching, you’re not growing.
Second, be intentional about who you surround yourself with. Put yourself in rooms with people who are smarter than you, more experienced than you, and willing to challenge you. That’s where real growth happens.
I also think it’s critical to be kind to yourself and recognize your wins. In sales—and really in any industry—there can be a lot of rejection. It’s easy to focus on what didn’t happen, but celebrating your progress and your successes is what keeps your momentum going and gives you the confidence to pursue the next opportunity.
Another important lesson is to pay it forward. As you grow in your career, take the time to support and develop others who are coming up behind you. Mentorship and guidance are powerful, and we all benefit when we invest in the next generation.
Finally, commit to being a lifelong learner. Especially in a space like mine, where industries, strategies, and opportunities are constantly evolving, staying curious and continuing to learn is essential. The more you invest in your growth, the more value you bring—to yourself and to those around you.
04What are the biggest challenges or opportunities in your field right now?
One of the biggest challenges right now is the financial pressure facing school districts and businesses. We’re seeing a combination of declining enrollment, rising operational costs, and reductions in federal funding—all happening at the same time. In fact, federal funding for schools is projected to drop significantly as pandemic relief funds expire, creating billions in lost revenue nationwide.
At the same time, many districts are dealing with budget shortfalls, rising healthcare and staffing costs, and funding formulas that simply haven’t kept pace with inflation. These pressures are forcing leaders into difficult decisions—often cutting programs, staff, or resources that directly impact students.
But with that challenge comes a major opportunity.
The opportunity is to rethink how organizations approach their budgets. For so long, the mindset has been to cut or ask for more funding. What I see emerging—and where I focus my work—is helping leaders uncover savings that already exist within their operations.
There’s a growing shift toward:
- Data-driven decision making
- Operational efficiency
- Alternative funding and savings strategies
- Solutions that don’t require additional cost or disruption
That’s where innovation is happening.
I believe the organizations that will thrive are the ones willing to challenge traditional thinking and look at their finances differently—not just asking “Where do we cut?” but instead asking, “Where are we missing opportunities?”
Because in today’s environment, the biggest opportunity isn’t finding more money—it’s uncovering what’s already there.
05What values are most important to you in your work and personal life?
The values that matter most to me are honesty, integrity, and accountability.
I believe in doing what you say you’re going to do—every time. Trust is built through consistency, and whether in business or in life, people remember how you show up and whether you follow through.
I also believe in giving as much as you can based on your circumstances. That doesn’t always mean giving more time or resources than you have—it means being intentional, present, and generous in the ways you’re able. Sometimes that’s offering support, making a connection, or simply showing up for someone when it matters.
At the end of the day, how you operate matters just as much as what you achieve. For me, success is grounded in staying true to your values, treating people the right way, and always doing the right thing—even when no one is watching.
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