Don’t take no for an answer: How self-advocacy shaped my career

When I was a few years into my insurance career, a sales rep told me, “You’re going to hear ‘no’ all the time. Don’t take no for an answer.”

At the time, I assumed he was talking about sales. I didn’t realize he was giving me the best career advice I would ever receive. I didn’t yet understand how every aspect of this career comes with a “no.”

In the 10-plus years since then, I’ve seen how building a career in insurance, especially as a woman, requires self-advocacy and not taking no for an answer. I’ve gone from part-time receptionist to managing partner of my agency by pushing for opportunities before they were offered, speaking up when my role grew, and advocating for myself and the people I lead.

Finding my place in the industry

I started at Webb Insurance in 2015 as a part-time receptionist. I quickly realized this position was just a stepping stone – the real action was happening in the back office, where the agency’s owners, Randy and Christie Webb, were working with clients and selling policies. I told them I wanted to work back there, too. I wanted to learn insurance, not just answer phones.

Six months later, I moved into a sales role, and two years later, I became the office manager. I loved the pace and variety. Nothing stayed the same from one day to the next.

Growing with the agency

Webb Insurance grew consistently. When I started, it was a three-person operation bringing in about $30,000 in written premium each month. Today, we have 10 employees, and our goal is $165,000 a month.

My responsibilities grew too. As office manager, I helped team members find their strengths and roles. A few years later, Randy and Christie wanted to move to Florida to spend more time with family, so I became a partner and took over day-to-day operations so they could scale back and work remotely.

The transition wasn’t simple. For a while, I was still doing sales while managing operations and trying to support the team. I was switching between quoting, handling renewals, stepping into service issues, and guiding staff, but it got to be too much. I couldn’t coach the team while I was still playing on it.

Advocating for leadership

As I juggled sales and operations, the advice from the sales rep came back to me. I needed to advocate for myself and my team. I sat down with the founders and explained that we couldn’t keep moving forward if I stayed buried in production. I needed to step fully into leadership.

That conversation set me up to effectively lead the agency and make meaningful changes. In the last few years as managing partner, I successfully:

• Designed a retention department to reduce pressure on our sales team
• Created a maternity program to support new moms
• Led an agency rebrand, changing the name to Webb & Winkelman Insurance to better reflect who clients will meet in the office

Leading a women-centered agency

The representation in the agency name mattered a lot to me, not because of vanity but because it signals that women are leading here. For so long in our industry, the heads of agencies have been men, and women have been in the background quietly working.

When I first got into the industry, people would ask to speak to a man – the type of person they assumed would be leading a business. I don’t see that much anymore.

Now, our agency is almost entirely women – and none of them came from an insurance background. I hired for personality, work ethic, and willingness to learn. Insurance can be taught, but those basic skills are key to success in any role.

One of my missions is to make our agency a great place to work, especially for working moms, who often juggle priorities between their work and their families. We allow a lot of flexibility and do our best to show every employee that they are valued. We have an amazing team of women who support each other, share the load when life gets hard, and bring their full selves to work.

As a woman leading women, I want to make sure they see their own potential and keep leveling up. I want my team to see leadership as an option for them too. One of my goals is for someone on my staff to eventually say they want my job. To me, that would signal success.

What I’ve learned on the path to partner

Reflecting on my journey, here are the three most important lessons that have guided me:

Design the role you want. Don’t wait for the perfect opportunity to be offered to you. The only way I went from being a receptionist into sales is because I asked for it. And when the agency needed a full-time leader, I made that push. See the need, create the solution, and show how you are the right person to lead it.

Build your network of allies. Career growth is never a solo effort. Knowledge is power in our industry, and it’s built on shared experience. I found mentors in my own agency, but I also built relationships with competitors, like a captive agent in my town who sent business she couldn’t write. Find the people who will teach you, challenge you, and cheer you on.

Don’t take no for an answer. I can’t emphasize it enough. You will always hit barriers. But the more you practice bouncing back, the easier it becomes. Refusing to accept “no” has been the engine of my career, clearing a path not just for myself, but for the women who will come after me.

Keep pushing. Your own breakthrough is waiting on the other side of a “no.”