Name a woman.
Now name a woman who’s also a leader.
Now name one who’s never second-guessed herself, never felt like she didn’t belong in the boardroom, never been undermined or underestimated. Doubt you can.
Jennifer McGuinness, CEO of Pivot Financial, gets it. “I failed at every single thing I'm about to tell you,” she said at the inaugural Breaking Barriers webinar. “Through those failures, I learned how to navigate the complexities of leadership and build a career I'm proud of.”
We all know failure is supposed to be a lesson, a stepping stone, a necessary evil. But for women, failure is often a scarlet letter. We’re expected to be twice as prepared, twice as competent, twice as everything – without being too much of anything.
Strong but not pushy. Smart but not arrogant. Approachable but not too nice. And don’t forget those exclamation points, ladies!!! (Three is too many, in case you were wondering).
The Breaking Barriers webinar, hosted by the Mortgage Women Leadership Council (MWLC), is designed to dismantle that impossible balancing act. It’s an open forum for women in leadership to talk about what’s actually holding them back – and how to move forward anyway.
McGuinness, a veteran of the mortgage industry with nearly three decades of experience, is no stranger to these challenges. She’s heard the comments, fought the biases, and earned every seat at every table she’s sat at. And yet, she’s been called an “ice queen.”
“This person had never met me,” she said, laughing. “Don't assume you know someone unless you’ve actually met them.” The reputation, of course, came from her no-nonsense approach to negotiation, a skill she’s honed over years of pushing past every “no” in her way.
And let’s talk about no. McGuinness remembers sitting in an annual review, where her bosses told her she wasn’t getting a promotion – but they were giving her a $100,000 raise instead. Their reasoning? “The money puts you in line with the title.”
Her response? “You’re giving me the title, too.” And she got it.
Women in leadership have to advocate for themselves. They have to ask for what they deserve because no one is going to hand it to them. And sometimes, they have to walk away from the places that refuse to see their worth.
It’s not just about climbing the ladder. It’s about defining success on your own terms. McGuinness calls it a “CEO achievement,” but acknowledges that doesn’t always mean literally becoming a CEO. For some, it’s a flexible schedule. For others, it’s a clear career trajectory. The key is owning that choice.
Motherhood, in fact, is something McGuinness calls her greatest achievement. When an interviewer once told her they couldn’t publish that answer, expecting something more “businesslike,” she stood firm. Women in leadership are not all the same. There is no single right way to define success.
That’s what Breaking Barriers is about – creating space for those conversations, building a support system, and making sure that the women who come next don’t have to figure it out alone.
Perfection isn’t real. But power? That’s something you can own.
For access to the full webinar, and to join the Mortgage Women Leadership Council, visit MWLCouncil.com.
