At Rise HiER, we’re committed to sharing real stories from real leaders who’ve dared to challenge the status quo—and themselves. During our recent webinar, we had the honor of hosting Katy Carrigan, CEO of Goody, for an intimate and insightful conversation about leadership, self-doubt, and what it really takes to rise above imposter syndrome.
Katy’s journey from Dropbox to the helm of a rapidly growing startup is not just a story of professional ascent—it’s a lesson in self-belief, grit, and growth. Here are the biggest takeaways from our time together.
From “Why Me?” to “Why Not Me?”
When Katy was unexpectedly tapped to be considered for the CEO role at Goody, she was already on the interview panel…for external candidates. It wasn’t a position she had been pursuing. In fact, her first instinct was disbelief.
“I was like, ‘What are you talking about?’” she told us. “I didn’t feel ready. I had all the reasons why it shouldn’t be me.”
But that hesitation eventually evolved into a powerful mindset shift: Why not me?
Katy realized she already knew the business inside and out, had deep relationships across the team, and possessed the operational instincts that startups thrive on. That reframing—from disqualifying herself to recognizing her readiness—was a key moment in her rise.
Navigating Imposter Syndrome: The “Winning Ugly” Years
Even after stepping into the CEO seat, imposter syndrome didn’t immediately go away. In fact, Katy admitted it lingered far longer than expected.
“It took me about three years to fully own the role. I was still wondering if I was the right choice.”
What changed? Experience. Katy described her early CEO years as a series of “winning ugly” moments—getting through lawsuits, navigating accounting issues, dealing with the unknown. They weren’t glamorous wins, but they were deeply formative.
Each obstacle proved to her that she didn’t need to have all the answers—she just needed a clear compass and a willingness to figure it out.
The Power of Putting Yourself Out There
One of the most powerful moments in our Q&A came from Rise HiER member Belinda Barnes, who opened up about a missed opportunity. She’d wanted to apply for a director-level position but talked herself out of it after hearing who else was applying.
Katy’s response was firm but supportive:
“Always apply. Even if you don’t get it, you’ve shown your interest. You’ll get feedback. You’ll get noticed.”
This sentiment resonated deeply across the group. Too often, we pre-reject ourselves from opportunities because we assume we’re not “ready.” Katy encouraged us to reject that narrative.
Rise With Confidence, Not Caution
When asked what advice she’d give herself on the day she became CEO, Katy didn’t hesitate:
“Take more risks.”
In hindsight, she realized she had spent too much time trying to prove herself, playing it safe to protect the company. She contrasted this with a male peer who, in a similar position, projected immediate confidence—even overconfidence.
Katy challenged us as women, to project our potential more boldly. “Don’t hedge. Don’t wait to be perfect. Bet on yourself out loud.”
Tactical Tools: How to Get Noticed in Bigger Organizations
Katy didn’t just share mindset shifts—she offered actionable tools. For those looking to rise in larger companies, she emphasized the value of skip-level meetings—connecting with leaders above your direct manager.
Her pro tips:
Always bring an agenda. Include it in the invite.
Send a short pre-read with context and key topics.
Link your insights to broader team or company goals.
Come with solutions, not just problems.
Visibility, she reminded us, isn’t self-promotion—it’s leadership in action.
Final Reflections
From building generational wealth by moving to Florida, to restructuring Goody’s pricing model by trusting her gut, Katy Carrigan’s journey is rich with lessons in courage, conviction, and continuous learning.
She reminded us that the pathway to leadership is rarely paved with certainty. More often, it's marked by moments where we choose to believe in ourselves before anyone else does.
“It’s not about being fearless,” she said. “It’s about being willing to grow in the face of fear.”
At Rise HiER, that’s exactly what we’re here to help you do.
Want to keep growing?
Join us at Rise HiER for more transformative conversations, expert-led coaching, and a network of women rising—together. Let’s build the confidence to say “Why not me?”—and then go after what’s next.