Sales, leadership, and carving your own path

The one thing Bridget Gleason knew, beyond a shadow of a doubt, was that she wanted to be a stay-at-home mom. She dreamed of providing her kids and her family with an incredible life.

And then the universe handed her something completely different.

When Bridget’s boys were one and three, her husband left—and she had no choice but to go back to work. So she interviewed for a sales position, negotiating a flexible part-time schedule in which she would be compensated based on performance rather than hours spent in the office.

When career meets motherhood

Motivated to spend as much time with her sons as possible, Bridget’s unanticipated status as a single mother afforded her a crash course in productivity. From this, she learned to prioritize the handful of to-dos that were most impactful. Going back to work also taught her to reframe the unexpected as a gift. She could have a rewarding career AND be a good mom. She didn’t have to choose one or the other.

Today Bridget shares her resilience in the face of uncertainty, explaining how that process continues to this day. I ask her about the role emotions play in her work life and how she defies expectations to behave a certain way as VP of Sales. Listen in for Bridget’s advice around prioritizing self-care, ‘sharing the real’ when your kids are struggling, and reframing surprises as opportunities rather than obstacles.

The Startup Pregnant Podcast Episode #027

Some quotes from the episode

  • “My passion? I wanted to be home with my kids when I had them. It’s what I wanted to do. I had this vision of doing a very traditional role and being that sort of stalwart for the family and raising my kids … and life gave me something different.”
  • “As soon as I started [working], I thought, ‘Oh, this isn’t so bad. There’s this other part of me that’s very much alive when I’m here at the office.’”
  • “It’s really hard to nurture and give to others if we haven’t done that first for ourselves.”
  • “I often feel that they want me to show up a certain way, they want me to be a certain kind of VP of Sales … because it makes them feel more comfortable if I’m doing the role like they expect, if I beat my chest, and I’ve got it under control, and I know what we’re doing. If I behave the way they expect, they feel better—but that’s inauthentic to me because there are a lot of times I don’t know what to do.”
  • “I’ve got to be true to the full complement of who I am. Sometimes there’s a lot of emotion in it.”
  • “People that perform at their best and stay at jobs, often they’ve got somebody in the workforce … that thinks of them as something more than a tool to get a job done.”
  • “All right, I’ve got 4 hours, and I’ve got 38 things. What are the things that are going to be the most impactful? Okay, do those.”
  • “How do we reframe? That we go with this flow that … the universe is not out to make life miserable for me, and to see the things that come my way as opportunities, not obstacles. And that takes an incredible amount of deliberate thought and conversation and great friends and people who’ve done it in other circumstances.”
  • “This is not a one-and-done, this growth stuff.”
  • “Let’s share the real. Let’s be real about the struggles because that’s where we, as parents, need help … and we can’t support each other if we don’t know what those struggles are.”


Bridget Gleason is the Vice President of Sales at, the world’s most popular open-source log analysis platform. Her strengths lie in accelerating sales for startups and early-stage SaaS and PaaS technology companies, delivering significant revenue increases, forecast predictability and customer retention. An industry thought-leader, Bridget is a sought-after presenter at sales, leadership and women’s conferences. She is most recognized for her phenomenal success in building and leading high-velocity sales organizations.




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