• Tell me about a time you had to have a conversation with a senior team member or investor that you kept delaying. What finally made you do it, and what changed after?

• You’ve said automation should free people to be more human at work. What does “more human” actually look like inside Chaser? What are people able to do now that they couldn’t before?

• If you could go back and give your 28-year-old self one piece of advice about building a career in tech, what would it be? Why?

• What’s the difference between surface listening and deep listening in leadership, and why does it matter?

• What’s something you get to do as CEO that you genuinely love? Why?

• What’s a bet you made on your team that completely paid off, a moment when you trusted someone before they fully trusted themselves?

• When did you personally become convinced that automation was a people strategy, not just an efficiency strategy? Was there a specific moment or experience that made it click?

• Can you share a story about a customer whose cash flow situation genuinely transformed because of what Chaser does? What did their reality look like before and after?

• What’s something about being a woman building a career in fintech or SaaS that people don’t really talk about openly, but should?

News and Updates

• What book(s) or article(s) did you read this past month that stayed with you? What takeaways do you have?

• What event(s), talks or experiences did you attend this past month that stayed with you? What takeaways do you have?

• What podcast(s) did you listen to this past month that stayed with you?