• You advocate that automation makes organizations leaner but more human. How does Chaser keep from sterilizing customer relationships when automating sensitive moments like collections?

• You strongly advocate that new or aspiring CEOs spend a year embedded directly with the sales team. What did you learn from prospects in the sales trenches that changed how you evaluated Chaser's product roadmap?

• You describe yourself as an overarching perfectionist. How do you reconcile that with being a CEO who has to make rapid decisions across ten different departments?

• Chaser serves finance teams across different countries and currencies. What has that taught you about leading a distributed, international team versus a single-market business? Is there a leadership skill that only shows up once you're operating globally?

• Where have you had to be kind but direct with your own expectations of yourself, as a CEO, a mother, and a person under constant scrutiny?

• What does kindness look like in a client relationship built around debt collection and chasing money owed? How does Chaser's product balance firmness, getting paid, with treating the debtor with dignity? Is there a client story where kind but direct collections work changed the outcome for the better, for both sides?

• How has kindness shown up this past month internally, across teams?

• Tell me about a recent win at Chaser. What do you want to highlight for your audience? A leadership win, an integration, something else?

• What's a leadership instinct or lesson you've been focusing on lately? How did you shape it, and how is it serving you?

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?