Hosted by Lauren Bailey, Founder of Legacy Executive Club, this episode features Anna Baird, Operating Partner at Madrona and former CRO/COO/CFO who helped scale Outreach to unicorn status and was the global lead partner for Google at KPMG during its IPO years. With decades of Silicon Valley leadership across Intuit, McAfee, and more, Anna shares candid lessons for leaders who want to grow careers and companies.

Key Takeaways

2:20 – 3:18 Imposter syndrome never goes away, even at the top

6:23 – 7:26 Taking risks and fixing what’s broken: the art of the possible

8:28 – 9:52 The biggest career “train wrecks” and lessons learned

10:26 – 12:24 Why listening to customers, product, and employees is a leader’s superpower

14:09 – 16:14 The danger of manipulating data and the need for one source of truth

17:16 – 18:49 Spotting and repairing the “relationship gap” at the executive level

22:19 – 24:40 Legacy lessons: teaching, listening, and being remembered for impact

This is a masterclass in strategic listening, resilience, and building trust from someone who’s sat in nearly every C-level seat.

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And check out the community behind this show: https://legacy.wearegirlsclub.com/

Connect with our host on LinkedIn.