Explore every episode of the podcast After The Title

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.

If you liked this episode, share it with a colleague or work friend who’s ready to lead differently.

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

Connect with our host on LinkedIn. 

Climbing the ladder is one thing. Learning what really matters on your way to the top is another.

After the Title is a podcast for high-achieving leaders, and those on their way, who want the truth about what leadership really looks like. Hosted by Lauren Bailey, these are unfiltered conversations with executives who’ve hit the top and started asking deeper questions:

What truly matters now?

Is anyone else dealing with this? 

What will I leave behind?

Each week, Lauren sits down with leaders to explore the stories, pivots, and defining moments that shaped their legacy — and the humans they became along the way.

If you’re craving purpose beyond performance, mentorship beyond metrics, and meaning beyond the title... you’re in the right place.