GTM 54: Resilience is Your Willpower with Anna Baird

Anna Baird started her career in Accounting helping with IPOs of companies like Google. She then moved to become an SVP at McAfee and when they sold to Intel she decided to work at start-ups so that she could help build the foundations at scale from the beginning. She became a CFO and then a COO and finally a CRO. Anna is now working on Boards to help other executives take advantage of the opportunities that they saw earlier and avoid some of the mistakes that she’s faced at early stages. ◡̈

What You Will Learn:

  • The importance of leveraging your relationships to bring in revenue.
  • Practicing resilience to surpass those who doubt your capabilities.
  • Knowing when to walk away from a company.
  • Understanding where your hires’ skillsets are to be successful within your organization.


(6:13) What Anna has learned throughout her career selling into large strategic accounts.

(11:45) A walk through of Outreach’s deal review calls as a successful strategic tactic.

(15:45) How to prepare folks to make a strong ask that garners results.

(19:20) Anna’s impactful story that fueled her.

(22:55) A moment in time where Anna faced a struggle with misalignment.

(32:40) Anna’s advice to female leaders struggling to get promoted.

(37:40) Understanding where your hires’ skillsets are to be successful in your organization.

(42:10) Working in silos no longer works.


“I just wanna work with interest people, solving interesting problems, with people I enjoy and respect being around.”

“The only reason why we exist as a company, is because we’re solving a pain. Never lose track of why you exist and what is it that you’re building for.”

“Everyone wants to work for a place where they feel has a great foundation of innovation, great ideas, and different perspectives, and I feel that’s what the younger generation is excelling at.”

Guest Speaker Link:

Host Speaker Links:

The GTM Podcast
Don’t miss The GTM Podcast dropping every Tuesday discussing true stories and experiences including trials and tribulations in the Go-To-Market world.

Before helping found GTMfund, Scott spent 4 years at Outreach as Director of Strategic Engagement. He was in charge of aligning key relationships with VCs, BoDs, ecosystem partners and community members to drive revenue and strategic initiatives across Outreach. Scott initially ran revenue/partnerships for Sales Hacker (which was acquired by Outreach in 2018). Prior to Sales Hacker, he led and built outbound Business Development teams at Payfirma and MediaValet. Scott also advises for a number of high growth start-ups and is the host/author of The GTM Podcast and The GTM Newsletter. At GTMfund, Scott leads all fundraising efforts and runs the media arm of the firm. He’s also responsible for assessing investments, team management, LP/community relationships and GTM support for founders.

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