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On this episode of the Sunny Side Up podcast, guest Anna Baird—Outreach’s CRO of Sales and Development—shares her tips on moving from the VP role to the C-Suite, how to make sure you’re in alignment with the company you’re working for, and why taking time off to replenish your soul is so important. Anna is an executive with a rich level of experience that has led to her current role as CRO and on to the board of directors for Ticketmaster competitor, Screen Geek. Anna’s biggest piece of advice for leaders? Always be looking ahead to the future of your company. 

About the Guest

As Outreach’s CRO, Anna leads all sales and revenue operations. With a wealth of experience in finance and executive leadership, she specializes in accelerating high-growth companies and has led startups through significant fundraising events. Prior to Outreach, she served as CFO of Livongo, Senior Vice President at McAfee, and Partner at KPMG. There she was the Global Lead Partner on several premier technology companies, including Google and Intuit. Anna is a CPA and is Six Sigma Green Belt certified. When she’s not crushing it in the C-suite, Anna loves to travel. She has checked off a few bucket list items, including standing at the edge of Victoria Falls in Africa, scuba diving in Fiji, and skydiving in Hawaii, but she asserts she is just getting started.

Connect with Anna Baird

Key Takeaways

  • A little about Anna’s background and how she went from being a CPA to a CRO. 
  • Anna’s thoughts on taking time off to replenish and refresh your soul. After she left McAfee, Anna took nine months off to travel with her family to some of the places she’s always wanted to go. She believes you have to make time for rest, no matter what job title you have. 
  • Anna’s tips on moving through the executive ranks: 
    • It’s not all about relationships 
    • Look for opportunities 
    • Look for things that are broken and try your best to fix them
    • Do an excellent job right where you’re at 
  • When moving from a VP to a C-level role, the playbook isn’t hugely different. Anna believes understanding the company and a desire to understand is critical to moving up. 
  • If you don’t understand something or you’re wrong, just admit it, Anna says. People will respect you more if you ask questions, plus you’ll learn more in the end. 
  • To do well at a company, Anna believes it’s critical to be in philosophical alignment not only with the company’s vision but also with the CEO’s vision. 
    • The three things that will trip you up on day 1 if you don’t do your research: 
      • Alignment as a human 
      • Alignment as a leader
      • Alignment on vision 
  • It’s important to know what your role actually is within the company. Agree on your role and its parameters before you say yes. 
  • Once you’re a successful C-level executive, the next phase of the journey is joining a board of directors—the phase Anna currently finds herself in. 
  • Anna shares why she decided she wanted to be on a board of directors and why she felt like Screen Geek was the right fit for her resume and experience. 
  • Anna’s last piece of advice is to think about your career on that three-year horizon—always looking ahead to the future. 
  • Anna tells us about two great books, one old and one new, that she recommends (see below). 
  • The three people in B2B Tech Anna would recommend for Sunny Side Up: 
    • Hilary Hadley of Zoom 
    • Ed Calnan of Seismic 
    • Erica Schultz of Confluence 


“Your job as a leader is not to think about this quarter, it’s to think about the next 36 months, and are we building the things that make us successful 36 months from now?”  


Highlights From the Episode

On Taking Time Off

Anna talks about how she’s learned the hard way to take time to rest and replenish her soul, whether that’s through extended vacations and time off with her family, or weekly hikes, cooking, or gardening. If you lose yourself in your work, it’s hard to come back. 

If it’s Broken, Try to be the One to Fix it

One of the keys to Anna’s success has been her willingness to step up and fix things that were broken in an organization. If you want to move up and show your managers that you can take on more responsibility, be the one to step up and take initiative when something isn’t working in the company. 

Asking Questions to Understand

Even leaders don’t know all the answers to every question, and that’s okay! Take the time to listen as you’re moving up the ranks, and make sure you’re leading with intellectual curiosity and a genuine desire to learn from those above you. Don’t be afraid to ask questions. 

Moving from the C-Suite to the Board

Anna’s career has led her to the board of directors level. But even when you’re a high-level executive like Anna, she emphasizes doing your research before signing a board contract to make sure the board is right for you and you’re able to add a significant level of ROI to the team. A board is its own community—make sure you’re holding up your end of the contract and don’t burn the bridges you’ve built. 

Be Looking 36 Months Ahead

Anna’s last piece of advice for listeners is to always be looking 36 months ahead as a leader. Even when many executives are focusing on the fiscal year 2022, Anna is already making things happen for 2023. It’s always about what’s next when you’re a top leader. 

Recommended Reading/Resources

The Art of War by Sun Tzu
The Qualified Sales Leader by John McMahon


Hilary HeadleeHead of Global Sales Ops + Enablement at  Zoom


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