--- title: Wine Down Wednesday with Anna Baird description: Ernest Hemingway was an American novelist. 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[2022 Top 25](https://info.wearegirlsclub.com/top-25-2022) - [2021 Top 25](https://info.wearegirlsclub.com/top-25-2021) - [2020 Top 25](https://info.wearegirlsclub.com/top-25-2020) - [About Us](https://wearegirlsclub.com/about-us?hsLang=en) - [Contact Us](https://info.wearegirlsclub.com/contact-us) - [LEARNING CENTER LOGIN](https://wearegirlsclub.litmos.com/account/login) [CONTACT US](https://www.hubspot.com/) [LEARNING CENTER LOGIN](https://www.hubspot.com/) [Community](https://info.wearegirlsclub.com/blogs/tag/community) [Career Development](https://info.wearegirlsclub.com/blogs/tag/career-development) # Wine Down Wednesday with Anna Baird [![](https://info.wearegirlsclub.com/hs-fs/hubfs/f5f7a0fbefaac3de3b1d4ff2b57b188e-1.png?width=50&height=50&name=f5f7a0fbefaac3de3b1d4ff2b57b188e-1.png)](https://info.wearegirlsclub.com/blogs/author/lauren-bailey) [Lauren Bailey](https://info.wearegirlsclub.com/blogs/author/lauren-bailey) May 2, 2025 9:40:27 AM One of my favorite things in [#GirlsClub](https://z2l.27e.myftpupload.com/)is bringing top women in business to our community for an intimate conversation and Q&A. We call it Wine Down Wednesday as we all sip, chat and enjoy the girl talk. --- Recently, [Anna Baird](https://www.linkedin.com/in/anna-baird-38966513/), CRO for [Outreach](https://www.outreach.io/)joined me from their Seattle offices. Fresh from her transition from COO to CRO (she’s also been a CFO!), she talked about her journey to head of sales at one of our industry’s favorite companies. As always, Anna was smart, direct, and authentic. It’s why we love her. Allow me to share a few of her golden nuggets for up and coming women in sales: 1. **Anna was helped early and often in her career by key mentors.** Her advice: invest time with these people consistently. The time we spend at a coffee, a lunch, or a conversation is the best deposit we can make in the bank. Too often we get the help and move on. Anna consistently invests her time and attention to the men and women who have been behind her during her career. 2. **Wondering if management is right for you?** Try mentoring someone coming up behind you. It could be a new rep on your team. If the experience feeds you…you belong in management! 3. **Find your replenishment source and dip into it often.** I tried a few times to get Anna to share a breakdown with us. I mean, who of us hasn’t cracked under the pressure of doing it all – especially during COVID?! Not this powerhouse. She learned early to find her source of replenishment and she’s not shy about taking it. What’s Anna’s? “Baking! I love it.” 4. **Take something broken:** When we’re looking for an opportunity to prove ourselves, a path up the ladder, or a challenge, volunteering for the scary broken project almost guarantees a win. What a perspective! We all have those projects, departments, processes, etc. at our offices. Find one. Volunteer to own it. Then knock it out of the park. All throughout our conversation, I heard examples of how Anna played to win while still maintaining her values, her personality – her femininity. This really impressed me. I admit, as I came up in sales departments as the only woman, I spent more time being one of the guys than myself. Anna shared many examples of how she brought balance and human perspective to executive meetings. It’s a perspective her leadership and her entire company has embraced, and it’s one of many reasons we love [Outreach](https://www.outreach.io/)at [#GirlsClub](https://www.linkedin.com/company/girlsclub/). We’re grateful for your time, your advice, and your example [Anna Baird](https://www.linkedin.com/in/anna-baird-38966513/)! I’m an even bigger fan today. ###### Topics - [LB's Corner](https://info.wearegirlsclub.com/blogs/tag/lbs-corner) - [Career Development](https://info.wearegirlsclub.com/blogs/tag/career-development) - [Confidence Advice](https://info.wearegirlsclub.com/blogs/tag/confidence-advice) - [Community](https://info.wearegirlsclub.com/blogs/tag/community) - [Uncategorized](https://info.wearegirlsclub.com/blogs/tag/uncategorized) - [Sales Leadership](https://info.wearegirlsclub.com/blogs/tag/sales-leadership) - [Women Empowerment](https://info.wearegirlsclub.com/blogs/tag/women-empowerment) - [Events](https://info.wearegirlsclub.com/blogs/tag/events) - [Gender Pay Gap](https://info.wearegirlsclub.com/blogs/tag/gender-pay-gap) - [Hiring Tips](https://info.wearegirlsclub.com/blogs/tag/hiring-tips) - [Announcements](https://info.wearegirlsclub.com/blogs/tag/announcements) - [Diversity & Inclusion](https://info.wearegirlsclub.com/blogs/tag/diversity-inclusion) - [Imposter Syndrome](https://info.wearegirlsclub.com/blogs/tag/imposter-syndrome) - [Job Promotion](https://info.wearegirlsclub.com/blogs/tag/job-promotion) - [LGBTQIA+](https://info.wearegirlsclub.com/blogs/tag/lgbtqia) ###### Popular Post - [Sales’ Biggest Problem IS Solvable!](https://info.wearegirlsclub.com/blogs/sales-biggest-problem-is-solvable) - [Fireside Chat: How to Be an Ally to the LGTBQIA+ Community](https://info.wearegirlsclub.com/blogs/fireside-chat-lgbtqia-ally/) - [Four Things That The SaaStr Did To Build Diversity And Inclusion](https://info.wearegirlsclub.com/blogs/saastr-build-diversity-inclusion/) - [Seven common misconceptions about graphic design](https://info.wearegirlsclub.com/blogs/seven-common-misconceptions-about-graphic-design-2) - [#GirlsClub Guide to: Asking for a Promotion](https://info.wearegirlsclub.com/blogs/girlsclub-guide-to-virtual-sales-ask-for-a-promotion/) ###### Subscribe Previous Post ###### [I Said Yes](https://info.wearegirlsclub.com/blogs/seven-common-misconceptions-about-graphic-design-3) Next Post ###### [#GirlsClub Summer Camp: Should I Stay or Should I Go?](https://info.wearegirlsclub.com/blogs/girlsclub-summer-camp-august-recap/) ### Similar Blog Posts [![](https://info.wearegirlsclub.com/hs-fs/hubfs/Image-1.png?width=352&name=Image-1.png)](https://info.wearegirlsclub.com/blogs/tips-for-remote-networking/) ##### [Tips for Remote Networking](https://info.wearegirlsclub.com/blogs/tips-for-remote-networking/) [Read More](https://info.wearegirlsclub.com/blogs/tips-for-remote-networking/) [![](https://info.wearegirlsclub.com/hs-fs/hubfs/Image-1.png?width=352&name=Image-1.png)](https://info.wearegirlsclub.com/blogs/seven-common-misconceptions-about-graphic-design-3) ##### [I Said Yes](https://info.wearegirlsclub.com/blogs/seven-common-misconceptions-about-graphic-design-3) [Read More](https://info.wearegirlsclub.com/blogs/seven-common-misconceptions-about-graphic-design-3) [![](https://info.wearegirlsclub.com/hs-fs/hubfs/Image-1.png?width=352&name=Image-1.png)](https://info.wearegirlsclub.com/blogs/conversation-evereve-ceo-megan-tamte/) ##### [A Conversation with Evereve CEO, Megan Tamte](https://info.wearegirlsclub.com/blogs/conversation-evereve-ceo-megan-tamte/) [Read More](https://info.wearegirlsclub.com/blogs/conversation-evereve-ceo-megan-tamte/) #### Join us! 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