Ep 4: Anjarae Hamilton - The Through Line

Guest: Anjarae Hamilton, Head of Retailer Sales & Account Management at FaireTwo engineering degrees. Leads a sales team. Make that make sense.Anjarae Hamilton built the kind of resume that comes with a very specific implied promise: you will go be this thing. Vanderbilt undergrad. Stanford master's. And then she walked away from engineering entirely -- not because she couldn't do it, because she found something that fit better.What followed was consulting at Bain, operations at Caviar, Square, and DoorDash, and eventually Faire, where she now leads retailer sales for one of the most interesting wholesale marketplaces in the country. Kate and Anjarae overlapped at DoorDash, which makes this one feel less like an interview and more like catching up with someone you genuinely admire.Bio: Anjarae Hamilton is Head of Retailer Sales and Account Management at Faire, where her team works alongside thousands of independent retailers, helping them discover brands, place orders with confidence, and build lasting relationships with the makers they love. She grew up in a small town in Tennessee, where most of the businesses were owned by someone she knew. That early window into Main Street shaped a career spent helping small businesses grow, first at Square, then at DoorDash, and for the last five years at Faire. She lives in Los Angeles with her filmmaker husband, her 4-year-old daughter, and her 2-year-old son.In This Episode06:19 - How growing up in a small Tennessee town with an Air Force engineering base shaped who she became06:45 - What made her choose civil engineering -- and why the reason was more intuitive than logical15:09 - How she stumbled into Bain without knowing how competitive it was, and why that might have been the thing that got her in17:52 - What consulting gave her that engineering never could: the language, the frameworks, and the ability to influence without authority25:27 - The mentor who told her to pay attention to what she read in her free time -- and how that led her to Caviar41:49 - Why coming back from maternity leave to build a brand new team was actually easier than returning to her old one45:30 - Her annual life OKRs, the vision boarding tradition, and how she thinks about fulfillment without using the word balance52:23 - The through line she sees connecting all of it -- and what she tells her mom when she says Anjarae never uses her engineering degreeMemorable Quotes"Throughout every major decision, it would be: here's the pros and cons list rationally, and then how does it feel? Intuitively in my body.""My mom says I don't even use my engineering degree. I'm like -- I do kind of. I'm solving problems.""No one thinks about you as much as you do. I use that to quiet the overthinking, and as a reminder that I have to advocate for myself.""Almost all these decisions are two-way doors. Maybe you choose something and it sucks. You're still going to learn so much and be in a different spot to make a new decision."Resources MentionedRadical Candor by Kim ScottFaire -- faire.comConnect with AnjaraeLinkedIn: https://www.linkedin.com/in/anjarae/Follow Direction Over PerfectionInstagram & TikTok: @directionoverperfectionA podcast for early-career professionals, career changers, and parents helping young adults find their footing. Hosted by Kate Crane.