Across her career in tech, Anne Raimondi hasn't stayed comfortable for too long. A quick scan of her stacked resume shows tours at top-performing startups, including eBay, SurveyMonkey, Zendesk, and her current role as Chief Customer Officer at Guru. But dig a little deeper, and what stands out most is the breadth of these roles, from founder, operator, C-Suite executive, and now board member at Asana, Gusto, and Patreon. She's tackled consumer and enterprise challenges and headed up functions all over the org chart, including product, marketing, revenue and operations.

Put simply, she's seen startups from nearly every altitude, so we were over the moon when she agreed to sit down with us again. (Previously, Raimondi's appeared on the Review's digital pages sharing a tactical look at diagnosing and repairing team trust that's gone sideways.) This time around, she pulls on threads from across her career in tech to dole out leadership lessons for executives and board members looking to level up.

From Exec Roles to Board Seats — Lessons for the Startup C-Suite from Zendesk, Guru, eBay, & More

First, she turns her attention to how new executives can find the right company fit, craft 30, 60, 90-day plans that give you a boost, and get the whole team bought into your vision.

Next, she puts on her talent development hat, sharing how founders can hone an eye for spotting and recruiting the best external talent, while building up a stable of internal leaders. Finally, she takes us inside the board room and dives into the healthy habits that any startup can borrow.

Whether you're a founder, executive or board member looking to sharpen up your skills — or someone who wants to step into these same shoes someday — it's a must-read. Raimondi's clearly crystallized the lessons and stumbles from each chapter of her career, with a healthy dose of modesty. “Great leaders and executives have enough humility to recognize, ‘I was on a rocket ship, and these are the mistakes I made on that rocket ship that I wouldn’t do again,” she says.

As always, thank you for reading and sharing!

-The Review Editors

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