Deborah Poole
Tech executive, Board Director, and Advisor to High-Growth Companies
Builder of big teams and big businesses from scratch. Most recently served as Chief Business Officer at WHOOP leading enterprise sales, bizdev, customer service, and government affairs during a period of 6x growth. Previously had a nearly 10-year career at Wayfair, running and scaling multiple business units including the launch of Wayfair Canada to hiring 10,000 people in 18 months as head of global recruiting. Current board member of Drizly through a wild period of growth, fundraising, and Uber acquisition. Started her career in management consulting with McKinsey and is a graduate of Harvard (BA) and Georgia Tech (MS). Lives in Newton with her family, pandemic puppy, and beehive.
Domain Expertise: Multi-disciplinary GM
Most passionate problem sets:
Cross-functional problems and dependencies
Designing orgs for scale
Driving teams to move faster than they are comfortable with
New market launches / BizDev
Career Experiences: WHOOP, Wayfair, McKinsey, Drizly
Charities I support: Southern Poverty Law Center, Save the Children
💪🏽 COACHING COURSES
1X1: Scaling Global Teams
No two orgs look the same, and yet… Hypergrowth companies in rapid expansion mode have many of the same design characteristics to enable flexibility, identify emergent talent, and pivot along with market demands. If you're heading into (or already in) a period of turbo-charging your business, this session provides a useful framework for planning hiring, scoping roles, communicating across an increasing number of time zones, and designing for evolution so your org isn't outdated by next quarter.
$2,500 per month
(Typically two sessions per month + prep work + follow-up email/text time)
GROUP SESSION: Coaching Female executives
Frank, open discussion about how to get into and drive effective change as a woman in the boardroom, the C-suite, or in front of a large room. Special focus on real experiences, practical and tactical considerations, and how to identify an environment where you'll most likely thrive. Intended for mid-senior and senior professionals.
2.5 hours
$325 per person
⭐ CORE VALUES
Theme
If I had more time, I would have written a shorter letter.
There are no more than three things that really matter right now, and you must be able to identify them in order to do them.
Lack of sleep is not a badge of honor.
Interests
🏍️ Passion areas: NY Times crossword (Fri/Sat), mentoring mid-career women, home improvement.
📚 Favorite books: A Wealth of Pigeons by Steve Martin. No business book on any topic, though that does not stop people from giving them to me. I wrote my undergraduate thesis on William Faulkner. It's really hard to bring that up in casual conversation.
inquire about deborah
For coaching, advisory board, or endorsement opportunities.