Richard H.
1,185 min coaching
VP of Strategy at High Growth Startup | Career Coach
I’m a seasoned strategy and business operations leader with experience across consulting and high-growth consumer tech. I’ve grown my career extremely quickly—starting with three years in management consulting at Deloitte, followed by three years at Stitch Fix (where I was promoted three times to Director), and most recently serving as VP of Strategy & Analytics at AllTrails, where I sit on the senior leadership team.
In these roles, I’ve led long-term strategy development, annual planning, OKRs, business reviews, board materials, analytics, and research. I’ve also acted as a general manager for top company priorities including international expansion, monetization, and retention.
My strength lies in balancing EQ and IQ—reading the room, understanding what matters to stakeholders, and adapting accordingly, while applying deep strategy and operations expertise to solve a company’s most complex, high-stakes challenges.
As a coach, I can help with interview prep (including take-home projects), career navigation, or thought partnership on live projects. I’ve coached dozens of people into roles while also building teams from scratch and managing orgs of ~20 people.
Looking forward to connecting and building a tailored plan for you!

Works at Menlo School
$250/hr
Available Jun 1, 2026