Richard H.
5.0
(6)
Studied at Claremont McKenna College
Works at Menlo School
Available tomorrow at 10:00 PM UTC
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About Richard
I’m a business leader, coach, and educator with a career that spans strategy & operations, consulting, education, and purpose-driven career pivots. I specialize in helping people navigate moments of transition: whether you’re stepping into a bigger leadership role, applying to school, or rethinking your career. Additionally, I help businesses in growth mode add structure and forward momentum when hit with ambiguous problems. My own path has taken me through multiple chapters. I started my career in consulting at Deloitte, then pivoted into marketing at Stitch Fix, where I was promoted three times and eventually led a team of 20+. From there, I transitioned into strategy and business operations and rose to VP of Strategy & Analytics at AllTrails and sitting on the senior leadership team. Most recently, I made a values-driven shift into education and now work as a high school teacher. Throughout, I’ve had a consistent through-line: helping people, and businesses, get unstuck, think bigger, and move forward with clarity. I bring a mix of EQ and IQ, blending strategic rigor with empathy and real-world experience across multiple domains. As a coach, I work with professionals at all stages: whether you’re accelerating your current path, navigating a pivot, or looking for more meaning in your work. I also bring years of experience as a mentor, team builder, and strategic advisor to growth businesses, helping business leaders adopt the right structure and thinking to grow. If you’re looking for a thoughtful partner to help you chart your next chapter, with intention and momentum, I’d love to connect and build a tailored plan together.
Why do I coach?
Being a coach is one of the most meaningful ways I know to give back. I’ve been lucky to have mentors who guided me through key inflection points in my life: people who helped me navigate uncertainty, ask better questions, and move forward with purpose. Coaching is my way of paying that forward. I find deep joy in helping people make sense of moments where they are stuck. There’s something incredibly satisfying about using structure (whether it’s a strategic framework, a roadmap, or the right set of prompts) to help unlock clarity and momentum. Watching people grow into the fullest version of themselves is a privilege I don’t take for granted.
Work Experience
Math Teacher
Menlo School
August 2025 - Present
Vice President, Strategy & Analytics
AllTrails
October 2024 - July 2025
Leading strategy, business operations, analytics, and international expansion for the world's most popular and trusted platform for outdoor exploration
Vice President, Marketing
AllTrails
April 2022 - October 2024
Leading product marketing, brand marketing, lifecycle marketing, and marketing strategy & operations for the world's most popular and trusted platform for outdoor exploration.
Director of Marketing
Stitch Fix
November 2021 - April 2022
Grown scope and size of direct team 7x since joining; hired and managed team of ex strategy consultants and functional experts who have since become high performers. Responsible for lifecycle marketing, vertical demand strategy and execution, marketing strategic planning for 150+ person org, integrated marketing, consumer analytics & insights, and high priority / cross functional strategic demand initiatives for CEO / CFO / SVP of Marketing.
Senior Manager - Marketing Strategy & Operations
Stitch Fix
November 2020 - November 2021
Manager - Marketing Strategy & Operations
Stitch Fix
December 2019 - November 2020
Strategy Consultant
Deloitte
2016 - 2019
Solved strategic and operational challenges for executives of various sized businesses (angel investor funding to $1B+ in revenue) in retail, technology, hospitality, media, telecom, and healthcare industry sectors. Select Project Experiences Include: Customer growth strategy for $1B+ retailer | Marketing strategy for multi-billion dollar technology business | Customer growth strategy for Pre-K ed tech business | Project management of customer-facing technology platform for high growth telecom business | Investment strategy for early-stage telecom start up | Corporate M&A strategy for multi-billion dollar media and advertising business | Deloitte Retail POV - The Great Retail Bifurcation
Management Consulting Analyst
Mercer
2015 - 2015
Investment Banking - Analyst
Osborne Clarke
2014 - 2014
Education
Claremont McKenna College
Bachelors of Arts, Economics
Activities and societies: Admissions interviewer, Director of Tours, Varsity Men's Basketball (four year varsity athlete and team captain), Student Government, Student Investment Fund, Robert Day Scholar, Delta Epsilon International Honor Society in Economics, Cum Laude
6 Reviews
Overall Rating
5.0
Richard has helped Leland clients get into AllTrails