Madison Leonard ☀️ — CEO
I'm an end-to-end GTM architect who specializes in uncovering strategic market positioning. My superpower? Spotting patterns across buyer behavior, competitive landscapes, and product adoption. I merge data with intuition to craft compelling narratives that drive technical understanding, articulate business value, and highlight competitive differentiation. Over the last 10 years, I've built 0-to-1 GTM strategies that drive meaningful business results: - Transformed a traditional sales-led motion into a hybrid GTM approach, reducing sales cycles by 25% and increasing qualified pipeline by 15% - Architected a complete product-led growth strategy that increased platform retention by 3.4x through targeted segmentation and optimized user journeys - Built high-performing product marketing functions from scratch at multiple startups, establishing processes that scaled with 100%+ YoY growth - Developed positioning frameworks that successfully differentiated products in crowded markets, leading to $9M+ in influenced revenue - Launched new products that achieved 186% adoption growth within 8 weeks through strategic narrative development and cross-functional alignment I'm passionate about the intersection of data, storytelling, and customer experience -- transforming technical capabilities into compelling value propositions that inspire action. Recently, I've become deeply curious about how AI is reshaping the GTM landscape -- from how we uncover market insights to how we personalize customer journeys. I'm actively exploring how these emerging technologies can amplify strategic positioning and create even more differentiated market narratives while staying grounded in human-centered storytelling. --- On a personal note, I'm a big personality framework nerd. I love everything from Enneagram to CliftonStrengths to Big Five and more. I believe the more we can harness our unique strengths, the more efficient we can be towards accomplishing our goals and working together as a team.
Stackforce AI infers this person is a SaaS Product Marketing expert with a strong focus on growth strategies and market positioning.
Experience: 11 yrs 3 mos
Career Highlights
- Transformed sales-led motion into hybrid GTM approach.
- Architected product-led growth strategy increasing retention by 3.4x.
- Launched products achieving 186% adoption growth within 8 weeks.
Work Experience
theSkimm
Interim, Head of Product & Brand Marketing (1 yr 3 mos)
Stensul
Interim, Director of Product Marketing (1 yr)
GTM Happy
Fractional Product Marketer & GTM Consultant (3 yrs 2 mos)
Vanta
PLG Product Marketing Lead (5 mos)
ClickUp
Platform Product Marketing Lead (11 mos)
Founding Product Marketer (11 mos)
Bred Ventures Inc.
Head of Product Marketing and User Engagement (4 yrs)
Buyerly
Senior Product Marketing Manager (1 yr)
City of Thousand Oaks
Product Marketing Manager (1 yr)
Florence University of the Arts
Event Producer (1 yr)
Evolutionary Media Group (EMG PR)
Event & Marketing Associate (1 yr)
DreamWorks Animation
Product Research Assistant (1 yr)
Education
Bachelor of Arts (B.A.) at California Lutheran University
Continued Education at Stanford University
Special Events Management focus at Florence University of the Arts
Marketing at General Assembly