Ashleah Wilson
North Vancouver
Summary
High-velocity Growth Executive with 25+ years of experience architecting B2B and SaaS platforms from inception to over $125 million in annual recurring revenue. A specialist in narrative simplification, bridging the gap between complex technical engineering and market-ready value propositions. Recognized as a pioneer in AI Acceleration, operationalizing generative technology to drive enterprise efficiency and category dominance. Cumulative P&L contribution exceeds $1 billion.
Overview
19
19
years of professional experience
Work History
Partner & AI Strategist
THE NOW OF WORK
01.2025 - Current
- AI Transformation: Architecting "Post-Search" GTM strategies for enterprise clients; ranked in the Top 1% of ChatGPT power users (2025).
- Executive Advisory: Synthesizing AI complexities for C-suite leaders in Finance and Tech.
- Keynote Leadership: Delivering simplified AI roadmaps to global audiences of 800+, defining the future of AI-augmented B2B marketing.
Vice President of Marketing
JANE APP
01.2019 - 01.2024
- Revenue Velocity: Engineered the GTM engine that scaled ARR from $5M to $125M in 48 months, resulting in Jane App becoming a top-tier North American growth leader.
- Complexity Management: Unified diverse product features into a singular Practice Management narrative, specifically tailored to high-LTV B2B healthcare enterprises.
- Performance Excellence: Maintained 104% NRR by shifting marketing focus toward high-retention "best-fit" segments.
VP of Marketing & Client Success
CHIMP.NET (CHARITABLE IMPACT)
01.2014 - 01.2018
- Marketplace Scaling: Accelerated transaction volume from $8M to $250M by simplifying complex financial giving instruments for corporate and individual donors.
- Go-To-Market: Built an integrated Marketing and Client Success function to reduce churn and maximize lifetime donor value (LTV).
Managing Director, Marketing
MOVE, INC. (REALTOR.COM & TOP PRODUCER)
01.2007 - 01.2012
- Enterprise Oversight: Managed a cross-functional team of 13 and a portfolio generating $220M in annual revenue.
- Sales Transformation: Built the "Sales Translation" layer that enabled 150+ reps to articulate complex SaaS value, leading to the 3 highest revenue days in the firm's 30-year history.
Education
Post-Graduate Diploma - Business Administration
Simon Fraser University
Bachelor of Arts - Political Science
University of British Columbia
Skills
- AI strategy
- GTM strategy
- Operational savings
- Executive advisory
- Data analysis
- Scalability planning
Websites
Accomplishments
- $1B+ Career Revenue Impact: Strategic lead for high-growth programs across SaaS, Media, and Real Estate.
- Global Media Reach: Secured international coverage for Capilano Suspension Bridge, reaching 76M+ viewers (MTV, China Park Avenue, Europe InCite).
- B2B Content Engine: Developed a content ecosystem that generated 350,000+ high-intent leads and inbound calls.
Board Leadership And Education
- Board Member, Golden Buffalo Development Inc., Strategic oversight of a $300M project portfolio
- Graduate Diploma in Business Administration, Simon Fraser University
- Bachelor of Arts (Political Science), University of British Columbia
Core Executive Competencies
- B2B Growth Architecture: Multi-channel Go-To-Market (GTM) Strategy, Enterprise Sales Cycle Optimization, Category Creation.
- Strategic Simplification: Distilling complex technical stacks into high-conversion narrative frameworks for business audiences.
- Revenue Operations: Net Revenue Retention (NRR) at 104%, Unit Economics (LTV/CAC), AI-Driven Growth Workflows.
Timeline
Partner & AI Strategist
THE NOW OF WORK
01.2025 - Current
Vice President of Marketing
JANE APP
01.2019 - 01.2024
VP of Marketing & Client Success
CHIMP.NET (CHARITABLE IMPACT)
01.2014 - 01.2018
Managing Director, Marketing
MOVE, INC. (REALTOR.COM & TOP PRODUCER)
01.2007 - 01.2012
Post-Graduate Diploma - Business Administration
Simon Fraser University
Bachelor of Arts - Political Science
University of British Columbia