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Jasper Cannon MSMKT, CSSGB, CSM

Managing Partner

Dallas-Fort Worth Metroplex · 1 connection

Chesterton Hills

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About

Reach out to me! => 📧: jasper@chestertonhills.com | I lead high-impact strategy and special projects for multibillion-dollar enterprises and startups. Named a Top Strategy & Management Consulting Voice by LinkedIn, I’ve helped leadership teams navigate complex challenges, drive transformation, and accelerate growth. From building new departments to enterprise-wide initiatives like international expansion, I bring a disciplined, execution-focused approach that moves work from idea to impact. Recognized not only by clients but by the broader business community, I’m also invited to speak internationally on strategy, leadership, and transformation. ✅ Launched products and services generating over $120M in revenue and acquiring 3M new customers across markets ✅ Averted $200M in losses for clients across industries ✅ Steered $700M FY marketing investments, aligning business goals with market realities and customer demands ✅ Negotiated over $1.2 Billion in strategic partnerships across clients ✅ Executed 20 international and 10 domestic organization expansions ✅ Built new analytics departments that recovered $50M+ in 6 months ✅ Advised and coached founders and executives at over 100 start

Experience

Managing PartnerChesterton Hills
Jul 2025
Venture PartnerMedStartr Ventures
Jan 2025
Vice President, Strategic Partnerships & InitiativesMedStartr Ventures
Jan 2025
Senior Venture Capital AssociateMedStartr Ventures
Jan 2022 to Jan 2025
Venture Capital AssociateMedStartr Ventures
Jan 2020 to Jan 2022
Technology & Healthcare Council MemberSpringboard Enterprises
Jun 2025
Strategic Startup Advisor (FRACTIONAL)Springboard Enterprises
Apr 2025
Venture Capitalist in Residence (FRACTIONAL)LvlUp Ventures
Jun 2026
Deals (FRACTIONAL)SWAN Impact Network
Aug 2026
OpenAI Forum Member *CANNOT REFER YOU FOR JOBS OR PROGRAMS*OpenAI
Nov 2024
Deal Partner (FRACTIONAL)Ganas Ventures
Jan 2026
Founding Board MemberStealth Startup (AI)
Jun 2026
Strategic Startup Advisor (FRACTIONAL)MedTech Innovator
Apr 2026
Admissions Ambassador (FRACTIONAL)The Johns Hopkins University
Oct 2025
Strategic Startup Advisor (FRACTIONAL)The Johns Hopkins University
Jul 2024
Strategic Startup Advisor (FRACTIONAL)NYU Stern School of Business
Apr 2026
Strategic Startup Advisor (FRACTIONAL)Emory University
May 2025
Strategic Startup Advisor (FRACTIONAL)The University of Texas at Dallas
Oct 2024
Strategic Startup Advisor (FRACTIONAL)The DEC Network
Aug 2023
Strategic Startup Advisor (FRACTIONAL)Happy Valley LaunchBox powered by PNC Bank
Jul 2019
Strategic Startup Advisor (FRACTIONAL)The Cannon Community
Aug 2024
Strategic Startup & Small Business Advisor (FRACTIONAL)EQALL Business Solutions
May 2024
Author, Career Guide (FRACTIONAL)Indeed
Jul 2024
Strategic Startup Advisor (FRACTIONAL)Sky's the Limit
Jul 2024 to Jul 2026
Strategic AdvisorStealth Mode AI Fintech Startup
Aug 2025 to Dec 2025

Education

The Johns Hopkins University
Master’s Degree Marketing/Marketing Management
The Johns Hopkins University - Carey Business School
Master's Degree Marketing/Marketing Management
Penn State University
Bachelor of Science - BS BUSINESS, MANAGEMENT, MARKETING, AND RELATED SUPPORT SERVICES
IES Abroad
Study Abroad Business Administration and Management, General