I'm a data-driven digital strategist and growth marketing leader with 20+ years of experience helping organizations overcome revenue stagnation, low visibility, and operational inefficiency. I'm also known for blending strategy, technology, and execution to deliver measurable growth, with a track record of scaling teams, leading P&L, and applying AI-powered workflows and Generative Engine Optimization (GEO) to stay competitive in evolving buyer journeys.

Jessica Hennessey

I'm a data-driven digital strategist and growth marketing leader with 20+ years of experience helping organizations overcome revenue stagnation, low visibility, and operational inefficiency. I'm also known for blending strategy, technology, and execution to deliver measurable growth, with a track record of scaling teams, leading P&L, and applying AI-powered workflows and Generative Engine Optimization (GEO) to stay competitive in evolving buyer journeys.

Available to hire

I’m a data-driven digital strategist and growth marketing leader with 20+ years of experience helping organizations overcome revenue stagnation, low visibility, and operational inefficiency.
I’m also known for blending strategy, technology, and execution to deliver measurable growth, with a track record of scaling teams, leading P&L, and applying AI-powered workflows and Generative Engine Optimization (GEO) to stay competitive in evolving buyer journeys.

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Language

English
Fluent

Work Experience

CEO | Head of Digital Growth & Strategy at 3 Media Web
January 1, 2025 - October 8, 2025
Set strategic vision, managed full P&L, and scaled operations for a high-performance digital agency. Drove 28% annual revenue growth and increased net profit by 90%. Integrated AI and GEO strategies into workflows, accelerating delivery and improving client visibility.
Vice President of Growth & Strategy at 3 Media Web
January 1, 2021 - October 8, 2025
Directed agency-wide growth planning, digital strategy, and business development. Introduced data-driven frameworks for delivery, improving efficiency and client outcomes.
Director of Digital Strategy at 3 Media Web
January 1, 2020 - October 8, 2025
Led SEO, CRO, UX, and paid media strategies for B2B/B2C clients. Lifted conversions by 48% while cutting ad spend 56%, delivering 9:1 ROI.
Lead Digital Strategist at Wakefly
January 1, 2019 - October 8, 2025
Drove 100% growth in lead generation through demand generation strategies. Developed SEO strategies for 60+ global websites and achieved 12% YoY revenue growth in eCommerce.
Sr. Mgr, Online Marketing at Earthwatch Institute
January 1, 2017 - October 8, 2025
Increased monthly leads from 200 to 800 within 100 days. Reduced PPC spend by 90% while improving CTRs and conversions.
Manager, Online Marketing at Ipswitch
January 1, 2014 - October 8, 2025
Increased qualified inquiries by 500% through web optimization. Delivered 25% higher email campaign CTR via testing and optimization.
Manager, Web Strategy at Rapid7
January 1, 2013 - October 8, 2025
Guided web strategy during 800% company growth. Project-led a rebrand covering 350+ pages and 800+ assets.
CEO | Head of Digital Growth & Strategy at 3 Media Web
January 1, 2025 - October 8, 2025
Set strategic vision, managed full P&L, and scaled operations for a high-performance digital agency. Drove 28% annual revenue growth and increased net profit by 90%. Integrated AI and GEO strategies into workflows, accelerating delivery and improving client visibility. Achieved a 49% increase in net profit margin through scalable delivery and operational efficiency.
Vice President of Growth & Strategy at 3 Media Web
January 1, 2021 - October 8, 2025
Directed agency-wide growth planning, digital strategy, and business development. Introduced data-driven frameworks for delivery, improving efficiency and client outcomes.
Director of Digital Strategy at 3 Media Web
January 1, 2020 - October 8, 2025
Led SEO, CRO, UX, and paid media strategies for B2B/B2C clients. Lifted conversions by 48% while cutting ad spend 56%, delivering 9:1 ROI.
Lead Digital Strategist at Wakefly
January 1, 2019 - October 8, 2025
Drove 100% growth in lead generation through demand generation strategies. Developed SEO strategies for 60+ global websites and achieved 12% YoY revenue growth in eCommerce.
Sr. Mgr, Online Marketing at Earthwatch Institute
January 1, 2017 - October 8, 2025
Increased monthly leads from 200 to 800 within 100 days. Reduced PPC spend by 90% while improving CTRs and conversions.
Manager, Online Marketing at Ipswitch
January 1, 2014 - October 8, 2025
Increased qualified inquiries by 500% through web optimization. Delivered 25% higher email campaign CTR via testing and optimization.
Manager, Web Strategy at Rapid7
January 1, 2013 - October 8, 2025
Guided web strategy during 800% company growth. Project led a rebrand covering 350+ pages and 800+ assets.
Head of Digital Growth & Strategy at 3 Media Web
December 31, 2025 - October 8, 2025
Set strategic vision, managed full P&L, and scaled operations for a high-performance digital agency. Drove 28% annual revenue growth and increased net profit by 90%. Integrated AI and GEO strategies into workflows, accelerating delivery and improving client visibility. Achieved 49% increase in net profit margin through scalable delivery and operational efficiency.
Vice President of Growth & Strategy at 3 Media Web
December 31, 2021 - October 8, 2025
Directed agency-wide growth planning, digital strategy, and business development. Introduced data-driven frameworks for delivery, improving efficiency and client outcomes.
Director of Digital Strategy at 3 Media Web
December 31, 2020 - October 8, 2025
Led SEO, CRO, UX, and paid media strategies for B2B/B2C clients. Lifted conversions by 48% while cutting ad spend 56%, delivering 9:1 ROI.
Lead Digital Strategist at Wakefly
December 31, 2019 - October 8, 2025
Drove 100% growth in lead generation through demand generation strategies. Developed SEO strategies for 60+ global websites and achieved 12% YoY revenue growth in eCommerce.
Sr. Mgr, Online Marketing at Earthwatch Institute
December 31, 2017 - October 8, 2025
Increased monthly leads from 200 to 800 within 100 days. Reduced PPC spend by 90% while improving CTRs and conversions.
Manager, Online Marketing at Ipswitch
December 31, 2014 - October 8, 2025
Increased qualified inquiries by 500% through web optimization. Delivered 25% higher email campaign CTR via testing and optimization.
Manager, Web Strategy at Rapid7
December 31, 2013 - October 8, 2025
Guided web strategy during 800% company growth. Project led a rebrand covering 350+ pages and 800+ assets.
Head of Digital Growth & Strategy at 3 Media Web
January 1, 2025 - October 8, 2025
Set strategic vision, managed full P&L, and scaled operations for a high-performance digital agency. Achieved 28% annual revenue growth and a 90% net profit increase by optimizing positioning, scalable delivery, and operational efficiency. Integrated AI and GEO strategies to accelerate delivery and client visibility.
Vice President of Growth & Strategy at 3 Media Web
January 1, 2021 - October 8, 2025
Directed agency-wide growth planning, digital strategy, and business development. Introduced data-driven delivery frameworks to improve efficiency and client outcomes.
Director of Digital Strategy at 3 Media Web
January 1, 2020 - October 8, 2025
Led SEO, CRO, UX, and paid media strategies for B2B/B2C clients. Increased conversions by 48% while reducing ad spend by 56%, delivering 9:1 ROI.
Lead Digital Strategist at Wakefly
January 1, 2019 - October 8, 2025
Drove 100% growth in lead generation through demand generation strategies. Developed SEO strategies for 60+ global websites and achieved 12% YoY revenue growth in eCommerce.
Sr. Mgr, Online Marketing at Earthwatch Institute
January 1, 2017 - October 8, 2025
Increased monthly leads from 200 to 800 within 100 days. Reduced PPC spend by 90% while improving CTRs and conversions.
Manager, Online Marketing at Ipswitch
January 1, 2014 - October 8, 2025
Increased qualified inquiries by 500% through web optimization. Delivered 25% higher email campaign CTR via testing and optimization.
Manager, Web Strategy at Rapid7
January 1, 2013 - October 8, 2025
Guided web strategy during 800% company growth. Project-led a rebrand covering 350+ pages and 800+ assets.

Education

Certificate in Web Design at Boston University
January 11, 2030 - October 8, 2025
BS in Finance at Bentley University
January 11, 2030 - October 8, 2025
Certificate, Web Design at Boston University
January 11, 2030 - October 8, 2025
BS in Finance at Bentley University
January 11, 2030 - October 8, 2025
Certificate, Web Design at Boston University
January 11, 2030 - October 8, 2025
BS in Finance at Bentley University
January 11, 2030 - October 8, 2025
Certificate, Web Design at Boston University
January 11, 2030 - October 8, 2025
BS in Finance, Magna Cum Laude at Bentley University
January 11, 2030 - October 8, 2025

Qualifications

Certificate in Web Design
January 11, 2030 - October 8, 2025
Certificate, Web Design
January 11, 2030 - October 8, 2025
BS in Finance
January 11, 2030 - October 8, 2025
Massachusetts CEO of the Year: Web Design & Development
January 1, 2023 - October 8, 2025
Massachusetts CEO of the Year: Digital Marketing
January 1, 2024 - October 8, 2025
Forbes Communications Council Member
January 1, 2018 - October 8, 2025
Women Applying AI, Founding Member
January 1, 2025 - October 8, 2025

Industry Experience

Media & Entertainment, Professional Services, Software & Internet, Education, Other, Retail