I help businesses improve the way their websites attract, engage, and convert the right customers. With 25+ years of experience in web strategy, SEO, UX, CRO, analytics, and digital growth, I work with organizations to identify what is holding their website back and create a clear plan to fix it. My work often includes website audits, AI visibility and GEO strategy, content and messaging improvements, user experience recommendations, conversion optimization, analytics review, and digital growth planning. I bring a mix of strategic thinking and practical execution, helping teams move from “we know something isn’t working” to a focused, actionable roadmap.

Jessica M. Hennessey

I help businesses improve the way their websites attract, engage, and convert the right customers. With 25+ years of experience in web strategy, SEO, UX, CRO, analytics, and digital growth, I work with organizations to identify what is holding their website back and create a clear plan to fix it. My work often includes website audits, AI visibility and GEO strategy, content and messaging improvements, user experience recommendations, conversion optimization, analytics review, and digital growth planning. I bring a mix of strategic thinking and practical execution, helping teams move from “we know something isn’t working” to a focused, actionable roadmap.

Available to hire

I help businesses improve the way their websites attract, engage, and convert the right customers. With 25+ years of experience in web strategy, SEO, UX, CRO, analytics, and digital growth, I work with organizations to identify what is holding their website back and create a clear plan to fix it.

My work often includes website audits, AI visibility and GEO strategy, content and messaging improvements, user experience recommendations, conversion optimization, analytics review, and digital growth planning. I bring a mix of strategic thinking and practical execution, helping teams move from “we know something isn’t working” to a focused, actionable roadmap.

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Language

English
Fluent

Work Experience

CEO | Head of Digital Growth & Strategy at 3 Media Web
December 31, 2024 - September 12, 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.

Education

Bachelor of Science in Finance at Bentley University
January 11, 2030 - June 9, 2026
Certificate in Web Design & Development at Boston University
January 11, 2030 - June 9, 2026

Qualifications

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, Non-Profit Organization