Digital Strategy & AI Executive

Helping teams
grow what comes next.

For the last decade, I've been in the tech weeds with teams at JFrog, Okta, and DocuSign, figuring out how to translate strategy to launch. Now with AI, you can build almost anything, but I'm here to help you figure out what's worth shipping.

Jennifer Chase at a sunlit desk with a laptop, notebook, and coffee mug

Career experience

Each role taught me something different. Here's the path that got me here.

JFrog

Senior Director, Web Strategy

April 2024 – Present

  • Inherited a distributed team and rebuilt it into a cohesive, cross-functional group spanning SEO/AEO, content, design, analytics, and engineering
  • Introduced AI across our web operations — from content production to personalization — and cut production cycles by 30%
  • Found and deployed an AI chat solution that ended up increasing sales pipeline by 150%, which honestly exceeded my expectations

Okta

Senior Manager, Digital Strategy

June 2022 – April 2024

  • Led the team behind the Okta.com redesign — a project that taught me a lot about navigating large-scale digital transformation
  • Built an AI-driven chatbot that reduced support costs by 22% and genuinely improved the user experience
  • Grew digital engagement 30% quarter over quarter by focusing on self-service and making things easier for the end user

DocuSign

Senior Manager, Marketing Websites

November 2019 – May 2022

  • Took on a full website redesign and replatforming — the kind of project that either makes you or breaks you
  • Over two years, our team tripled web traffic and grew the digital business by 250% YoY. It was a lot of late nights, but the results spoke for themselves
  • Built a global A/B testing and personalization program that lifted landing page conversions by 18%

Mindbody

Manager, Web

March 2018 – October 2019

  • Managed a complex site migration during a global rebrand and M&A integration — a crash course in stakeholder management
  • Built and led a cross-functional team of 15+ specialists who I'm still proud to have worked with
  • Launched a CRO program that improved monthly KPIs by 25%

eCommerce Ventures Inc

Co-Founder & Web Product Manager

Prior to 2018

  • Co-founded a digital commerce company and built the product from scratch — the experience that taught me what it really takes to ship
  • Designed the eCommerce web experience from the ground up, learning customer acquisition by doing it every day
  • Recruited and led a small but mighty team across product, engineering, and marketing

About me

Jennifer Chase, Digital Strategy & AI Executive

I started my career as a Mechanical Engineer, which isn't the most obvious path into marketing and digital strategy. Engineering taught me how to think and how to get from a messy problem to something real. Now I'm drawn to the fast-paced world of digital and AI, where products ship in minutes, not years. And I've never looked back.

Over the past decade I've worked at enterprise-level tech companies like JFrog, Okta, and DocuSign, sitting between engineering, product, and strategy, doing the kind of digital work that has to hold up technically and still drive pipeline for the business. The part that keeps drawing me toward these transformations is the hard part: building teams where everyone can come together to deliver something people will love. We also happened to increase pipeline by 150% while we did it. That's the best part.

AI-First Strategy

I started integrating AI into web strategy before most teams were thinking about it. Not because I predicted the future — I just kept following the data.

Data-Driven Growth

I’m a firm believer that good strategy starts with good data. I measure what matters and let the numbers guide the decisions.

Cross-Functional Leadership

I’ve built global teams of 15+ across engineering, design, content, and analytics. The best work happens when people feel heard.

Pull up a chair.

Think of this less as “talking to an expert” and more like reaching out to a friend who's been knee-deep in web strategy and AI long enough to have strong opinions — but not so long that she's forgotten what it's like to still be figuring things out. Whether you have a question, a half-baked idea, or just want a second opinion, I'd genuinely love to hear from you.