Digital Strategy & AI Executive

Helping teams build
what comes next.

I've spent the last decade helping B2B SaaS companies like JFrog, Okta, and DocuSign turn their web platforms into real growth engines — and I love the work.

I've had the privilege of working with

JFrogOktaDocuSignMindbody

About Me

Jennifer Chase, Digital Strategy & AI Executive

I started my career as a Mechanical Engineer, which probably isn't the most obvious path into digital strategy. But that's kind of the point — I think differently about these problems because I came at them from a different angle. Over the past decade, I've had the chance to lead web transformation at DocuSign, Okta, and JFrog, and every one of those experiences taught me something new.

What I've gotten good at is sitting between engineering, product, and marketing and helping those teams actually work together. The results have been meaningful — tripling web traffic, deploying AI solutions that moved the pipeline needle by 150% — but honestly, the part I care most about is building teams that trust each other and do great work.

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.

Results I'm Proud Of

0%

Pipeline Increase

AI chat solution I sourced at JFrog

0%

YoY Growth

Digital business we built at DocuSign

0%

Faster Production

AI-driven ops I led at JFrog

0%

Cost Reduction

Chatbot project I led at Okta

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

Skills & Certifications

Strategic

  • Web Strategy & Roadmap
  • Customer Journey Optimization
  • Full-Funnel Conversion
  • AI Integration (SEO/AEO)
  • Personalization

Technical

  • CMS (HubSpot, Contentful, WordPress, Drupal)
  • Web Analytics
  • A/B Testing
  • Digital Transformation
  • AI for Marketers

Leadership

  • Cross-functional Team Management
  • Global Team Building
  • Stakeholder Collaboration
  • Vendor & Agency Management
  • Mentorship

Certifications

  • Certified Scrum Master (CSM)
  • Business Communication Certificate — Cornell University

Education

BS Mechanical Engineering — Santa Clara University

Kind Words

I'm grateful to have worked with some incredible people. Here's what a few of them have said.

Jennifer was my manager for a number of years at DocuSign. Not only was she an incredible mentor, but always went above and beyond for her team, encouraging us to challenge ourselves, helping our career growth and most importantly, just being a fantastic inspiration for me. No matter what, she always made me feel part of the team, asked for my opinion on matters and was transparent with me.

Dervilla O’ Reilly

Lead Web Manager, Localization & International Operations @ DocuSign

Jennifer is responsible for DocuSign’s entire marketing website and has done such a wonderful job of managing the work. She is a doer and gets it done no matter what. I have enjoyed working with her and I know that all our cross functional teams think very highly of her. Her direct reports are also very fond of her and believe in her leadership and communication skills. She is an expert in third party integration, content management systems, localization, SEO, accessibility and more.

Talieh Rohani

Product Management Lead @ Airbnb | Marketplace Strategy, Growth Strategy

Speaking & Media

I enjoy sharing what I've learned. More to come here soon.

Conference Talk

Details coming soon

Podcast Feature

Details coming soon

Published Article

Details coming soon

Interested in having me speak at your event? Get in touch.

Get In Touch

Whether you have a question, an idea, or just want to say hello — I'd love to hear from you.