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October 27, 2025
Episode 88: Why an AI Critic Joined a Tech Company

Why an AI Critic Joined a Tech Company

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About the Episode

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About the Episode:

In this episode of Higher Ed Pulse, host Mallory Willsea sits down with Joel Goodman, former founder of Bravery Media and now the new VP of Growth Strategy at Squiz. The conversation dives into Joel’s bold career transition from agency life to a global EdTech company, his evolving views on AI in higher education, and the future of digital strategy in a consolidating industry. With nearly two decades of experience in higher ed web strategy, Joel offers a critical — and refreshing — perspective on what's next for institutions looking to actually move the needle.

Key Takeaways

  • AI in higher education isn’t failing because of bad tech — it’s failing because of poor implementation, broken cultures, and lack of process.
  • Joel Goodman’s move from agency owner to tech company VP reflects a broader shift in how digital strategy leaders are rethinking their roles.
  • Web strategy in higher education needs more than chatbots and templates — it needs personalization, creativity, and cultural innovation.
  • Institutional websites powered by AI must prioritize accuracy and context, not just flashy UX.
  • Consolidation in the higher ed vendor space could threaten innovation unless new voices and smaller players are protected.
  • Joel remains optimistic thanks to authentic, strategic conversations happening at conferences like Digital Collegium and EDUCAUSE.

Why Did Joel Goodman Leave Bravery Media?

After running Bravery Media for nearly a decade, Joel Goodman decided to make a career leap into a role with Squiz, a global tech company that specializes in digital experience platforms for higher education. Why the change? Joel was candid about the pressures agency owners face in a shifting market — declining funding, rising institutional skepticism, and a consolidating vendor landscape. Rather than push against the tide, he saw an opportunity to drive deeper change from within a tech company, especially one that aligns with his values around innovation and accountability.

For Joel, the move wasn’t just about job title or financial upside. It was about influence — being in the room where product development decisions are made and ensuring that technology actually serves the real needs of institutions. In this episode, he shares how stepping into a VP role enables him to zoom out, apply his years of digital strategy expertise at scale, and make higher education better from the inside out.

Interestingly, Joel joins the ranks of several higher ed leaders who are choosing to swap traditional leadership titles for roles that give them more room to innovate. Mallory draws a great parallel to a past episode featuring Lindsay Nyquist, who stepped away from a CMO role to become a strategist. For professionals wondering what career growth really looks like in 2025 and beyond, this episode offers some compelling food for thought.

How Does an AI Skeptic Fit Into an EdTech Company?

If you’ve followed Joel on social media or read his writing, you know he’s not shy about challenging AI hype — especially in higher education. So how does someone who openly critiques AI end up working for a company that’s actively investing in AI tools? Joel answers this head-on: context matters.

Squiz’s approach to AI in higher education is one of cautious innovation. Their tools don’t pull data from Reddit or the open web — they use institutionally approved content and layer in validation agents to reduce hallucinations. This, Joel explains, is AI that’s not just cool — it’s useful. It reflects a strategic, outcomes-driven approach to digital transformation that aligns with Joel’s long-held belief: technology should empower users, not distract them.

Joel also critiques the current obsession with generative AI as “low-hanging fruit.” A chatbot isn’t innovative just because it can talk. Instead, he sees real value in using AI to identify patterns in data and drive smarter decision-making. He cautions that too many vendors are chasing AI for the sake of AI, without thinking critically about long-term ROI, which is why thoughtful dissent within tech companies is more valuable than ever.

What’s Wrong With Digital Strategy in Higher Ed — and How Can It Be Fixed?

Joel has been in the trenches of web strategy in higher education for two decades — so when he says things are starting to feel “homogenized,” it’s worth listening. His concern? Institutions are outsourcing too much of their digital thinking to the same handful of vendors, leading to cookie-cutter websites, generic chatbots, and strategies that all start to look the same. In a world where brand should be a differentiator, higher ed is at risk of becoming indistinguishable.

This consolidation isn’t just aesthetic — it impacts student experience, engagement, and even enrollment pipelines. Joel and Mallory discuss the recent Ankura/RNL acquisition as an example of how fewer players controlling more of the stack could lead to less innovation, not more. Mallory notes that while institutional leaders might not be voicing their concerns publicly, the quiet unease is real.

But Joel offers a path forward: empower smaller vendors, encourage institutional risk-taking, and challenge conventional UX patterns. Web strategy isn’t just about flashy interfaces — it’s about how we use digital tools to actually meet student needs. The industry doesn’t need another chatbot. It needs better questions, stronger leadership, and more courageous experimentation.

What Gives Joel Hope About the Future of Higher Ed Tech?

Despite his critiques, Joel isn’t pessimistic. In fact, he ends the episode on a hopeful note. What gives him optimism? Conversations. The real ones — happening at events like Digital Collegium, EDUCAUSE, and soon AMA. He’s encouraged by the level of thoughtfulness he’s hearing from peers, vendors, and campus leaders alike. It’s not just about selling software anymore. It’s about reducing burnout, simplifying tech stacks, and designing tools that actually help people do their jobs better.

He believes that we’re moving past the AI buzzword phase and into an era of more thoughtful deployment. Joel sees smart people asking better questions, and that gives him confidence that higher education is starting to find its footing again.

And maybe most importantly? He believes in the power of bold, small teams to drive big change. Whether you’re a marketer, a strategist, or a VP, your voice matters — especially when you’re willing to question the status quo and build something better.

Connect With Our Host:

Mallory Willsea
https://www.linkedin.com/in/mallorywillsea/
https://twitter.com/mallorywillsea

About The Enrollify Podcast Network: The Higher Ed Pulse is a part of the Enrollify Podcast Network. If you like this podcast, chances are you’ll like other Enrollify shows too!  

Some of our favorites include Generation AI and Confessions of a Higher Education Social Media Manager.

Enrollify is produced by Element451 —  the next-generation AI student engagement platform helping institutions create meaningful and personalized interactions with students. Learn more at element451.com.

People in this episode

Host

Mallory Willsea is a strategist and consultant working at the intersection of higher education.

Interviewee

Joel Goodman

Joel Goodman is now the VP of Growth Strategy for Squiz.

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