Will Eagle of Lyft: How AI Is Disrupting Our Industry, and What We Can Do About It

Artificial Intelligence is no longer the future; it is the present. It’s reshaping landscapes, altering industries, and transforming the way we live and work. With its rapid advancement, AI is causing disruption — for better or worse — in every field imaginable. While it promises efficiency and growth, it also brings challenges and uncertainties that professionals and businesses must navigate. What can one do to pivot if AI is disrupting their industry? As part of this series, we had the pleasure of interviewing Will Eagle.

Will Eagle’s career began with a 28.8 bps dial-up modem his father gave him in 1995, which sparked a fascination with the internet that led him to teach himself HTML and build early websites. That curiosity launched him into a career at the intersection of technology and creativity, starting as a web developer at Virgin.com in London and moving into digital marketing at Virgin Mobile in Toronto. He went on to work in entertainment with MTV and MuchMusic, spent time on the agency side at Leo Burnett as Director of Digital Planning for TD Canada Trust, and later joined Google, where he served as Chief Facilitator at the GooglePlex in Mountain View, leading strategy sessions with top C-Suite clients. Google’s Los Angeles office became his home, and he has since held roles at Pinterest, Collab, and now Lyft. Will is also a published author with several books available on Amazon focused on marketing, digital platforms, and audience growth.

Thank you so much for joining us in this interview series! Before we dive into our discussion our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?

My career really started with a modem. In 1995 my father gave me a 28.8 bps dial up modem. I was fascinated by the idea that a computer in our house could connect to the wider world. Very quickly I started teaching myself HTML and building early websites. At the time the internet felt like a frontier. There were no rules and no playbook, just people experimenting with what this new medium could become.

That curiosity led to my first professional role at Virgin.com in London as a web developer. From there my career evolved alongside the internet itself. I moved into digital marketing at Virgin Mobile in Toronto during the early days of online customer acquisition, worked in entertainment with MTV and MuchMusic, spent time on the agency side at Leo Burnett, and later joined Google. Google eventually relocated me to Los Angeles, which became home. Since then I’ve spent time with Pinterest, Collab, and now Lyft.

What has always driven me is the intersection between technology and creativity. I’ve always loved both sides of the equation, the technical layer that makes something possible and the creative layer that makes people care. Early in my career that meant writing code and designing websites. Over time it evolved into thinking about how brands show up in people’s lives in ways that feel natural rather than intrusive.

The shift from marketer to strategist really happened when I joined Leo Burnett as Director of Digital Planning for TD Canada Trust, one of Canada’s largest advertisers. That role forced me to zoom out and think less about channels and tactics and more about human behavior, culture, and business outcomes.

Today at Lyft I get to apply those lessons in a unique environment. On average we have about 24 minutes with a rider. That’s an incredibly rich moment. Someone is moving through the world, often heading to something meaningful in their day. Lyft is a purpose driven, customer-obsessed company, and we think deeply about how brands can show up during that time in ways that are helpful, entertaining, or inspiring rather than interruptive.

For me, the through line from that first modem to today is the same question: how can technology and creativity come together to create experiences that genuinely add something to people’s lives?

What do you think makes your company stand out? Can you share a story?

Lyft stands out because we are truly customer obsessed. That might sound like a simple phrase, but inside the company it’s a real operating principle. We think deeply about the rider experience and the moments when someone is moving through their day.

On average we have about 24 minutes with a rider. That’s not just a transportation moment, it’s a life moment. Someone might be heading to dinner, a concert, the airport, or a big meeting. Because of that, we think carefully about how brands can show up in ways that are additive rather than interruptive.

One example was our campaign around the release of Wicked: For Good. We created a first of its kind experience where riders saw a magical flash of the two protagonists inside the Lyft app, which then transitioned into Lyft Ads’ proprietary Map Splash format and custom map vehicles themed to the film. Instead of a traditional ad, it felt like the story world of the movie briefly entered the rider’s journey.

Another example was a campaign we created with Sephora called “Delivered to Beauty.” The insight was simple but powerful: beauty lovers don’t actually want to wait two days for a box to show up on their porch. They want to experience beauty. They want to go to the store, test products, and get advice from people who truly know beauty.

So we partnered with Sephora to “deliver” people to Sephora stores using Lyft Ads. The campaign reframed Lyft not just as transportation, but as a bridge between digital inspiration and real world experience.

Those types of ideas are possible because Lyft sits at the intersection of technology, culture, and the real world. When you combine that with a rider first philosophy, it opens up a lot of creative possibilities.

At Lyft we say we don’t just move people from A to B. We help connect people to the moments that matter in their lives.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

Three traits that have shaped my career are curiosity, collaboration, and tenacity.

The first is endless curiosity about how people and the world work. I’ve always been fascinated by human behavior and emerging technology. That curiosity started early when I was teaching myself HTML and experimenting with the early internet. Over time it evolved into a broader question that still guides my work today: how do technology, culture, and human behavior intersect? That mindset has been incredibly valuable in marketing and strategy because the best ideas often come from connecting dots that don’t initially seem related.

The second trait is a deep love of collaboration. I genuinely enjoy working with other people and building ideas together. Some of the best work I’ve been part of happened in rooms where different disciplines came together, technologists, creatives, strategists, media planners, and clients all shaping something together. At Google, for example, I spent years facilitating workshops with brands and agencies to help them rethink how they approached YouTube and digital storytelling. Those sessions were often less about presenting answers and more about creating the conditions where great ideas could emerge from the group.

The third is tenacity. The marketing and technology industries move incredibly fast and things rarely work perfectly the first time. Over the course of my career I’ve seen platforms rise and fall, technologies evolve, and entire business models change. The ability to stay persistent, keep learning, and keep moving forward has been critical.

Taken together, curiosity keeps me exploring, collaboration brings the best ideas to life, and tenacity helps see those ideas through.

Let’s now move to the main point of our discussion about AI. Can you explain how AI is disrupting your industry? Is this disruption hurting or helping your bottom line?

AI is changing how we work, at nearly every step of the advertising journey.

The obvious place people see it is in creative asset production. AI can generate images, video, copy, and variations of creative work at a speed that would have been unimaginable even a few years ago. But the disruption goes far beyond that. We’re also seeing AI transform how strategists mine insights, conduct customer research, generate ideas, and even build pitch decks.

In many ways, the biggest shift is not just production efficiency, but cognitive amplification. AI can help teams explore more possibilities, pressure test thinking, and reach stronger ideas faster.

Personally, I view this shift as overwhelmingly positive. AI has become one of my strongest ideation partners. It pushes me to think more broadly and explore directions I might not have considered on my own. But it also reinforces something important: humans are still the editors, curators, and experience designers. AI can generate options, but judgment, taste, and context remain human strengths.

One skill that I believe will become essential is prompting. Prompting is not just about asking a tool for something. It’s about learning how to frame problems, guide systems toward useful outputs, and refine ideas through iteration.

For Lyft Ads, AI ultimately means we can deliver more value to both brands and riders. If AI tools cleared through our internal review process can help automate parts of research, deck creation, or concept exploration, it frees up more time for the work that really matters. That means spending more time understanding our clients’ businesses and designing experiences that genuinely enhance the rider journey.

Ironically, I’m finding that the result of using AI well is often more meaningful human thinking, not less.

Which specific AI technology has had the most significant impact on your industry?

What’s interesting right now is that it isn’t one single AI technology transforming the industry. It’s the combination of them.

Large language models like ChatGPT, Gemini, and Claude are incredible thinking partners. Generative tools are changing how we create images, video, and design assets. And new workflow tools are starting to stitch everything together. Each category has its own strengths.

The real shift happens when you begin combining them into systems.

Right now many teams, including ours, are building structured projects, agents, and proprietary workflows that connect these tools together. Instead of thinking about AI as a single tool you open in a browser, you begin thinking about it as an integrated layer across your workflow.

When these systems work together they can dramatically accelerate the early stages of strategy and creative development.

Can you share a pivotal moment when you recognized the profound impact AI would have on your sector?

I don’t think there was just one moment. I have those moments almost every day.

AI evolves so quickly that you constantly see new examples of what’s possible. One day it might be a breakthrough in research. Another day it might be a new creative tool.

One of my favorite examples is watching colleagues build a pitch deck for the first time with AI assistance. Traditionally creating a strong strategy deck could take days. Now someone can start with a blank page, use AI to pressure test their thinking, explore angles, and structure the story, and suddenly they have the bones of a strong presentation much faster than before.

What’s powerful is that the person becomes a stronger editor and thinker in the process. Instead of wrestling with a blank page they can focus on refining the idea.

When you start seeing that acceleration across many parts of the workflow, you realize this isn’t just a new tool. It’s a fundamentally new way of working.

How are you preparing your workforce for the integration of AI, and what skills do you believe will be most valuable in an AI-enhanced future?

At Lyft we’re not just preparing for AI. We are actively integrating it into how we work.

There are many initiatives across the company helping teams thoughtfully adopt AI tools while still moving with momentum. The mindset is experimentation with intention.

Interestingly, many of the most valuable skills in an AI enhanced future are still deeply human ones.

Rapport building and relationship building remain essential. Creativity is still central. And the ability to design thoughtful solutions to complex business challenges continues to matter enormously.

If anything, AI raises the bar for those human skills.

What are the biggest challenges in upskilling your workforce for an AI-centric future?

Creative strategists are actually a little lucky because our work already demands mental flexibility.

That said, there are still hurdles. One is psychological. Many people initially feel guilt, as if using AI is cheating.

Another challenge is discernment. AI can generate a lot of output, but not all of it is good. Learning to recognize what is insightful versus mediocre is critical.

What ethical considerations does AI introduce into your industry, and how are you tackling these concerns?

Protecting client information is paramount. During RFP processes we often handle sensitive business information, so strict governance and protected systems are essential.

Another concern is quality. AI can generate enormous amounts of content quickly, but without a strong editorial eye the output can become derivative or shallow.

Ok super. Here is the main question of our interview. What are your “Five Things You Need To Do, If AI Is Disrupting Your Industry”? If you can, please share a story or an example for each.

1. Start experimenting immediately

You have to use the tools. The people learning fastest are the ones actively experimenting in their daily workflows. So how do you start?

If you have a question or task at hand, ask yourself: “Could AI help me here?” Typically the answer is a resounding yes. Just try it out. You can even ask ChatGPT something like “I’m going to redo my patio space. How could you help me?” and let it outline all the ways it could assist with a problem that might seem inapplicable for AI at first.

2. Develop prompting as a core skill

Prompting is becoming a foundational form of digital literacy. I think the people who will work the quickest and most effectively with AI will be the ones who have experience briefing an intern. The best results come when you’re clear and comprehensive, although I do love giving tools like Claude as little information as possible just to see how they handle a query.

A top tip: have your AI tool of choice help you write your prompts. You can start somewhere rough, have the tool round out the prompt, make your selections and edits, and align on a final version you’re happy with.

Really, the most underrated skill in the AI era isn’t knowing which tool to use. It’s knowing how to talk to it. I’ve found that verbal prompting, whether that’s speaking directly to an AI or transcribing notes from a client call, team brainstorm, or meeting recap, creates a natural foundation for generating polished outputs. Rather than starting from scratch with a blank page, I record the conversation, extract the key details and decisions, and feed those notes directly into a prompt. That messy human context becomes the scaffolding for whatever comes next, whether it’s a pitch deck, a strategic brief, or a follow-up document. The conversation itself is the thinking, and the AI simply translates it into structure.

3. Focus on editing, not just generating

I’m proud to say I drafted 130,000 words for my first book, eventually cutting it down to about 100,000 words. I lost a book’s worth of content to the editing floor. That’s fine, because it leads to a better, more focused product. The same is true with AI. You have to hone your skills as an editor: guiding the conversation, judging which ideas should move forward, and knowing how to package everything into an output for your audience. Because AI delivers content at such speed, it’s easy to generate a volume of ideas and then edit down to the best possible selections. That’s why Claude and ChatGPT are two of my best ideation partners.

I was Google’s Chief Facilitator at their GooglePlex in Mountain View. That meant I would lead and facilitate sessions with our top C-Suite clients. One repeating theme in facilitation and ideation is the idea of flipping between expansive thinking (generating ideas) and reductive thinking (selecting ideas.) AI is fantastic at generating, but terrible at selecting. It has no compass for what’s truly good from a human lens.

4. Protect data and maintain integrity

It’s critical to be aware of your company’s policy (and your clients’ policies) around AI usage before you jump in. If you’re working with sensitive client data, like their brief for a marketing campaign, be cautious before uploading it to an AI tool. They might have a policy against it.

5. Stay obsessed with the human outcome

At Lyft we always ask: is this best for riders and drivers?

We can avoid AI slop by reminding ourselves of our purpose here at Lyft: service and connection. “Does this AI solution serve our rider/driver best?” If the answer is no, we ditch it. Don’t forget your audience, and train yourself to recognize content that reads as AI. I used AI to help me with portions of this article, such as arranging my thinking into order, but everything was written or dictated and transcribed from my raw content during the interview.

What are the most common misconceptions about AI within your industry, and how do you address them?

One misconception is that AI only produces low quality content. With thoughtful direction it can elevate thinking.

Another is that creative people should avoid AI. I believe the opposite. Creative thinkers often become the best AI collaborators.

And finally, AI is not a shortcut. It is an accelerator.

Can you please give us your favorite “Life Lesson Quote”? Do you have a story about how that was relevant in your life?

One of my favorite quotes is deceptively simple: “What gets packaged, gets sold.” It came from my former boss at Pinterest, Jason Wire, a brilliant and thoughtful creative mind.

What it really asks is: what is the insight? What experience are you trying to create?

In marketing and strategy, ideas don’t live in isolation. They need to be communicated in a way that inspires action.

At Lyft that means packaging ideas so clients succeed and riders ultimately have a better experience.

Off-topic, but I’m curious. As someone steering the ship, what thoughts or concerns often keep you awake at night? How do those thoughts influence your daily decision-making process?

Like most leaders, I think about scale, efficiency, and growth. But more than anything I think about the health, happiness, and growth of my team. If people feel supported and energized, creativity flourishes and the work tends to take care of itself.

If I look after the team, the business will usually be looked after too.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

I would focus on teaching facilitation and ideation skills to kids.

When people learn how to collaborate effectively, listen to each other’s ideas, and build on them constructively, the quality of thinking improves dramatically.

Creativity is not just a talent. It is a process.

If we taught those skills earlier in life, I believe we would see more collaboration, more empathy, and better problem solving across society.

How can our readers further follow you online?

Readers can connect with me on LinkedIn: https://www.linkedin.com/in/willeagle/

You can also find several of my books on Amazon where I share ideas about marketing, digital platforms, and audience growth.

Thank you for the time you spent sharing these fantastic insights. We wish you only continued success in your great work!