My 2017 iPhone videos taught me about AI in 2025 (Exit Five Newsletter)

Hello and welcome to the Exit Five Weekly Newsletter — read by 42,000 B2B marketing professionals around the world. Exit Five is a membership site designed to help you build a successful career in B2B marketing. Join 5,700 other members at exitfive.com.

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TOGETHER WITH KNAK

📧 Here’s How to Write a Great Email

Follow CHEETAH, the 7 Key Elements to High-Performing Emails.

I don’t need to cite a laundry list of statistics to convince you email is one of the most important channels in B2B Marketing.

I know it and you know it – so let’s help you get better at it.

Pierce Ujjainwalla (co-founder & CEO at Knak) is an email expert… and after writing and studying thousands of emails, he’s identified the seven things that create emails that aren’t just read, they’re acted on.

It’s called the CHEETAH framework, and it breaks down how to:

• Captivate attention before the email is even opened
• Make your email feel like it’s coming from a real person, not a faceless company
• Increase conversions by matching email to landing page

If you’re planning to send more than one email this year, check out the free (and ungated!) guide to the CHEETAH framework here.

🤳 Why I Started Recording Videos on My iPhone in 2017 (And What That Taught Me About AI in Marketing Today)

Back in 2017, I did something that felt ridiculous at the time.

I'd drop my daughter off at school, start walking to the Drift office, pull out my iPhone, and just...start talking. About marketing. About what we were working on that day. About a copywriting tip I wanted to share.

No script. No production team. Just me, walking down the street, rambling into a camera. I'd post it to LinkedIn and the video would get 50,000 views.

Now it’s obviously not that easy today, but here's what I learned: being early on a new channel or technology creates an outsized advantage. And right now, we're at that exact moment with AI and video.

That's why I sat down with Holly Xiao, who leads B2B marketing at HeyGen, to talk about where this is all going. Not the hype. Not the fear-mongering. Just two marketers trying to figure out what actually works.

The Real Reason Video Works

Let me tell you what happened after I started posting those walking videos.

People at events would come up to me and say they felt like they already knew me. Prospects would reply to our emails mentioning something from a video. The engagement was completely different from anything I was getting with written content.

And here's why: we process video differently than text

Think about what happens when you get home and sort through your mail. You immediately separate everything into two piles. The A pile (handwritten notes, personal stuff) and the B pile (marketing, promos, things you'll deal with later). Your brain does the same thing with content online.

When something feels like marketing, you tune it out. But video, when it's done right, bypasses that filter. You get my voice, my personality, maybe there's music or animation. It's multidimensional in a way that written content just isn't.

Why Your Videos Probably Suck (And How to Fix Them)

Gary Vee has this great moment where someone tells him, "I've been posting videos every day to Instagram for a year like you said, and you're wrong. These videos aren't working."

His response? "I mean this in the kindest way possible, but maybe your videos suck."

And that's usually the answer.

Just because you made a launch video doesn't mean it's going to work. There's an art to this. We've tried to over-science everything in marketing, but creativity still matters.

Here's what I see kill most B2B videos:

The Time Suck
“We're working on the product launch video. It's gonna take us six weeks.”

Why? Too many rounds of feedback. Too much consensus-building. Maybe there wasn't even a good idea to begin with.

The Wrong Recipe
Every B2B company goes to their LinkedIn channel and every video has like 73 views. Why? Because they're all following the same template. Stock music. Piano comes in. Show the product. Who's actually watching that?

Not Enough Reps
I posted a ton of video content. We have these highly edited podcast clips we post on LinkedIn. But you know what my most-watched video was in the last year? A seven-second clip of me on a hike with my wife. Zero editing. No strategy. Just real.

You need volume to figure out what works. Look at any successful YouTube creator. It’ll be 83 views, 16 views, 100 views, 200 views, then suddenly 20,000 views. It takes time and feedback.

The fix? Use organic social as your testing ground.

Post your ideas for free. See what gets engagement. See what topics make people stop scrolling. Then invest in production for the concepts that already have signal.

If I came up with a tagline and people responded to it (like they did for Exit Five’s: "Nobody goes to school for B2B marketing"), I'd feel good about making a funny skit-style video around that concept. But I wouldn't spend $17,000 on a launch video without testing the core ideas first.

How AI Changes the Game (Without Replacing Creativity)

Here's what has me excited right now: AI is giving marketers a renewed sense of energy because it's making marketing relevant again.

But let's be clear about what AI actually does.

AI is trained on everything we've already created. It excels at handling the mundane, repetitive, tedious tasks quickly and efficiently. That frees us up to focus on the meaningful creative work.

There's this book called "Audacious: How Humans Can Win in an AI World" by Mark Schaefer. His whole point is that the opportunity with AI is actually to be MORE creative, MORE human, take MORE chances.

Let AI run the business systems and processes. Let it do things at scale. But the last mile? That's always going to be human creativity.

Think about it this way:
In the late '90s, there were people who didn't believe the internet was going to be a thing. Obviously lots of hype. Some things didn't come true. But at the fundamental layer, could you see how the technology was going to disrupt everything?

That's where we are now. And the marketers who figure this out early are going to have a massive advantage.

How Small Teams Can Use AI to Punch Above Their Weight

Before, if you wanted to make a video, the conversation went like this: "This is going to cost $7,500 in production. Where are we going to film it? We need B-roll. We need footage. It'll take 4 weeks."

That's why most marketing teams make one big video every few months and pray it works.

Here's what changes with AI:
You can actually test ideas now. Holly has a customer with a marketing team of less than four people competing against major companies. They're using AI to compress the production cycle from weeks to days.

Want to test five different hooks for your product demo? You can. Want to remake a video because the script needs tweaking? You can do it in an afternoon instead of rebooking a shoot.

That's what's exciting about where things are going. It's shrinking the cycle.

What About Personalization at Scale?

Here's where this gets really interesting.

Right now, most ads are the same for large segments of audiences because of production costs. What you see is probably what I see.

But AI makes it possible to individualize videos at scale. Tailoring every ad specifically to individual viewers based on their unique interests and behaviors, automatically.

As a marketer, you'd create a single template and script that automatically adapts personalized elements for each viewer. That’s how personalized we can get with AI.

The Thing Nobody Talks About: We're Going to Crave More Human Connection

Here's the weird paradox I'm feeling right now.

I love tech. I'm a believer in AI. I want to use ChatGPT, get ideas, build systems. But at the same time, I just want to go on a hike with three friends and be offline.

And we're seeing this in our business and with other companies. People want more in-person events. They want to get out of their house and hang out with each other.

In a world of AI solving business stuff for us, humans are going to crave more real-life experiences.

So there are these two poles. AI and computers and automation on one side. Human connection and offline experiences on the other. Both are becoming more important, not less.

The companies that figure out how to do both well are going to win.

Do People Even Care If It's AI?

Holly's team did a consumer study. They surveyed over 2,500 people and found that over 90% of consumers don't have a problem with brands using AI to generate videos in marketing content.

What they care about is quality. If it feels too robotic, alarm bells go off. But if it looks realistic and the content is good, people are open to it.

The medium doesn't matter. The story does.
If you're using AI to create videos that aren't informational, educational, funny, useful, entertaining...then yeah, it's going to suck. But that's not an AI problem. That's a marketing problem.

You still need to nail the angle, the hook, why you're doing this. If you do that, whether it's created by AI or a human might not actually be the differentiator.

Your Action Plan: How to Start Using AI for Video Right Now

Here's what I'd do if I were starting from scratch:

1. Stop Thinking About Production First
Don't think about cameras and editing yet. Think about: What's the hook? What's your angle? What's the niche? What are you making videos about?

It's like starting a YouTube channel. You don't just say "I'm going to make videos." You need a concept. A point of view. Something that makes people want to watch.

2. Test Your Ideas in Writing First
Everything we've ever created at Drift started with writing. We'd frame it like a blog post or article: What are we announcing? Why is it valuable? Who's it for? Why does it exist? How do you use it?

Then we'd use that as the jumping-off point. Product marketers would make emails and landing pages from it. The video team would write scripts from it.

Writing first is cheaper. You can test what resonates before you invest in production.

3. Put AI Tools in Your Bookmarks Bar
I have ChatGPT, Claude, Perplexity, and one other tool at the top of my browser. Every time I open a window, it's a reminder: "Is there a way I could use one of these tools for this task?"

Push yourself to be an early adopter. This is one of those rare moments where you can get an advantage by moving fast.

4. Give Yourself Permission to Suck at First
Remember what I said about YouTube creators? They all have videos with 80 views in the beginning. That's part of the process.

You're not going to make one video in the next six months and have it be a smash hit. You need reps. You need feedback. You need to figure out what works.

5. Use the Right Tool for the Right Job
If you want to create an overview video or product explainer, tools like HeyGen let you do that completely from scratch without a camera. The best part? If anything changes last minute (which it always does), you can easily edit the script and video to keep it current.

You can also turn written content into video in a few clicks. Most of you are sitting on a goldmine of blog posts, landing pages, and articles. Why not repurpose them?

But here's the key: Start with the story. The tool doesn't matter if you don't have something worth saying.

The bottom line? We're at one of those rare points where early adopters get an outsized advantage.

It's like being the first person in 2008 to bet on inbound marketing and HubSpot. Or being early on LinkedIn video in 2017. The people who move first and figure it out get a huge head start.

The companies winning with video aren't trying to be everything to everyone. They're not waiting for perfect conditions. They're testing, iterating, and using every tool available to tell better stories faster.

So here's my challenge: Take a bet that this is where the world is going. Use this as an opportunity to reinvent yourself, rethink your workflows, question your assumptions.

Try to use these tools. Be an early adopter. Push yourself to move fast.

Because very few opportunities in life let you get ahead just by being willing to try new things before everyone else does.

- Dave

P.S. You know what's wild? I became a VP of Marketing then CMO only to realize that it wasn’t actually my job to write any of the copy anymore or focus on storytelling. The things that are actually my superpower. My job as a marketing leader was to manage the team, do performance reviews, build board decks, be in spreadsheets. That's the reason I got burnt out. AI gives us a shot at getting back to that. And honestly? That has me super excited about the future of marketing.

📺 UPCOMING EVENTS

[OCTOBER 7TH] Beyond Copy: How To Use AI to Build GTM Systems That Scale

OK, we get it. You can do cool things with AI in marketing. But what? Do you have any examples beyond the fluff? Beyond just writing copy? Beyond creating more AI slop? Yes we do and I think you’ll get a ton of examples from this one.

In this free live session, we’ll skip the theory and dive straight into practical implementation of AI for B2B marketers. No endless slide decks — expect live builds and no-BS demos tackling real marketing challenges.

Dave Gerhardt (Founder & CEO, Exit Five), Eoin Clancy (Head of Growth, AirOps), and Dan Guenet (GTM Engineering Lead, Compound Growth Marketing) will share practical frameworks and examples of how B2B marketers are using AI to drive real results. From automating insights out of sales calls, to creating content humans actually want to read, to increasing visibility in AI search, you’ll see it all in action.

What we’ll cover:

• How to build AI workflows that tie directly to your GTM strategy
• Real examples of scaling content and insights without sacrificing quality
• Where AI can automate the manual parts of marketing (and where it can’t)
• Frameworks for evaluating AI tools and picking what’s worth your team’s time
• Live demos of AI in action

This is a free, live session open to all B2B marketers, Exit Five members and non-members alike. Can’t make it live? Register anyway and we’ll send you the recording after.

Save Your Spot

🏢 Open Roles

Who's hiring right now?

Vapi is hiring a Head of Marketing to build and scale marketing from the ground up. You’ll own demand gen, growth, and brand storytelling, shaping how Vapi shows up in the enterprise AI market and turning developer momentum into qualified pipeline. The ideal candidate is a data-driven, strategic B2B SaaS marketer who can balance hands-on execution with high-level growth strategy in a fast-moving startup.

Knak is hiring a Senior Manager Brand & Content Marketing, an Email Marketing Lead, and a Digital Marketing Manager. Learn more about the roles here.

Other open roles on the Exit Five job board this week:

• TLDR is hiring a Senior Growth Marketer - Paid Acquisition
• TLDR is hiring a Senior Growth Marketer - Lifecycle & Automation
• Dragon360 is hiring a Demand Gen Strategist
• Tatari is hiring a Senior Manager, Customer Marketing
• Paramark is hiring a Marketing Manager
• Doist is hiring a Lifecycle Marketer
• Tatari is hiring a Digital Marketing Manager
• Enumerate is hiring a Senior Product Marketing Manager
• Red Stag Fulfillment is hiring a Director of Growth Operations
• Dynamic Lifecycle Innovations is hiring a Director of Marketing

See all open roles

Have an open role and want to make sure the best B2B marketing talent sees it? Just reply to this email and we'll send over more info on how you can post it on our job board + get it in front of 42k+ marketers.

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