Dave Gerhardt

Hey I'm Dave Gerhardt. I created Exit Five, which has turned into the top community for B2B marketing professionals. Before starting Exit Five I had a 10 year career in marketing and grew from PR intern to CMO. I even once had hair! My wife says I'm more handsome now though, and she's quite pretty so that means a lot -- but the internet just boxes me in as the typical bald guy tech bro. So oh look, another bald tech guy writing on LinkedIn! whoopty freaking do.

Anyway. Where was I... OH. Receipts! I wanted to talk about receipts, because in a world of fluff and online influencers, I actually have some receipts and I want to tell you about them here because it signals power, credibility, and makes it seem like I'm super rich, so: I used to be pretty good at marketing, and my work as a marketer played a key role (at least I think so) in helping two software companies to successful exits: Drift for $1B+ and Privy for $100M+. I certainly helped the founders make a bunch of money, and I was able to comfortably purchase a brand new Toyota Sienna minivan for my family in 2021.

Today I spend my time working on Exit Five, and it's actually been super fun and given me a bunch of purpose. We're a team of six full-time team members now, and we have a private online community and host in-person events around the world. Plus there's a popular podcast and newsletter for marketers. We reach something like 20 MILLION marketers with our content every year, and we've got a pretty special thing going on. I hope to keep it going. You can learn more about it all at exitfive.com.

I spent most of my life in the Boston area but now live in the woods in Vermont with my wife, two kids, two cats, and one dog.

You can reach me at dave@exitfive.com if you want, but TBD if I reply. Depends on the message. But please don't send me any more swag or books. But if for whatever reason you do want to send me something, I play the ProV1x golf ball and like the low numbers.

PS. Find my podcast “The Dave Gerhardt Show” on Spotify

Founder & CEO

Exit Five is a media company focused on B2B marketing. We help B2B marketers build successful careers through our content and community. Learn more at exitfive.com

We polled ~100 CMOs at companies $50M - $500M+ ARR on what their top marketing challenges are right now. Here are the top takeaways.

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1. AI. No surprise. 85% said AI adoption is # 1 priority for 2026.

But this goes beyond the cute use cases you see on LinkedIn and from the AI creators showing you all the new things to do with the new tools.

"I need practical use cases and quick wins to show” - VPM $25M ARR

“We are expected to be using AI to scale marketing  efficiently” - VPM $30M ARR

“We are under pressure to demonstrate hard savings and additional value created via AI adoption.” - CMO $450M ARR

“Wondering am I moving fast enough on AI transformation — not just adopting tools, but truly rethinking how marketing works from the ground up.” - CMO $600M ARR

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2. Everyone said some version of this: "We need to grow more, spend less, & prove marketing did it.”

Grow more. Spend less. And PROVE that marketing did it. That is the key word there.

They all talked about revenue growth, but the framing has evolved beyond "drive more MQLs."

The dominant language was:

• Marketing-sourced and marketing-influenced pipeline (not just leads)
• Pipeline quality over volume
• Tying marketing to ACV expansion and retention, not just new logos

“We ned to tie marketing more directly to revenue outcomes — not just MQLs, but marketing-sourced and marketing-influenced pipeline, ACV growth, and expansion revenue” - VPM $85M ARR

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3. The other repeat topics we heard included:

• Team too small for scope of work
• Feeling  caught between strategic work (positioning, GTM, C-suite influence) and heavy day-to-day execution
• Structural misalignment after acquisition or reorg
• AI search disruption
• Moving upmarket
• Moving from single product to multi-product

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PS. We run a private group for in-house B2B marketing leaders. If you're running the marketing team at a company doing $50M+ ARR you should check this group out. Apply here:

exitfive.com/cmo-council

LinkedIn is the number one channel for B2B marketers (for content, social, ads, you know we love it here) so I had LinkedIn VP Marketing Davang Shah on the podcast this week to go right to the source about what's working, what's not, and trends across the platform.

We covered: 

- What actually works with LinkedIn ads right now
- Brand vs performance marketing strategies and how they differ
- How to think about measurement beyond last-click attribution on ads
- Why 95% of your buyers aren't in market at any given time and what to do about it

Davang also shares the data behind thought leader ads, what most marketers get wrong about the buyer journey, and how he's leading his own team through the AI shift at LinkedIn.

Listen here:

https://lnkd.in/erc8w2vM

PS. Did you know the average B2B deal takes 211 days and involves 22 people?

Tom Wentworth

High growth SaaS executive with expertise in both enterprise product-led and enterprise GTM models. I infrequently post advice on tech marketing at https://tomwentworth.com and used to host a podcast called Scaleup Marketing.

Chief Marketing Officer

I’m on the marketing team at Recorded Future, a $300m+ ARR, high growth cyber security company focused on securing our world with intelligence. 

Everyone loves Claude, but do you know why Claude is called Claude? 

Claude is a tribute to Claude Shannon, the greatest scientist you've probably never heard of. In 1948 Shannon figured out how to measure, compress, and transmit information reliably. He introduced the "bit" as the fundamental unit of data. 

His MIT masters thesis was how Boolean logic could be implemented with electrical switches i.e. the theory behind the semiconductor.

Without him, there are no computers, no Spotify, no internet, and no Claude.

Shannon lived in my home town of Winchester, MA and I walk by his house on Upper Mystic Lake a few times a week; reminding me of the impact one person can have on the future of humanity. 

Put some respect on his name 💜

CMO @ incident.io 🔥 --dangerously-skip-permissions

Hey Dharmesh Shah HubSpot

I know you love to delight customers, here's one for you that will make the crowd go wild. 

On a Hubspot form, add the option to block free email providers AND misspellings. I'm fine with people using personal emails but accidental misspellings creates HAVOC in our CRM. And you'd be amazed at how many possible ways there are to misspell Gmail. 

p.s. I'm friends with Patrick Shea so that should put this at the top of your priority list :)

Glad to see all the marketers using Claude Code. But don't sleep on Claude Cowork. 

My preferred pattern for new marketing AI apps is to build them as Claude Cowork plugins. 

Cowork can handle both markdown instruction-based skills (like how to write AEO-optimized content) but even better, you can have it run Python apps for you. 

So anything that has an API can easily be turned into a Cowork plugin. Have Claude Code build the plugin for you, telling it to turn API endpoints into Python scripts. Cowork will then will run the scripts in a virtual environment for you. 

Push the plugins to a Github repo and you can make them one-click installable across the team. 

Code is my first love but Cowork is probably the future of this stuff for mere mortals.

Managing LinkedIn ads in the campaign manager is brutal. There's a better way: Claude Cowork. 

I've got a simple plugin for you to install that can do everything you can do via the UI. Create campaigns. Clone them. Set audiences. Start/stop. Manage budgets. 

It can even create new ads for you. Give it an image and tell it to create 5 copy variations and it will. 

Want more? Use Claude Cowork scheduled tasks and have it send you a daily performance update every morning (like in the screenshot). 

All you've got to do is figure out how to generate access tokens (instructions are in the repo). 

Ben Cope is a happy reference customer. 

Comment WENTWORTH IS AN AI GENIUS to get access. 

Or just take a look at my Github link in the comments.

Sometimes I can't sleep at night because I know there are people who still use points-based lead scoring in Marketo to tag MQLs. 

"if webinar then 10 points, if email open then 2 points" is probably the dumbest thing ever to happen to SaaS marketing.

Want to know if a lead is good fit or not? Have Claude (via Clay) look at the raw data and tell you. It's great.

Ok a non Claude post for once. 

The most important thing I've learned about marketing in the past 10 years or so is that design is much more important than I ever gave it credit for.

If I were starting a team from scratch today I might make design my first marketing hire. 

AI can automate a lot of things, but great design stands out. Brings clarity. Cuts through the noise. So much more than "making things look clean". 

Here's to you Chloe Livesey Lucas Clauser Hannah Morton Ilija Vujinović Erik Z. Tom Petty and all the great designers I've worked with. I underestimated you. Never again.

Sign of the times: I spend more time in Github now than Hubspot.

While we're at it, here's a Reachdesk plugin for Claude Cowork. Just got to feed it an API key. Check stats, send gifts, etc. Right from the comfort of a prompt. 

Link in the comments.

Alarmalade not red but I’ll take it 😇

LinkedIn content that builds trust and drives pipeline | Founder @ black tofu | Content Strategist

A red coffee cart just outsmarted a $30K billboard.

Yesterday while creating content around San Francisco, I saw this:

"Rough night on-call? Free coffee for tired engineers."

It was incident.io, parked on the street, handing out coffee.

It wasn't anything fancy, and that's why it's a win. It's not intimidating like lots of booths are. 

Just free caffeine for their exact target audience.

I talked with Sophia Luna and realized I've seen incident.io before. We obviously connected on LinkedIn, and she asked how I knew Mohit Bijlani, their CRO. 

We used to work together at Cloudflare! Small freaking world! 

In B2B, buyers need 10-15 touchpoints before they even take a meeting. A red coffee cart in SF just became one.

I see marketing teams do the craziest things to get attention.

When in reality, sometimes the most basic thing, handing out free coffee in the morning, is what makes you memorable.

You don't need to spend thousands on a billboard.

You need to put yourself in front of the right people, at the right moment.

This is exactly why I create content on LinkedIn. By the time someone talks to me, they already know who I am.

If you're in SF, and want some free solid coffee, check them out!

Ya’ll know I’m pretty aggressive at trying to build AI tools for marketing. 

But did you know there’s a team at incident.io doing the same across our entire GTM org? Dedicated actual engineers (not pretend engineers like me) doing actual engineering work to build AI tooling to improve the output of our GTM efforts. 

What they are building makes my stuff look like the amateur hacky stuff it is. 

They are keeping me on my toes, and inspired me to figure out how to get more of tooling available from Claude Cowork (which is really great btw). 

Follow Tom A. Oni Bhaumick to hear about capital E GTM Engineering.

Applied AI Lead · Product Engineer at incident.io 🔥

One of my favourite things about being an engineer is that I have a license to ask nosy questions about other people's jobs — and then get to build stuff to help them out.

At incident.io, I'm working on a team-of-two called Applied AI, rolling out best-in-class use of AI across the company. Today, our focus is GTM: sales, BDR, CSM. The brief: raise the floor; raise the ceiling.

I used to play rugby in the front row, and as a prop I knew only one way to run: route one. So we went direct: give everyone access to Claude Cowork with a single plugin containing the best skills and resources we could assemble.

Why Cowork? Claude Code showed us that a smart model plus files on disk is an incredibly powerful paradigm — powerful because it's simple. Cowork brings that philosophy to knowledge work. Our plugin brings the best available knowledge as markdown, plus our best recipes for success as skills, directly into Cowork.

Choosing Cowork also felt like the most go-with-the-flow option. Skills for reusable recipes and MCP servers for data access really work, and Claude is good at using them. We're betting on where this ecosystem is heading, orienting towards what the models are already good at.

We accept we don't know and can't control all the ways our skills will be used: we hire great people, they will innovate and push the boundary. We want that. These models are getting smarter all the time — why fight that with rigid workflows and the straightjacket of automation?

Data, knowledge and skills, knit together by intelligence. That's where we're going.

taplio

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