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.

_________________________________________________________

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

_________________________________________________________

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

_________________________________________________________

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

_________________________________________________________

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?

Andrew Capland

Coach for heads of growth | PLG advisor | former growth @ Postscript, Wistia, HubSpot

I help heads of growth have more influence and impact with 1:1 coaching -  and I help early-stage SaaS teams scale as a product-led growth advisor.

After coaching more than 50 clients, it's become clear... Most Growth Teams face the same struggles:

You’re not always sure which lever to pull to drive meaningful impact.

You don’t have a repeatable operating system, so there's no structured process for prioritizing experiments, aligning across teams, or scaling execution

You're spending too much time convincing instead of executing. You're constantly selling ideas internally, securing resources, and fighting for buy-in.

Your role feels misunderstood because your boss has never done your job, and leadership sees the numbers but doesn’t always recognize the full impact of growth.

You’re ready for the next level but don’t have a clear roadmap to get there.

I'm Andrew

I’m the former growth lead at two high-volume PLG businesses: Director of Growth at Wistia, and Head of Growth at Postscript.

I’ve been where you are.

I’ve built and scaled growth teams from scratch, run hundreds of experiments, and made every mistake in the book. I know what "good" looks like, and I know how overwhelming it can feel without mentorship from someone who's done your job.

Now, I take everything I've learned to help other growth leaders increase their impact and influence.

☎️ Book a call to work with me ☎️
https://deliveringvalue.co/get-started

Founder

Delivering Value offers coaching & advising for product-led growth teams.

Because scaling a product-led business is hard. It's a really effective go-to market model, when done right. But, it’s still relatively new and most companies don’t have someone with extensive PLG experience. 

That means you spend a lot of time and money making mistakes trying to figure it out. Or, you feel overwhelmed by all the content out there, trying to teach yourself.

That’s were the idea of Delivering Value was born. To help early-stage tech companies save time by avoiding common mistakes, learn proven frameworks & methods instead of trying to figure it out themselves, & ultimately grow faster.

Services include:
* 1:1 coaching for heads of growth
* PLG advising for SaaS teams
* Digital products for the growth community

I specialize in helping clients who work at small to mid-sized SaaS companies (usually starting around $8-$10 million in ARR), not tech unicorns. If that sounds like you, send me a message!

5 minutes before our call, I got an email from the Head of Growth at one of the largest vibe coding apps in the world.

"Dude, I'm really sorry."

"My daycare just called. My daughter has a fever. I'm in the car on the way to pick her up right now. I gotta cancel our call today"

I wrote back: "Hey, no problem at all. Totally understand. Hit me back when she feels better and we'll get something on the books."

That was last week.

Then yesterday, I found myself on the other end of that exchange.

I didn't have to cancel, but I was running late to a sales call because my wife and I were juggling our sick 20mo sick daughter at home.

She woke up over the weekend throwing up. And I made one of those 2:30am drives to the 24-hr CVS. 

My wife and I got maybe 4 hours of sleep. So yesterday morning, I was the one asking for a few extra minutes, as we passed her off between our meetings.

Last week I was on the receiving end. 

This week I was the one asking for grace.

A lot of millennials are growing into their leadership chapter right now. Some are parents. Some aren't. But every single one has stuff outside of work that bleeds into it.

A sick kid. An aging parent. A health scare. Family living in a war zone. Or something else personal they haven't told anyone about.

Without the context, it's easy to look at last minute cancellation, or someone running late - and be annoyed about the inconvenience.

It's worth remembering, whether you're managing a team or just on one. 

Always assume best intentions.

Everybody has stuff. Everybody deserves grace.

Coach for heads of growth | PLG advisor | Former 2x growth lead (Wistia, Postscript) | Co-Founder Camp Solo | Host Growing Forward Pod 🎙️

I was coaching a Head of Growth who had scaled his team to 37 people. And somewhere along the way, his biggest superpower was becoming his biggest problem.

He didn't see it yet.

I always joked that even though he lived on the west coast, he had east coast energy. He talked fast, made quick decisions, and was always thinking three steps ahead.

But what came naturally to him didn't translate to his team.

His execs didn't understand his strategy. His team struggled to execute the way he did. So in every meeting, he was the one pushing everything forward, involved in every detail.

Sound familiar?

First, we translated his strategy into language his executives understood. Framed it to earn buy-in and resources. And built an operating system so his team could execute without him involved in every project.

Once that clicked, everything accelerated. 

He built a 25-person overseas contractor team that let him validate ideas in days instead of quarters. Without breaking his budget.

In the process, Philip went from being the bottleneck to building a word-class growth team that didn't need him in every decision.

He got so good at building high-performing overseas teams that he turned it into a company.

Hire Overseas helps growth teams build pre-vetted contractor teams: growth marketers, paid ads specialists, SEOs, designers, content creators. Built for teams that need to move fast without full-time headcount.

When you're ready to scale your team 👉 https://lnkd.in/evUTZXW3

Created by a former member of our tribe, for people just like us.

I'm sharing this on a Saturday. So if nobody sees it, I can tell myself it's not a failure.

I've been sitting on an idea for 2 years. Too scared to do anything about it.

Partly because things were going well and I didn't want to mess with that. Partly because if I tried it and it didn't work, I'd have to explain that to my college friends when we meet up for dinner.

But this past year, things changed.

My roster has been full for a while. I have more demand for 1:1 coaching than I can take on.  And at some point, everyone says the same thing. 

They feel alone in their role. 

They have no one to bounce ideas off of. 

The new Directors, VPs, and Heads of Growth are working remotely, juggling young families, fighting off burnout, and sick of making decisions with AI that agrees with everything they say.

They want to be surrounded by other A players on the same journey. People who'll be honest with them.

That's exactly what I wanted when I was in-house. 

I didn't have it either.

I'm calling it the Growth Council. A small room where you can share your real challenges with people who understand your job and will be honest with you.

I'm opening the doors in the next few weeks.

If you want to be first to know 👉🏼 deliveringvalue.co/council

I was scrolling LinkedIn on my way into the gym when I almost spit out my coffee.

One of my old clients (head of marketing) had just been promoted to CEO.

(I wasn't surprised she made it - just that it happened so fast)

And when her boss made the offer, she actually did spill her coffee.

She was leading the marketing org at a PLG company with millions of users when we worked together. And she'd built her whole career on saying yes to things she didn't know how to do yet.

Say yes first. Figure it out later.

Never run a campaign? Yes, I'll figure it out. 
No idea what an integrated marketing calendar is? Yes, I'll figure it out. 
Head of marketing at a scaleup with no infrastructure? Yes, I'll figure it out.

It worked. In 6 years, she went social media manager to CEO.

But somewhere in the middle, that habit became a liability.

The skills that get you to head of marketing, head of growth, VP of whatever - can be the same skills that hold you back once you're there.

You said yes to everything. You raised your hand before you knew the answer. You out-worked everybody in the room.

And then you land the leadership role.

Suddenly you're drowning in great ideas you can't execute. You're in every meeting. Every decision flows through you.

That job requires something different. 

Sequencing. Prioritization. Saying no to things that feel important. Being okay with mediocre in some areas so you can be exceptional in the ones that actually matter.

That transition is hard. And some people never make it. 

Because your superpower and your kryptonite are usually the same thing.

She figured it out. 

This week on Growing Forward, Arielle Johncox walked me through the whole journey - and everything she had to unlearn to get there.

Catch it here 👉 https://lnkd.in/eeYqaNqg

My dad: "Hey buddy, how's it going?"

Me: "I feel really anxious, but I can't figure out why."

Also me: "Have you ever felt like that?"

My dad, after a pause: "Uh, no. I don't think so."

Then we both laughed. But I wasn't really laughing.

That was me at peak imposter syndrome + burnout. I woke up tired and anxious almost every morning during that time. 

Always focused on what I hadn't done.
Ways I was falling short. 
Goals I hadn't hit.

I didn't even realize how much my focus was impacting my confidence until my coach asked me a question during one of our sessions:

"What was a win you had this week?"

I gave her one. 

She said: "What else?"

And I came up with another. 

She kept pushing. By the time I had three, I realized - I actually had been doing okay. I was just ignoring my wins. And instead focusing on what I hadn't done well.

She gave me an assignment: 

Write down 3 wins every day.

Didn't have to be big. Praise from a teammate. An experiment that moved the needle. A hard conversation I didn't avoid. A KPI headed in the right direction.

And after a few weeks of this exercise I realized that my brain started scanning for wins during the day instead of scanning for everything I hadn't done yet. 

Like a muscle. The more I trained it, the stronger it got.

I've given this same assignment to almost every client I've coached. It's not a cure for imposter syndrome. But it's one of the most underrated tools I know for rebuilding your confidence over time.

If you're a growth leader who's been silently carrying that "general state of uneasiness" - you're not alone. 

Most people just don't have the courage to say this stuff out loud.

And if nobody's asked you how you're actually doing lately, I'm asking.

If I didn’t care about hurting your feelings, here’s what I’d tell you about running a growth team.

1. Your boss has no idea what you do - and it's probably your fault. A huge part of the job is making it clear.

2. Nobody understands what your team is working on, or why. If you can’t explain it simply, you shouldn't expect support and resources.

3. Don’t get fooled by the fancy jargon and acronyms. Most are just complicated ways of saying “deliver value to your users.” Focus on that, and you'll be okay.

4. Unless you're also a customer - stop making decisions based on your personal preferences, or leadership’s. Anchor on the user and the data.

5. You don’t have to say yes to everything. Your real job is figuring out which opportunities deserve a yes.

That’s my starter list anyways.

A few minutes before the scariest call of my week, I prepped my battle station. 

Microwaved my coffee. Put my notes on the second monitor. Then nervously clicked my pen. Waited for everyone else to sign-in.

By the time all 10 joined, I could feel my body entering that mode where you're not sure if it's peak performance or you're about to have a panic attack.

I've spent dozens of hours with each of these people individually. But I'd never had them all in the same room before.

I've publicly shared that I'm starting a group coaching program in Q2. Privately, I have no idea how to run one. This was my first attempt at figuring it out.

I invited 10 growth leaders onto a Zoom. 

Directors, VPs, Heads of Growth, all navigating similar challenges right now. I picked a topic relevant to everyone, set up the call, and hoped for the best.

A few minutes in, something happened that slowed my heart rate down.

People just started talking. Jumping in. Problem-solving. Connecting. All the things I was hoping would happen - started happening on their own.

About 20 minutes in, two of them realized they'd lived through the exact same situation. Just in different order.

One had just been asked to step into an interim VP of Marketing role after their boss was let go. The other had just come out the other side of that exact situation a few months earlier.

So he shared everything he had learned.

That's the room I'm building. A place where the person who just solved your problem is sitting right next to you.

The Growth Council opens 5 spots in Q2. 

I'm reviewing applications personally. If you're a Director, VP, or Head of Growth ready to stop figuring it out alone, apply at the link in bio.

"Julie" is a VP of Growth who told me she was waking up at 3am to refresh her dashboards every night. 

She was putting lots of pressure on herself to win - fast.

She'd just stepped into the role from a more traditional VP of Marketing background. And she was figuring it for the first time, and alone.

She had been working with an executive coach when I met her. 

But generic leadership wisdom can only go so far when the actual challenge is leading a cross-functional growth team through AI, shifting channels, resource constraints, and an evolving concept of product-market fit.

At some point, she stopped working with the exec coach and worked with me.

She jokingly called our sessions "growth therapy." 

She'd show up to our calls feeling overwhelmed by all the competing priorities. By the end of the hour, she'd have clarity on what to tackle first and a growing "not right now" list for everything else.

I'm not a certified executive coach (though my mom is and probably how I fell into this). 

But I've just done this job twice and coached 90+ other people through it. 

It was clear she needed someone who had seen her exact challenges before and help her develop processes and frameworks to solve them.

A year later, her team hit 40%+ year-over-year growth. 

The only thing that changed was she stopped figuring it out alone.

I spent years pushing for a promotion - and felt completely lost after I got it.

I was leading a cross-functional growth team at a cool tech startup. The title I'd been chasing. Director of Growth. 

I'd told myself everything would be way easier once I got that title. People would finally trust my decisions. I wouldn't have to fight so hard for budget, justify extra headcount, or sell my strategy up down and sideways.

But within a few weeks I realized I was having the same debates - with a new title. It was frustrating.

I just wanted to quietly do good work. 

I didn't want to complain. Because who complains after a promotion? 

But on the inside I was really frustrated because I had pushed so hard for something I wasn't enjoying.

My team could hear about it - that would impact their motivation. My execs definitely couldn't know - they'd question if I was the right person for that job. And talking about it at dinner with my wife felt crazy.

It wasn't until I started working with a coach that I learned this is actually a documented thing. High performers who've spent years working toward a goal often fall into a low-grade depression after they achieve it.

The person chasing the goal was their identity. When the goal is gone, so is the motivation and sense of self.

That conversation didn't fix everything. 

But it was the first time I'd said it out loud to someone who didn't need anything from me. Someone I could think out loud with without it costing me anything.

It took me months to figure out a new title wasn't the finish line.

"Dude, I've had the SAME arguments with the SAME people in the SAME ways so many times that I'm just exhausted... I've stopped pushing as hard."

A VP of Growth said that on our call.

He'd been questioning if he was focused on the right things. But I thought the real challenge was something else.

So I asked him a simple question:

"If you were fired tomorrow and they hired someone new for your exact job, do you think they'd do something drastically different than what you're doing?"

He thought about it for a while. 

"No. I think they'd probably see the same opportunities I do."

Then he gave the answer above, which meant his instincts weren't the problem. He'd stopped trusting himself.

Confidence erodes slowly. 

The idea you pitched that got ignored and then credited to someone else 6 mos later. The meeting where you had the answer but didn't want to risk being wrong. The quarter you missed your numbers, while other teams hit theirs.

Those all chip away.

Then one day you realize the swaggy version of you that walked in 18 months ago (who wasn't scared to push, make mistakes, or ask for permission) is gone. 

You're still there. But you're quieter. Less swag.

So we built him a trophy file.

A running doc of his wins, thank-you's, Slack claps, screenshots, and data points to remind himself all of the value he brings every day. And we added three things every single day.

It's a small activity. But a huge tool.

Because your edge doesn't come back on its own. You have to find it, one win at a time.

One of my best clients got leveled after 16 months.

They didn't hire someone to replace her. They hired a more senior growth advisor to work directly with her CEO instead.

She was understandably frustrated. 

The advisor recommended most of the same things she'd been pushing for internally. They saw the same opportunities. 

But they shared them in a way that made it easier for the execs to get behind.

In retrospect, her CEO never understood what she was working on, or why. And by the time that was clear, it was too late. The trust was already gone.

Growth is still a relatively new discipline. 

And unlike marketing or product, where most executives think they understand the playbook, growth sits across all of it.

You might push for product changes to drive usage that conflicts with the product team roadmap. Or see an acquisition opportunity in a channel marketing hasn't prioritized. 

You're often doing work that bumps into other teams. 

That's the nature of the job.

If you're not constantly managing alignment, you end up in a million meetings, getting blocked, or both.

The average Head of Growth I meet lasts in their role around 18 months. 

But the ones who last 3-4 yrs treat communication as core part of the job. 

They market what they're doing and why. They make trade-offs visible. They get alignment before they ship, and rebuild it every time something changes.

The ones who don't run into challenges.

Full breakdown on youtube 👉 https://lnkd.in/ew4VYZBA

You probably don't have a career path - and it's not your managers fault.

- Growth means something different at every company
- Your manager has probably never done your job
- No formal criteria to get promos
- Still a new/emerging disciple

The truth is, nobody has a "path" for you anyway.

It's on you to take control...

- Advocate for what you want
- Be clear about your expectations
- Ask for feedback as much as possible
- Use every opportunity to deliver value
- Hold your employer accountable to your plan

Your manager is there to help you. But your job is to let them know where you want to go.

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