Why VP of Marketing is a Brutal Job - Even When You're Crushing It
The real reason April Dunford started her consulting business and reinvented her career in her 40s
Hey 👋 I’m Andrew - and welcome to Delivering Value Substack. This is where I write about the stuff growth leaders don’t always talk about: lessons from the trenches, honest convos with other leaders, and what I’m learning as I build my business solo.
This post is part of my Candid Convos series, where I chat with SaaS leaders to unpack the toughest moments in their careers - and explore how they navigated ‘em.
“The VP of Marketing job kinda sucks.”
“At least at a startup anyways. It’s a better job at larger organizations. But at a startup, it’s really rough.”
That’s what April Dunford shared during our conversation. Today, she’s known as the GOAT of Product Positioning, and one of the most successful marketing consultants. So I was shocked to hear she never planned to be a consultant. The real reason she started her business was because she couldn't survive another VP of Marketing gig.
After working her way up the marketing totem pole, from product marketer to VP, she realized her job was totally misunderstood by her bosses and board. Nothing was ever enough.
“I can remember times where I pulled something off that felt like a magic trick from a marketing perspective. And the reaction from the rest of the executive team was, 'yeah, that's great. Can you do double that?'"
That’s what motivated April to burn the boats and begin her second act.
But it wasn’t a sure thing. April originally thought going solo might be the end of her career.
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April grew-up in a small town outside Peterborough, Canada.
It’s a quiet town that tourists love to visit in the summer.
From a young age, she was always working. Not because she was overly ambitious, but because if she wanted money, she had to earn it.
Her parents weren’t thrilled when she said she wanted to go to university. They tried to talk her out of it. But she was smart and deeply curious about how things worked. So she went, and eventually transferred from pre-med into the engineering school.
The engineering program had lots of group projects, but there weren’t many women in the program, so April found herself getting blocked out of the code by her male peers.
“They were like, who are you from this small town? You suck. Do not touch code. And so I sat there for the entire term and sat on my hands, and they wouldn't let me touch code. It was terrible. It was awful, actually, because I considered myself a pretty good programmer at the time.”
Instead, she found herself writing the group reports and giving the team presentations.
That skillset eventually became her superpower and helped her land her first job at a startup doing product marketing. She didn’t ever study marketing, but she could write a SQL query, and explain technical concepts in plain english. That was enough to get her in the door.
Her professional first job at a software company was deeply technical (selling databases to database people) and right in her wheelhouse.
Everyone on the marketing team had an engineering degree - but none of them had studied marketing. They didn’t need to. It was B2B in the ‘90s. If you wanted to explain your product to technical buyers, you had to be technical yourself.
From there, April jumped to more startups - seven in total.
Along the way, she helped build messaging, designed the pitches, and supported sales teams. She also lived through integrations, layoffs, restructures. She even fired herself during one brutal round of cuts at a large company when she couldn’t justify letting anyone else on her team go.
Eventually, she landed at IBM where being an executive meant playing politics, managing up, and learning how to navigate invisible hierarchies.
She’d finally achieved the thing she set out to do: become a senior leader at a respected global company.
That’s when she realized… it wasn’t that great.
She loved marketing, but being a VP at Microsoft meant she couldn’t get her hands dirty anymore. They looked down on it.
One day, her boss pulled her aside and asked, “April, do you want to be a doobie (someone who’s doing the work), or do you want to be an executive here?”
Execs played the political game. They negotiated for budget. They spent lots of time getting aligned. That’s when it clicked: to succeed here, she’d have to give up the parts of the job she actually loved.
Because real execs, at that level, didn’t “do” the work anymore. She didn’t last long after that.
April took on a string of VP roles where she helped scale teams, and pulled off what she calls “marketing magic.”
“I can remember times where I pulled something off that felt like a magic trick from a marketing perspective. And the reaction from the rest of the executive team was, 'yeah, that's great. Can you do double that?'"
She realized that most CEOs didn’t really understand marketing.
“And if they don’t understand it, they won’t value it. You can be smashing your numbers… and still get let go,” she shared.
She saw that happen to peers, colleagues, and people she managed.
The last VP job was the breaking point.
They violated her employment contract.
“They just decided not to honor it,” she told me. “A bunch of stuff happened, and I left there thinking, man I don’t think I can do another one of these [VP of Marketing jobs].”
“I ran out of the burning building,” she said. “I wasn’t going back in.”
She didn’t have a master plan to become a Product Positioning consultant. She originally offered Fractional Marketing Leadership.
That’s what everyone told her to do. But it never felt right. Clients expected five days of strategic firepower on a two-day budget. The expectations were full-time. The authority was part-time. And the business model made her feel like a second-tier employee.
“It was just a bad deal for everybody.”
Eventually, she realized:
She didn’t want to be a freelancer.
She didn’t want to be an “advisor.”
She didn’t want to be a part-time exec, circling the same problems from the outside.
She wanted to teach.
“If you’re going to bring in an outside expert,” she said, “the only reason is to learn something your team doesn’t already know - something you only do once or twice in the life of a company.”
She started to narrow her focus on product positioning.
“I wanted to be the best person on the planet at one small thing,” she said. “To the point where if you were a B2B tech company and you needed to get this right, everyone would say: ‘You should call April.’”
But it wasn’t easy from the start.
I needed to burn the boats.
“I do think I really needed to burn the boats,” she shared.
“The last [VP marketing job] was so bad, it kind of sustained me through the first two years of consulting being really rough. I’d never have got to year three if I wasn’t like, ‘Look, we're not going back. My plan B is way worse than this.’”
Hearing April’s story reminded me of something I've seen with other successful consultants, fractional folks, and solopreneurs: they have to figure out how to make it work, because going back isn't an option.
If you’re a marketing leader quietly wondering “is this it?” I hope your take the take to listen to April’s full story below.
Catch April’s story on YouTube
Listen on Spotify
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