This Growth Marketing Expert Quit a Toxic Job and Gave a Middle Finger on the Way Out
The instagram vs reality of working in tech.
Hey 👋 I’m Andrew. Welcome to Delivering Value - the newsletter and podcast where I share stories from SaaS leaders about the toughest moments of their careers, and explore how they turned them into success stories. You get to learn from their mistakes, without the pain.
This is a story about the instagram vs reality of working in tech.
The Instagram version? An impressive title at a unicorn startup with a brand name most people in tech would recognize. Loads of responsibility and accountability - and the opportunity to make a big impact. On the surface, a picture of career success.
The reality? Sleepless nights. Stress that’s out of control. Burnout you can’t shake.
Tiffany DaSilva thought she had landed a perfect role. A chance to grow, to lead, to make an impact. Something she thought would help her career for years down the road.
Instead, it almost killed her.
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Tiffany was obsessed with how people found information online, how search engines worked, and how great marketing could connect the right audience to the right message.
Tiffany didn’t just work in marketing, she loved it.
She started young, making websites and learning how to get them ranked on Google, before she even knew what SEO was. Over the years, she built her expertise in PPC, SEO, and CRO. She worked both in-house and at agencies. She loved the craft, the strategy, the endless learning.
She also knew, deep down, that one day she wanted to build something of her own.
But first, she needed to prove herself at the highest levels of the marketing world. To get a few more impressive logos on her resume. So she kept climbing. Bigger companies, more responsibility, new challenges. She pushed herself to master every angle of digital marketing.
So when a unicorn startup opportunity came along, she saw it as the next big step in her career.
She hoped this job would take her career to the next level.
Instead, she was thrown into an understaffed, high-pressure environment with no clear roadmap.
If you’ve worked at early-stage companies, you know the drill.
She was expected to build a team, drive impact, and deliver wins, but didn’t have the resources she needed. To compensate, she worked long hours and pushed herself hard. She told herself the wins would come. But they didn’t seem to come fast enough.
The company had a highly competitive culture, which made it hard to get buy-in. And because she had always been successful before, she blamed herself for the challenges instead of recognizing the systemic issues.
Then, she started to hear offhanded comments in the hallway.
"I thought we’d be seeing more results by now."
"I figured you’d be better at this."
For the first time in her career, she felt like she was failing.
Tiffany eventually realized the company culture wasn’t a match and left to a smaller company, looking for a reset. A place where she could catch her breath after the unicorn craziness.
But it wasn’t a reset.
This company moved really fast, and if you didn’t deliver immediate wins, you were left behind. The pressure, that she was trying to take a break from, started to build even faster.
After running from one stressful startup environment to another, she was exhausted. She was revving too high from the stress and couldn’t get decent sleep.
Then, one weekend at her parents' house, things took a terrifying turn.
Her parents found her in her bed. Her body was blue and she had stopped breathing.
Her Dad had to bring her back to life!
She woke up in the hospital and could hear what people were saying. But when she tried to speak the wrong words came out.
For a month, her brain refused to process language the way it always had.
Emails looked like gibberish. Conversations didn’t come out the right way. She had built a career around communication, but suddenly she couldn’t send a coherent message anymore.
During all this time, her company kept calling to ask, “when are you coming back?”
Her parents had to answer for her, because she physically couldn’t respond.
During her recovery, she realized something major needed to change. She needed a totally different work arrangement. She hoped to stay at the company, but with fewer hours, a slower pace, and less stress.
But when she returned to the office, instead of compassion, her leaders punched down.
A senior leader said, “I don’t think you’ll ever be a successful entrepreneur. You just don’t have what it takes.”
She had given her health to this job and nearly died from the stress. And in return, they used it against her?
She walked out of that meeting knowing she was done.
A year earlier, Tiffany had met Joanna Wiebe, the Founder of Copyhackers, and a group of women at a conference. They formed a bond around being highly motivated women in tech - and developed a pact to lift each other up, push each other forward, to refuse to stay in places that dimmed their light. They called it a shine crew.
(I’ve interviewed several amazing members of the shine crew, like Gia Laudi, Talia Wolf, and Lauren Schuman)
She told them what had happened.
Their response? “You’re leaving. And here’s exactly how you’re going to do it.”
Tiffany followed their advice - and walked into the office the next day to gave her notice. The company asked her to stay on for 2 months to transition her work, which she agreed to.
But then suddenly, a week after that conversation, they called her into a meeting and said they changed their minds. Instead of a two month transition, “you’re leaving next week.”
Then one of the partners said, “I’m doing this for your health.”
That was it. Years of frustration, of being unheard, of fighting for her place in an industry that refused to see her all came to the surface.
She started counting down. Five. Four. Three.
It was a glass room, so he co-workers could see (and hear) everything going on.
Two. One.
She looked at each partner and said,“f-ck you, f-ck you, goodbye.”
Then she walked out of the office… and something crazy and unexplainable happened.
She was still wiping away tears when her phone rang. It was an old boss - one that she loved working for.
“Hey, I know this is out of the blue, but we have a PPC problem. Do you consult?”
She walked straight from the stairwell of her old office to his.
She sat down, helped his team solve their problem, and then told him exactly what happened a few hours earlier. He listened. Then he asked her a question that would change everything: “How many clients do you need?”
By the end of the day, she had three clients. By the end of the year, she had built a thriving business.
And today she's known as one of the top growth marketing consultants in the world.
Catch Tiffany’s whole story on YouTube
Or listen on Spotify
I help product-led growth leaders and teams scale smarter with:
1:1 Coaching for Growth Leaders – Guidance for heads of growth to maximize your strategy, operation system, and impact.
Advising for Product-led Teams – Strategic growth guidance for product-led teams to remove uncertainty and execute smarter