10/10/2025
What's the fastest way to lose a founder's trust? I accidentally automated the process in 2022. Here's the story.
Back in 2022, I was leading a high-stakes lead generation campaign for a B2C Saas company. Our entire quarter was riding on it. After days of crafting the perfect personalized email, I loaded a list of 500 ideal prospects—mostly Founders and CEOs—into our ESP, queued the sequence, and hit send with a confident smile.
The feeling of triumph lasted about 47 seconds.
A reply popped into my inbox. It was from a Founder named Mark, and it was just two lines i assume this was a mass email, but you should probably check your merge fields. Not a great look.
My heart stopped. I frantically checked the sent folder. The first email was to Mark, but started with Hi Sarah. The next was to another CEO, but also began with Hi Sarah. I had committed the cardinal sin of cold email i sent a bulk blast and forgot to toggle the personalization tags. The {{First Name}} field was just plain text. I had just emailed 500 Founders and CEOs, calling most of them by the wrong name. Our credibility was evaporating in real-time.
That disaster taught me the most valuable lesson of my career true personalization isn't about writing one good email; it's about building a system that automatically makes each recipient feel like your only one.
The fix wasn't to scrap automation, but to master it. We rebuilt our entire process within our ESP, using:
- Smart Segmentation: No more blasting. We grouped leads by industry, role, and a specific pain point they exhibited.
- Dynamic Content Blocks: The body of the email would change to mention a relevant case study or result based on the recipient's company size.
- Behavioral Triggers: If a lead clicked a link about a specific feature, their next email would automatically follow up on that topic, by name.
The result? Our reply rate tripled. We didn't just recover from the Sarah incident; we built a pipeline that was both massively scalable and deeply human.
The real kicker? That founder, Mark, became our first major deal. He said our new outreach was the first that didn't feel like a copy-paste job.
PS: That's the power of getting it right.
