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I quit my job last week
Reflections on 8+ years

I quit my job last week
Reflections on 8+ years
Read Time = 3 minutes
Eight years. One hell of a run.
I joined the company right before our Series A — we’ve grown into a $60M+ business owned by a relentless PE firm.
Yesterday was my last day.
I was hired as an AE and bounced around reporting to our Founder, CEO, COO, and Director of Sales. It was a struggle at the beginning, but I was good at building pipeline. I knew CRM reporting, cold email, cold calling, and how to run discovery. I won with volume.
Eventually, the Founder asked if I wanted to build the outbound channel. I took the job so I could learn how to manage people and build a team.
(Side comment — sports helped me a ton here. I hadn’t managed people, but I had been on teams. Playing sports taught me how to perform under pressure, be coachable, and work as part of a team. The most underrated thing about sports is that it teaches you how to fail in public.)
I scaled the BDR team to 10 people. It was a lot of work and fun as hell. I hired a buddy from college as my Team Lead and my brother as our intern haha.
My job became creating processes, hiring, running 1:1s, and coaching. I was building the playbook as I went. The team was performing well, contributing 40% of the company’s revenue. A couple of years in, we got bought by a PE firm.
As part of the transaction, the PE firm merged us with another company. “Mergers” are weird because everyone kind of feels equal at the start. It took months to integrate people, quarters to integrate processes, and years to integrate technology.
I got promoted to Director a couple of months in and was responsible for managing my 10 BDRs plus six from the other company (they were inbound).
I was overwhelmed and immediately hired two Managers. A couple of years went by — the post-COVID tech run slowed, and we were heading for a RIF. The next year or so sucked, and I realized my dream of managing a team of 25+ was over.
In 2022, I was bored of managing a shrinking BDR team. That’s when I started writing online. My goal was to share my learnings and experience to help founders and startups build outbound GTM channels. It took six months, but I started gaining traction, bringing in $3–5K a month.
I kept my W2 throughout and went to my boss asking if he’d help me transition out of the role. He asked what I wanted to do, and I told him: “Partnerships”
(This was an asymmetrical bet for me. The average company in our industry was generating 20–30% of revenue from channel partners. We were at 2%)
Over the next three months, I groomed my replacement on the BDR side. In the evenings, I built partner relationships — mostly by cold emailing PEs and accounting firms where we shared three or more mutual customers.
Finally, I presented my case for running the partner channel to the CEO and ELT team. Since I was already doing the job, it made it easier for them to say yes. I was off to the races building partnerships alongside our Head of Strategy.
(Another side note — I’m often asked about getting hired. The biggest thing I’ve learned: do the job to get the job. For an SDR, that might mean prospecting hiring managers, reaching out, starting conversations, and selling yourself. Easier said than done, I know)
Building our partner channel was a grind for the first 6–12 months. It took way longer than I thought to generate consistent referrals. Eventually, I started meeting more people in person and developing real relationships that helped move the ball forward.
It took about 16 months for the flywheel to really start moving. We had a dozen partners sending 2–4 referrals each quarter. We hit $1M in revenue generated and finally got some budget and additional headcount.
What I learned throughout this journey is that I thrive on building GTM process. I helped grow three separate channels to $1M+ in revenue during my time. I’ve also realized I’m a bit of a sicko in that once things reach a certain level of stability or success, I start to get bored.
So when company growth slowed and we cleaned out the C-suite, I started looking around. Then an old connection called - and a 30-minute conversation opened the door to a new adventure.
#moretocome
Until Thursday,
TSG
P.S. I reply to all emails.