From Salesforce Client to Practice Lead: My Journey and Lessons Learned (Part 1)
This is Part 1 of a four-part series on my career journey in the Salesforce ecosystem.
My path into the Salesforce ecosystem didn’t start with a grand plan. It started with a Scrum Master role at Hagerty Insurance — a specialty insurer for classic cars — where I was leading technical teams implementing Salesforce. The project was high-profile. The work was meaningful. But I found myself increasingly disconnected from the hands-on technical work that had defined my earlier career in data and SQL.
That disconnection turned out to be the catalyst for everything that came next.
The Turning Point
I read Extreme Ownership by Jocko Willink and Leif Babin during this period, and something in it shifted how I approached my work. The core principle — taking full ownership of everything in your world — made me more proactive about identifying gaps and doing something about them instead of waiting for direction.
The gap I noticed was specific: Hagerty didn’t have internal expertise in Marketing Cloud. I’d never worked with Salesforce before. But when I looked at the platform, I recognized the underlying architecture — relational databases, SQL foundations. The technical concepts weren’t foreign. They were familiar in a new wrapper.
So I started learning it on my own.
Making the Move
That decision to self-direct into a new technology — without anyone asking me to, without a clear career path in front of me — eventually led to transitioning into the Marketing Cloud Architect role at Hagerty. It was a significant shift, and it happened because I chose to take ownership of a problem the organization had rather than staying in my lane.
What I Took Away
Four lessons from this phase have stayed with me:
Hard work generates opportunity. What looks like luck from the outside is usually preparation meeting circumstance. The foundation I built in data and SQL made Marketing Cloud learnable faster than it would have been otherwise.
Independent learning matters. Self-directed skill development isn’t just valuable early in your career — it becomes essential in consulting, where you’re often expected to get up to speed without being handed a roadmap.
Know when to seek help. Independence and collaboration aren’t opposites. The times I’ve grown fastest were when I combined my own effort with guidance from people who knew things I didn’t.
Build relationships. Trust with colleagues creates foundations that outlast any single project. The connections I made at Hagerty opened doors I didn’t anticipate for years afterward.
In Part 2, I share what the transition into consulting actually looked like — and what the first year taught me about surviving and thriving in the partner ecosystem.