From Salesforce Client to Practice Lead: My Journey and Lessons Learned (Part 1)
Share on LinkedInThis 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 and 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.