How My Entry Level Sales Job Helped Me Find A Huge Opportunity Years Later

My early struggles as a legal tech SDR forced me to identify first principles that eventually guided me to Ironclad

When I first joined Logikcull as an entry level sales rep in 2016, I had no idea what it would all lead to. I’d just left the practice of law for a small job at a small company, in an industry that was largely viewed by most lawyers as kind of a backwater. But the “smallness” of my role gave me the opportunity to develop some foundational insights about sales that guided me to an incredible opportunity years later.

Today I’ll share the story of how I developed those insights, and the role they played in helping me make the pivotal decision to leave sales for a community role at Ironclad.

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In late summer 2016, about a week before I started my sales job at Logikcull, I got a call from Connor,¹ my future manager. “We’re super excited to have you join, but I wanted to share some news. Our VP of Sales just left the company.”

Author’s Note: If you want more context about how I landed that job, check out How I Found My First Legal Tech Job

I told Connor it was fine—I mean, what else could I say? But after we got off the phone I couldn’t stop thinking about it. Our VP of Sales just left the company. Should I be worried? I was new to the legal tech startup space and had no idea how things worked. Was it normal to change VPs of Sales often? Or did he know something that the rest of us didn’t?

I guess I’d be lying if I wasn’t a little concerned. A big reason why I took the Logikcull job over a much higher paying alternative, was so that I could learn. I knew Connor had no experience in the legal industry and just a few years of sales experience in the technology space. I was also aware that he got his job because of a personal relationship with that VP of Sales. In that situation, would I still be able to develop as a salesperson? Or was I completely screwed?

I guess I’d find out.