Embracing Change: My Journey from Sales to Pricing

During my time at London Business School, I often heard the advice: "When making a career shift, try to change only one of these—your role, your industry, or your geography—but never all three at once." It’s a smart, pragmatic approach, one that many of my brilliant classmates have followed. And yet, here I am, doing exactly what I was told not to, leaving sales for consulting (or maybe even founding something of my own), moving from niche B2B SaaS into a broader consulting space, and relocating from London back to Colorado.

A major driver of my decision to pursue an Executive MBA in late 2022 was the realization that I wanted to move beyond sales. I was good, but not great and I knew deep down that I lacked the drive to push myself toward that final 1% that separates the best from the rest. My interests had started shifting. Instead of focusing solely on closing deals, I was thinking about bigger, systemic issues—how prospects evaluated our product, where our packaging and pricing fell short, and how we could capture more value.

I’m also a numbers guy. Yes, sales is a metric-driven profession, but it often comes down to a binary outcome: did you hit your number or not? The cycle of living from quota to quota, deal to deal, felt increasingly unfulfilling. Then, in the fall of 2023, my employer decided for me, letting me go and push me to fully commit to a new path.

Why Pricing?

During my 11 years in B2B SaaS, I led international expansion twice and brought a new product to market. I often worked in uncharted waters with no historical data, no established client base, just a small team, a strategy, and a lot of execution. I mapped out the addressable market, created GTM content, built pricing sensitivity models, ran demos, attended conferences, and negotiated deals with some of the top investors in the world.

As I move from sales into consulting, I’m leaning into this experience—the years spent understanding prospects, uncovering pain points, and figuring out what truly drives buying behavior.

So, why pricing? Because it’s a fascinating, often misunderstood lever that can make or break a company. Pricing in B2B SaaS is particularly complex, with the added layer of subscription services creating an ongoing exchange of value between vendor and customer. Businesses don’t buy like individuals, and pricing strategy isn’t just about setting a number, it’s about monetization, incentive structures, packaging, and the mechanics of the exchange itself.

How should a company charge for its product? How do you incentivize a sales team to maximize value capture? How does pricing affect retention, expansion, and overall company health? These are the questions I encountered daily in sales, but never had the bandwidth to fully explore. Now, they’re the questions I want to dedicate my career to answering.

The Road Here

Committing to this new direction wasn’t easy, and it didn’t happen overnight. The past year and a half have been a grind, moving my family across the Atlantic, searching for answers about what’s next, and hitting more than a few dead ends along the way. At one point, I even considered taking one more sales gig, convincing myself it might be the safer choice.

Then came the final interview, a seven-hour marathon that I completely bombed. Halfway through, they dropped me from the process. It was a low point, one that led to a lot of questioning and self-doubt. But in hindsight, it was exactly what I needed.

That moment forced me to be honest with myself: I wasn’t just looking for a new job—I was looking for a new challenge, a new way to apply my skills, and a space where I could make a real impact.

So here I am, taking the path that’s not recommended, making the leap that many would call risky. But I’m doing it with conviction, with a clear sense of why, and with the belief that pricing is where I can make a real difference.