Case Studies
A closer look at what enterprise GTM work looks like in practice.
Why I Made This Move
A former Bluecore co-founder left to start something new, raised seed funding, and called me. He said: "I need someone who can build GTM from scratch. You're the first business hire. Interested?" I had just spent two years managing a team at Bluecore. I was good at it. But I wondered: could I do the 0→1 thing? Could I build something from nothing?
The Challenge
Zero revenue. Zero product. Zero brand. Three engineers and a founder. I hired a team of 3 (sales, marketing, CS) and we had to figure out everything: positioning, ICP, pricing, messaging, sales process, demo strategy. Oh, and we launched a conversational shopping agent for ecommerce retailers—six months before Amazon launched Rufus to do the exact same thing. Great idea, tough timing.
What I Did
We bootstrapped everything. I built the go-to-market strategy with the founders, created the first pitch deck, ran discovery calls, closed the first deals, hired the team, and managed up to investors. We went all-in on conference presence—bootstrapped two major shows ourselves for demand gen. Took every meeting. Iterated constantly. Grinded to $1M ARR in 18 months. Then our old friends at Bluecore acquired us in October 2024.
The Numbers
- •First business hire (non-founder, non-engineer)
- •$0 → $1M ARR in 18 months
- •Built team of 3 from scratch
- •88% pilot-to-paid conversion
- •Post-acquisition: Leading 15-person GTM org at Bluecore
What I Learned
Zero-to-one is humbling. At Bluecore I had brand, product-market fit, inbound leads, and budget. At alby we had none of that. It taught me what founders deal with every day. It also taught me that relationships matter—getting acquired by Bluecore was a full-circle moment and a testament to the trust I'd built over the years. Now I'm back at Bluecore leading the combined GTM team for their AI agent product. Turns out you can go home again.
Why I Made This Move
I built the SE function, proved I could hire and lead, and learned the product inside-out. But I wanted to carry a number. I wanted to see if I could actually close. So I switched to Enterprise New Business—the hardest role in the company. Fresh territory, long sales cycles, seven-figure deals.
The Challenge
The perfect storm of timing, territory, and maybe some talent. I had deep product knowledge (former SE) and understood the technical side better than any rep. But I quickly learned: you can't do everything yourself. I had to trust my SE team. I also learned how hard it is to build pipeline—not just close deals that land in your lap.
What I Did
I leaned into MEDDIC qualification hard. I became the most accurate forecaster on the team because I refused to put garbage in my pipeline. If it didn't meet qualification criteria, I killed it early or handed it to SMB. I focused on fewer, bigger deals with real champions and economic buyers. And I leveraged my SE team ruthlessly—I stopped trying to be the technical hero.
The Numbers
- •FY'19: #1 Rep, 323% of $1.00M quota, President's Club
- •FY'20: #1 Rep, 512% of $1.00M quota, President's Club
- •FY'21: #1 Rep, 176% of $1.25M quota, President's Club
- •Promoted to Director, led team of 6 reps with $6M team quota
- •FY'23: 112% of $6M team quota as first-time manager
What I Learned
Individual contributor excellence doesn't automatically translate to management. It took me two years as a manager to figure it out—my first year (FY'22) we hit 77% and I had to exit 3 reps. The second year (FY'23) we hit 112%. Leadership is different from selling. But the foundation—qualification, forecasting accuracy, leveraging resources—that's what scales.
Why I Made This Move
After three years at Oracle, I wanted to build something from scratch at a smaller company. Bluecore had strong product-market fit but was stuck doing transactional deals. Reps were running their own demos and closing $50K deals. I saw an opportunity: what if we built a real enterprise sales motion?
The Challenge
Sales Engineering didn't exist at Bluecore. Reps were doing everything themselves, which worked when the product was additive (add our email tool to your stack). But the product had evolved into a replacement sale—rip out your existing platform and replace it with ours. That's a different motion. It requires technical depth, custom demos, and someone who can overcome objections without the desperation of a quota-carrying rep.
What I Did
I convinced the SVP of Sales to let me build it. Hired and ramped 5 Sales Engineers in the first 6 months. Installed a qualification framework so we only brought SEs into real opportunities. Built demo environments, pitch certifications, and a technical discovery process. The result? Average deal size went from $50K to $250K+.
The Numbers
- •Founded SE org reporting to SVP of Sales
- •0→6 people in first year
- •Standardized technical sales process
- •Enabled team to close first ever $1M+ deals
What I Learned
Two things: First, building a function from zero is incredibly satisfying. Second, I realized I wanted to be even closer to revenue. I loved seeing deals close, but I wanted to own the number. This was my path to VP of Sales or CRO—not staying in engineering/product. So I made the switch to carrying a bag.
Why I Made This Move
I joined Oracle the way 80% of Oracle employees do—through acquisition. When Responsys got acquired, I could have left. Instead, I saw an opportunity to learn how enterprise software actually works at scale. I wanted to understand the machine before trying to build one.
The Challenge
Big tech is organized chaos. Overlay sales reps, overlay sales engineers, competing internal priorities, and a thousand cooks in the kitchen. Meanwhile, customers just want their problems solved. The challenge wasn't the technology—it was figuring out how to deliver value while hiding all the internal complexity from the customer.
What I Did
I became a translator. Externally, I learned to run enterprise sales cycles—discovery, demo, business case, RFP, negotiation. Internally, I learned to navigate Oracle's matrix and rally the right resources without exposing customers to the mess. I also became GTM owner for Gartner and Forrester reports, learning how to position products for analysts. Most importantly, I invested in world-class training: Challenger Sale and Demo2Win. That training shaped everything that came after.
The Numbers
- •FY'14: 114% of $1.0M SE quota
- •FY'15: 151% of $1.4M SE quota
- •FY'16: 91% of $1.6M SE quota
- •Promoted to Principal SE within 3 years
What I Learned
Process and structure aren't the enemy—they're what enable scale. The best salespeople protect their customers from internal chaos. And if you want to sell enterprise software, you need to understand how buyers actually evaluate and buy it. Oracle gave me the foundation I've built everything else on.
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