War stories
Every seller has wins they're proud of and losses that taught them the most. These are mine, told honestly.
Head of Advertising Creative Studio
Met in the office again and closed the pilot, then introduced us to the Marketing team for the campaign side
Partnerships Manager
Met in person at the Uber office
Strategic Partnerships Manager
Met at the in person conference eTail Boston
Marriott started as inbound PQLs: low-tier or free trial users signing up for the platform at the individual property level, far below the enterprise deal we were really selling.
Instead of treating those sign-ups as small one-off accounts, I packaged their usage into pre-built user experiences that could easily be deployed at a macro level across the portfolio. That built a strong, active user base that was ready to be switched on at the corporate level when the Head of Brand & Creative at Marriott approached us for their 2027 campaign launch.
Lesson: Free and low-tier users are not small deals; they are proof of value waiting to scale. Nurture PQLs and the enterprise deal writes itself.
As AE, Onboarding, demo-to-close conversion sat at 25% and prospects were treating demos as passive show-and-tell.
I changed the format so clients used the product inside the demo instead of watching it. Conversion metrics moved from 25% to 33%, and the play was rolled out to the entire sales org.
Lesson: Getting the client hands-on turns a demo into a purchase decision. Small process changes can outperform any pitch deck.
The pandemic shut down every event venue overnight. There was no playbook for selling a virtual event platform, and I was carrying pipelines from other verticals at the same time.
I built the sales motion from zero: the methodology, the partnership with product and dev on functionality, and the onboarding of the entire sales org to the new platform. Over the three years that followed it generated $10M in revenue and I beat targets by 10%.
Lesson: When the market changes faster than the company, the rep who writes the playbook first owns the category.
I joined Uber Eats Strategic Partnerships managing 800+ high-value East Coast accounts in the middle of significant organizational restructuring.
I missed my first quarter ramping at 70% and my second at 95%. The restructuring kept changing who I sold to and how, and I tried to run my old playbook instead of rebuilding for the new reality. By the third quarter I had adjusted, hit 130%, and was pacing at 100% when I left.
Lesson: When the org changes around you, rebuild the motion immediately instead of forcing the old one. Constant change is a skill, and I learned it the expensive way.
A BDR booked a meeting with the events team at JetBlue. In my initial research on the ICP, she seemed to sit on the wrong team: conferences and events instead of the experiential events and marketing side we typically target.
I slacked on my preparation, figuring I would give a high-level overview and use the call to find the right people on the marketing side. When I joined, there were 3 additional people I didn't recognize, and they immediately identified themselves as the exact individuals I should have been pitching to. My materials weren't built for them: I pitched the wrong use cases, and they weren't interested because the preparation wasn't built for their needs. I was unable to recover and never secured the next meeting. Afterward, I went through the call with my manager to comb through how I could have approached it differently.
Lesson: Always be overprepared and stay on your toes for wherever the conversation may take you.