Coworking with Jonathan Wagner

Every month, we feature you, our talented and insightful Revenue Brew readers! Want to be featured in an upcoming edition? Introduce yourself here. This interview has been lightly edited for style and clarity.

Jonathan Wagner is chief growth officer at Alianza.

What’s the most ridiculous expense you’ve filed? Eighty dollars for a room service salad and fries at 2am—after flight delays, cancellations, and no open restaurants. The food itself was about $40. The other $40? Taxes, service charges, and what I can only assume was a line item called “because we can.”

What’s the hardest deal you’ve closed/worked on? A renewal with a legacy [telecommunications company] that genuinely believed their 2007 perpetual license included cloud-native AI upgrades, future innovation, and maybe immortality. It was like selling Spotify to someone still clinging to their iPod Classic and insisting it should update itself. It took six months, three executive escalations, and a whiteboard session titled, “What you actually bought.” Time travel wasn’t in scope, but somehow we landed it.

What’s your favorite deal you’ve closed/worked on? A deal where we helped a customer realize they didn’t have to just enable the user experience, they could actually own it again. Watching a 100-year-old telco rediscover its relevance? Better than quota relief.

One thing we can’t guess about your job from your LinkedIn profile: What you won’t see on LinkedIn: I split my time between navigating tough escalations and celebrating big wins—same steakhouse, same Napa Cab, different vibe. Either way, we’re raising a glass, though the quality (and quantity) of the wine may vary. Because that’s where trust gets built and where the real work happens.

What’s the best piece of work-related advice you’ve gotten? “Bad news doesn’t get better with age.” Rip the Band-Aid, take the hit, and get to work. Nobody wins when you wait.