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. 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.


Coworking with Jonathan Wagner

He’s the chief growth officer at Alianza.

Mike Valli is chief commercial officer at symplr.

What’s the most ridiculous expense you've filed?

 I spent $100k on a single expense in a prior role. It was an executive forum I was hosting at a nicer location that was considered to be a bit of a destination with golf, amazing food, and a whole lot of face time. My goal was to bring as many of our customers together as possible so we could all engage, network, and learn from one another.

I’m a huge believer that developing relationships and earning trust comes from spending quality time together in person. What I found is that customers often get just as much out of interacting and learning from their peers than with the so called “experts.” Sometimes the best insights come simply from swapping stories over a drink or on the back nine.

So these types of events that also throw in some fun and appreciation for customers are just a win-win all around. Can they be over the top? Sometimes, but it’s always worth every penny.

I closed a billion-dollar managed services deal with a rural health system. It was the kind of deal where the contract alone was over 1,000 pages and the negotiation took 9 months.

What’s your favorite deal you’ve closed/worked on?

 Actually, the same deal as referenced above. It’s the most complex, creative, and innovative deals where you often learn and grow the most.

I spend a fair amount of time with other parts of the business and supporting broader organizational initiatives. I spend a ton of time in areas like M&A, sales, delivery, operations.

What’s the best piece of work-related advice you’ve gotten? 

“Eat change for breakfast.” Change can feel scary and it’s easy for negative feelings to creep in, but it’s important to realize it is just a perception of a situation.

Mike Valli is chief commercial officer at symplr

He’s the chief commercial officer at symplr. 

Coworking with Mike Valli

Dana Lacey is the founder of Dana Lacey Consulting.

What’s the most ridiculous expense you've filed? 

Approximately 1 million chicken sandwiches from LGA’s Shake Shack, over six years, as I travel often.

My most difficult deal took about two years to close. I had to convince more than two dozen companies to work together to create a unique product partnership. A lot of time was spent helping executives grasp an entirely unfamiliar mental model. There was a ton of risk and a significant engineering challenge. If we were successful, nobody would see any ROI for at least a year.

The hardest part was creating urgency. No one wanted to be first, and trust never comes easily. I built confidence by being direct and setting see-through expectations. My trusty sales dek went through dozens of iterations to tackle confusion and existential concerns. I had to develop a range of incentives, from thought leadership to user research to straight up cash. I convinced my leadership team to invest in product, marketing, and engineering resources that lightened the load for our partners. I even hosted meet-cutes that inspired friendships and vibes across roles and businesses.

 I closed a deal with a major publisher literally a minute before the go-live deadline for Twitter Blue, a brand new consumer subscription. I was on three conference calls at once: the publisher’s lawyers, our lawyers, and an extremely antsy product team. The redlines had everyone tripped up. Our engineers wanted to launch without them, my manager wanted me to be meaner, and the lawyers wanted what lawyers always want—to get their way.

Ultimately I made everyone comfy with the trade-offs, and we flipped the switch just in time.

What’s one thing we can’t guess about your job from your LinkedIn profile?

 Inadvertent therapy for clients facing change.

 “You don’t have to do anything you don’t want to do.” This had never occurred to me as an option. A lot of my bosses have wanted me to be more aggressive with prospects and partners. Ignoring that advice has helped me build trust, transparency, and empathy—key ingredients to equitable, long-lasting relationships. It has also served me well as an entrepreneur, where the pressure to build is blinding. I’m proud to say I no longer work with assholes, I don’t cross my boundaries, and I never abandon my values. Best of all: zero meetings on Fridays.

Coworking with Dana Lacey

 She’s the founder of Dana Lacey Consulting. 

Veronica Tello is senior team lead, product support at Squarespace.

Getting people to care about development. I talked about it nonstop for a year until it became part of our team’s DNA. I could see the path to development. I just helped clear the way there.

 A wellness challenge that raised $2,000 for women’s rights and made work fun again (and not too, too cringy). Authentic engagement with impact is my jam and what invigorates me for work.

 Most of my job happens in small moments over months of one-on-ones and hard convos that eventually lead to big shifts. We celebrate the big shifts, but the magic really happens when it is just me, my direct report, and the problem we’re facing.

 We’re blind to our own expertise; lean into what you love and what comes easy because that’s where you add the most value; things don’t have to be hard for us to deserve it, we just have to be.

Coworking with Veronica Tello

She’s senior team lead, product support at Squarespace. 

Coworking is our Q&A for revenue organization leaders, managers, and employees. Sound like you? Share your career highlights with Revenue Brew, and you may be featured in an upcoming newsletter and on our website.

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Coworking

Coworking with Jonathan Wagner

Coworking with Mike Valli

Coworking with Dana Lacey

Coworking with Veronica Tello

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