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Coworking

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. This interview has been lightly edited for style and clarity.

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.

What’s the hardest deal you’ve closed/worked on? 

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.

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

 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.

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

 “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.

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

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 Dana Lacey

Coworking with Veronica Tello

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