Why Outmarket AI?
At first, it was the role. Founding Head of Marketing – building an entire marketing function from zero to one. That’s my dream job. I’ve done it once before, and it really was a dream. But this time, it would be bigger: leading a team like an orchestra, watching strategy take shape while keeping my hands on the baton.
So I tailored my resume, applied, and started recording video responses to the screening interview questions. And then I got bold: I booked a flight to San Diego to connect with the Outmarket team at a WSIA conference.
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The Bold Flight
Here’s a confession: WSIA is a members-only event, and I’m not a member. But I was about to be. As Outmarket AI’s Founding Head of Marketing, of course.
When the registration form asked for a company, I chose: Outmarket AI.
When it required a company email, I… provided mine.
I’d already booked the flight and hotel, so at that point it was: “Why not see if this works?” I assumed it wouldn’t, and I would just have to cancel my plans. No big deal.
But it did work. My credit card was charged $1,000, and I was registered. Okay then, here we go!
I arrived in San Diego listening to Soundtracks by Jon Acuff. If you’ve read it, you know why. Here’s my 500th recommendation: grab the Audible version – Jon reads it himself.
When badge pickup asked, “Outmarket AI?” I smiled and said, “Yep!” because yes, that is the company I’m interested in here.
The Sideways Landing
That morning — this morning — sitting in my hotel room, ready to head to the conference, I refreshed LinkedIn one last time to review names and faces.
And there it was: a post from CEO Vishal Sankhla announcing Outmarket AI’s very first Head of Marketing.
The post was fifteen minutes old.
I laughed out loud. Sometimes timing is poetic. Sometimes bold moves land… and sometimes they land sideways.
I went back to check my application. Sure enough, I could still record more video screening responses before they started reviewing applications in 3 days.
Well, good news for the hiring team: you don’t need to review my responses after all. The role’s already filled.
But wait…
Katherine’s going to need a team, right?
Beyond the Role
I had to ask myself… was it just about the role, or is there something about the product and vision that makes me want to be part of Outmarket no matter what?
The answer is yes. Definitely yes.
It’s not that I’ve spent my career in insurance; I haven’t. But I’ve spent my career in SaaS, building systems, telling stories, and helping customers win. That’s the lens I bring.
More to the point, I’ve seen what an industry-defining narrative looks like, and Outmarket has it.
Infusionsoft (now Keap) created and dominated the category of all-in-one sales and marketing automation for small businesses. If you’ve ever heard of Lifecycle Marketing, that’s them. Google it, and here’s what you’ll find:
Outmarket AI reminds me of Infusionsoft in those early days, but with even more potential.
Outmarket AI Will Win
Outmarket has a product that will redirect the flow of the insurance industry the way a seismic event causes a river to cut a new course. The efficiency gains are staggering, and their early adopters are already saying so out loud:
They have the right product for the right problem at the right time, and advisors like Alpesh Patel, who scaled DocuSign’s enterprise business from $200M to $2B. That kind of experience is rocket fuel, and developing hand-in-hand with early adopters is key to building a great product.
I see it. Alpesh sees it. Katherine sees it. Outmarket AI is going to win, and they’re going to shake up an entire industry. It’s just a matter of building the systems to keep up and then course-correcting along the way.
Always Building
So yes, the Head of Marketing role I had my eye on is filled. I’m sitting here in San Diego with an “Outmarket AI” badge, equal parts eager and uninvited. But I’m still working, still serving my SaaS clients, still creating.
By the way, if you ever need to find me at a conference full of company-issued laptops, I’ll be the one with the stickers, still building.
Because sideways isn’t failure. Sideways is movement.