The category didn’t exist yet, but my job was to convince Fortune 500 CIOs it already did

From 2008 to 2012 — through Apptio‘s $50M Series D round — I led communications and PR (while at Barokas PR) for a startup with a problem most founders would kill for: real product, real customers, real traction. But founder Sunny Gupta also had a problem most never see coming: the market had no name for what Apptio’s technology provided its ICP: Fortune 500 CIOs.

We weren’t selling against a competitor. We were selling against a blank space. Enterprise IT departments had never been asked to justify their spend the way a sales team justifies pipeline or a marketing team justifies CAC. IT was a cost center. IT got a budget, IT spent the budget, and nobody asked it to defend the return the way they’d interrogate any other line of business.

The cobbler’s children have no shoes

Sunny and the team built the software to change that. My job was to convince the people who ran IT at Fortune 500 companies – CIOs who’d spent their entire careers being asked to cut budget, never to account for it like a business — that a whole new discipline was worth their time, their credibility, and eventually their budget line. As we often put it, the cobbler’s children had no shoes.

From the near beginning, we called it Technology Business Management, but nobody else called it — or asked for it — by name. Not right away. That was the whole problem. We’d most often hear “IT cost transparency” or IT financial management (ITFM), and even “cloud costing” or the IT economics.

The facts were never the problem

Here’s what I learned: the facts were never in dispute. Every CIO in the room already knew IT spend was opaque, that they couldn’t answer basic questions like “what does this application actually cost us” or “are we overspending relative to peers.” That wasn’t news to them. What they didn’t have was a frame—a way to talk about IT that let them walk into a board meeting and sound like a business leader instead of a request line.

Giving them the data wasn’t the persuasive act, but giving them the language was.

How the category sold itself

We didn’t lead with product specs. We convened the people who’d become the category’s first believers — hosting CIOs in the same room to compare notes on a problem they’d each assumed was theirs alone — and let them discover, out loud, to each other, that this was a shared, nameable, solvable thing. By the time that group formalized into what’s now known as the TBM Council, the persuasion had already happened. Nobody needed to be sold anymore; they’d co-authored the pitch.

That’s the part of PR nobody puts on a “traits of successful founders” list. It’s not enough to have the truth on your side. You have to build the frame that lets someone else say the truth out loud, in their own voice, to their own boss — and believe it was their idea to say it.

While I only worked with Sunny and Apptio to Series D, if you fast-forward to 2023, you’ll see that IBM acquired Apptio for $4.6 billion.

Full circle: IBM, and what Sunny’s building next

If you’re interested in following Sunny’s entrepreneurial journey, he recently reunited with his former Apptio cofounder, Kurt Shintaffer, at Thira (an enterprise AI startup) — which recently announced $21M in seed funding led by Madrona and Matt McIllwain, a multi-round Apptio investor who also served on its board of directors. Matt and Madrona are calling it the “biggest opportunity yet”. Can’t wait to see what happens.

FWIW, the company says, “Thira is AI to handle the behind-the-scenes tasks that keep big companies running, like setting up a new hire’s laptop, resetting a locked account, or approving a software purchase. The pitch is to enable a “back-office that runs itself.”

Five things that experience taught me about persuasion (and rhetoric)

1. Name the problem before you name the product. CIOs didn’t wake up wanting “Apptio.” They woke up unable to answer a question their CFO kept asking. We built the vocabulary for that question before we ever pitched the software that answered it.

2. Let your believers become your validators, not just your references. A customer quote in a press release is nice. A customer standing up in a room of their peers, unprompted, saying “we have this exact problem” is category-defining. If your buyers won’t say it to each other, they’re not ready to say it publicly yet.

3. Borrow the vocabulary your buyer already trusts. We didn’t invent new language from nothing. We applied the logic CIOs already respected (supply chain thinking, cost accounting, business-unit accountability) to a category they’d never had permission to think about that way. Persuasion is easier when you’re reframing something familiar, not asking someone to learn a new language from zero.

4. Build the case for the category before you push the product. If people don’t yet believe the problem is real and urgent, your product pitch is premature and you’re answering a question no one’s asked yet. Get agreement on the problem first.

5. Time your rhetoric to your proof. We didn’t push the category message before we had real customers wrestling with the real problem in the room. Persuasion without evidence is just a good story; persuasion timed to proof is a movement people want to join.

Long story short, none of this shows up on Harvard or other lists of founder traits. While curiosity and risk tolerance will get you to a good product, they won’t get a room full of skeptical Fortune 500 executives to adopt a category that didn’t exist six months earlier. That takes persuasion and rhetoric. Not great at either? Don’t worry, both are crafts (not personality traits) and 100% learnable.

Let’s work together

If you’re a founder trying to build category language, land press, or get a room of skeptics to say your problem out loud before you’ve pitched them anything — that’s exactly the kind of work I do. Shoot me an email: lindsey at lindsbcomms dot com.