Rebuilt Dealroom's GTM From Scratch and Grew ARR From $3.5M to $12M In Under 3 Years

Out of all the ranking and back and forth, we landed on a clear ICP: PE-backed roll-ups doing 3+ acquisitions per year in North America.

Rebuilding the positioning around pain

I came up through product marketing (Salesforce, then building PMM teams), so my move was to go straight into positioning and messaging. What Dealroom was saying wasn't wrong. It just wasn't differentiated, and it wasn't speaking to that ICP. Nothing we were putting out would "stop the scroll." If you were in corp dev and saw it, you'd think, meh, okay.

I interviewed a bunch of customers, and I listened to individual Gong calls filtered by prospect type. I'm a big believer in aspirin versus vitamin messaging, something I learned from Greg. You don't need a vitamin, but you need aspirin. So I dug into three layers: what are your pains, what's the negative business impact of those pains, and what does that mean when you're talking to your CFO, who is the final decision maker.

That last layer is where a lot of messaging falls flat. People stop at the pain and never tie it back to the business, so the champion can't sell internally. We worked it all the way through. Dealroom makes you faster. Okay, so what does that mean? I can do more deals. How many more in a year? What's your PE target? Now you can talk to a CFO and sell the positive business impact of DealRoom

Testing it with sales first

My first step was to test the new messaging with the sales team. I'd built it alongside our VP of Sales and the sales and CS folks who were most involved, so we enabled the team on a core slide deck, had them pitch it to prospects, and watched what stuck. We learned a ton and made a lot of tweaks.

From there we pushed it to the website, starting with the homepage, then the platform and pricing pages since those were our top pages. We watched conversion to make sure nothing dropped. It didn't, and we saw positive momentum. Only after that did it go into paid social, email, and the video content we were doing on YouTube.

Building it with sales instead of handing it to them mattered a lot. At a company this size there's no space for marketing and sales not being aligned, because it just blows up. We created key alignment and good will that stands to this day between teams. It bought sales in on what marketing could do.

Building the measurement layer

We rolled out campaigns, UTMs where relevant, basic reporting, and lead scoring to lay the foundation. My team owned the full pipeline number (sales qualified leads), not just marketing-influenced. I think it's silly to only own marketing, and owning all of it meant our starting point with sales was always "if inbound is down, how can I help you with outbound?"

Results

In my time at Dealroom, ARR grew from about $3.5 million to $12 million. Our quarterly new bookings targets went from around $400K to $500K when I started to about $1 million when I left. SQLs went from about 63 a quarter to 150 per quarter.

Figuring out what to sell was a big part of it too. We used to sell a single piece of the platform on its own, and those customers would churn. We stopped. Q1 this year was a tough retention quarter because of all the non-ICP customers we'd sold to earlier, but by Q2 and Q3 things had leveled out. Obviously this feels tough initially to a sales team, but they are now seeing that selling to the right ICP meant bigger, multi-year deals.

I can't take all the credit. We had a great new sales leader, a great sales team, and CS figuring out their part. But it started with getting focused on who we were for.

Key metrics

• ARR: ~$3.5M to $12M

• SQLs per quarter: ~63 to 150

• Quarterly new bookings target: ~$400K to $500K to ~$1M