Freehand CRO Jim Hilbert on how AI speeds GTM workflows

Jim Hilbert, chief revenue officer of agentic AI studio Freehand, is no stranger to the CRO role, having headed up revenue multiple times over his decades-long career in the B2B SaaS world.

Thanks to AI, the last few years have brought some of the most consequential changes to go-to-market organizations he’s seen.

“More so than ever for me, I have this thing on my shoulder: ‘Jim, you’ve got to go faster on AI,’” Hilbert told Morning Brew. “I’ve just hired three sellers in the last month, which normally would have taken me six months, [and] in two weeks they were able to get on the phone and start having conversations with customers, just by going through the onboarding that we built through AI…That’s a huge change.”

Freehand (formerly Pando) launched in February. The San Francisco-based startup uses AI to automate supply chain spending and procurement. With AI dramatically speeding up the pace at which the revenue organization operates, Freehand recently launched a growth expansion team and is eyeing new geographies and markets beyond freight. Freehand says it’s already working with Fortune 500 clients, and can cut manual procurement and sourcing work by up to half and reduce reconciliation and accounts payable cycle times by up to 90%.

“Our go-to-market is very focused on very, very large strategic enterprises,” Hilbert said. “With AI, this year I’m also starting to go down into the lower enterprise mid-market space and really getting focused on having more logos as well as just the largest brands on the globe.”

This conversation has been edited for length and clarity.

How have AI and automation changed your job?

It’s mostly just given me productivity gains to-date. All the things that I would work with my sales or rev ops teams on, they’re now using AI to get better dashboards for me. We can focus more on the different segments, whether it’s SMB, mid-market, enterprise, strategic, what’s working, what’s not working, do analysis of the [total addressable market] better than we’ve ever had before.

When I look at my current customers, how do we expand in those, and what are the opportunities to expand, doing the research on those large companies. We’ve sold into one division or one [geography] of a very large brand. How do I penetrate and go further?...Just using AI is able to help me keep up with that more on a real-time basis, instead of after the quarter or after the year end. And then just managing the funnel, whether that’s early pipeline or that’s late-stage, figuring out, how do I get movement within the funnel faster, how do I convert faster, and how do I close faster? And tying all that back to the product. In the past, there was a middle group, product—it was between me and engineering. With AI, that’s all now come together—engineering, product, and the go-to market team. It’s hard to know where the boundaries are, because we’re all working within each other’s lines, trying to drive productivity and efficiency across the org.

What’s the importance of driving predictable, sustainable growth?

Predictable, consistent growth is key. When we started, we went very hard after the large enterprises…That’s kind of where I sit at the intersection of right now: How do I get into the lower-level enterprise, call it $1 billion to $5 billion companies, and continue to have those very, very large whales that we’re closing at the $5 billion [mark] and above, and I think the biggest thing for me to get total consistency on that is going to be getting into the mid-market. We were prevented from mid-market only because the product was so complex when it was a SaaS product…The implementation time was the same, whether it was a $50,000 deal or a million-dollar ARR deal. There wasn’t much time difference, so we kind of pulled back from that market. But with AI now, the speed of AI, I can do the same thing for a mid-market that I can for a large enterprise, and the timing is almost identical.

How big an opportunity does that open up?

It’s big, because sales cycles used to be, in the large enterprise, nine months to a year. We can get those done in three to six months now. The implementations used to take a year; we can get those done in under three months, in some cases…And however fast [the customer is] wanting to go, we can go as fast or faster than they even expect. So it’s important: It really shortens sales cycle, time to revenue, everything gets a better push with the AI leverage.

What goals are you and your team focused on right now?

Funnel, funnel, funnel, right? And pipeline conversion is super, super important. Landing those logos is more important, quite frankly, this year, and probably into next year, given the size of our company, than getting the big seven-figure deals. They’re almost equal. If I could do 20 logos and get to seven figures versus one and get to seven figures, those 20 are pretty important to us.

The second would be, we just broke out this year with the growth expansion team, and it’s going to be very important for us, back to this pipeline consistency of making sure we’re growing our customer base with all the new products that we’re putting out. Products are coming out much faster because of AI as well. What used to take maybe months for me to get a new product, a customer can have an idea that comes to our customer advisory board or comes from the field, and we can turn a product around in 30 days.

What do the AI-driven productivity gains mean for your approach to hiring, training and retaining employees?

That’s all changing. Even using AI to research the candidates and things that I didn’t have time to do before, now I have time to do. It changes everything. I’m really today looking for people that have had the last year, year and a half, and they’ve done something with AI, they can actually come to the interview and show me use cases of what they’ve done to improve their own productivity, or what they did to do research on an opportunity, or what they’ve done with a customer implementation. If I’m hiring somebody on the delivery team, how have they used AI to make things go faster, and what is their competency level? Everyone at Freehand gets a Claude license, and we’re measured on tokens as well. That’s a new thing. As I look at productivity and look at what the sellers and the solution consultants are doing, I can look at tokens now as to how fast they’re really running toward their goals.

What has been helpful for you to evolve with the role and stay up to speed?

Really relying on Claude, literally questioning Claude: “What are my peers doing, what is the market doing right now? I want to go enter this new vertical. What are going to be my challenges entering that vertical? Tell me about that vertical. What’s the size? What’s the TAM? What’s the average revenue? Are these guys running on 5% margin or is it an 80% margin business? Show me the high growth companies within this vertical.” All of that I’m doing through Claude today.