The Software Cowboy and me: The non-negotiables of AI in sales

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1. HubSpot acquired Warmly, an AI-powered pipeline generation platform, earlier this year. Its founder and former CRO’s LinkedIn headline reads “Keegan Otter (Software Cowboy 🤠)” — with his headshot above it, superimposed over an AI-generated desert backdrop, in a John B. Stetson hat. He was wearing a similar one when I met him at the HubSpot office a few weeks later (and again in the Zoom call we did for this interview). Going into our first conversation, I wondered how seriously he took his shtick. Was he like a professional wrestler, hard-committing to his gimmick when hardly anyone’s watching? Not quite. Keegan’s extremely smart, incisive, and self-aware about the personal-branding mileage his “Software Cowboy” persona affords him. He’s also very clearly an authority on folding AI into sales workflows — so when I was asked to find an internal SME to interview on exactly that, he was an obvious pick. We talked about: The four agents your sales org needs to have The three nice-to-haves The one tool you can skip How to drive adoption Who you should have training your agents Here’s how it went. My Talk With the Software Cowboy I started by asking Keegan to roleplay as a consultant tasked with developing an AI-supported workflow for a relatively AI-ignorant B2B sales org. It turns out Keegan has actually done that for multiple startups — so this wasn’t exactly a “role” for him … and if you saw the rack of cowboy hats and “GET S*** DONE” poster he keeps visible behind him on Zoom, you’d know he doesn’t “play” about anything. Here’s the stage I set: The company is mostly unfamiliar with AI beyond the occasional ChatGPT-drafted email. Leadership has heard terms like “adapt or die” and “paradigm shift” enough to know leveraging AI is officially a necessity in sales, but they’re still skeptical. They ask him to start by developing an AI-supported workflow for one pod — four SDRs, two AEs, and one manager with floating RevOps support. “Traditional inbound lead generation is a quantity play — firehosing reps with contacts.” Many salespeople (and humanity at large) worry about mass AI-driven job displacement. Some might find an agent with their literal job title in its name unsettling. Keegan made it clear that this agent wouldn’t solo-replace an SDR team. He says it takes the grunt work, freeing up AEs and SDRs to focus on accounts they need and want to prioritize. Inbound Chatbot Agent Keegan’s third essential agent — and the one he’s most excited about — is an inbound chatbot agent. Any time a company is running ads, has an LLM/AEO/GEO presence driving referrals, or has landing pages for events, people are on its website at all hours. Without an agent, those off-hours leads go unattended. This agent has three key functions: Answering questions outside of working hours, non-stop Qualifying inbound leads automatically Routing them appropriately (to sales if they’re a fit — self-serve if not) During his time at Warmly, Keegan saw its inbound agent start to book more inbound meetings than human SDRs (don’t worry, this is a happy “robots outperformed humans” story!) The shift allowed reps who’d been focused on inbound prospecting to dial in on outbound. And with a different AI agent helping identify signaled accounts for outbound, those reps ended up booking more meetings with higher ACV, qualification rates, and closed revenue. Lower-Segment / Self-Serve Agent Finally, Keegan described an agent that handles leads that aren’t quite ICP fits or fall into lower segments. You still shouldn’t jump ship on them, so you give them some room to figure things out for themselves.

   In Inbound and outbound mix

2. Agents aren’t there to replace salespeople. They’re there to free up time for human-centric strategic work that drives results. However, he also mentioned that leaders should be frank about AI’s place in the future of sales, saying: “AI will not replace you — but it will replace the person that’s resistant to new efficiencies, resistant to learning how to use AI.” The Hard Evidence to Reference I pointed out that not all reps would be immediately convinced by that framing, and it might help leaders to have more concrete proof on hand to support it. I asked if he could recommend metrics or evidence that highlights how agents can positively influence an individual rep’s performance. He brought me back to the example he shared when we discussed inbound chatbots, walking me through the evolution of Warmly’s inbound agent. It started as a robotic chat tool that could route leads to a human rep for a live conversation. Eventually, AI took the process over end-to-end and started independently booking meetings in off-hours — outpacing human SDRs for inbound meeting volume. Naturally, the team thought, “Wait a second, AI is taking my job,”but ultimately, the workflow let reps focus more on outbound prospecting and accounts. They booked more meetings with higher ACV and qualification rates. That meant more pipeline, higher contract deal sizes, and more closed-won revenue — a trend that continued across customers who bought the inbound agent. I mentioned it sounded like “finding the pockets” is key. As with so many other fields, thriving in sales will be a game of proactively identifying the activities where AI can’t replicate human capability and directing reps to them. Keegan and I agreed — and both felt that the responsibility there should mostly land on managers. Who actually trains the agents? I asked Keegan who he felt should train AI agents. I figured it would also be on management, but he pushed back. “Organizations’ AI tech stacks are often bloated, and agents function better as a cohesive motion than a suite of disparate resources.”

   In Outbound stack design