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. “An AI SDR assistant (outbound agent)to work alongside SDRs/AEs on lower-tier outbound” 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 AI SDR agents

2. If all goes well, they’ll scale his setup org-wide. I started by asking him which activity he’d address first, and how he’d get there. The 4 Agentic Essentials Keegan laid it out plainly. Every sales org should prioritize four key AI agents: A qualification/enrichment agent to qualify and prioritize inbound leads An AI SDR assistant (outbound agent)to work alongside SDRs/AEs on lower-tier outbound A self-serve/lower-segment agent to automate non-ICP or lower-tier leads An inbound agent to route, qualify, and convert website visitors 24/7 Qualification / Enrichment Agent He’d start by building an agent, housed where a company’s CRM data lives. Traditional inbound lead generation is a quantity play — firehosing reps with contacts. Orgs that leverage it often drop 10 meetings on a rep’s calendar at once, and only three wind up being qualified. He gave the example of a rep selling to service businesses (think HVAC installers and plumbers), getting excited about a fintech provider booking time with them. And they wind up sitting through a 30-minute meeting with a prospect who’s all the way off ICP. Keegan suggests orgs need an agent that automatically checks whether an inbound lead fits: If it does: Neat! Flow it to the rep. If it doesn’t: No sweat! Flag it and route it to another agent (like a prospecting or self-serve one) that either further qualifies it or takes it end-to-end via self-checkout. This kind of agent can trim those 10 meetings to five while still preserving the three with potential, safeguarding rep efficiency and time. AI SDR Assistant (Outbound Agent) Next, Keegan would build an outbound-type agent that worksalongsideICs on the team, not instead ofthem — also known as an AI SDR assistant. This one goes after accounts where there isn’t enough context for meaningful manual personalization, handling the lower tiers while human SDRs and AEs focus on tier 1 and 2 accounts. I mentioned that reps might find this one unnerving. “Routing them appropriately (to sales if they’re a fit — self-serve if not)” This agent: Takes the leads that the qualification enrichment agent flags as non-ICP or lower-tier Tries to qualify them further or takes them end-to-end through a self-checkout/self-serve flow Can go as far as presenting a quote and letting the prospect swipe a card without ever touching a human rep Can flag whether the prospect wants to talk to sales (mostly at larger companies) How to Make It All Come Together Keegan described this fleet as a connected system and recommended a crawl, walk, run rollout. Start with agents on lower-tier projects overseen by a couple of human reps and a RevOps manager. Next, expand automation as the agents improve. Have humans confirm they only need to review a small percentage of outputs throughout. If you successfully cover those bases, your sales org will have a functioning agentic workflow. The “Nice to Haves” If the four elements I just listed are the steak of Keegan’s AI-supported sales workflow, these are the crushed peppercorns and rich brandy-and-cream sauce that can kick it into full-blown “au pouivre” mode. Side note: That was my god-awful analogy. Please don’t blame Keegan. Content Creation Agent Keegan says this is the most valuable second-tier addition to an AI-supported sales workflow, saying: “Once you have the [lead capture, lead routing, enrichment, and follow-up] systems in place and can ‘get prospects in the store,‘ you should address the question of, ‘How can I pump out more content?‘” His ideal content creation agent covers both sales and marketing collateral — from vertical-specific decks to conference-promoting LinkedIn posts. He sees content as a vital supplementary element once you have those first four pillars built out. Voice Agents Keegan was careful to flag these as “hit or miss” — suggesting they’re worth experimenting with, but not a sure thing.

   In AI SDR agent conversation handling

3. 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. “If it does: Neat! Flow it to the rep. If it doesn’t: No sweat! Flag it and route it to another agent (like a prospecting or self-serve one) that either further qualifies it or takes it end-to-end via self-checkout.” 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 Lead routing and assignment

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