AI isn’t a buzzword to Ryan Milligan, VP of Sales, Marketing, and RevOps at QuotaPath. Oh no, it’s more like… a wrench. A wrench he uses to tighten the revenue machine, not wave around at conferences. (Hey, watch it, that’s dangerous!)
In fact, Ryan’s got one rule: Start with the problem. Not the pitch deck.
While everyone else is busy trying to “AI” their way into relevance, he’s just asking, Where’s the leak? And will this fix it?
In a time where it’s unclear whether AI is going to live up to all of its promises or will totally reshape how go-to-market teams operate, collaborate, make decisions, and scale: one could forgive Ryan for taking a cautious-yet-AI-forward approach. After all, these times are indeed uncertain.
Ryan explained that his approach cuts through all the marketing noise with sharp focus: AI isn’t valuable unless it drives a meaningful result.
And that means starting with the problems first.
A pretty solid framework for any of us deciding on what’s next.
Don’t lead with AI. Lead with the problem.
Ryan’s philosophy is clear: stay focused on the business’ needs. He doesn’t start with what AI can do, he starts with the outcome he wants to improve.
“My focus has been on identifying the problem we can solve and then injecting AI to solve that problem versus starting with the AI injection for all things. Problem-first versus AI-first.”
In Ryan’s world, the objective is simple: maximize ARR per rep. That’s the north star. Everything else, whether it’s automation, AI, or process design, serves that goal.
“[The] goal for my team is maximizing ARR/rep, so my focus is 100% on how I make my reps more efficient.”
This mindset leads to highly selective use of AI. He doesn’t sprinkle it across the org, he applies it exactly where it helps reps move faster and smarter.
“AI is key to this in automating next step/form field updates, sending tailored responses post demos, all things to automate processes where the rep doesn't add unique value.”
Resistance? Anchor the convo in outcomes
AI can be QUITE polarizing — especially when it’s introduced as a shiny new object. Ryan takes an equally grounded approach to overcoming skepticism: keep the conversation rooted in real pain points.
“[When] I have encountered resistance, my focus has been on identifying the problem we can solve and then injecting AI to solve that problem,” he says. By focusing on the tangible outcomes rather than abstract possibilities, he can shift the chat from fear or fatigue to relevance and utility. This problem-first framing helps with stakeholder alignment and it ensures AI actually solves something useful. And that’s a win.
There are still places AI doesn’t belong. Ryan knows where.
He’s not drinking the fully autonomous Kool-AI-d. Not yet. Some things — like deeply technical demos — still require a human brain, a human voice, and a human-sized serving of nuance.
“Demoing our product,” he says, “ It's an incredibly technical and tailored demo, I don't think an AI agent could do it.”
You don’t use a wrench to paint a wall. Not if you want to get done by dinner.
Use AI to extend your team’s strengths, not replace them
Ryan sees AI not as a replacement, but as a complement. It’s a tool to accelerate people, not to remove them.
“AI is great for supplementing the skillsets of humans,” he explains. “Use it as a tool, not a replacement.”
This balanced, practical mindset keeps his team aligned and confident and ensures that AI implementation supports, rather than disrupts, the broader GTM strategy.
Operator takeaway: Let outcomes lead, and AI will follow
Ryan Milligan’s approach to AI is a masterclass in operational discipline. It’s not about being early. It’s about being effective.
By starting with the business case, choosing his targets carefully, and maintaining a clear sense of what not to automate, Ryan is able to ensure that every AI investment earns its keep. He reminds us that in a fast-moving space, clarity is your best accelerant.
It ain’t flashy. But it is focused. And in a world chasing the next shiny thing, that’s a true competitive advantage.
