James Aspinwall | February 2026
Notes on a conversation between John Biggs and Jason Ambrose of People.ai
People.ai has been around long enough to watch multiple waves of enterprise software crest and break. Now it’s repositioning for the agent era — and the way Jason Ambrose frames the shift is worth paying attention to.
The Gap Between CRM and Reality
Most CRM systems tell you what was entered. They don’t tell you what’s actually happening.
People.ai takes a different approach. Instead of relying on manual updates, their AI analyzes the communications that define modern sales — emails, Slack messages, meetings, chat transcripts — and maps that activity to accounts, contacts, and opportunities.
That sounds straightforward until you scale it up.
A startup selling to a small business has one salesperson talking to one buyer about one product. Simple. But when Microsoft sells to Verizon, you might have dozens of people on both sides — legal, technical, procurement, executive — with conversations happening everywhere. Mapping that complexity into a clean CRM record is genuinely hard. People.ai uses its own models, trained on billions of transactions, to reconstruct what’s really going on inside a sales organization.
What Is an Agent, Really?
A chatbot answers a question. An agent has an objective.
Ambrose frames it in terms of business process automation. Old-school automation works when the logic is predictable — if this, then that, stay inside one system, follow a defined workflow. Agents step in when reasoning is required. They cut across systems. They pursue a goal. They have to decide what to do next.
But that only works if they’re plugged into real expertise.
Public LLMs are trained on public data. Enterprise expertise lives in private systems. If you want an agent to act intelligently inside a company, it needs access to proprietary data. That’s a big trust ask. You’re effectively saying, “Let our AI read your emails.” That’s not a small decision.
The Corporate Fortune Cookie Problem
Anyone who has used a generic LLM for business advice has seen it. You ask for guidance and you get vague platitudes. “Build trust with stakeholders.” “Accelerate the deal.” “Engage the customer.”
That’s not actionable.
This is where expert agents earn their keep. Instead of generalized advice, they ground recommendations in specific deal data. Who hasn’t responded in three weeks? Which technical blocker hasn’t been addressed? Where did the last conversation stall?
Without that grounding, AI defaults to corporate fortune-cookie language. The difference between a useful agent and a useless one is whether it has access to what’s actually happening.
The Capital Markets Shift
SaaS is being repriced. Public markets adjusted first, private markets followed. Companies that once enjoyed premium multiples are being reevaluated in light of AI disruption.
Capital is flowing into AI-native plays. If you look like “just another SaaS company,” you need a credible AI story. If you genuinely sit at the center of AI transformation, you’re in a stronger position. The market is asking a simple question: who is being disrupted by AI, and who is using it to build something new?
Is AI Replacing Jobs?
Ambrose’s take is pragmatic. Technology changes work. It always has. He remembers downloading Mosaic when the web first launched. Some jobs disappear. Most jobs change.
His line: people should work with people, and let AI do the rest.
Sales, at its core, is still about relationships. AI can summarize, surface risks, and suggest next steps. It can’t replace trust, empathy, or judgment. At least not yet.
The Copy-Paste Tell
If you’re in sales and you haven’t started using AI, Ambrose’s advice is simple: start. Use ChatGPT, Claude, Gemini — whatever. Have it rewrite emails, summarize meeting notes, draft follow-ups.
But don’t copy and paste.
He pointed out something many executives are quietly thinking: if you send a clearly AI-generated email without tailoring it, you’re signaling that you didn’t invest the time. And if you didn’t invest the time, why should the recipient?
AI can amplify your work. It can’t replace the part that makes you human.
The Takeaway
People.ai is betting that the future of sales is agentic, cross-system, and grounded in real communications data. Not dashboards — reasoning systems that understand what’s actually happening inside complex deals.
Whether you buy that vision or not, one thing is clear. The next phase of enterprise AI won’t be about novelty. It will be about integration, trust, and measurable outcomes.
And that’s a much harder problem than writing clever emails.