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TechnologyMarch 28, 20268 min read

Why We Built an AI Sales Force

10 AI salespeople cover every continent. Here's why a $2M seller now gets Goldman Sachs-level execution.

Robert Kessler
Robert Kessler

Head of Sales, Bulletin · Napkin Deals

The Problem: Elite Execution Was Reserved for Elite Deals

In traditional investment banking, the quality of your representation is a direct function of your deal size. A $500M transaction gets a team of 12 — seasoned bankers, analysts, junior associates working around the clock to build models, source buyers, and negotiate terms. According to Pitchbook, firms like Goldman Sachs and Morgan Stanley deploy an average of 8–14 professionals per mandate above $250M.

A $2M transaction? You get a broker with a spreadsheet and a prayer.

This creates an enormous gap in the lower-middle market. Business owners with $1M to $20M in enterprise value are systematically underserved. They deserve real representation — competitive processes, professional materials, global buyer outreach — but the economics of traditional banking make it impossible to deliver that at scale. The International Business Brokers Association estimates that fewer than 20% of listed businesses under $5M ever close a transaction with professional intermediary support.

The Thesis: AI Can Collapse the Cost of Execution

We asked a simple question: what if we could give every seller the same quality of execution that a $500M deal receives, but at a fraction of the cost?

The answer was not to hire more bankers. It was to build AI agents that could perform the highest-leverage activities in the M&A process — buyer identification, outreach, qualification, and follow-up — at a level of consistency and scale that no human team could match.

Today, Napkin employs 10 AI salespeople. Each one is assigned a geographic territory. Together, they cover every continent. They work 24/7, they never forget a follow-up, and they operate within a structured framework that ensures every interaction meets institutional standards. This is what we describe in our Humans + AI workforce model — technology that amplifies human capability rather than replacing it.

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How It Works

Each AI salesperson is a specialized agent built on top of our proprietary deal intelligence layer. They are not chatbots. They are autonomous systems that can:

  • Source and qualify potential buyers from our verified acquirer database
  • Generate personalized outreach based on the buyer's acquisition history, sector focus, and geographic preference
  • Manage multi-step follow-up sequences across email and platform messaging
  • Track engagement signals and escalate high-intent buyers to human bankers
  • Produce weekly pipeline reports with conversion analytics

The human team focuses on what humans do best: relationship management, negotiation strategy, and closing. The AI handles the volume work — the 200 emails, the 50 follow-ups, the continuous pipeline management that would otherwise require a team of analysts.

The Results

Since deploying our AI sales force, we have seen a step-change in execution quality across the board:

  • Far more buyers reached per engagement than a human team could contact manually
  • Faster paths from listing to first qualified conversation
  • Geographic coverage expanded from a handful of markets to global
  • Follow-up that never sleeps, never forgets, and never lets a warm buyer go cold

More importantly, we are now able to offer competitive-process M&A to sellers who were previously too small to warrant one. A business owner selling a $2M company now receives the same structured outreach process as a $200M deal — because the marginal cost of adding another engagement to the AI pipeline is effectively zero. This is the core of our M&A for the rest of us thesis.

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Why This Matters for the Industry

The M&A advisory industry has been slow to adopt technology. Most firms still operate on the same model they used 30 years ago: senior bankers source deals, junior analysts build models, and everyone works on a handful of transactions at a time. According to Deloitte's 2025 M&A Technology Survey, only 12% of advisory firms have deployed AI in any part of their deal execution workflow.

This model works at the top of the market. It fails everywhere else. And "everywhere else" is where 95% of business transactions happen.

By deploying AI at the execution layer, Napkin is not replacing bankers — we are extending the reach of every banker we have. Our human advisors can now manage more relationships, provide more strategic guidance, and close more deals because the operational burden has been lifted.

This is what we mean when we say AI creates human jobs. The AI handles the scale. The humans handle the judgment. Together, they deliver something that neither could alone: institutional-quality M&A for the rest of the market.

What Comes Next

We are currently expanding our AI workforce beyond sales into other high-leverage areas: deal analysis, document preparation, due diligence support, and buyer matching. Each new capability compounds the value we deliver to sellers and the efficiency of our human team.

The vision is straightforward: any business, anywhere in the world, should have access to the same quality of M&A representation that was previously reserved for nine-figure transactions. AI makes that possible. We are building it.

Knowledge is one thing. Execution is another.

When you're ready to move, our team of bankers and advisors will guide you through every step.

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