I have watched this industry sprint toward automation like it is the answer to everything. AI-powered outreach tools, automated email sequences, predictive analytics platforms — all promising to flood your pipeline with acquisition targets. And some of it genuinely works.
We use AI and proprietary tech-enabled search tools every day at 90North. But here is what concerns me: too many firms are confusing the ability to find a target with the ability to engage one. And for business owners who built something from nothing over 20 or 30 years, that distinction is everything
Technology Grants Us Reach. Experience Grants Us the Ability to Engage.
Let me be specific about what technology does well in our world. When a PE client comes to us with a thesis — say, commercial HVAC services in the Southeast between $5M and $20M in revenue — our research team uses subscription databases, AI-driven search capabilities, and direct diligence to triangulate across multiple data sources. We can build a curated, thesis-aligned target list in one to two weeks. That is genuinely powerful.
Five years ago, that same exercise took months. So I am not here to argue against technology. I am here to argue against the idea that technology finishes the job. It starts it. The target list is the beginning. What happens next is the only part that actually matters.
Business Owners Can Smell Automation in the First Ten Seconds
I spent years as a senior operating executive on the receiving end of M&A outreach. I know exactly what it feels like to get a call from someone reading a script, or to open an email that was clearly sent to 500 other business owners with a first name swapped in. You feel it immediately. And for a business owner who has spent decades building something, hiring people, surviving downturns, making payroll when things got tight, that impersonal touch is not just ineffective. It is insulting. These are people who built their companies on relationships. They chose their vendors based on trust. They retained employees because they knew their names. When someone reaches out about the most significant financial decision of their life with a templated email that reads like a robo-call, the conversation is over before it starts.
I hear this constantly from the business owners we speak with. They tell us: ‘You are the first person who actually asked me about my business before jumping into what your client wants.’ That is not a sophisticated sales technique. That is basic respect. But it has become rare enough that it stands out.
Director-Led Outreach Is Not a Luxury. It Is the Mechanism That Works.
At 90North, every outreach conversation is personally led by a director with 25-plus years in executive sales, business development, and M&A. That is not a marketing line. It is how we operate, and it is the reason our conversations go differently than what most business owners are used to. When I call a founder, I am not reading from a script. I have run businesses. I have sat in the chair they are sitting in. I understand the weight of what they are considering. That shared experience changes the dynamic entirely. It turns a cold call into a peer-to-peer conversation. And honestly, it is the only dynamic that produces real, qualified introductions, not just names on a spreadsheet. The firms that have replaced this with automation are optimizing for volume. We are optimizing for the conversation that actually leads to a closed transaction. Those are fundamentally different goals.
Where AI Fits in a Relationship-Driven Process
I want to be clear about something: we are not technophobes. Our research team, led by Melinda Gracey, uses AI capabilities and multiple subscription databases daily to build proprietary target lists that are exclusive to each client. The technology makes us faster, more precise, and more thorough in identifying companies that genuinely fit a client’s investment thesis. But we draw a hard line.
The technology informs the research. It never touches the relationship. No automated email sequences to business owners. No AI-generated voicemails. No chatbot follow-ups. When a business owner picks up the phone or opens an email from us, there is a real person on the other end who has personally vetted their company, understands their industry, and is prepared to have an honest conversation about what a transaction might look like, or whether it makes sense at all. That combination, proprietary tech-enabled search on the back end, experienced human beings on the front end, is what produces quality introductions, not just lists.
This Is Their Life's Work. Act Like It.
Every time our team picks up the phone or drafts an outreach email, we remind ourselves of one thing: we are reaching out to someone about their life’s work. The company they built is not a line item on a target list. It is their identity, their legacy, their employees’ livelihoods. The moment you forget that, the moment you treat outreach as a numbers game to be optimized and automated, you lose the very people you are trying to reach. The best business owners, the ones running companies that PE firms actually want to acquire, are not going to respond to volume. They respond to credibility, to patience, and to someone who demonstrates they have done the work before the first conversation even starts. I have seen too many firms invest heavily in AI-powered outreach platforms and then wonder why their conversion rates are falling. The answer is straightforward: business owners are not conversion rates. They are people making the hardest decision of their professional lives. And they want to make it with someone they trust.
Technology is a tool. A powerful one. We use it aggressively on the research side and it makes us better at what we do. But the transaction itself, the conversation that moves a business owner from curiosity to confidence, will always be a human event. The firms that understand this will close the deals that matter. The ones chasing automation all the way to the finish line will keep wondering why the best targets never call back.
If your current sourcing approach is heavy on technology but light on real conversations, let's talk about what director-led outreach looks like in practice. Reach out to me directly at tfigurelli@90north-partners.com.