As a founder of a SaaS business, I’ve spoken with countless smart, thoughtful, and accomplished private equity investors. Recently, after recording an episode of The Dakota Way Sales Coaching, I was asked a simple question:
“Do you think in person versus Zoom is better?”
“From an efficiency standpoint,” I said, “Zoom hands down. From a relationship perspective and the prospect of winning business, in-person 100% of the time.”
I’ve done hundreds of calls and meetings with private equity firms, and the ones that resonated most were always the in-person conversations. In a world increasingly shaped by AI, relationships are still how you win… and relationships are built face to face.
If you want to systematize in-person meetings, book a demo of Dakota Marketplace to start city scheduling.
Why City Scheduling Is the Ultimate Advantage for Private Equity Deal Sourcing
AI can write emails, scrape founder databases, and score leads faster than any BD rep ever could.
But AI can’t sit across from a founder, look them in the eye, and build trust.
And in private equity, trust still closes deals.
That’s why, in a world of automation and scale, the smartest thing a deal sourcing professional can do is go in the opposite direction: get in the room, shake hands, and have the conversation.
Enter city scheduling: A system for building in-person relationships at scale.
The Real Edge in Sourcing? It’s Still Human
Yes, AI can help identify which founder to reach out to. It can even write the outreach email.
But when a CEO decides whether to respond, whether to take the meeting, and ultimately whether to partner with your firm, they’re not choosing based on an algorithm. They’re choosing based on trust, rapport, and gut instinct.
Nothing builds that faster than being there in person.
City Scheduling: The Playbook for Building Relationships AI Can’t
City scheduling is a tactical approach to deal sourcing where you proactively book four to six meetings in one metro area on a single day, and you do it in person.
You sit down with CEOs. You hear their story. You look them in the eye. You ask real questions and share real perspectives.
Zoom is a powerful tool and part of everyone’s workflow. But when it comes to building long-term founder relationships, face-to-face conversations still win.
Why Face-to-Face Still Wins in 2025
Founders aren’t selling a product, they’re selling their life’s work. Being in the room signals that you take that seriously.
Trust is still a human emotion. It isn’t built through automation. It’s built through listening, eye contact, tone, and presence. In-person conversations go deeper, faster.
And in an AI-saturated world, this is your differentiator. Founders receive templated emails from dozens of funds every week. Only a few show up, sit down, and spend thirty minutes getting to know them.
That’s your edge.
How Dakota Marketplace Makes City Scheduling Easier Than Ever
City scheduling only works if the research and list-building don’t slow you down. That’s why it’s built directly into Dakota Marketplace.
The Metro Areas tab allows private equity deal teams to quickly see all sponsor- and founder-owned private companies by city, industry, and sector, along with company descriptions, estimated revenue, employee count, and CEO contact details.
Want to target every logistics and supply chain technology company in Dallas that’s founder-led? That takes less than sixty seconds.
Need to line up five CEO meetings in Chicago next month? Filter by metro, shortlist companies, pull contacts, and start emailing.
With Dakota Marketplace, the hardest part of city scheduling (research and list building) is already done.
Book a demo of Dakota Marketplace to see how easy city scheduling can be.
The City Scheduling Framework for PE Deal Sourcing
Start by picking five high-priority cities that align with your industry focus and total addressable market. Dakota’s metro data quickly shows where company density lives.
Block one full day for each city and plan five meeting slots: 9:00 a.m., 11:00 a.m., 1:00 p.m., 3:00 p.m., and 4:30 p.m.
Then email roughly thirty CEOs per city using a simple, respectful, direct approach. Let them know you’ll be in town, explain who you are, and make it clear you’re not calling with an offer… just looking to introduce yourself and learn their story.
While you’re meeting in one city, you’re booking the next four. It becomes a constant, disciplined rhythm of outreach and travel.
Why This Matters More Than Ever
Every private equity fund is getting more efficient. Every CRM is getting smarter. Every BD rep has access to the same lists.
But very few are consistently sitting down with founders.
City scheduling turns in-person meetings into a system, not a one-off. And when a deal is on the line, founders don’t choose the best algorithm – they choose the firm that showed up, listened, and built a relationship.
In a World of Machines, Be the Human
Private equity is still a people business.
Yes, use AI. Use automation. Use Dakota Marketplace to work faster and smarter. But then get on a plane, walk into the office, and have the meeting.
That’s how you stand out. That’s how you source better. And that’s how you win the deal.
Book a demo of Dakota Marketplace to start city scheduling and build real relationships at scale.
