July 28, 2025
In a world full of complex CRM systems, expensive lead generation tools, and AI-driven automation, the most powerful sales tactic we’ve ever used at Dakota is also one of the simplest:
City Scheduling.
It’s a tactic that brings structure to chaos, turns strategy into execution, and, most importantly, drives real results.
If you’re in investment sales, you know how chaotic the calendar can get. You’re juggling outreach, meetings, travel, and often it feels like you’re just reacting. That’s where City Scheduling changes the game.
City Scheduling is the practice of organizing your sales outreach and meetings by metro area, and executing a systematic outreach campaign to fill your calendar in that city.
Instead of working a national list randomly, you bring order to the madness by focusing on one market at a time. You proactively book five meetings in one city for one day, then move on to the next city.
Simple? Yes.
It might sound simple. But trust me, it’s incredibly effective.
Here’s why it’s so powerful:
1. It Shrinks the Problem
Trying to call on 3,000 RIAs across the country is overwhelming. Calling on the 85 RIAs in Chicago? Totally doable.
2. It Creates a Repeatable System
Instead of reactive outreach, you have a clear, structured playbook. Every week, you know what cities you’re scheduling for and what emails you’re sending.
3. It Keeps You Focused
With five cities on your calendar at any given time, your outreach becomes targeted and intentional. You’re not bouncing around aimlessly. You’re executing a plan.
4. It Builds Market Awareness
The more often you visit a city or reach out to a specific Metro Area, the more familiar your name becomes. Even if they don’t meet with you today, they remember you tomorrow.
5. It Fuels Your Pipeline
City Scheduling fills your calendar with qualified meetings. That’s how you build momentum, drive pipeline, and raise capital.
Here’s the exact system we use:
Step 1: Pick Your Cities
Choose 5 cities based on the concentration of target accounts in your TAM.
Step 2: Create Your Daily Schedule
Block 5 meeting slots per day:
9:00 a.m. • 11:00 a.m. • 1:00 p.m. • 3:00 p.m. • 4:30 p.m.
Step 3: Start Outreach 3–4 Weeks in Advance
Send ~30 emails per day per city using a clear, concise meeting request (more on that below).
Step 4: Work 5 Metro Areas at a Time
While you’re filling meetings in one city, you’re prepping the next four behind the scenes.
Step 5: Track Progress
Use a CRM to track outreach, confirmations, and follow-ups.
Your email should be short, specific, and include a clear CTA. Here’s an example:
Subject Line: Meeting Request – March 7 at 3:00 p.m.
I’ll be in Boston on March 7 with my colleague Sarah Greene from Horizon Partners and would love to stop by and introduce our firm.
Horizon manages $4B in a concentrated, high-conviction large cap strategy that’s outperformed its peer group since 2012.
Would you be available to meet at 3:00 p.m.?
That’s it. Clean. Focused. Effective.
Even if they say no, they now know your name, your brand, and your strategy.
Sales leaders: your job is to help your team win. Requiring them to always have five cities on the calendar is not micromanagement.
It’s accountability for activity.
It’s the most practical way to ensure your team is consistently filling the top of the funnel. If they’re stuck, City Scheduling gets them unstuck. If they’re succeeding, City Scheduling scales their effort.
City Scheduling works because it removes complexity. It gives you a system to follow every day, every week, every month.
You’re not throwing darts at a map or waiting for leads to come in. You’re executing, moving with purpose, and filling your pipeline with high-fit prospects.
In the end, City Scheduling isn’t just a sales tactic, it’s a mindset. A mindset of structure, discipline, and relentless execution.
You want to raise more capital? Start here. Pick five cities. Block your calendar. Start the outreach. Then do it again. That’s how you build momentum.
Book a demo of Dakota Marketplace to learn how fundraisers are using the platform for cold outreach and City Scheduling!
Gui Costin is the Founder and CEO of Dakota.
