Allocators are still taking meetings. Cold emails still get opened. Cities still need to be worked. What's changed is the operating system underneath all of it, and the fundraisers paying attention are pulling ahead fast.
In the May 2026 edition of The Dakota Way Sales Coaching, I went solo to talk about exactly that. The episode walks through the 4 core principles of The Dakota Way, with a fresh layer on top: how Slack, Claude, and a system-of-record CRM are quietly rewriting the day-to-day life of the individual fundraiser.
Below are ten of the most important takeaways from the episode.
Book a demo of Dakota Marketplace to start applying these to your fundraising workflow!
1. You Are Your Own Inc.
Whether you're a solo fundraiser at a boutique investment firm or part of a larger distribution team, my advice is the same: think of yourself as Your Name, Inc. That means systems, processes, and technology. You just can't wing it.
A lot of my coaching is targeted at the individual salesperson raising capital at a single-product firm. No senior leadership guiding the sales motion, no playbook handed down, no one to ask. That's my job here, to help you figure it out. The four core principles of The Dakota Way are the operating system we use to do exactly that.
2. The CRM Is Becoming a System of Record, Not a User Interface
The world has changed considerably with AI, and the most immediate place we're feeling it is in the CRM.
For decades, the conversation around Salesforce, ACT, SalesLogix, and everything in between was about customizing fields and tweaking the user interface. That's why people hate Salesforce, despite it being the safest, most secure, and most flexible CRM on the planet. The UI isn't intuitive, the data is poor, and pulling a report feels like a chore.
That era is ending. The CRM is becoming a place to dump information. The retrieval happens through Claude, ChatGPT, Copilot, Gemini, or whatever LLM you prefer. Structure matters less. Getting the data in matters more.
It's why we built Dakota Joe, the natural-language layer on top of Dakota Marketplace.
3. Slack Plus AI Is the Underrated Power Move
At Dakota, we run Slack channels for Marketplace Good News, Investment Meeting Notes, Software Meeting Notes, and dozens of others. Every time we renew a customer, sign a new contract, or replace a competitor, it goes in the channel.
Connecting Slack to Claude turns that archive into something we can actually use.
A few real examples from our team:
- "How many times did we replace a competitor in 2026?" 20 seconds, full list returned.
- "What's the average contract value of all the new contracts signed in 2026?" 20 seconds, answered.
- "How many multi-year deals did we close?" Same speed.
The old version of this question, sent to an intern, would have taken days of manual review. The new version takes the time it takes to type the prompt.
4. Dictate, Don't Type
Once you've decided on a system of record, the friction of getting information into it goes away.
You don't need to type call notes anymore. Dictate them. Then ask Claude to clean it up, format it properly, and include the key constituents. Then tell Claude to put it in Slack or your CRM.
That's the workflow. The win isn't AI as a productivity tool on the margin. The win is having a system where every conversation gets captured and becomes searchable across the team.
5. You Have 18 Months. Plan Accordingly.
No one in HR walks in on day one and tells a new fundraiser: figure this out in 18 months or you're gone. But that's the reality of investment sales.
The problem: investment sales cycles run 9 to 36 months. If you spend the first 6 to 9 months on the website, the pitch deck, or other after-5 PM activities, you've burned a third of your runway on the wrong work.
The pitch deck is not the asset. A PM told me in 2013, after a partner pushed to redo the deck: "We've raised $10 billion using that deck. I'm not convinced they're hiring the deck." Allocators hire the team and the strategy, not the design. Focus on what matters most.
6. Set Expectations Before You Set Meetings
Core principle number 1 is setting expectations. Day one, write down a sales plan: which channels you'll focus on, why those channels fit the strategy, and what you can realistically commit to in terms of activity.
Then sit down with your boss and get agreement on what good looks like. I've never held our investment sales team to fundraising goals, because no one controls fundraising goals. What you can control is who you're getting in front of and how often.
Set a weekly check-in. 5 to 10 minutes. Walk through meetings set, meetings completed, feedback from prospects, and pipeline status. That weekly cadence is a forcing mechanism. It protects you from yourself, because no one wants to show up to a sales meeting empty-handed.
For our sales team, that check-in happens daily at 7:45 AM.
7. Five Cities. Always.
Core principle number 2 is knowing who to call on, and the practical implementation is a city schedule.
At any given time, you should have five cities on the board with 9, 11, 1, 3, and 4:30 circled as meeting slots. The point isn't the specific cities. The point is that the empty slots give you purpose. They tell you what to do every morning when you sit down at your desk or in a Starbucks: fill the slots.
No one went to college to be a professional meeting setter-upper, but that's the job. Whether the meetings are with Harvard, the largest RIAs, a sovereign wealth fund, or a family office, the cadence is the same. Five cities, five slots per city, always.
8. Cold Email Is Branding in Disguise
The cold email format I recommend is built for one purpose, with two tangential benefits.
The format:
- Subject line: Meeting request, date, and time.
- Body: Two sentences. Who you are, what you do, why someone should care.
- Close: A clear ask. "Can you meet May 4th at 3 o'clock?"
The primary purpose is to book the meeting. But here's what most fundraisers miss:
Tangential benefit #1: Even when the allocator can't take the meeting, they now know you manage $2 billion in a private credit real estate strategy with a 16% net return target. They drag your email into their private credit folder. You just delivered an investment idea.
Tangential benefit #2: When you do this consistently, month after month, allocators see your brand show up over and over again. Combine that with a quarterly update webinar (20 minutes, with replay and transcript sent after), and they start to think: I should probably take this call.
9. Be a Master Messenger
Core principle number 3 is being a master messenger, and the structure has four parts. Stacey Havener's masterclass on storytelling is the deeper version of this, but here's the high-level framework:
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Center the conversation in the first 2 minutes. Tell them exactly what to listen for. "We're a concentrated 22-stock large-cap growth strategy. 30 years old. $7 billion in assets. The team's been together 25 years." No confusion about who you are or why they should care.
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Ask them their investment decision-making process before you pitch. "I did a lot of work on your website, but I want to hear it from you, what's your process?" That answer tells you how to run the rest of the meeting.
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Let them talk. Stacey's target is 70% them, 30% you. That's hard. Aim for 50/50 minimum. Use Keith McDowell's rule: short answer first, then let them ask the follow-up.
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Close with two questions before you leave. "Do you see our strategy fitting in your asset allocation mix? Can you make our 12/31/26 close, or do you anticipate doing a search in the next 12 months?" If the answer is no, mailing list. If yes, you have your next step. No ghosting.
And the banned phrase when your boss asks how the meeting went: "Great meeting." We banned it at Dakota in 2011. Tell them what actually happened.
10. The Lobby Is Where the Killer Follow-Up System Lives
Core principle number 4 is having a killer follow-up system, and the entire workflow has been rebuilt by AI.
Walk out of your meeting. Get to the lobby. Pull out Claude (or ChatGPT, or Copilot) and dictate:
"Just finished a meeting with XYZ. My calendar's connected, so include all the attendees. Pull a description of the firm. Here's what we talked about: our large-cap growth strategy, this was the feedback, here's who they currently use, these are the next steps. Please clean this up and format it as call notes."
Under two minutes. Detailed, searchable call notes, ready to drop into your CRM or your Slack.
Then make sure every opportunity in your CRM has two custom fields: Current Status and Next Step. Run the pipeline report weekly. Email the link to your boss before your check-in. That's the loop.
It connects directly back to core principle number 1: setting expectations and reporting back against the plan.
The Bigger Picture: Process Plus AI Wins
The 4 core principles of The Dakota Way are:
- Have a killer follow-up system
None of them have changed. What's changed is the toolkit you have to execute them.
Slack and Claude turn every conversation into a searchable record. Your CRM becomes a place to dump information instead of a place to format it. Dictation in the lobby replaces an hour of typing at the hotel. Pipeline reports get written in plain English.
The discipline still has to be there. But for the solo fundraiser sitting at a boutique investment firm with no playbook and no senior guidance, the AI layer makes the discipline a lot easier to maintain.
Getting information that's currently not recorded into a system where it can be retrieved will change your business. We've seen it firsthand at Dakota.
Book a demo of Dakota Marketplace to join the thousands of fundraisers using it daily to help raise capital!
