In the March 2026 edition of The Dakota Way Sales Coaching, Gui Costin, Founder and CEO of Dakota, sat down with Rob Robertson, President of the Dakota Marketplace business, to talk process, discipline, and the systems that separate world-class fundraisers from everyone else.
The conversation covered the 4 core principles of The Dakota Way — and opened with a candid editorial on what happens when salespeople are left to their own devices.
Below are ten of the most important takeaways from the episode.
Book a demo of Dakota Marketplace to start implementing these best practices into your workflow!
1. Salespeople Left to Their Own Devices Will Drift
It sounds simple, but it's true: without structure, salespeople go off the rails.
Opportunistic selling is the default for most organizations. Gui and Rob estimate that 90% of sales teams operate this way. The 10% who outperform are the ones who combine opportunistic selling with a disciplined, consistent process — and never veer from it.
The goal is not to eliminate instinct. It's to make sure instinct operates inside a system that keeps the most important activity front and center.
2. Daily Check-Ins Are Non-Negotiable
The Dakota software team runs a 7:45 AM check-in five days a week. It takes 13 minutes. It covers the calendar, good news, and each rep's plan for the day.
It sounds easy. It isn't.
The discipline required to maintain this cadence — every single day, no exceptions — is what makes it work. Rob, who was skeptical of the early call when he first started, put it simply: ten years later, he can't imagine a day without it.
If you have a team, build the infrastructure. If you're a solo fundraiser, run that meeting with your boss.
3. Your Weekly Meeting Should Have One Job: Accountability
The Dakota investment sales team runs an 11:30 AM Monday check-in. The agenda is tight and non-negotiable:
- How many new meetings did you set last week?
- How many total meetings did you set?
- Did you move anything into red zone?
- Did you advance anything into finals?
- What did you close?
That's it. Not call notes. Not long-winded recaps. Just the numbers that prove the pipeline is healthy and moving forward.
4. Spiking the Ball Requires a Touchdown
One of Gui's most direct points from the episode: you get to celebrate when you close. Not before.
If you're still celebrating a win from three weeks ago, that's not excitement — it's avoidance. Sales is hard. The job is to close and move on to the next one. Celebrate the touchdown, then get back to work.
5. Focus on What Matters Most — Always
The overarching principle behind The Dakota Way is focus on what matters most. It sounds obvious. It's surprisingly rare in practice.
Long-winded meeting updates, irrelevant commentary, celebrating without progressing — these are all symptoms of losing the thread. As Rob put it, the daily check-in forces you to the mat. You're preparing for it every morning, which means you're asking yourself: is what I'm doing today actually what I should be doing?
That question alone has compounding value.
6. Process + Opportunistic Selling Is the Gold Standard
Neither process nor opportunism alone gets you there.
Pure process without flexibility misses opportunities. Pure opportunism without process creates chaos. The best fundraisers — the top 10% — do both. They follow a system with discipline while staying alert to what's happening in the market, in their relationships, and in their pipeline.
That combination is the gold standard. And it's teachable.
7. Know Your TAM and Let It Drive Your Channel Focus
Core Principle 2 of The Dakota Way is know who to call on. Product structure drives channel focus.
Mutual fund or ETF? Your buyer is the RIA channel. Private credit strategy? You're talking to family offices, consultants, and institutions. A hedge fund already approved on the Morgan Stanley platform? Your TAM just became a highly targeted list of qualified teams — and the diligence is already done.
Clarity on your TAM saves 80% of the time that most fundraisers waste calling on the wrong people.
8. Keep Five Cities on the Calendar at All Times
City scheduling is a daily discipline at Dakota. Five cities, always active. The moment one drops off, the next one goes on.
The point isn't that you'll travel to every city. It's that the habit of scheduling forces coverage, identifies your gaps, and keeps cold outreach going even when you don't feel like doing it.
As Gui says, if someone in Birmingham responds and you only have one meeting — convert to Zoom. You still generated the idea, you still made the connection, and you still kept your pipeline moving.
9. Your CRM Is 10x Leverage — Use It That Way
Core Principle 4 is have a killer follow-up system. The CRM is the engine.
Every meeting scheduled goes into the system. Every opportunity gets logged. Pipeline reports get shared at the weekly check-in. The data compounds over time, and with AI now layered on top — through Slack, through Dakota Marketplace's Claude-powered intelligence — that logged activity becomes meeting prep, pipeline analysis, and sales coaching material.
If you've built good data habits, you're at a significant advantage right now. If you haven't, start today.
10. Ask the Two Toughest Questions at the End of Every Meeting
Most fundraisers leave meetings without knowing where they actually stand. Gui's prescription: don't.
Before you walk out the door, ask two questions:
- "Would you see our strategy fitting in your asset allocation mix?"
- "Is there a close date — search timeline or fund deadline — that you could realistically hit?"
If the answer to either is no, put them on the mailing list and move on. If yes, establish next steps before you leave.
This eliminates ghosting, eliminates false buying signals, and keeps your pipeline honest. It also gives you something real to report at Monday's check-in.
The Bigger Picture: Process Wins
The 4 core principles of The Dakota Way are:
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Set expectations
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Know who to call on
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Know what to say
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Have a killer follow-up system
None of them require perfect market conditions. None of them require extraordinary talent. They require consistency — and the courage to hold yourself accountable to the things that actually matter.
As Gui put it: if you set up the process, stick to it, and always focus on what matters most, it works. We've proved it.
Book a demo of Dakota Marketplace to join the thousands of fundraisers using it daily to help raise capital!
