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New fundraisers get 18 months to prove themselves, and the ones who waste the first six to nine getting organized never catch up.
That's the opening warning from Dakota founder and CEO Gui Costin and VP of Institutional Sales Tim Dolan in the latest episode of The Dakota Way Sales Coaching.
It sets up a systematic approach to fundraising built around four core principles: set expectations, know who to call on, be a master messenger, and build a killer follow-up system. Here are 10 takeaways fund managers can put to work immediately.
1. Set expectations with your boss in week one
Before any cold outreach or city scheduling, sit down with your boss and agree on a sales plan: what you'll do daily, weekly, monthly, and quarterly, and what KPIs define success. Costin and Dolan are direct about why this matters early: if you're still figuring this out six months in, you've already fallen behind the 18-month clock most fundraising roles run on.
2. Report against your plan weekly, not quarterly
Dolan reports to his partners every Monday, and he calls the discomfort of showing up with nothing to say a feature, not a bug. Weekly (or at minimum biweekly) reporting forces activity and pipeline movement between check-ins. Costin's line: you never want your boss wondering what you've been up to for the past two months.
3. Establish your TAM before you start calling anyone
Your product structure should drive your channel focus, not the other way around. A long-only mutual fund strategy points toward RIAs, banks, and broker-dealers; a 3(c) private structure points toward foundations, endowments, and institutions. Costin's warning: a lot of salespeople waste time chasing big brand-name allocators whose mandates don't actually fit their product, and there's no end zone to win in that game.
4. Always keep five cities on the books
Once TAM is set, run a constant cadence of city scheduling: five cities in motion at all times, with meeting slots at 9:00, 11:00, 1:00, 3:00, and 4:30. When a day of meetings in one city wraps, add another city to the list. Costin frames it simply: you're your own professional meeting scheduler, and that is the job.
5. Turn your outreach email into a marketing exercise
The Dakota Way email format is specific: subject line reads "Meeting Request, [Date and Time]," followed by one to two sentences on who you are and what you do, then a clear ask. Done well, recipients drag that email straight into their Outlook asset-class folders, which means every outreach email is quietly building brand familiarity alongside booking the meeting.
6. Open every meeting with a tight, factual introduction
Skip the small talk. In the first 30 seconds, cover who you are, what you do, and your structure: founding year, strategy, ownership, headquarters, AUM. Dolan's guidance is to check the box fast so the allocator has full context before you move into questions.
7. Learn their investment process before you pitch yours
Before diving into your own strategy, ask the allocator to walk through how they currently invest in that asset class or strategy type. Understanding their decision-making process first is what makes the Q&A that follows land instead of turning into a one-way pitch.
8. Let them talk 70% of the time
Once you're in Q&A, the goal is a back-and-forth, not a monologue. Dolan and Costin put a number on it: aim for the allocator talking 70% of the meeting. The more they talk, the more you learn about fit, and fit is what determines whether a follow-up is worth your time.
9. Close every meeting with the two tough questions
This is the piece Costin says 99.9% of fundraisers skip, and it's the difference between a "great meeting" and a meeting that actually moves a deal forward. First: does this strategy fit your asset allocation mix? Second, if yes: for a long-only strategy, are you doing a search in the next 12 months? For a private strategy, can you make the final close by the target date? A "no" saves you weeks of chasing a dead lead. A "yes" tells you exactly what the allocator needs to keep moving through due diligence.
10. Use your CRM, and AI, to 10x your follow-up leverage
Log every call and meeting immediately (Costin notes that waiting more than 24 hours cuts your notes' detail by roughly 60%), and use tools like Claude to dictate notes on the way out of a meeting so nothing gets lost. Every opportunity in the CRM needs two fields filled in without fail: current status and next step, pulled straight from the two tough questions above. Those opportunity reports, reviewed weekly with your boss, are what close the loop back to principle number one.
Dakota Marketplace gives fundraisers the account and contact data behind principle number two: knowing exactly who to call on within your TAM, updated in real time across every institutional and intermediary channel. See how it fits into your sales plan, book a demo.
