Sales, fundraising, and deal sourcing teams are under more pressure than ever to move quickly, stay organized, and personalize every interaction. At the same time, the amount of data sitting inside CRMs has exploded… far beyond what traditional reporting methods were designed to handle.
This is where large language models (LLMs) are starting to change the sales process. Instead of forcing teams to adapt to rigid reporting tools, LLMs allow teams to interact with their data the same way they think – by asking questions and getting answers instantly.
Below are three reporting pitfalls that hold investment sales and deal teams back and the best practices emerging as LLM-powered tools like Dakota Joe become part of modern sales workflows.
Want AI-powered reporting built directly into your sales process? Book a demo of Dakota Marketplace!
CRMs were meant to make sales teams more efficient. But for many fundraising and deal teams, they’ve become systems of record instead of systems of insight. Data is there, but accessing it often requires exporting spreadsheets, remembering filters, or relying on someone else to pull reports.
Across Dakota Marketplace, we’re seeing a clear shift: teams are adopting LLMs inside their sales workflows to remove that friction. Rather than learning how to “build reports,” sales and IR professionals can simply ask questions in natural language and stay focused on conversations, not tooling.
That’s the role Dakota Joe plays inside Dakota Marketplace: Turning CRM data into immediate, usable insight without slowing teams down.
Three Pitfalls Holding Your Team Back, And How to Avoid Them
Pitfall #1: Working From Reports That Are Out of Date the Moment They’re Created
Spreadsheet-based reporting relies on snapshots. The moment data is exported, it begins to age. New conversations happen, notes are added, and deal momentum shifts. But the report stays frozen.
For fundraising and sourcing teams, this creates unnecessary risk. Decisions get made based on yesterday’s context, and opportunities can be mistimed or overlooked entirely.
The best teams are moving away from static files and toward live, question-driven reporting. With LLM-powered tools like Dakota Joe, teams can ask questions against real-time CRM data and get answers immediately, without rebuilding reports or chasing down the latest version.
Pitfall #2: Reporting That Slows the Team Down
In spreadsheet-heavy environments, reporting often becomes centralized around one or two people. Everyone else waits. Over time, that waiting turns into hesitation… teams stop asking questions because it feels easier to keep moving than to request another report.
This is where LLMs make a meaningful difference in the sales process. By allowing anyone on the team to ask questions in plain language, reporting becomes self-serve instead of a bottleneck. Fundraising and deal professionals don’t need to know filters, formulas, or report logic – they just need to know what they want to understand.
Dakota Joe was built with this reality in mind, helping teams move faster without adding complexity or pulling people away from active conversations.
Pitfall #3: Insight That’s Disconnected From Action
Spreadsheets live outside the CRM, which creates distance between insight and execution. A report might highlight a promising allocator or a stalled relationship, but acting on that information requires switching tools, finding context, and reconnecting the dots.
In competitive fundraising and sourcing environments, that friction matters. When insight isn’t immediately actionable, momentum slows and follow-through suffers.
LLM-powered reporting works best when it lives inside the same system where relationships are managed. Dakota Joe keeps insight tied directly to accounts, contacts, and activity history within Dakota Marketplace, making it easier for teams to move from insight to action while context is still fresh.
Why These Best Practices Matter in Today’s Fundraising Landscape
Fundraising and deal sourcing teams are operating in a market where allocators are more selective, pipelines are more crowded, and expectations are higher across the board. Old reporting methods weren’t built for this environment.
The teams adapting fastest aren’t abandoning structure, they’re modernizing it. By using LLMs inside their sales workflows, they’re reducing friction, improving visibility, and staying more responsive to what’s happening in real time.
This isn’t about chasing the latest technology trend. It’s about making the sales process feel more natural, more efficient, and more aligned with how teams actually work.
What is Dakota Joe?
Joe is Dakota Marketplace’s AI-powered report builder that lives directly inside your existing environment. With Joe, you can generate custom reports on Accounts, Contacts, Investments, and Dakota Recommends data in a consistent, presentation-ready format. Just tell Joe what you’d like to see — by segment, time period, or strategy — and it builds the report for you.
Instead of building reports manually or exporting spreadsheets, teams can interact with their data the same way they think… by asking questions like who they’ve spoken to recently, where momentum is building, or which relationships need attention.
Because Dakota Joe lives inside Dakota Marketplace, insights stay connected to allocator profiles, activity history, and relationship context. That means less time preparing reports and more time focusing on conversations that move deals and fundraising forward.
How Dakota Marketplace and Dakota Joe Support This Shift
Dakota Marketplace gives fundraising and deal teams the intelligence, visibility, and workflows needed to operate effectively in a competitive market. Dakota Joe extends that foundation by using an LLM to simplify CRM reporting, allowing teams to ask natural-language questions and turn data into insight without manual work.
Together, they help teams spend less time preparing reports and more time building relationships, advancing conversations, and staying focused on the opportunities that matter most.
Ready to move beyond spreadsheet-only reporting? Book a demo of Dakota Marketplace.
