Knowing that client entertainment closes deals is the easy part. Knowing which experience fits this opportunity, with this contact, at this stage — and whether it's even worth booking — is where most reps stall. Today we're shipping AI experience suggestions directly inside your CRM to answer that question for every deal you're working.
For a long time, the hardest part of running a client entertainment program wasn't approvals or budget. It was the blank page. A rep opens an opportunity, knows a touch in person would help, and then has no idea what to actually do — a dinner? box seats? a round of golf? — or whether the moment is right at all. So nothing happens, and the deal stays in the inbox.
The problem: the right move, at the wrong time, for the wrong person
Reps aren't experience curators. Even the ones who believe in face-to-face selling rarely know that the VP they're courting is a wine collector, that the account went quiet right after a renewal last year, or that a steakhouse dinner sits comfortably under their manager's approval limit while a suite does not. That knowledge lives in scattered places — past notes, LinkedIn, finance policy, tribal memory — and almost never surfaces at the moment a rep is deciding what to do next.
The result is predictable. The deals that get an in-person touch tend to be the ones with a rep who happens to be well-connected or naturally social. Everyone else defaults to another email. Pipeline that could have moved sits still, not because the play doesn't work, but because no one knew which play to run.
What's new: suggestions on the record, not in a separate tool
Dealgrounds now reads your opportunity and contact records and surfaces a specific, ranked experience recommendation right on the record. No new tab, no separate app to remember. Open a deal and you'll see a suggestion like "Invite the economic buyer to a wine dinner this month" — with the reasoning attached, so it's a recommendation you can trust rather than a black box.
How it works
Each suggestion is built from the signals you already have, weighed together:
- Deal stage and momentum: a stalled late-stage opportunity gets a different recommendation than an early discovery call.
- Contact seniority and interests: who you're trying to reach, and what they actually care about — sports, food, music, golf.
- Account history: what's worked (or fallen flat) with this account before, so you don't repeat a miss.
- Budget and approval limits: only experiences that fit your policy and your manager's threshold, so suggestions are always actionable.
The model uses those inputs to recommend a specific experience and, just as importantly, to explain why — "this contact is a champion, the deal has slipped twice, and a relaxed dinner is the fastest way to surface the real objection." When the timing isn't right, it says so, instead of pushing spend for its own sake.
The best recommendation isn't the most impressive experience. It's the right one, for this person, that you can actually get approved this week.
What reps see and do
The whole point is to remove the friction between "good idea" and "booked." When a rep likes a suggestion, requesting it is one click. That click routes straight into the same Dealgrounds approval workflow your team already uses — manager sign-off, budget check, compliance log — with the deal context and the AI's reasoning carried along automatically. Approvers see why the experience was chosen, not just a line-item expense, which means faster yeses and a cleaner audit trail.
For revenue leaders, that turns an inconsistent, rep-by-rep habit into a repeatable motion. Every open opportunity now comes with a defensible suggestion for the next in-person move, and every accepted suggestion is attributed back to the pipeline it influences.
- Where: AI suggestions live on the opportunity and contact record, inside your CRM.
- Signals: deal stage, contact seniority and interests, account history, and budget/approval limits.
- Why you can trust it: every suggestion explains its reasoning — and flags when to wait.
- One click: requesting an experience routes straight into your existing approval workflow.
- Availability: rolling out now to Pro and Enterprise plans.
Availability
AI experience suggestions are rolling out now to Pro and Enterprise customers, with no setup required beyond your existing CRM connection. As more of your team accepts, declines, and books suggestions, the recommendations sharpen to your accounts and your buyers. If you're on a Starter plan and want early access, talk to your account team.