How I use AI
Same principle as the rest of the job: work myself out of repetitive work so I can spend time on the deals that actually need a human call. I don't ask AI to decide a discount or talk to a customer — I ask it to read the pipeline every morning, tell me what changed, and draft the first message, so my first move of the day is a decision instead of a search.
The Deal Strategy Assistant to the right is the clearest example: a Claude plugin for Deal Desk analysts. Every morning it reads the analyst's covered pipeline, picks the handful of deals that most need deal strategy help, explains what it sees and why it matters, and drafts the first message to the AE. It's advisory only — it reads the CRM and never writes to it, drafts messages and never sends them.
Read the open opportunities in the analyst's confirmed coverage, with the relevant account, contract, case, activity, and change-history context. Optional connectors (Slack, Gmail, meeting notes) add evidence.
Check each deal against flags and signals: total contract value (TCV), timeline to close (in the month, in the quarter, or beyond), possible bottlenecks such as tax-exemption documentation, private equity ownership, or a cloud-marketplace or partner route, and whether Sales has already opened a Deal Strategy case.
Surface up to five priority deals each morning. Skip deals raised in recent briefs (21 days by default, configurable) unless something material changed, such as a customer who is ready to buy now asking for a wet-ink signature instead of DocuSign. If nothing qualifies, the brief says so.
For each deal: what the flags and sources show, why help matters now, and a proposed next step, plus a draft Slack message to the AE. Skipped checks and missing connectors are listed in the brief.
Gets a new analyst from “installed” to a correct brief the next morning. The analyst gives their name. The skill finds their Salesforce user and proposes their region, sales leaders, and reps from the territory, role, or team data it can read. The analyst confirms or edits that coverage. Ambiguous name matches and missing manager data are raised as questions, never guessed, and the confirmed coverage feeds the daily brief from the first run.
Scans the whole pipeline within the analyst's confirmed coverage each morning and surfaces up to five deals that need Deal Desk or Deal Strategy input. Each entry says what is happening, what the deal looks like, and why it needs the desk, with sources the analyst can check: the opportunity record, relevant Slack conversations, and credible outside information, such as whether a customer is owned by a private equity firm. Ownership or geographic-risk signals are shown as evidence for the analyst to escalate, never as automatic conclusions.
Writes a friendly, proactive message to the AE: what the analyst noticed on the deal, an offer to help or suggest options, and a low-pressure next step. Drafts are saved unsent. Draft-only is the install default. Automatic sending is not built; it would need an explicit configuration and permission change, and only after the drafts have proven their quality.
Checks connected, authoritative sources for policy changes: the internal wiki (such as Confluence), designated policy Slack channels, and messages from policy owners, including leadership announcements. Each rule is stored with its source, so the brief can compare deals against current policy and promotions and flag conflicts for the analyst. An announcement that conflicts with an approved policy is flagged, never treated as an automatic override. It runs on request or on a weekly schedule the analyst sets up.
These are examples, not a complete list.
Requires a CRM connection. The current demo uses Salesforce; other CRMs, such as HubSpot, require an appropriate connector and field mapping. Optional: Slack, Gmail, a meeting-notes tool. Each missing connector is listed in the brief header with what the brief loses without it.
One static export of a fictional Salesforce Developer Edition org, dated 2026-09-26. 40 open deals reviewed, 5 surfaced. Every name and number is invented. Amounts are total contract value (TCV), and days to close count from Sep 26.
1. Halvorsen Energy — Expansion
$450K TCV · Expansion · closes 2026-09-29
Close date slipping · No deal strategy engagement
Ask Derek what the budget approval is contingent on. If funding the full expansion at once is the block, offer a 90-day ramp on the new hosts so the order form can sign before the full amount is funded.
2. Pinecrest Software — New Logo
$330K TCV · New Logo · closes 2026-10-09
Cloud marketplace route · Signature path mismatch · No deal strategy engagement
Line up the marketplace paperwork now: confirm the AWS account ID, the private-offer terms, and who signs. Move the internal target to Sep 30.
3. Lakeshore County — New Logo
$410K TCV · New Logo · closes 2026-10-12
Possible tax-exempt entity · Signature path mismatch · No deal strategy engagement
Send Maya the vendor packet (including the W-9) and start the tax-documentation request with Finance/Tax today. Ask procurement whether a cooperative purchasing vehicle is required.
4. Brightwater Logistics — New Logo
$640K TCV · New Logo · closes 2026-10-28
Private equity ownership · Affiliate with pricing on file · Multi-year ask
Before the 3-year proposal goes out, ask whether Harborline wants pricing that covers other portfolio companies. Structure the multi-year rate as a give against a sponsor-level commitment, not a standalone discount.
5. Corvane Financial — Renewal (commitment reset)
$1.15M TCV · Renewal · commitment reset · closes 2026-11-03
Reset or renewal approaching · Consumption ahead of commitment · No deal strategy engagement
Pull nine months of usage and model the run rate forward. Bring Priya three reset options (12, 24, 36 months) before the kickoff so the customer's finance team hears a plan, not an overage bill.
Not surfaced: Lumenfield Media — Renewal ($380K TCV; a Deal Strategy case is already open). Watching: Oakridge Mutual — New Logo (tool consolidation) ($760K TCV); Tallis Retail — Expansion ($520K TCV).
An authored example for deal #4, written in the tone and structure deal-outreach-draft is built to produce. It is not unedited assistant output. In the plugin, a draft like this is saved unsent for the analyst to review.
Hi Maya, hope you're doing well. I had a chance to review Brightwater Logistics and noticed it's part of Harborline Capital Partners' portfolio. Ridgeway Haulage is also in that portfolio and is already a customer, so it may be worth exploring whether the sponsor wants a coordinated approach before the three-year proposal goes out. I'm happy to help assess the options and structure a recommendation. This is simply a proactive suggestion for you to consider. Happy to discuss it over a 20-minute Zoom call this week if useful. Let me know if you have any questions.
What it does: opens warmly, names the fact and where it came from, offers help before the proposal goes out, and closes with a low-pressure ask. No discount numbers on first touch.
Demo videos and the interactive brief, all on fictional data.