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Play · Negotiation & closing
For sales leadersDust agents, Momentum (automatic CRM updates)

Have AI draft the CFO email so the no comes on day 3, not day 73

Picked and checked by Olga Pearson, SalesUpLevel

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The resultas reported

ARR per rep 3x, average deal size up 40%, mid-market win rate doubled, selling time from about 25% to nearly 50%, and reps carrying about 40 deals instead of 20.

First ask each rep to walk you through yesterday and automate the non-selling work. Then have an AI agent draft short emails to the CFO or CEO on every live deal; reps check the facts and leaders send, so you hear no on day 3, not day 73.

By Ryan Milligan, CRO of QuotaPath, interviewed on the GTM Science podcast · GTM Science podcast, CRO Stories ↗ · Jun 9, 2026

If you sell: run it before your 10am

  1. Ask each rep to “walk me through yesterday” and list every non-selling task.
  2. Automate the biggest ones first, like CRM updates from calls.
  3. For each open deal, have an agent draft a short exec email from the call notes.
  4. The rep checks the facts; the leader sends it to the CFO or CEO.
  5. Track deals per rep, win rate and time to a clear yes or no.
Copy-paste prompt · Our template version (the source gave no prompt)
Here are my notes from calls on this deal: [paste]. Write a 90-word email from me, [title], to the prospect’s [CFO/CEO]. Say what their team is evaluating, the business outcome they told us they want, and ask one direct question about whether this is a priority this quarter. Use only facts from the notes; flag anything you had to guess.

If you lead a team: roll it out

  1. Run the “walk me through yesterday” audit before you buy any tool.
  2. Keep the rule: the rep checks every fact, the leader sends.

Watch out for

  • The results are team-wide, from several changes together, not from the exec email alone.
  • Vendor tools are named, but this is the CRO’s own interview, not a vendor case study.

Source: Ryan Milligan, GTM Science podcast, CRO Stories, Jun 9, 2026. Results are as reported by the source; we did not measure them.

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