Today’s plays › All plays › Negotiation & closing
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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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
- Ask each rep to “walk me through yesterday” and list every non-selling task.
- Automate the biggest ones first, like CRM updates from calls.
- For each open deal, have an agent draft a short exec email from the call notes.
- The rep checks the facts; the leader sends it to the CFO or CEO.
- Track deals per rep, win rate and time to a clear yes or no.
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
- Run the “walk me through yesterday” audit before you buy any tool.
- 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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