What Teams Do With Their Wingmen

The solve. "Improve paid subscriptions from 18% to 20%." The Wingman measures with the team's own conversion metric, walks the paywall funnel with the design system, sizes the exhausted free-tier users, ships a discount campaign and the discount API through Jira tasks with named owners, and launches the team's dashboard on its own domain.

The watch. A Campaign Monitor AI Employee checks conversion and redemptions daily and reports what's working and what isn't — pausing sends and flagging the PM when the code fails on annual plans.

The teaching. The Paid Conversion Playbook — by Emma — joins the Company Brain; the next growth question starts from it.

The solve. Leads were dying in a 4-day silence after the first call. The Wingman found it, applied the team's follow-up cadence and qualification gate — approved expertise from Sales Ops and RevOps — and put pricing before the demo, where the stalls stopped.

The watch. A Lead Follow-up AI Employee checks every new lead each morning and nudges the owner in Slack. No lead waits four days again.

The teaching. The Lead Conversion Playbook joins the brain — cadence, gate, and pricing-first, each cited to its author.

The solve. Every escalation triaged the way the team's best handler does it: root cause, owner, customer communication — captured once as approved expertise instead of living in one person's head.

The watch. An Escalation Triage AI Employee classifies new escalations as they land, flags repeat offenders and SLA risk, and reports the day's picture.

The teaching. The triage playbook — and every hard case that refines it — compounds in the brain.

The solve. Something's off-trend; the Wingman runs the root-cause analysis with the company's real data and definitions and posts the diagnosis, not a dashboard link.

The watch. A Checkout Drop-off (or any off-trend) AI Employee runs the RCA every morning and reports the diagnosis to the team in Slack — escalating with a named owner when it finds something real.

The teaching. Each RCA's method joins the brain, so the next anomaly starts from everything already ruled out.

The solve. The pricing review done with the company's actual definitions — which discounts count, which margins matter, which exceptions apply — instead of a fresh spreadsheet argument each quarter.

The watch. The review runs on schedule as an AI Employee, with changes highlighted and anything anomalous escalated to the owner.

The teaching. The definitions themselves become approved expertise — the end of "which number is right?"

The solve. The WBR assembled from live data with the team's own definitions; the competitor brief built from the sources the team actually trusts.

The watch. Both run as AI Employees — on schedule, reporting deltas rather than data dumps, escalating surprises.

The teaching. What counts as "worth reporting" is itself approved expertise — tuned once, reused every week.