How Daybreak Health turned a 4-hour-per-account renewal prep cycle into a 15-minute self-serve workflow — and built a system the GTM team actually uses.
A 30-person GTM team renewing and upselling 100+ school districts had everything they needed — except hours in the day to prep each conversation properly. CSMs were spending 3–5 hours per renewal on data pulls, slide formatting, and proposal assembly.
The Renewal & Upsell AI Workflow encodes that prep cycle into a self-serve Claude skill. One uploaded PDF in. A pre-meeting briefing, personalized deck, and pricing proposal out — in under 15 minutes.
CSMs had the data, the district relationships, and the pitch. The friction lived entirely in production — assembling the assets for each conversation from scratch, every time.
Encode the workflow once in AI infrastructure. Let the team self-serve. Free the strategists to strategize.
A CSM uploads a district's utilization report. The system returns three deliverables — all branded, all personalized, all ready to use without rework.
HTML dashboard with the district's ARR, contract type, risk flags, utilization summary, and the strategic angle to lead with. CSM reads this in 5 minutes before the call.
15–18 slides, fully personalized: district name, real funnel data, clinical outcomes, ADA recovery math, parent quotes, and the right ROI framing for the contract type.
Branded Word doc with the right template for the contract type, pre-filled with district contact info, plan structure, and contract terms. CSM adds the pricing.
After every session, the CSM rates prep quality and asset quality. Results route directly to the marketing lead via Slack DM for continuous improvement.
The skill reads the district's current plan, ARR, contract type, state, and Looker data — then routes to the right deck pathway and proposal template. The CSM never sees the logic. They just see the right output for the right account.
| Current plan | Renewal goal | Deck pathway | Key framing |
|---|---|---|---|
| Unlimited | Renew at current ARR | Deck 1 — Unlimited Renewal | Outcomes validation + ADA recovery |
| Unlimited (at risk) | Prevent downgrade | Deck 2 — Downgrade Defense | Coverage equity + parent voices |
| No-Cost | Upsell to Unlimited | Deck 3 — No-Cost → Unlimited | The 30% access gap |
| No-Cost | Upsell to budget option | Deck 4 — No-Cost → Uninsured | Equity bridge + low-cost entry |
| CYBHI No-Cost (CA) | Upsell to CYBHI Unlimited | Deck 5 — CYBHI Path | CA-specific funding + state alignment |
Slides adapt their framing based on the data underneath them — automatically.
A structured workflow encoded as modular Claude skill files, paired with project-level data sources and tight integration with the tools the GTM team already uses.
Three modular skills (deck, proposal, brand kit) encode every routing rule, layout spec, copy guideline, and QA step. Logic lives in version-controlled markdown — readable, refineable, shippable.
Revenue tracker, template library, brand assets, positioning research, benchmark data — all pre-loaded in the project, fetched on demand. No re-uploading per session.
The skill reads district plan, ARR, contract type, state, and Looker data, then routes to the right deck pathway (1 of 5) and proposal template (1 of 8).
Intake widget, tracker lookup, and skill load all fire simultaneously. By the time the CSM finishes intake, the dashboard is already rendering.
Content library lookups happen via Notion MCP. Post-session feedback routes via Slack MCP. The workflow closes the loop without manual handoffs.
New CSMs ramp faster. Senior CSMs spend their time on strategy and relationships. The production work comes out of the equation entirely.
Daybreak Health · 2025–Present