You will recognize these
You found product-market fit through self-serve. Now enterprise deals are closing and every one is a bespoke exercise.
- Enterprise deals quoted in Google Docs with pricing invented per deal.
- VP Sales is the human router for every discount and approval request.
- CS finds out about $60K customers from a Slack message weeks after close.
- Stripe handles self-serve. Manual invoices handle enterprise. Nobody can produce one ARR number.
What “done” looks like
For the VP Sales
Your founding AEs have a structured, repeatable way to quote and close enterprise deals. Pricing precedents are documented, not accidental.
For the CEO
The enterprise motion has real infrastructure. Board sees enterprise ACV moving. Operational maturity is credible before the next raise.
For VP Customer Success
Structured enterprise handoff with full context on every closed deal. No more finding out about large customers from a Slack thread.
What gets built
6 weeks. Fixed scope, fixed timeline. Here is exactly what you get.
Audit & Motion Roadmap
Review of your first 5 to 15 enterprise deals, pricing decisions made so far, and dual-motion analysis. Interviews with VP Sales, CEO, AEs, CS, and Finance. Prioritized roadmap delivered on Day 5.
Enterprise Quoting & Deal Desk
First formal enterprise pricing structure with SKU separation from self-serve. Quoting path configured with discount guardrails and a lightweight approval workflow. Designed for a team of 3 to 10 reps.
Handoffs & Provisioning
Structured Sales to CS handoff for enterprise accounts: kickoff checklist, context transfer template, implementation plan, and automated CS notifications.
Dual-Motion Billing
Stripe (self-serve) and enterprise invoicing reconciled into one unified ARR view. CRM configured as the single source of truth across both motions.
Rollout & Enablement
Live training session with the sales and CS teams. Go-live transition. Runbook and enablement recordings for onboarding future hires.
What we need from you
We work autonomously. Your leadership team provides alignment. Total effort: 6 to 8 hours per week across the buying committee.
VP Sales / CRO
2 hours per week. Pricing decisions, quoting parameters, approval policy.
CEO
1 to 2 hours per week. Early pricing decisions and enterprise motion strategy alignment.
Finance
1 hour per week. Dual-motion billing walkthrough and ARR reconciliation validation.
Common questions
We only have 5 to 10 enterprise reps. Are we too small for this?
This service is scoped for 5 to 10 rep teams. Lightweight by design. We install only what protects the enterprise motion today, not infrastructure built for a 50-person sales org.
Will this slow down our PLG motion?
PLG stays PLG. We add enterprise infrastructure alongside your self-serve motion, not on top of it. Dual-motion billing reconciliation protects both flows and gives you one unified ARR number.
We just hired our VP Sales. Is it too early for this?
It is the ideal time. Bad precedents set in the first 10 enterprise deals compound across the entire motion. Every week of ad-hoc pricing and discount drift creates patterns that are hard to unwind at $25M ARR.
We do not have a RevOps person to maintain this.
Everything we build is documented in a runbook. The 30-day warranty covers early issues. The infrastructure is designed to work within your existing CRM workflows without a dedicated ops hire.