Enterprise Sales

Enterprise Sales

Scope

Covers

• Running a single enterprise deal (mid-market → enterprise) from qualification to signature
• Mapping the buying committee and empowering a champion
• Preventing “no decision” outcomes (status quo / ghosting) with decision enablement + MAP
• Procurement + contracting workflows (forms, vendor onboarding, preferred-vendor objections)
• Security reviews + security questionnaires (packaging answers, coordinating stakeholders)
• POCs/pilots framed as a business case + ROI model (not just technical fit)
• Product-led sales escalation (self-serve usage → enterprise expansion narrative)

When to use

• “Build a mutual action plan for an enterprise deal.”
• “My deal is stuck in procurement/security—help me run it.”
• “We need a champion kit for IT/legal/economic buyer.”
• “They want a POC—help me scope it and build the ROI case.”
• “We have usage but can’t convert to enterprise—build an escalation story.”

When NOT to use

• You’re still validating ICP / getting first customers (pre-product-market-fit) -> use founder-sales
• This is a transactional SMB sale without buying committee / procurement / security
• You have self-serve PLG usage and want to convert it into sales pipeline -> use product-led-sales
• You need a lead qualification or scoring framework (MQL/SQL definitions) -> use sales-qualification
• You’re building a channel/partner/reseller deal structure -> use partnership-bd
• You’re building a full sales org / forecasting system (use building-sales-team)
• You need legal advice or final contract language (coordinate with counsel)

Inputs

Minimum required

• Product + value: what it does, for whom, and the measurable outcome
• Account: company, segment, current state (existing tools/workflows), urgency/trigger
• Deal context: target package/ACV range, desired timeline, stage, and what “closed-won” means
• Stakeholders known so far: champion candidate, economic buyer, IT/security, legal/procurement, users
• Current friction: what is blocking progress (no decision risk, procurement, security, POC request, etc.)
• Constraints: what you can offer (pilot scope, services, security docs), internal resourcing, red lines

Missing-info strategy

• Ask up to 5 questions from references/INTAKE.md.
• If answers aren’t available, proceed with explicit assumptions and label unknowns in Assumptions & unknowns, plus a short Validation plan.

Outputs (deliverables)

Produce an Enterprise Deal Execution Pack in Markdown (in-chat; or as files if requested):

1. Deal snapshot (account, use case, stage, timeline, success definition)
2. Buying committee map + champion plan (roles, incentives, concerns, next actions)
3. Champion enablement kit (internal pitch + stakeholder one-pagers + objection answers)
4. Decision enablement plan (reduce “no decision”: do-nothing cost + decision guide + MAP)
5. POC/pilot plan + ROI business case (30-day plan; success metrics; ROI model; decision criteria)
6. Procurement + security packet plan (forms tracker, required docs, owners, timelines)
7. Close + implementation handoff (commercials, signature plan, kickoff + first value milestones)
8. Risks / Open questions / Next steps (always included)

Templates: references/TEMPLATES.md

Workflow (7 steps)

1) Intake + enterprise qualification (what “enterprise” means here)

• Inputs: User context; references/INTAKE.md.
• Actions: Confirm deal type (buying committee, procurement/security, ACV, timeline). Capture the core use case and desired business outcome. Identify the #1 stall risk (no decision vs procurement vs security vs POC).
• Outputs: Deal snapshot + assumptions/unknowns + validation plan.
• Checks: There is a clear outcome, buyer, and timeline (even if assumed).

2) Map the buying committee + pick the champion

• Inputs: Account org context; known stakeholders.
• Actions: Build a buying-committee map (5–7 common roles) and identify a champion (the person who can drive internal consensus). Define each stakeholder’s goals, risks, and required evidence.
• Outputs: Buying committee map + champion plan (what the champion needs next).
• Checks: A single “primary champion” is named (or a plan to find one within 1–2 calls).

3) Arm the champion (enable internal selling)

• Inputs: Use case, value narrative, stakeholder concerns.
• Actions: Produce a champion enablement kit: internal pitch memo, stakeholder one-pagers (IT/security, procurement, legal, economic buyer), and objection/FAQ answers. Include proof artifacts (case studies, security docs list, ROI assumptions).
• Outputs: Champion enablement kit.
• Checks: The champion can forward/share these materials without editing (copy/paste ready).

4) Beat “no decision” with decision enablement + MAP

• Inputs: Current stage; risks; target decision date.
• Actions: Make “do nothing” concrete (cost, risk, missed goals). Define the decision to be made, options, and decision criteria. Build a Mutual Action Plan (MAP) with dates, owners, and required outputs (incl. procurement/security milestones).
• Outputs: Decision enablement plan + MAP.
• Checks: MAP includes a decision meeting date and explicit buyer commitments (not just seller tasks).

5) Design the POC/pilot as a business case (not a feature test)

• Inputs: POC request; success criteria; data available; integration constraints.
• Actions: Reframe the POC as a 30-day pilot to co-create a business case/ROI model. Define measurable success metrics, required data, responsibilities, and decision criteria. If appropriate, propose a paid pilot/POC as a seriousness filter.
• Outputs: POC/pilot plan + ROI model + decision criteria.
• Checks: The pilot produces a decision-ready business case, not just “it works.”

6) Run procurement + security like a project (do the paperwork)

• Inputs: Procurement process; security requirements; contract constraints.
• Actions: Create a tracker for forms, security questionnaires, and vendor onboarding steps. Offer to pre-fill buyer forms to reduce their load. Prepare a minimal security packet checklist and coordinate internal SMEs. Consider contract structuring options (e.g., separate services vs software agreements) where appropriate—without giving legal advice.
• Outputs: Procurement/security tracker + packet checklist + comms plan.
• Checks: Owners and dates exist for every procurement/security task; blockers are explicit.

7) Quality gate + finalize (close-to-implementation)

• Inputs: Draft pack.
• Actions: Run references/CHECKLISTS.md and score with references/RUBRIC.md. Add a signature plan (who signs, when) and an implementation handoff (kickoff, first value milestone). Always include Risks / Open questions / Next steps.
• Outputs: Final Enterprise Deal Execution Pack.
• Checks: Next steps are executable this week; assumptions are explicit; “no decision” risk is actively managed.

Quality gate (required)

• Use references/CHECKLISTS.md and references/RUBRIC.md.
• Always include: Risks, Open questions, Next steps.

Anti-patterns

Avoid these common failure modes when producing an Enterprise Deal Execution Pack:

1. Single-threading the champion — Relying on one internal contact without mapping the full buying committee. Champions leave, get overruled, or lose political capital. Always map 5-7 stakeholders and have a backup path.
2. POC as a feature demo — Letting the POC become an open-ended technical evaluation without success criteria, timeline, or a business case. Every pilot must produce a decision-ready ROI model, not just “it works.”
3. Treating procurement as passive waiting — Sending forms and waiting instead of proactively project-managing procurement, security, and legal like a joint workstream with owners, dates, and escalation paths.
4. Ignoring “no decision” risk — Focusing on beating competitors while the real enemy is status quo inertia. The do-nothing cost must be made explicit and concrete with a decision guide and MAP.
5. Stopping at signature — Declaring the deal done at contract signing without an implementation handoff, kickoff plan, or first-value milestones. Failed implementations destroy expansion and references.

Examples

Example 1 (procurement + security stall): “Use enterprise-sales. We’re selling a workflow automation tool to a 5k-employee fintech. We have a champion in Ops, but procurement sent vendor onboarding forms and security wants a questionnaire + SOC 2. Output: an Enterprise Deal Execution Pack with a MAP, procurement/security tracker, and champion enablement one-pagers.”

Example 2 (POC request, ROI focus): “Use enterprise-sales. A healthcare enterprise wants a POC. ACV target $120k. They’re asking for a technical test, but we want to make it a business-case pilot. Output: a 30-day pilot plan with success metrics, ROI model, and a decision-ready business case.”

Boundary example (redirect to founder-sales): “We’re pre-seed with no customers yet. Help me figure out how to sell to my first 5 design partners.” Response: This is founder-led early-stage sales, not enterprise deal execution. Use founder-sales for ICP wedge development, diagnostic discovery scripts, and a learning-oriented outreach plan for your first customers.

Boundary example (redirect to product-led-sales): “We have 2,000 self-serve users and want to figure out which ones to reach out to for enterprise contracts.” Response: This is a product-led sales problem about converting PLG usage into pipeline. Use product-led-sales to define PQL/PQA signals, routing rules, and a sales-assist workflow. Once you have a qualified enterprise opportunity with a buying committee, return here.

Anti-pattern example: “Just write a generic enterprise sales script that closes anyone.” Response: This skill is deal-specific and evidence-driven. Request account context + stakeholders and produce a tailored MAP, champion kit, and pilot/business-case plan instead.