founder-sales

- Founder-led sales for early-stage products (typically pre-seed → Series A)

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Install skill "founder-sales" with this command: npx skills add oldwinter/skills/oldwinter-skills-founder-sales

Founder Sales

Scope

Covers

  • Founder-led sales for early-stage products (typically pre-seed → Series A)

  • Getting initial design partners / first customers (incl. first 10–30)

  • Outbound + warm intro outreach design (not high-scale automation)

  • Diagnostic discovery (problem-first; demo later)

  • Decision enablement (your #1 competitor is often “no decision”)

  • Closing-to-activation (white-glove onboarding to prevent “yes → silence”)

  • Building a simple, repeatable learning loop (message → calls → iteration)

When to use

  • “Help me get my first customers / first 10 customers.”

  • “Create a founder-led sales playbook.”

  • “Write a discovery call script (diagnostic, no demo).”

  • “Create an outreach sequence for my ICP.”

  • “Prospects go dark / end in no decision—help me close with a clear next step.”

  • “We close deals but onboarding stalls—create an activation/implementation plan.”

When NOT to use

  • You need to define the product, ICP, or positioning from scratch (do that first; then return here)

  • You’re scaling a full sales org (SDRs, AEs, quotas, forecasting, territories) rather than founder-led learning

  • You want scraped lead lists, spammy outreach, or anything deceptive/manipulative

  • You need legal/privacy/security advice or contract language (coordinate with qualified experts)

Inputs

Minimum required

  • Product: what it does, for whom, and the core “pain → outcome”

  • ICP hypothesis: target roles + company type (and who pays vs who uses)

  • Stage + goal: “first X customers” and timeframe (e.g., 10 customers in 8 weeks)

  • Offer: pricing hypothesis (or pilot structure) + what “success” looks like in 30 days

  • Proof: founder credibility and 1–3 proof points (results, prior work, early users)

  • Constraints: founder time per week + preferred channels (warm intros, email, LinkedIn, communities)

Missing-info strategy

  • Ask up to 5 questions from references/INTAKE.md.

  • If answers aren’t available, proceed with explicit assumptions and label unknowns. Include an Assumptions & unknowns section and a short Validation plan.

Outputs (deliverables)

Produce a Founder Sales Sprint Pack in Markdown (in-chat; or as files if requested):

  • Context snapshot (stage, goal, constraints, time box)

  • ICP wedge + founder POV (who, what pain, why now, why you, what you won’t do)

  • Targeting plan + target list (criteria + initial list table + next actions)

  • Outreach kit (warm intro request + cold message + follow-ups + meeting ask)

  • Diagnostic discovery kit (agenda + question bank + call notes template; “no demo first”)

  • Decision enablement kit (reduce “no decision”: decision guide + risk reversal + mutual action plan)

  • White-glove activation plan (implementation checklist + 30-day success plan + follow-up cadence)

  • Learning loop (tracking + weekly review + message iteration plan)

  • Risks / Open questions / Next steps (always included)

Templates: references/TEMPLATES.md

Workflow (7 steps)

  1. Intake + stage gating (founder-led focus)
  • Inputs: User context; references/INTAKE.md.

  • Actions: Confirm the goal (e.g., first 10 customers), time box, ICP hypothesis, and founder availability. Identify “must-not-do” constraints (ethics, brand, compliance). Decide what a successful 30-day customer outcome looks like.

  • Outputs: Context snapshot + success definition + constraints list.

  • Checks: The goal is measurable and time-boxed (who/what/by when). Founder involvement is explicit.

  1. Craft the founder POV + ICP wedge
  • Inputs: Product + founder credibility + early signals.

  • Actions: Write a founder POV that leads with insight (not features): the problem, why existing approaches fail, and why now. Tighten to 1 primary ICP wedge (plus 1 secondary) with exclusion criteria.

  • Outputs: ICP wedge statement + founder POV one-pager.

  • Checks: A target buyer can self-identify in 10 seconds. The POV is specific enough to repel non-ICP prospects.

  1. Targeting + outreach plan (warm first, then cold)
  • Inputs: ICP wedge; channel constraints; any existing network.

  • Actions: Define targeting criteria and build an initial target list. Create a “warm intro ask” and a cold outreach sequence designed for learning, not volume. Specify personalization hooks (“budding moments”) to test in messaging.

  • Outputs: Target list table + outreach kit (warm + cold + follow-ups).

  • Checks: Each message has a single clear ask and a believable reason for the recipient to respond.

  1. Run diagnostic discovery (no demo first)
  • Inputs: Discovery goals; references/TEMPLATES.md (Discovery kit).

  • Actions: Write a diagnostic call script that keeps the first conversation problem-first. Use questions that help the buyer self-diagnose and quantify impact. Capture language verbatim for future messaging.

  • Outputs: Discovery agenda + question bank + call notes template.

  • Checks: The script does not default to a product demo. The call ends with a concrete next step.

  1. Beat “no decision” with decision enablement
  • Inputs: Common objections; buyer risk profile; desired next step.

  • Actions: Create decision-enablement assets: (a) a short decision guide (options + criteria), (b) a risk-reversal / pilot framing, and (c) a mutual action plan (MAP) that makes the path forward easy and safe.

  • Outputs: Decision enablement kit (decision guide + risk reversal + MAP).

  • Checks: The buyer has a low-risk path to try/decide. The “do nothing” option is explicitly contrasted with its cost.

  1. Close-to-activation (white-glove implementation)
  • Inputs: What “implemented” means; onboarding steps; resources available.

  • Actions: Define activation milestones and an onboarding plan. Prevent “yes → silence” by scheduling implementation during the close, assigning owners, and creating a follow-up cadence. Treat the sale as complete only after activation.

  • Outputs: Activation/implementation checklist + 30-day success plan + follow-up cadence.

  • Checks: Every “closed” customer has a scheduled kickoff and clear activation criteria.

  1. Quality gate + finalize (learning loop)
  • Inputs: Draft pack.

  • Actions: Run references/CHECKLISTS.md and score with references/RUBRIC.md. Add a lightweight tracking + weekly review loop. Always include Risks / Open questions / Next steps and a short validation plan.

  • Outputs: Final Founder Sales Sprint Pack.

  • Checks: Assumptions are explicit; next steps are executable; artifacts are copy/paste ready.

Quality gate (required)

  • Use references/CHECKLISTS.md and references/RUBRIC.md.

  • Always include: Risks, Open questions, Next steps.

Examples

Example 1 (first 10 customers, B2B SaaS):

“Use founder-sales . We’re building scheduling automation for outpatient clinics. Goal: 10 paying customers in 8 weeks. ICP: clinic ops managers. Offer: $500/mo pilot. Output: a Founder Sales Sprint Pack with outreach sequences, a diagnostic discovery script, a MAP, and a white-glove onboarding plan.”

Example 2 (design partners, new category):

“Use founder-sales . We’re a security workflow tool for SOC teams. Goal: 6 design partners in 6 weeks. We have strong founder credibility but no case studies yet. Output: target list criteria + outreach kit + decision enablement assets that reduce buyer risk.”

Boundary example:

“Write a generic cold email that works for any product, and send 10,000 emails.”

Response: explain this skill is for founder-led learning and ethical, targeted outreach; request an ICP wedge + proof points and produce a small, testable sequence and learning plan instead.

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