product-led-sales

- Designing a product-led sales (PLS) motion: converting self-serve usage into a sales opportunity that can close larger contracts

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

Product-Led Sales

Scope

Covers

  • Designing a product-led sales (PLS) motion: converting self-serve usage into a sales opportunity that can close larger contracts

  • Defining product-qualified entities (PQL/PQA), signals, thresholds, scoring, and routing rules

  • Designing the sales handoff workflow (alerts, SLAs, dispositions) and a Product↔Sales feedback loop

  • Creating a usage-triggered outreach kit (helpful, compliant, not “creepy”)

  • Planning instrumentation, reporting, and a pilot-to-scale rollout

When to use

  • “We’re PLG/self-serve, but we want to add sales without breaking the low-touch funnel.”

  • “Define PQLs/PQAs and the product signals that should trigger outreach.”

  • “Create a product-led sales playbook for sales to act on usage signals.”

  • “Sales says MQLs are low quality—build a product-qualified pipeline instead.”

  • “Design a PLS pilot (routing + SLAs + measurement) before scaling.”

When NOT to use

  • You don’t have meaningful activation or self-serve usage yet (fix onboarding/activation first)

  • You want a purely enterprise, relationship-led motion with minimal product usage signals (use enterprise-sales )

  • You need ICP/positioning or pricing/packaging from scratch (do that first, then return)

  • You want spammy outreach, deception, or dark patterns (not supported)

  • You need legal/privacy/security advice or production data/CRM implementation (coordinate with qualified experts)

Inputs

Minimum required

  • Product + model: freemium/trial, typical onboarding path, who uses vs who buys

  • ICP/segments: target roles + company types + ACV bands (and which segment is in scope for PLS)

  • Objective: conversion to paid, expansion, ACV lift, pipeline creation (pick 1 primary)

  • Current funnel baseline: activation rate, trial-to-paid, expansion rate (even rough)

  • Usage data reality: what events/attributes exist, and whether you can map users → accounts

  • Sales capacity + workflow: SDR/AE/CS roles, SLAs, and where activity is logged (CRM)

  • Constraints: regions/compliance, “don’t use these signals,” messaging tone/brand rules

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 a Product-Led Sales Motion Pack in Markdown (in-chat; or as files if requested):

  • Context + goal snapshot (segment, objective, success metrics, constraints)

  • PLS funnel + ownership map (stages, intervention points, RACI, SLAs)

  • PQL/PQA definition + signal spec (signals table, thresholds/scoring, false-positive controls)

  • Routing + workflow spec (alerts, assignment rules, CRM fields, dispositions, feedback loop)

  • Usage-triggered outreach kit (email templates + call opener + follow-up rules)

  • Instrumentation + reporting plan (tracking plan, dashboards, leading indicators)

  • Pilot + scale plan (timeline, experiment design, rollout guardrails)

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

Templates: references/TEMPLATES.md

Workflow (7 steps)

  1. Intake + readiness gate (PLS is a layer, not a substitute)
  • Inputs: User context; references/INTAKE.md.

  • Actions: Confirm the primary objective and target segment(s). Run a readiness gate: do you have activation/usage depth + identity/account mapping to create reliable signals? Capture constraints (sales capacity, SLA expectations, privacy/compliance).

  • Outputs: Context snapshot + readiness verdict (Ready / Needs prerequisites) + assumptions/unknowns.

  • Checks: Objective is measurable; segment is explicit; prerequisites and constraints are documented.

  1. Map the PLS funnel and decide where sales intervenes
  • Inputs: Current PLG funnel, user journey, pricing/packaging, sales coverage model.

  • Actions: Map stages from first value → sustained usage → qualification → sales assist → purchase/expansion → onboarding. Pick intervention points where a human can increase deal size or reduce time-to-value, and define guardrails to keep a low-touch path intact.

  • Outputs: PLS funnel + intervention points + guardrails + ownership map (RACI).

  • Checks: Low-touch conversion path remains viable; ownership is explicit at every stage.

  1. Choose the qualified unit (PQL vs PQA) and write the definition
  • Inputs: Buyer/user model, account structure, pricing driver (seats/usage).

  • Actions: Decide the qualified unit:

  • PQL for user-led buying (a user’s intent/need)

  • PQA for account-led expansion (account adoption/coordination) Write a crisp definition: required signals + thresholds + exclusions.

  • Outputs: PQL/PQA definition (inclusion/exclusion + examples).

  • Checks: Definition is computable from data, not vibes; includes anti-gaming/false-positive controls.

  1. Build the signal spec, scoring, and routing/SLA rules
  • Inputs: Available events/properties, identity graph, sales capacity, CRM workflow.

  • Actions: Create a signal catalog (activation/aha, depth, breadth, integrations, invites, admin actions, billing intent). Set thresholds and scoring, define routing (who gets alerted, when), and specify a triage/holdout path for ambiguous signals.

  • Outputs: Signal spec table + scoring model + routing + SLA + disposition taxonomy.

  • Checks: Signals map to intent and value potential; routing matches capacity; false positives are addressed.

  1. Design the sales workflow and Product↔Sales feedback loop
  • Inputs: Sales roles, CRM fields, enablement constraints.

  • Actions: Define the operational workflow: alert delivery, assignment rules, what context reps see, required actions, logging, dispositions, and a weekly tuning loop with Product/RevOps to improve signals and messaging.

  • Outputs: Workflow spec + RACI + weekly review agenda.

  • Checks: Every alert has a next best action; outcomes are measurable and feed back into tuning.

  1. Create the usage-triggered outreach kit (helpful, not creepy)
  • Inputs: Use case narrative, common objections, signal context.

  • Actions: Write email templates that reference helpful context (“noticed you’re setting up X”) without surveillance language. Provide variants for early vs high intent. Add a call opener + discovery prompts anchored to the user’s likely goal.

  • Outputs: Outreach kit (emails + call opener + follow-up rules).

  • Checks: One clear ask per message; tone is respectful/compliant; personalization uses only approved signals.

  1. Pilot, measure, iterate, and scale
  • Inputs: Draft pack; baseline metrics; pilot constraints.

  • Actions: Propose a pilot (segment + duration + sample size), define success metrics and leading indicators (time-to-first-touch, meeting rate, conversion, expansion, retention). Run references/CHECKLISTS.md and score with references/RUBRIC.md. Finalize with Risks / Open questions / Next steps and a rollout plan.

  • Outputs: Final Product-Led Sales Motion Pack + pilot/measurement plan.

  • Checks: Pilot is bounded; dashboards are specified; iteration cadence is scheduled and owned.

Quality gate (required)

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

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

Examples

Example 1 (trial → sales assist):

“Use product-led-sales . We’re a B2B analytics tool with a 14-day trial. We get lots of signups but low trial-to-paid. We have usage events and can map users to companies via email domain. Sales: 2 SDRs + 2 AEs. Output: a Product-Led Sales Motion Pack with a PQL definition, routing rules, outreach emails, and a 4-week pilot plan.”

Example 2 (expansion via PQA):

“Use product-led-sales . We’re seat-based SaaS. Teams start self-serve at $20/seat but we want to land-and-expand into 100+ seat contracts. We can detect invites, admin setup, and integration activation. Output: a Motion Pack that defines PQAs, scoring, and a sales workflow + outreach kit for expansion.”

Boundary example:

“Write a generic cold outbound sequence for any product and send it to 50,000 people.”

Response: explain this skill is usage-signal-driven and must be targeted and compliant; request product + ICP + available signals and produce a small, testable sequence and pilot instead.

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