sales-playbook

When this skill is activated, always start your first response with the 🧢 emoji.

Sales Playbook

A structured, methodology-driven approach to the full B2B sales cycle - from first touch to closed-won. This skill covers outbound prospecting, discovery, qualification, demos, objection handling, and closing. It draws from proven frameworks (MEDDIC, SPIN, Challenger) and translates them into actionable templates and decision trees an agent can apply immediately.

The core philosophy: selling is problem-solving. Every outreach, question, and response should be oriented around the buyer's pain - not your product's features.

When to use this skill

Trigger this skill when the user:

• Wants to design or improve an outbound email or LinkedIn sequence
• Needs help handling a specific sales objection
• Is preparing for a discovery or qualification call
• Wants to apply MEDDIC, BANT, or another sales framework
• Asks how to write a cold email that gets replies
• Needs help structuring a product demo
• Is trying to close a deal or enter negotiation
• Wants to build a repeatable sales process from scratch

Do NOT trigger this skill for:

• Marketing campaign strategy or paid acquisition (use a marketing skill)
• Customer success or post-sale retention (different motion, different triggers)

Key principles

1. Discovery before demo - Never pitch before you understand the problem.

Run a full discovery call first. A demo presented to an unqualified prospect is a waste of both parties' time. Earn the demo by demonstrating you understand their situation.

1. Multi-thread every deal - Relying on a single champion is a single point

of failure. Map the buying committee early. Build relationships with economic buyers, technical evaluators, and end users in parallel.

1. Follow up relentlessly - 80% of deals close after 5+ touches. Most reps

stop at 2. A structured, value-adding follow-up sequence - not just "checking in" - is a primary differentiator between top performers and average ones.

1. Sell to pain, not features - Buyers don't care about features; they care

about outcomes. Always connect capabilities to specific pains the buyer has articulated. Feature-led pitches commoditize your product.

1. Document everything in CRM - Verbal commitments evaporate. Every call

insight, next step, and stakeholder detail must live in the CRM. This enables forecasting accuracy and deal handoffs without information loss.

Core concepts

Sales funnel stages

| Stage | Definition | Exit Criteria | |---|---|---| | Prospecting | Identifying and researching target accounts | ICP match confirmed | | Outreach | First contact via email, phone, or social | Meeting booked | | Discovery | Understanding pain, current state, and goals | Qualified or disqualified | | Demo / Evaluation | Showing product value against confirmed pain | Verbal buy-in from champion | | Proposal | Formal pricing and scope presented | Proposal accepted in principle | | Negotiation | Terms, pricing, and contract finalized | Legal/procurement engaged | | Closed Won / Lost | Deal signed or walked away | CRM updated with outcome and reason |

MEDDIC qualification

MEDDIC is the gold standard for enterprise deal qualification. Use it to assess deal health and identify gaps before forecasting.

• M - Metrics: What quantifiable outcome does the buyer want? (e.g., "reduce

churn by 15%", "save 10 hours/week per rep"). No metrics = no business case.

• E - Economic Buyer: Who has budget authority? Have you met them? Their

priorities must align with your value prop, not just your champion's.

• D - Decision Criteria: What criteria will be used to evaluate vendors?

Technical fit, security, price, integration? Get this in writing if possible.

• D - Decision Process: What is the step-by-step process to get to a signed

contract? Who reviews, who approves, what does legal look like, what is the timeline?

• I - Identify Pain: What is the specific, urgent, business pain? Pain that

is not urgent or not quantified will not drive a deal to close.

• C - Champion: Who inside the account is selling on your behalf when you

are not in the room? A champion has influence, believes in your solution, and has a personal stake in the outcome.

Buyer personas

| Persona | Primary concern | What they want from you | |---|---|---| | Economic Buyer | ROI, budget, risk | Business case, proof of value, trust | | Technical Buyer | Integration, security, reliability | Specs, security docs, references | | End User | Daily workflow, ease of use | Demo, trial, peer reviews | | Champion | Internal credibility, career impact | Talking points to sell internally |

Sales cycle anatomy

A healthy B2B sales cycle follows this arc:

1. ICP research - Firmographic + technographic fit before first touch
2. Personalized outreach - Specific trigger or insight drives the first email
3. Discovery call - 70% questions, 30% talking. Uncover MEDDIC elements.
4. Tailored demo - Show only features that address confirmed pain
5. Mutual action plan - Written timeline co-created with the buyer
6. Proposal + business case - Numbers tied to buyer's stated metrics
7. Negotiation - Anchor high, give on terms not on price, protect margin
8. Close - Ask for the order. Silence is not a close.

Common tasks

Design an outbound sequence (5-touch template)

A multi-touch outbound sequence maximizes reply rates while respecting prospect attention. Space touches 2-4 business days apart.

| Touch | Channel | Angle | Length | |---|---|---|---| | 1 | Email | Personalized trigger (funding, hire, news) + one-liner value | 4-6 sentences | | 2 | LinkedIn | Connection request with brief context, no pitch | 2-3 sentences | | 3 | Email | Pain-led: "teams like yours struggle with X" + social proof | 5-7 sentences | | 4 | Phone + VM | 20-second voicemail referencing email, ask for 15 min | 20 seconds | | 5 | Email | Break-up email: "I'll stop reaching out. Curious if X is a priority." | 3-4 sentences |

Key rules:

• Every touch must add value or perspective - never just "bump this up"
• Personalization is non-negotiable on touch 1; touches 3-5 can be semi-templated
• Subject lines: 3-5 words, no caps, no punctuation (e.g., quick question)
• One call to action per email - asking for a 15-minute call, not a 30-minute demo

Run a discovery call (question framework)

Discovery is the most important part of the sales cycle. Use SPIN questioning:

Situation questions (understand current state - keep brief):

• "Walk me through how your team handles [process] today."
• "What tools are you currently using for [area]?"

Problem questions (surface pain):

• "What's the biggest friction point in that workflow?"
• "How much time does your team spend on [manual task] each week?"
• "What happens when [problem] occurs? What's the downstream impact?"

Implication questions (quantify the cost of inaction):

• "If nothing changes, what does that mean for [goal] this quarter?"
• "How does that affect your team's ability to hit [metric]?"

Need-payoff questions (buyer articulates the value themselves):

• "If you could eliminate [pain], what would that mean for [goal]?"
• "How valuable would it be to get [outcome] by [timeline]?"

Call structure:

1. Set the agenda and confirm time (1 min)
2. Build rapport and context (2-3 min)
3. SPIN questions (15-20 min)
4. Summarize pain in their words (3-5 min)
5. Tease the solution and book next step (5 min)

Handle common objections (response templates)

See references/objection-handling.md for full response templates on 15+ common objections. The meta-framework for any objection:

1. Acknowledge - Validate the concern without agreeing it is a dealbreaker
2. Clarify - Ask a question to understand the real root concern
3. Respond