claude-skills-reference/c-level-advisor/cro-advisor/references/sales_playbook.md

Sales Playbook

Frameworks for building, running, and scaling a B2B SaaS sales organization.

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Sales Process Design

A sales process is a repeatable series of steps that takes a prospect from first contact to closed revenue. Without it, you have individual heroics, not a scalable machine.

The Core Funnel

Lead Generation → Qualification → Discovery → Demo → Trial / POC → Proposal → Negotiation → Close → Handoff

Each stage has a clear entry criterion, exit criterion, and owner.

Stage Definitions

Stage 0: Lead / Suspect

• Entry: Contact exists in CRM with basic firmographic data
• Owner: Marketing or SDR
• Exit criterion: Meets ICP criteria (company size, industry, tech stack)
• Action: Research, prioritize, add to outbound sequence

Stage 1: Prospecting / Outreach

• Entry: ICP-qualified account, no contact yet
• Owner: SDR or AE (depending on model)
• Exit criterion: Meeting booked with a qualified contact
• Action: Multi-channel outreach (email + call + LinkedIn), 8-12 touch sequence
• Key metric: Meeting booked rate (benchmark: 2-5% of outbound contacts)

Stage 2: Discovery

• Entry: First meeting confirmed
• Owner: AE (SDR hands off or joins)
• Exit criterion: Confirmed: pain, budget range, decision process, timeline
• Action: Ask questions. Listen. Map the org. Don't pitch yet.
• Key metric: Discovery-to-demo rate (benchmark: 60-80% proceed)

Discovery question framework:

Situation:    "How do you currently handle [problem area]?"
Problem:      "What's the impact when [pain point] happens?"
Implication:  "If this continues, what does that mean for [business goal]?"
Need-payoff:  "If we solved this, what would that be worth to you?"

Stage 3: Demo / Solution Presentation

• Entry: Confirmed pain and fit from discovery
• Owner: AE (+ SE for complex products)
• Exit criterion: Prospect agrees to evaluate / trial; next step defined
• Action: Show the workflow that solves their specific pain (not a feature tour)
• Key metric: Demo-to-trial/proposal rate (benchmark: 40-60%)

Demo structure:

1. Recap their pain (show you listened) — 5 min
2. Show the "aha moment" (fastest path to value) — 10 min
3. Walk the specific workflow they described — 15 min
4. Handle objections, confirm fit — 5 min
5. Define clear next step (date, owners, criteria) — 5 min

Never show features they didn't ask for. Every additional feature is noise until they have a reason to care.

Stage 4: Trial / POC

• Entry: Prospect commits to evaluate with real data/use case
• Owner: AE + CSM or SE
• Exit criterion: Success criteria met, POC success confirmed
• Action: Define success criteria upfront (in writing). Set a tight timeframe (2-4 weeks max).
• Key metric: POC-to-proposal rate (benchmark: 50-70%)

POC setup requirements:

Before any POC:
  □ Signed NDA
  □ Written success criteria ("We'll move forward if X happens")
  □ Named champion who owns the evaluation
  □ Executive sponsor identified
  □ Defined timeline with end date
  □ Agreed next step if criteria are met

If you can't get written success criteria, you don't have a real opportunity. You have a "we'll see."

Stage 5: Proposal / Pricing

• Entry: POC success OR strong discovery fit for simple products
• Owner: AE
• Exit criterion: Proposal received, timeline to decision confirmed
• Action: Present in a live call, never email a proposal cold
• Key metric: Proposal-to-negotiation rate (benchmark: 50-75%)

Proposal structure:

1. Problem statement (their words, not yours)
2. Proposed solution (mapped to their workflow)
3. ROI summary (value delivered vs. investment)
4. Pricing options (give 2-3 options; anchors the decision)
5. Next steps with dates

Stage 6: Negotiation

• Entry: Verbal intent to proceed, price/terms discussion begins
• Owner: AE (+ VP Sales for large deals)
• Exit criterion: Mutual agreement on terms; contract sent
• Action: Never discount before they ask. Discount on scope, not on margin.
• Key metric: Negotiation win rate (benchmark: 70-85%)

Negotiation principles:

• Get something for everything you give. Discount → multi-year. Fast close → early pay discount.
• Don't negotiate against yourself. Silence after an offer is not rejection.
• Know your walk-away before you enter. If you don't have a BATNA, you have no leverage.
• Legal/procurement delay ≠ deal death. Keep the champion engaged.

Stage 7: Close

• Entry: Signed contract or PO received
• Owner: AE
• Exit criterion: Contract countersigned, kickoff date set
• Action: Celebrate with the customer. Immediately introduce CSM.
• Key metric: Average close rate (closed won ÷ all closed = won + lost)

Stage 8: Handoff to Customer Success

• Entry: Deal closed
• Owner: AE + CSM
• Exit criterion: Customer has met their assigned CSM, kickoff scheduled
• Action: Internal handoff call with AE + CSM. AE shares: deal context, key stakeholders, use case, success criteria, any promises made during the sale.

Handoff document (AE fills before first CS meeting):

Account: [name]
ACV: $X
Close date: [date]
Primary contact: [name, title, email]
Economic buyer: [name, title]
Use case: [specific workflow]
Success criteria: [what they said good looks like in 90 days]
Promises made: [anything specific committed during sale]
Risk flags: [competitive, budget, champion strength]

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MEDDPICC Qualification Framework

MEDDPICC is the enterprise qualification standard. If you can't answer every letter, you don't have a qualified opportunity — you have a conversation.

M — Metrics

What is the quantified business impact? What does winning look like in numbers?

• "What's the current cost of [the problem]?"
• "How do you measure success in this area today?"
• "If we achieve X outcome, what does that save or earn you?"

Red flag: No metrics = no business case = hard to get budget.

E — Economic Buyer

Who has final authority to approve the budget?

• "Who else will be involved in the final decision?"
• "Have you purchased solutions in this range before? Who approved that?"
• "When we get to final terms, who needs to sign?"

Red flag: You only know the user buyer. Economic buyer hasn't engaged.

D — Decision Criteria

What factors will they use to evaluate and select a solution?

• "What's most important in your evaluation?"
• "How will you compare options?"
• "What does the ideal solution look like to you?"

Why it matters: If you don't know their criteria, you're guessing what to prove. Define the criteria before you compete on them.

D — Decision Process

What are the steps from evaluation to signed contract?

• "Walk me through your process from here to signed agreement."
• "Does procurement get involved? Legal? InfoSec?"
• "Have you purchased software at this price before? How long did that take?"

Red flag: No defined process = unlimited sales cycle.

P — Paper Process

What's the contract and legal process?

• "Who manages vendor contracts on your side?"
• "What's your standard MSA, or do you use ours?"
• "How long does legal review typically take?"

Why it matters: Legal and procurement have killed many "done" deals. Start early. Route to your legal team simultaneously.

I — Identify Pain

What is the specific, felt pain driving this evaluation?

• "What triggered this initiative now vs. six months ago?"
• "What happens if you don't solve this in Q3?"
• "On a scale of 1-10, how urgent is this for your team?"

Red flag: Pain isn't felt by the economic buyer. User pain ≠ budget authority.

C — Champion

Who will actively sell your solution internally when you're not in the room?

• "Who else have you brought into this evaluation?"
• "Can you help us get access to [economic buyer / IT / security]?"
• "If the decision went the wrong way, who would be disappointed?"

Red flag: Your champion is enthusiastic but has no internal influence.

C — Competition

Who else are they evaluating? What's your position?

• "Are you looking at alternatives?"
• "What made you start with us?"
• "Have you used [Competitor X] before?"

Why it matters: Knowing the competitive field tells you what you need to prove and what to neutralize.

MEDDPICC Scorecard

Letter	Score 1	Score 2	Score 3
Metrics	No numbers	Approximate value	Specific ROI model
Economic Buyer	Unknown	Named, not engaged	Engaged directly
Decision Criteria	Vague	Partially defined	Written, weighted
Decision Process	Unknown	Verbal description	Steps confirmed, timeline known
Paper Process	Unknown	Basic awareness	Legal contacts, standard process known
Identify Pain	No urgency	User-level pain	Executive-level pain with consequences
Champion	No advocate	Friendly contact	Actively selling internally
Competition	Unknown	Identified	Position mapped, differentiation clear

Score each 1-3. Total 16+/24 = qualified opportunity. Under 12 = unqualified, do not forecast.

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Sales Compensation Plans

Comp drives behavior. Design it precisely.

Base / Variable Split

Role	Base %	Variable %	Rationale
SDR	60-70%	30-40%	Activity-based, not purely revenue
AE (Inside Sales)	50%	50%	Balanced risk/reward
AE (Enterprise)	55-60%	40-45%	Longer cycle, higher base for stability
VP Sales	50%	50%	Accountable for team results
CSM (retention focus)	70%	30%	Less variable, stable relationship role
CSM (expansion focus)	60%	40%	Expansion quota adds variable

Commission Structure

Standard AE plan:

Base: $80K
Variable: $80K (at 100% quota attainment)
OTE: $160K

Commission rate: OTE variable ÷ Quota
  If quota = $800K ARR: commission = $80K ÷ $800K = 10% of ARR closed

Accelerators (performance above quota):
  101-125% quota: 1.25x commission rate (12.5% of ARR)
  126-150% quota: 1.5x commission rate (15% of ARR)
  > 150% quota: 2.0x commission rate (20% of ARR)

Why accelerators matter:

• They keep top performers motivated past quota
• They make it possible for top reps to earn $200K+ (attracting talent)
• They create the "make it rain" culture

SDR Compensation

SDRs are measured on output (meetings booked, pipeline created), not closed revenue.

Quota: 20 qualified meetings booked per month (or $X pipeline created)
Commission: $150-300 per qualified meeting held

Accelerators:
  If a meeting converts to closed won: Bonus $250-500
  If monthly meetings > 125% of quota: 1.5x rate on upside meetings

Clawbacks

A clawback recovers commission paid on deals that churn or are fraudulently closed.

Common clawback rules:

• Full clawback if customer cancels within 90 days of close
• 50% clawback if customer cancels within 91-180 days
• No clawback after 180 days (AE shouldn't be penalized for future CS failures)
• Clawbacks vest: pay commission immediately but apply against next quarter's payout if triggered

Why clawbacks matter:

• Without them, reps are incentivized to close any deal, regardless of fit
• With them, reps self-qualify more carefully

SPIFFs (Sales Performance Incentive Funds)

Short-term tactical incentives for specific behaviors:

• $5K bonus for closing a new vertical deal this quarter
• 1.5x commission on annual prepay deals in Q4
• $1K for closing a deal in a new geographic territory

Use SPIFFs sparingly. Overuse trains reps to wait for the SPIFF before engaging.

Multi-Year and Prepay Incentives

Align rep behavior with company cash flow:

• Multi-year deals: Credit full TCV against quota, pay commission upfront on TCV
• Annual prepay: 10-20% uplift on commission rate
• Monthly billing: Standard commission rate

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Enterprise vs. SMB vs. Self-Serve Models

Self-Serve / PLG

Characteristics:

• Product is the primary acquisition channel
• Credit card required (no invoicing)
• No human touch in the initial purchase
• Sales engages only at enterprise signals (high usage, team expansion, compliance needs)

Funnel:

Website → Free trial / Freemium → Activation → PQL → Expansion → Enterprise

Key metrics:

• Free-to-paid conversion rate (benchmark: 2-5% of signups)
• Time to activation (first core action)
• PQL → expansion conversion rate
• NRR from self-serve base

Sales involvement triggers (PQL signals):

• Team size > 10 seats
• Usage spikes (power user patterns)
• Feature limit hits on core features
• Job title change (new economic buyer appears in account)

SMB Inside Sales

Characteristics:

• ACV $5K-25K
• 30-60 day sales cycle
• Inbound-heavy or light outbound
• SDR → AE → CS model
• Phone + email + video; no in-person

Funnel:

Inbound/MQL → SDR qualifies → AE discovery → Demo → Proposal → Close

Key metrics:

• MQL-to-SQL rate (benchmark: 15-25%)
• SQL-to-close rate (benchmark: 20-30%)
• Average sales cycle (30-60 days)
• AE productivity: $600K-$1M quota per rep

Team ratios:

• 1 SDR supports 3-4 AEs
• 1 CSM manages $1M-2M ARR

Enterprise Sales

Characteristics:

• ACV $50K+
• 90-365 day sales cycle
• Outbound prospecting + inbound from brand
• AE + SE + executive sponsor model
• Multi-stakeholder: champion, economic buyer, IT, legal, procurement

Funnel:

Account targeting → Executive outreach → Discovery → POC → Security review → Legal → Procurement → Close

Key metrics:

• Deals in pipeline (volume matters less, quality more)
• POC win rate (benchmark: 60-75%)
• Average sales cycle (3-12 months)
• AE productivity: $1.5M-$3M quota per rep

Team ratios:

• 1 SE supports 3-4 AEs
• 1 CSM manages $2M-5M ARR (named accounts, high-touch)

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Sales Hiring and Ramp

What "Good" Looks Like by Role

SDR (entry level):

• 1-2 years of outbound experience OR strong track record in customer-facing role
• Resilient: rejection is the job
• Coachable: SDR is a proving ground, not a final destination
• Can write clear, concise prospecting emails without templates

AE (inside sales):

• 2-4 years sales experience, preferably SaaS
• Can articulate their process for a discovery call
• Knows their numbers: quota, attainment, average deal size, sales cycle
• Shows how they build pipeline (AEs who only work inbound are a risk)

AE (enterprise):

• 4-8 years B2B sales, at least 2 in enterprise
• Has closed deals > $100K ACV
• Can name the stakeholders in a complex deal they navigated
• Understands procurement, security review, multi-year contracts

VP Sales:

• Has scaled a team from where you are to 2x your size
• Can build a comp plan from scratch
• Has hiring and firing experience
• Revenue from a repeatable process, not personal relationships

Interview Process

3-stage process:

1. Recruiter screen (30 min): Motivation, experience, logistics
2. Manager interview (60 min): Structured questions on process, examples, numbers
3. Panel / role play (90 min): Mock discovery call + debrief; team fit

Role play rubric:

• Did they prepare (knew your product, your ICP)?
• Did they ask before pitching?
• Did they handle pushback without capitulating immediately?
• Did they confirm a next step with a date?

Onboarding Structure (6-Week Ramp)

Week	Focus	Activities
1	Company, product, ICP	Onboarding sessions, product sandbox, shadow AE calls
2	Sales process, tools, messaging	CRM training, call review, write first prospecting emails
3	First outreach	Send first sequences, book first meetings, shadow closes
4	Independent discovery	Lead own discovery calls with manager reviewing
5	Full cycle	Handle pipeline independently, weekly coaching
6	Quota-bearing	25% of quota expectation; full accountability begins

Performance Management

Clear standards, no surprises:

Month 3: 25% of quota expected. Miss by > 50% → performance conversation.
Month 4: 50% of quota expected. Miss by > 40% → PIP warning.
Month 5: 75% of quota. Miss by > 30% → formal PIP.
Month 6+: 100% of quota. Consistent miss → exit.

PIP (Performance Improvement Plan) — not for show:

• Should include specific, measurable targets (not "improve attitude")
• 30-60 day timeline
• Weekly check-ins with manager
• If targets aren't met: exit, no extensions
• A PIP that doesn't lead to improvement or exit is a management failure

Rule: Low performers who stay cost you your top performers. They watch what you tolerate.