CONTENTS
A SALES-SYSTEM PLAYBOOK
What's inside
From why training alone fails to a sales system your whole team follows, plus the plans and scripts to run it.
01 Introduction
Why training without a system fails
07 Training & coaching
90-day onboarding, role-play, cadence
02 The MSP sales challenge
Why managed services are hard to sell
08 The sales playbook
The operating system for how you sell
03 The scaling inflection point
What breaks between 2 and 10 reps
09 Measure & scale
Metrics, pipeline and the path to 10 reps
04 The five-stage framework
From discovery to close, built into a system
10 Takeaways & next step
Seven principles, and how Salesbuildr helps
05 Beyond the funnel
Onboarding, adoption, expansion, advocacy A1-A2 Toolkit: 90-day rep onboarding plan Week by week, with a checkpoint at the end of each month
06 Value communication
Outcomes, ROI and the price objection
A3-A4 Toolkit: questions & objections A discovery question bank and six objection scripts
INTRODUCTION
Training without a system fails
The top performers have a system. Everyone else has a collection of habits.
The fastest path to better sales performance is a system that makes the right way of selling the only way, then training your people to use it.
THE GAP 6%
Average EBITDA across MSPs.
THE TOP 20%
14-25%
EBITDA of the top 20%. The difference is a system.
WITHOUT A SYSTEM
Templates scattered across someone's drive
Pricing that depends on who quotes
Pipeline trapped in an inbox
Every rep running their own process “Everyone talks about different theories in sales and marketing. But the crux of it is they do zero of it.”
DARREN STRONG
Written for MSP owners, sales managers and team leads. Built on interviews with 25+ MSP sales leaders on the Harvest MSP Sales Show, and on what we see across the hundreds of MSPs that use Salesbuildr.
CHAPTER 01
The MSP Sales Challenge
Why selling managed services is uniquely difficult, and why it gets harder as you grow.
Long sales cycles Deals take 60-120 days. Every week without momentum lets inertia kill the deal.
Two audiences The IT manager talks uptime. The owner or CFO buys lower risk and predictable cost.
Recurring revenue One contract can carry tens or hundreds of thousands in lifetime value, so qualify hard.
Sell solutions Sell outcomes: less downtime, predictable cost, stronger security, compliance readiness.
Trust comes first Transparent pricing, proof points and fast follow-up say more than any slide.
The margin gap. Top-20% MSPs earn $50 gross margin per $100 of service revenue. The average earns $38, James Davis. “You become a business advisor and a thought leader as opposed to a technology person with a tool belt that installs blinky lights.”
TIM THOMPSON
CHAPTER 02
The Scaling Inflection Point
At 50+ employees and several reps, the same challenges compound in ways founder-led sales never faced.
- Hero-rep dependency When one person holds the relationships, the pipeline and the pricing authority, you have a single point of failure.
- Buying committees IT director, CFO, CEO and often compliance, each with different concerns. A single-threaded deal is the fastest way to lose one you thought was won.
- Split selling from scoping Hand off to sales engineering above an MRR threshold, for multi-site or compliance-driven scope, or beyond two hours of technical deep-dive.
- Larger competitors CDW, Insight, consolidators and PE-backed platforms chase the same midsize accounts. Agility only wins when a system makes it repeatable. “Stop them being people driven and make them process driven.”
MIKE PARFITT
CHAPTER 03
The Five-Stage Sales Framework
A shared path from first call to signed agreement, embedded in the tools your team uses every day.
STAGE 1
Discovery
Environment, pains, triggers, goals, decision process and past MSP experience. Talk 20%, listen 80%.
STAGE 2
Qualification
Use BANTF (budget, authority, need, timeline and fit) to spend time on deals that can close.
STAGE 3
Needs & design
Technical assessment, gap analysis and solution mapping. Quantify the cost of inaction.
STAGE 4
Proposal
Customer first, pricing next, “about us” last.
Send within 24-48 hours and present it. Never just email it.
STAGE 5
Negotiation & close
Keep it a conversation.
Assumptive, cost-of-inaction or timeline close.
QUALIFY HARD
60% of inbound leads disqualified by Ian Groves (Startech), while growing 24% a year. The deals got better.
BUILD IT INTO THE SYSTEM
Put the framework in your CRM, proposal tool, templates and daily workflow. With templates and CPQ, every proposal follows the same structure, pricing logic and value narrative, and building one drops from 30+ minutes to under 5.
“Your proposal is never about you. Talk about your customer first.”
HANNEKE VOGELS
CHAPTER 04
Beyond the Funnel: The Bowtie
For recurring revenue the signature is the starting line. Two of three growth engines, retention and expansion, happen after it.
5-7× cheaper to grow an existing customer than to win a new one.
40-60% of potential revenue sits untapped in your existing base.
15-25% annual growth target per account through data-driven expansion.
STAGE 6
Onboarding
A formal pass from sales to delivery after the win: notes and solution design transferred, 30/60/90 day expectations set. Measure time to first value.
STAGE 7
Adoption & impact
QBRs as a structured demonstration of value. Watch adoption signals: a customer who stops engaging is at risk.
STAGE 8
Expansion
Whitespace: what does this customer not buy that your best customers already do? Your golden contract is the benchmark.
STAGE 9
Advocacy
Ask for referrals at month six, capture testimonials in QBRs, track NPS and act on detractors before they churn.
The Bowtie model, popularised by Winning by Design, extends your funnel. The funnel is only half the picture, and often the less profitable half.
CHAPTER 05
The Art of Value Communication
Turn features into business outcomes and defeat the status quo.
THE “SO WHAT?” TEST
“We monitor 24/7” → You'll never be surprised by a revenue-costing outage “Enterprise-grade backup” → Ransomware hits? You're back online in hours “Weekly endpoint patching” → Your compliance audit passes without scrambling
Start with their world
Show them you listened.
Problem-agitate-solve
Name it, amplify it, solve it.
Tell stories
Stories stick. Bullets don't.
Make it visual
Comparisons, ROI, timelines.
ROI
The ROI conversation Downtime costs SMBs $10K-$50K an hour. Add productivity, breach and compliance risk, and stalled projects. Most managed services are priced at 35-40% gross margin; best practice is 50-55% (James Davis).
PRICE
The price objection Rarely about price, mostly about perceived value. Never apologise: restate outcomes and quantify the risk of the cheaper option. Five orders a month at 10% off is £30K a year (Graeme Stead).
CHAPTER 06
Training & Coaching Your Team
Training is an event. Coaching is a habit.
THE FIRST 90 DAYS: ALAN LLOYD’S FRAMEWORK
WEEKS 1-2 Immersion and values
WEEKS 3-4 Product and market training WEEKS 5-8 Guided selling with real-time feedback WEEKS 9-12 Supervised independence Focus on pipeline
ROLE-PLAY
Awkward, and worth doing Run “deal autopsies” and practise the sceptical IT manager, the price-focused CFO, the burned prospect, “we're fine” and committee presentations. At least twice a month.
COACHING CADENCE
Daily stand-ups for focus and blockers
Weekly one-on-one pipeline reviews
Bi-weekly call or proposal reviews
Monthly performance deep dives
Quarterly career conversations
CHAPTER 07
Build Your Sales Playbook
The operating system for how your team sells.
Ideal customer profile Specific enough for a new rep to judge fit.
Qualification criteria
BANTF with clear thresholds.
Proposal templates
Pre-built for your common scenarios.
Buyer personas
Concerns and outcomes per buying role.
Objection handling
Frameworks for the top five objections.
Pricing guidelines
Discount authority and margin floors.
Discovery question bank 20-30 questions, organised by category.
Battle cards One per competitor, incl. the status quo.
Case studies Organised by industry, size and use case.
HOW TO MAINTAIN IT
The sales manager owns it; the team contributes; nobody ignores it.
Review quarterly with win/loss and competitive insight. Version it, make it searchable and keep it where reps work.
THE TEST
Can a new rep follow it and produce a competent proposal in their first week? If not, the playbook is not done.
CHAPTER 08
Measuring & Scaling Performance
KPIs, pipeline discipline and the path from 2 reps to 10.
LEADING INDICATORS
Discovery calls booked
Proposals sent
Follow-up response time
Outreach volume
LAGGING INDICATORS
Win rate and average deal size
Sales cycle length
MRR added
Customer acquisition cost
PIPELINE DISCIPLINE
3-5× coverage of target
Weekly reviews on deal movement
Ageing analysis for stuck deals
Separate commit vs. upside
SCALING FROM 2 REPS TO 5 TO 10
- 2 reps. The founder coaches directly. An informal process works, until it doesn't.
- 5 reps. A dedicated sales manager without a full quota. Formal weekly pipeline reviews. Standards become non-negotiable.
- 10 reps. Team leads or pods, hunters and farmers. One manager per 5-8 reps. Beyond 8, someone isn't coached.
- When to hire. When reps are at capacity with qualified pipeline left. If non-selling work tops 40%, invest in systems first.
James Davis's benchmark: 50%+ gross profit with operating expenses below 32% delivers best-practice 18-20% EBITDA.
KEY TAKEAWAYS
Seven principles to take away
Build the system first. Then train your people to use it.
- Systems beat talent Build the framework, then embed it in a system everyone follows.
- Discovery is the foundation Talk 20%, listen 80%. No fit with their top three priorities, no sale.
- Sell outcomes Decision-makers buy lower risk and predictable cost.
- Coach continuously First 90 days: pipeline first. Hire for coachability.
- Measure what you can still change Track leading indicators as well as win rate and revenue.
- Systems create speed Templates and CPQ take proposals from 30+ minutes to under 5.
- Grow the base you have Track what each client doesn't buy. Whitespace turns account management into growth. “Stop talking about which method to choose and just do something.”
DARREN STRONG
ABOUT SALESBUILDR
Turn your sales playbook into daily practice
One system for CPQ, portfolio management, PSA integration and whitespace discovery.
WHAT SALESBUILDR OPERATIONALIZES
Smart revenue discovery
Whitespace in your existing base
CPQ & templates
On-brand proposals in minutes
Native PSA integrations
Autotask, ConnectWise or Halo 50+ distributor feeds
Distributor pricing
Template system Your playbook as governed building blocks 30-day guarantee
Zero risk to get started
THE PEOPLE BEHIND SALESBUILDR
Meet the team behind the platform and this framework.
Victor Raessen
Founder
Micha Bos
Sales Director Europe
Ready to scale your MSP sales operation?
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TOOLKIT
TOOLKIT A1 · 90-DAY ONBOARDING · WEEKS 1-6
A 90-day plan to get new reps quoting and closing on their own
Bridge Group's 2026 study of 158 B2B tech companies puts the average ramp for a new account executive at 6.2 months. This plan aims to cut that by giving each week one job and one test.
WEEK, WHAT THE REP DOES, DONE WHEN
- Week 1. Values, ICP, how we deliver. Sit with the service desk for two days. Done when: Explain who we sell to and why in 2 minutes.
- Week 2. Shadow 5 discovery calls and 2 proposal meetings. Read the playbook. Done when: Write up one shadowed call in the discovery template.
- Week 3. Product training: core offers, bundles, what is and isn't included. Done when: Quote three standard deals from templates without help.
- Week 4. Market: competitors, the status quo, top five objections. Role-play twice. Done when: Day 30 check: pass a mock discovery call with the manager.
- Week 5. Run discovery calls with the manager on the line; debrief after each. Done when: Discovery notes complete for every call.
- Week 6. Build proposals from your own calls; manager reviews before sending. Done when: Proposal out within 48 hours of each call.
TOOLKIT
TOOLKIT A2 · 90-DAY ONBOARDING · WEEKS 7-12
A 90-day plan to get new reps quoting and closing on their own
The manager steps back each month. By week 12 the rep runs discovery, quotes from templates and presents without the founder.
The chapter 6 coaching cadence runs alongside.
WEEK, WHAT THE REP DOES, DONE WHEN
- Week 7. Present proposals live, with the manager attending. Practise the price objection. Done when: two proposals presented, not emailed.
- Week 8. Own a small pipeline (5-8 deals), with a daily stand-up and a weekly review. Done when: day 60 check, pipeline in the CRM, every deal with a next step.
- Week 9. Run deals alone. The manager joins only for committee meetings. Done when: follow-up within 24 hours on every open proposal.
- Week 10. Prospect your own leads. Ask existing clients for introductions. Done when: meetings booked from your own activity.
- Week 11. Pass the won deal to delivery: run one kickoff with the project team. Done when: a clean pass after the win, with notes and scope agreed.
- Week 12. Review the quarter: wins, losses, what to change. Done when: day 90 check, agree targets for next quarter.
TOOLKIT
TOOLKIT A3 · DISCOVERY QUESTION BANK
21 discovery questions, by category
Ask three or four from each row, then stop talking. Write their answers in their words; you will reuse them in the proposal.
Environment. How many users, sites and devices?
Which tools and licences do you run today?
What's coming up in the next 12 months (moves, hires, projects)?
Pain. What went wrong in the last three months?
How much time does your team lose when systems are down?
Who in the business ends up being the IT help desk?
Triggers. Why are we talking now and not six months ago?
Is an insurer, auditor or client asking for anything?
When does your current contract end?
Goals. What should be different in a year?
How will you judge whether a new provider is working?
What would make you renew?
Decision process. Who else needs to agree, and what does each of them care about?
Who signs, and what does finance need to see?
What happened last time you changed provider?
Budget and commercials. What do you spend on IT today, including surprise invoices?
Do you prefer a fixed monthly fee or pay as you go?
Is there a budget cycle we need to hit?
Past MSP experience. What did your last provider do well?
What made you start looking?
What would you never accept again?
TOOLKIT
TOOLKIT A4 · OBJECTION SCRIPTS
Six objections and what to say
Acknowledge it, ask a question, answer with their own facts, then agree a next step. Role-play each one twice a month.
THEY SAY, YOU ASK, THEN
“We're happy with our current provider.”
Good. What would they need to change for you to be even happier? · When did you last compare?
Offer a no-cost review against what they have. Book it before you hang up.
“You're more expensive.” Compared with what, exactly? Which items does the other quote leave out?
Put both quotes side by side by scope. Restate the outcome and the cost of the outage they told you about.
“We need to think about it.” What part are you still unsure about? Who else will weigh in? Agree a date to decide and offer a short call with the other decision-maker.
“Our IT person handles it.” What does that person spend most of their week on? What would they rather do?
Position co-managed support: you take the tickets, they keep the projects.
“Just send me a quote.” Happy to. So it's accurate, can I ask three questions first? Run a 15-minute discovery, then book a slot to present the proposal live.
“Switching sounds risky.” What went wrong last time? What would a safe switch look like for you?
Walk through the transition plan: phases, dates, who does what, the 30/60/90-day checks.