Sales training for MSPs — built for the reps selling Managed IT, not SaaS
Built for the reps selling Managed IT — not SaaS. Tactical training for MSP sellers in real territories with real renewals on the line.
MSP Sales Teams face challenges generic sales training was never built to solve
Most sales training programs were built for SaaS companies or inside sales teams. They don’t account for the realities of msp sales teams — territorial reps, in-person prospecting, replacement cycles, and competitive renewal cycles.
CHALLENGE 01
Pipeline depends on referrals
Most MSPs grow on word of mouth. When referrals slow, the pipeline dries up — and reps don’t have a prospecting muscle to fall back on.
CHALLENGE 02
Reps avoid cold prospecting
MSP reps came up technical. Cold calling and walk-ins feel foreign. Without the right training, they default to inbound and wait.
CHALLENGE 03
“We already have an MSP” kills meetings
Every prospect already has someone. Without a real framework, reps lose the conversation in the first 30 seconds.
CHALLENGE 04
Deals get won on price, not value
MSP buyers shop hourly rates. Reps who can’t articulate total value get pulled into price comparisons and lose on margin.
CHALLENGE 05
Renewals leak to competitors
Without a deliberate retention motion, renewals are vulnerable. Competitors quote 15% lower and the customer questions everything.
CHALLENGE 06
Sales hires don’t scale the way technicians did
Building an MSP on technical hires doesn’t translate when you bring on sales reps. Different skill set, different management approach — and most owners don’t know how to make the transition.
Sales Bootcamp, adapted for MSP sales teams
Sales Bootcamp is 12 live classes over 12 weeks via Zoom. Cohorts capped at 10. The curriculum has three phases — the same phases your reps will run on every deal, in order: prospect, run the meeting, build the value.
Phase 1 — Prospecting for Net New Business (Classes 1–5)
The first five classes build the prospecting engine your MSP reps need to generate their own pipeline — not wait on marketing leads.
- Class 1 — Preparation: The Qualifying Formula & How I Prepare for a Great Week. How to plan a prospecting week before it starts. The qualifying formula reps use to know which accounts to chase and which to skip.
- Class 2 — Cold Calling on Foot: Cold Calling in Person + Objection Handling. For MSP reps, this means walking into office parks and IT-buying decision-maker offices cold. How to do it. How to get past the gatekeeper. How to handle “we already have an MSP” without losing the room.
- Class 3 — Cold Calling over the Phone: Cold Calling over the Phone + Objection Handling. Phone prospecting that doesn’t sound like a script. Objection handling for the most common responses an MSP rep hears.
- Class 4 — Becoming Fearless: Mindset, Sequences & The Numbers Game. The mindset behind consistent daily activity. Multi-channel sequences that keep your rep in front of an account until the timing is right.
- Class 5 — Certification Day: Warm Calling over the Phone. Live skill check. Your rep certifies on the phone prospecting fundamentals before moving forward.
Phase 2 — Running Effective Meetings (Classes 6–8)
Three classes on running a discovery meeting that uncovers what’s actually broken in their IT environment.
- Class 6 — Preparation: How to Prepare for Your Blind Date. How to walk into a first MSP meeting prepared — research on the prospect, the buying group, the likely current state.
- Class 7 — During the Appointment: Coming Up with the Right Questions. The discovery framework that surfaces what’s actually broken in their IT environment — not just what they’ll volunteer.
- Class 8 — Certification Day: First Appointment Simulation. Your rep runs a live mock first meeting and gets coached on what to do differently before they’re in front of a real prospect.
Phase 3 — Building Value & Differentiation (Classes 9–12)
The closing phase. How to win MSP business without becoming the cheapest provider on the table.
- Class 9 — Strategy: Understanding Why Customers Buy + The Value of Comparisons. Why MSP buyers actually switch — and how to position against an incumbent.
- Class 10 — Strategy: The 5 Value-Building Pillars & Stacking Deals in Your Favor. The 5 ways to build value into an MSP proposal so price is no longer the deciding factor.
- Class 11 — Strategy: The Total Cost of Ownership & The Near Perfect Proposal. The TCO calculation that wins MSP renewals. The proposal structure that holds margin.
- Class 12 — Certification Day: Proposal Review & Analysis. Your rep brings a real proposal to class and gets it reviewed live — what’s working, what’s losing, what to fix.
AI tools are layered in across the program where they help your reps execute — prospect research, call prep, follow-up. Your reps don’t just learn the methodology. They leave with the modern toolkit attached.
Three tiers. One outcome — reps making more money than anyone else in their market.
TIER 1 — MOST POPULAR
Sales Bootcamp
The foundation program. Covers the complete B2B sales cycle — cold calling, territory management, discovery, value building, and closing. Every rep comes out with a written prospecting sequence and a target account list.
Best for: Companies wanting to build a complete, consistent sales process across their team. New reps and experienced reps both benefit.
Learn about Sales Bootcamp →TIER 2 — ADVANCED
Sales Spartan
For reps who have completed Bootcamp and want to go deeper. Advanced prospecting strategies, AI-powered territory planning, sophisticated deal structure, and profit improvement.
Best for: Experienced reps and Bootcamp graduates ready to operate at a higher level.
Learn about Sales Spartan →TIER 3 — LEADERSHIP
Sales Leaders Bootcamp
For the people running the team. Legendary Leadership, Mastering Your Management Process, and Coaching Your People to Success — plus a final assessment.
Best for: Sales managers, regional directors, VPs — and owners running sales themselves.
Learn about Leaders Bootcamp →
17 years. 13 President’s Club Awards. One methodology.
Derek Shebby spent 17 years as a top sales executive and director at one of California’s largest Xerox mega-dealers, winning the President’s Club Award 13 times and helping build the division from $40 million to over $100 million in annual revenue with a team of 120 salespeople.
When Derek trains your reps, he’s not teaching theory. He’s teaching exactly what he did to win 13 President’s Club Awards — and what he’s watched 30,000+ salespeople use to become the top producers in their markets.
Frequently asked questions
What if my MSP reps came up technical and don’t have a sales background?
That’s the most common situation we see. The Bootcamp is built for reps who don’t have a structured sales process yet. By week 12, they have a written prospecting sequence, a meeting framework, and a value-building playbook they’ll actually run on Monday morning.
Will this work for a small MSP with 2–5 reps?
Yes. Cohorts are capped at 10 across all companies — small MSPs get the same level of attention as larger ones. Many of our best client outcomes come from small MSPs who put their whole sales team through together.
Does the training cover MSP-specific topics like QBRs and SLAs?
We don’t train on MSP service delivery — that’s your internal job. We train the sales process around the services you sell. The methodology applies regardless of which RMM/PSA stack you run.
How fast do reps see results?
Activity changes in weeks 2–3 (more dials, more walks, more meetings). Pipeline metrics shift by weeks 6–8. Closed-deal impact follows your normal MSP sales cycle from there.
Do you train new sales hires or experienced reps?
Both fit in Bootcamp. New reps and untrained experienced reps benefit equally. Reps with 5+ years who’ve plateaued go to Sales Spartan (Tier 2) instead.
Can we enroll our whole sales team as a private cohort?
Yes. 6–10 reps from one MSP = private cohort at the 10-attendee rate. No other companies in the room. Full focus on your team, your market, your competitive set.
How is this different from MSP-specific sales coaches like Bigger Brains or MSP Sales Network?
Those programs are built by MSP veterans for MSP audiences — they know the technology side cold. We come at it from 17 years of B2B sales execution at scale. We’re a sales-first program adapted to the MSP buyer. Some teams use both.
How do I get started?
Book a 30-minute intro call with Derek. He’ll learn about your MSP, your reps, and your market before recommending a program. No sales pressure — just a direct conversation about whether this is the right fit.