Sales training for territorial sales reps — built for the person in the truck, not the cubicle
Built for the person in the truck — not the cubicle. Real prospecting, real meetings, real deals closed on the road.
Territorial Field Sales 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 territorial field sales — territorial reps, in-person prospecting, replacement cycles, and competitive renewal cycles.
CHALLENGE 01
Reps spend the day in the windshield, not in front of clients
Without daily prospecting discipline, the territory becomes a driving job. Lots of motion, no meetings.
CHALLENGE 02
Generic sales training assumes an inbound funnel
Most programs were built for SaaS. They train reps to wait for leads — not generate them. For territorial reps, that’s a dead end.
CHALLENGE 03
In-person prospecting feels obsolete — but it’s your real edge
Everyone else has abandoned the doorstep. Reps who still walk in own their territories. Reps who don’t are blending in.
CHALLENGE 04
Pipeline is concentrated in 2–3 reps
When two reps carry the team, the forecast is fragile. Train everyone else to prospect, and the business stops depending on one or two people.
CHALLENGE 05
New reps take 9+ months to ramp
Without structured training tied to real activity, new hires spend months figuring it out instead of producing. Turnover follows.
CHALLENGE 06
Discounting becomes the default play
When reps can’t build value, they cut price. Margin walks out the door deal by deal — and competitors notice.
Sales Bootcamp, adapted for territorial 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 every territorial rep needs.
- 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. The discipline most competitors have abandoned. How to walk into a prospect’s location cold. How to handle the gatekeeper. How to handle “we already have a supplier.”
- Class 3 — Cold Calling over the Phone: Cold Calling over the Phone + Objection Handling. Phone prospecting that doesn’t sound scripted. Objection handling for the most common responses a territorial 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 buying trigger hits.
- 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 first appointment that produces a real next step.
- Class 6 — Preparation: How to Prepare for Your Blind Date. How to walk into a first meeting prepared — research on the prospect, their current state, their likely pain.
- Class 7 — During the Appointment: Coming Up with the Right Questions. The discovery framework that surfaces what’s actually broken — not just what the prospect will 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 territorial business at full margin against the incumbent.
- Class 9 — Strategy: Understanding Why Customers Buy + The Value of Comparisons. Why 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 a 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 renewals. The proposal structure that holds margin under direct competitive comparison.
- 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
Will this work for our specific industry?
We’ve trained reps in office technology, mailing equipment, MSPs, manufacturers, distributors, furniture, irrigation, and a dozen other B2B segments. The methodology is industry-agnostic because the territorial sale — in-person prospecting, replacement cycles, margin defense, relationship-building — has the same shape across industries.
Do you customize for our company?
Bootcamp curriculum is consistent (the methodology IS the value), but examples, role-plays, and assignments adapt to your industry. For private cohorts (10 reps from one company), we go deeper — role-plays use your buyer personas, your competitors, your actual deal flow.
How fast will we see results?
Activity changes in weeks 2–3 (your CRM will show it). Pipeline metrics shift by weeks 6–8 (meetings booked, second meetings held, proposals delivered). Closed deals follow your normal sales cycle. The $30B client we trained saw a 23% YoY new business turnaround within 12 months.
Can my whole team train together as a private cohort?
Yes. 6–10 reps from one company = private cohort at the 10-attendee rate. No other companies in the room. Full focus on your team and market.
What if my reps are split between road and inside?
Both fit. Bootcamp covers in-person AND phone prospecting; reps take what applies to their role. Most territorial teams have some hybrid — pure road reps for major accounts, hybrid reps for mid-market, inside reps for SMB.
Do you only work with large companies?
No. Cohorts capped at 10 means small dealerships get exceptional attention. Our smallest client is a 3-rep dealership. Our largest is a $30B manufacturer running 50+ reps through parallel cohorts.
What if my rep is too senior for a “bootcamp”?
That’s Sales Spartan — the advanced tier. Bootcamp is for reps 0–3 years in or tenured reps who never had real training. Spartan is for closers who’ve plateaued and need the next layer.
How do I get started?
Book a 30-minute intro call with Derek. He’ll map your team against the three tiers, talk through your industry and market, and tell you honestly whether Modern Sales Training is the right call.