Enterprise sales training run by a closer, not a curriculum company. Drewbie Wilson has done $15M+ in personal sales over 20+ years, is a 7x best-selling author, and founded Call The Damn Leads®. He trains enterprise teams on the same C.A.L.L.S. Framework and 100/10/2 Standard he still runs himself — committee mapping, multithreading, and a follow-up cadence that survives a nine-month cycle.
Enterprise deals do not close the way transactional deals close. Six to twelve months. Five to eleven people in the room, most of whom your rep has never spoken to. IT, finance, legal, security review, procurement, and a champion who changes jobs in month four. Reps who are excellent on a one-call close go quiet the moment a deal has to be worked across a committee.
You are probably here because of one of these:
Deals stall in the middle. Great discovery, strong demo, verbal enthusiasm — then two months of nothing. Almost always the same cause: the rep sold one person and never multithreaded into the people who actually sign.
Your forecast is fiction. Half the pipeline is a champion’s opinion. Nobody has confirmed budget, authority, or a date, so every deal slips a quarter and nobody can say why.
Your team went upmarket and the motion did not. The reps who built the company on SMB velocity are now working deals ten times the size with the same three-touch follow-up habit.
You already bought training and it did not stick. Two days offsite, a binder, and ninety days later everyone is back to what they did before. That is a reinforcement failure, not a content failure.
Enterprise sales training fixes the motion, not the mood. It gives reps a repeatable way to map a buying committee, get a second and third thread going before they need it, and keep a long deal warm without becoming a pest.
Most enterprise sales training is a licensed methodology delivered by someone who has never carried an enterprise quota. Before you sign anything, hold the program up against these five.
Ask what the person in the room has personally sold and to whom. A facilitator reading a licensed deck cannot answer the question every rep asks on day two: “what do I say when procurement stalls me?” Practitioner experience is the whole difference.
Discovery training is table stakes. Enterprise training has to teach reps to name every role in the deal — economic buyer, champion, technical evaluator, blocker, procurement — and to know what each one needs before the deal reaches them.
Nine-month deals are won in the quiet months. The program should ship an actual cadence — what you send, to whom, how often, and what the touch is for — the same discipline behind our follow-up system training. If follow-up is one slide, walk.
Ask exactly what happens in weeks two through twelve. If the answer is a recording and a workbook, the behaviour will not hold. Reinforcement cadence, manager coaching, and live deal reviews are where enterprise programs earn back their cost.
Completion rates and satisfaction scores measure nothing. Agree up front on the numbers you will read ninety days out: threads per opportunity, stage conversion in the middle of the funnel, slipped-deal rate, and cycle-stage aging.
The honest version, so nobody buys the wrong thing. If any of these are what you are actually shopping for, say so on the call and we will point you somewhere better — including away from us.
A six-to-twelve month enterprise cycle is set by your buyer’s procurement, security and budget calendars, not by how well your reps sell. Training makes those months productive and the forecast honest. It does not make a committee decide faster.
If the plan pays reps to chase small fast deals, no workshop will make them work a nine-month enterprise deal instead. Comp, territory and quota design are a sales consulting problem, and they have to be fixed before training can pay off.
This is where most enterprise programs die. Skills learned in a room decay inside ninety days without reps, review and accountability. If you only have budget for a single session, buy a keynote and be honest that it is a kickoff, not a program.
Managers own reinforcement after the trainer leaves. If your front line will not run deal reviews or hold the standard, start with sales leadership training instead — training the reps under an absent manager is money set on fire.
Every engagement is scoped to your motion, your deal sizes and your actual pipeline. These are the pieces that show up in nearly all of them.
A one-page map per opportunity: who signs, who blocks, who evaluates, who benefits, and what each one needs to hear. Reps fill it in on live deals during the session, not on a case study about a company nobody works at.
The scripts and the internal-referral asks that get a second and third contact inside the account before the champion goes dark. Practised out loud, on your real accounts, until it stops feeling rude.
Confirm, Ask, Listen, Lay Out a Plan, Secure the Bag — the C.A.L.L.S. Framework rebuilt for deals where “secure the bag” is eleven conversations away and every stage needs its own confirmed next step.
The 100/10/2 Standard adapted to enterprise: the daily account-touch floor that keeps a rep working the top of the funnel while a nine-month deal sits in legal. This is the habit that stops feast-and-famine pipelines.
Your leaders get the deal-review format, the questions to ask, and the cadence to run it on, so the standard is still alive in month six. Pairs with sales team training when the whole floor needs the same language.
We read your real pipeline — deal sizes, stage conversion, where deals actually stall — and talk to two or three reps. The program gets built around what is breaking, not a standard curriculum.
Live sessions, in person or virtual, using your accounts. Committee maps, multithreading scripts and follow-up cadences are built in the room on deals that are open right now.
Reps run the motion on live deals while we review the work. Recorded calls, real emails, real committee maps — corrected weekly instead of graded once.
Managers take over the deal-review cadence with our format, and we stay on the reinforcement calls until the standard holds without us. That is the part that decides whether any of this was worth it.
Programs start at $1,000. Final pricing depends on team size, format, and how many sessions and reinforcement weeks you want — scoped on one call and stated up front, never a surprise invoice. If you want the program opened with a keynote, speaking fees run $2,500 to $7,500 plus travel, quoted separately.
Who you are working with. Drewbie Wilson has personally sold more than $15M over 20+ years, is a 7x best-selling author, hosts his own sales podcast, and is the founder of Call The Damn Leads®, a Crushing The Day company. He is not a licensed facilitator delivering somebody else’s methodology — the C.A.L.L.S. Framework and the 100/10/2 Standard are his, built on the phone, and he still runs them.
That matters in an enterprise room for one reason: when a rep asks what to do when procurement goes silent in month seven, the answer comes from someone who has been there rather than from the next slide.
Need the whole floor on one language and one standard, not just the enterprise pod? Start here.
Train the managers who have to hold the standard after the program ends.
Build the cadence that keeps a nine-month deal warm through the quiet months.
Open your sales kickoff with the energy, then run the program behind it.
One-on-one work for the individual enterprise closer who wants their own reps sharpened.
Buying-committee mapping, multithreading into accounts, running long cycles without losing the thread, stage-by-stage next-step discipline, and a follow-up cadence built for six-to-twelve month deals. It is delivered through the C.A.L.L.S. Framework and the 100/10/2 Standard, applied to your live pipeline rather than to case studies.
Standard sales training optimises a conversation. Enterprise sales training optimises a campaign across many people over many months. The skills that matter shift from closing one person to mapping a committee, building second and third threads, keeping momentum during silence, and forecasting honestly when no single person can say yes on their own.
Three common shapes: a single workshop for a sales kickoff, an ongoing program with live sessions plus reinforcement weeks, or a keynote that opens the event with the program running behind it. Most teams get the return from the ongoing shape, because reinforcement is where enterprise programs usually die.
On pipeline behaviour, not attendance. The usual set is threads per opportunity, mid-funnel stage conversion, slipped-deal rate and stage aging, read at ninety days against the same numbers taken before the program started. Those baselines get agreed during scoping so nobody argues about the scoreboard later.
Programs start at $1,000, with final pricing set by team size, format and program length, scoped on one call. If you want a keynote to open the program, speaking fees run $2,500 to $7,500 plus travel and are quoted separately.
Tell us your deal sizes, your cycle length and where deals are actually stalling. Drewbie will tell you straight whether enterprise sales training is the fix or whether something upstream needs to move first.
Related reading: When to hire a sales consultant · Sales coaching vs sales training
