OSR ACCELERATOR
Hire, Train, and Manage a Closer Who Sells MSP Services — Exceptionally Well
Fractional management for your outside sales rep. We document the process, build the playbooks, run the weekly call reviews, and hold the rep accountable — so deals get closed without you in every conversation.
15 minutes. No credit card. No pressure. If we're not the right fit, we'll be the first to tell you.
OSR ACCELERATOR
Hire, Train, and Manage a Closer Who Sells MSP Services — Exceptionally Well
Fractional management for your outside sales rep. We document the process, build the playbooks, run the weekly call reviews, and hold the rep accountable — so deals get closed without you in every conversation.
15 minutes. No credit card. No pressure. If we're not the right fit, we'll be the first to tell you.
Here's the situation.
You're somewhere between $5M and $15M. The MSP is real. The team is real. You've got marketing running, some referrals coming in, maybe an SDR feeding the top of the funnel.
But the closing seat is broken.
Either you're still in it — selling alongside running the company, capped at how many calls you can personally take.
Or you've got a rep in the seat who isn't getting it done. Calls go nowhere. Proposals stall. The pipeline looks busy and the close rate doesn't move.
You've tried hiring better. You've tried coaching them yourself. You've maybe even brought in a sales trainer for a workshop or two.
And you're still the bottleneck.
You've just created a more efficient way to stay stuck.
Here's the situation.
You're somewhere between $5M and $15M. The MSP is real. The team is real. You've got marketing running, some referrals coming in, maybe an SDR feeding the top of the funnel.
But the closing seat is broken.
Either you're still in it — selling alongside running the company, capped at how many calls you can personally take.
Or you've got a rep in the seat who isn't getting it done. Calls go nowhere. Proposals stall. The pipeline looks busy and the close rate doesn't move.
You've tried hiring better. You've tried coaching them yourself. You've maybe even brought in a sales trainer for a workshop or two.
And you're still the bottleneck.
You've just created a more efficient way to stay stuck.
Three places we usually find you
You're Still the Closer
Every deal over a certain size still ends up on your calendar. You can't promote out of selling because nobody else can replicate what you do on a discovery call. The business can't grow past your personal bandwidth — and you know it.
We document how you sell, turn it into a playbook, and put a closer in the seat who can run it without you.
You Have an OSR Who Isn't Closing.
The rep is busy. The pipeline looks fine on paper. But the close rate is soft, the deal cycle drags, and proposals turn into ghost-towns.
The problem is almost never the rep alone. It's the lack of a documented process, weekly call reviews, and someone whose job is to manage them. We install all three.
You're Building Real Sales for the First Time.
You've outgrown founder-led selling and you're done patching it together. You want the process documented, the playbooks built, and the management infrastructure in place from day one — not three years and two failed hires from now.
If you don't have an OSR yet, our Recruiting program finds and vets one. Then OSR Accelerator builds the system around them.
Three places we usually find you
You're Still the Closer
Every deal over a certain size still ends up on your calendar. You can't promote out of selling because nobody else can replicate what you do on a discovery call. The business can't grow past your personal bandwidth — and you know it.
We document how you sell, turn it into a playbook, and put a closer in the seat who can run it without you.
You Have an OSR Who Isn't Closing.
The rep is busy. The pipeline looks fine on paper. But the close rate is soft, the deal cycle drags, and proposals turn into ghost-towns.
The problem is almost never the rep alone. It's the lack of a documented process, weekly call reviews, and someone whose job is to manage them. We install all three.
You're Building Real Sales for the First Time.
You've outgrown founder-led selling and you're done patching it together. You want the process documented, the playbooks built, and the management infrastructure in place from day one — not three years and two failed hires from now.
If you don't have an OSR yet, our Recruiting program finds and vets one. Then OSR Accelerator builds the system around them.
What we install — and then run.
OSR Accelerator isn't a course or a coaching program. It's a fractional sales department layered onto your business
A Documented Sales Process
We map your full sales motion — qualifying, discovery, proposal, objection handling, follow-up, close — into a single playbook the rep actually uses. No more "everyone sells a little differently."
Custom Playbooks for Every STAGE
Qualifying call framework.
Discovery call framework.
Proposal template.
Objection handling guide.
Follow-up cadence.
Built specifically for how MSPs sell to SMB and mid-market IT buyers.
A 30-60-90 Ramp Plan
Whether the rep is brand new or already in the seat, we set the milestones, the metrics, and the accountability rhythm for the first 90 days. No guessing
Weekly Sales Meeting + Biweekly 1:1 Coaching
Every week, the rep meets with their MSP Sales Partners manager and peers from other MSPs to review live calls, work pipeline, and get group coaching.
Every other week, they get a focused 1:1 for individual development and deal-by-deal work.
This is the engine of the program.
Pipeline & Performance Tracking
A dashboard your rep updates and we manage.
You see exactly what's in the pipeline, where it's stuck, and what's coming
Monthly Business Reviews with Leadership
Every month, you and your MSP Sales Partners manager sit down to review what's working, what's not, and what's next.
Strategic, not status.
What we install — and then run.
OSR Accelerator isn't a course or a coaching program. It's a fractional sales department layered onto your business
A Documented Sales Process
We map your full sales motion — qualifying, discovery, proposal, objection handling, follow-up, close — into a single playbook the rep actually uses. No more "everyone sells a little differently."
Custom Playbooks for Every STAGE
Qualifying call framework.
Discovery call framework.
Proposal template.
Objection handling guide.
Follow-up cadence.
Built specifically for how MSPs sell to SMB and mid-market IT buyers.
A 30-60-90 Ramp Plan
Whether the rep is brand new or already in the seat, we set the milestones, the metrics, and the accountability rhythm for the first 90 days. No guessing
Weekly Sales Meeting + Biweekly 1:1 Coaching
Every week, the rep meets with their MSP Sales Partners manager and peers from other MSPs to review live calls, work pipeline, and get group coaching.
Every other week, they get a focused 1:1 for individual development and deal-by-deal work.
This is the engine of the program.
Pipeline & Performance Tracking
A dashboard your rep updates and we manage.
You see exactly what's in the pipeline, where it's stuck, and what's coming
Monthly Business Reviews with Leadership
Every month, you and your MSP Sales Partners manager sit down to review what's working, what's not, and what's next.
Strategic, not status.
The operating cadence
Sales reps don't fail because they're lazy. They fail because nobody's managing them. Here's what management actually looks like inside this program.
Cadence
What Happens
Weekly
Weekly Sales meeting with the rep — pipeline review, deal updates, group format with peers across other MSPs in the program
Weekly
Call reviews — live sales calls and proposals reviewed and coached
Biweekly
Biweekly 1:1 with the rep — individual coaching, deal-by-deal work, ramp and development planning
Monthly
Monthly Business review with you, the rep, and your MSP Sales Partners manager
Ongoing
Office hours — your rep can drop in mid-week for help on a live deal
This is the same operating system we run across 50+ MSPs. Your rep doesn't sell in a vacuum — they sell inside a network of MSP closers all working the same playbook.
The operating cadence
Sales reps don't fail because they're lazy. They fail because nobody's managing them. Here's what management actually looks like inside this program.
This is the same operating system we run across 50+ MSPs. Your rep doesn't sell in a vacuum — they sell inside a network of MSP closers all working the same playbook.
What it actually costs to manage an OSR
The OSR's comp is the OSR's comp. The real question is: who manages them, and what does that cost?
Who Manages the OSR
What It Costs
What You Actually Get
You, the founder
$0 cash, ~30% of your time
Inconsistent process. No scale. You become the ceiling.
Full-time VP of Sales / Sales Manager
$150K+/yr base, plus comp
Could be great. Often isn't. Industry data says 2–3 tries to find one who works. 6–12 month ramp.
A single fractional sales manager
~$5K/month
One person split across 3–4 clients. Reactive. No backup. No mastermind effect.
OSR Accelerator
Starts at $3,500/month
Documented process, weekly call reviews, full pod, 50+ MSP mastermind, and a system you own.
We're not the cheapest option on this list. We're the one with the lowest blended cost-per-closed-deal — because the rep gets ramped fast, managed weekly, and held to a standard.
What it actually costs to manage an OSR
The OSR's comp is the OSR's comp. The real question is: who manages them, and what does that cost?
We're not the cheapest option on this list. We're the one with the lowest blended cost-per-closed-deal — because the rep gets ramped fast, managed weekly, and held to a standard.
Stop being the only person in your MSP who can close a deal
A 15-minute Clarity Call walks through your current sales setup, where it's leaking, and whether OSR Accelerator is the right fit. If it isn't, we'll tell you what is
Stop being the only person in your MSP who can close a deal
A 15-minute Clarity Call walks through your current sales setup, where it's leaking, and whether OSR Accelerator is the right fit. If it isn't, we'll tell you what is
Don’t take our word for it.
Here’s what our clients say:
"Our salespeople learned a lot from the curriculum, and we were able to join a peer group where their live and recorded calls were reviewed by the coach and peers."
Jason Denton
Founder & CEO, Reliable Technology Services, Inc
"I love the coaching and call reviews. The feedback from fellow team members has been a game changer. Sometimes it's just a small adjustment that makes all the difference."
Eric
SDR Program Member
"I love the coaching and call reviews. The feedback from fellow team members has been a game changer. Sometimes it's just a small adjustment that makes all the difference."
Eric
SDR Program Member
Don’t take our word for it.
Here’s what our clients say:
"Our salespeople learned a lot from the curriculum, and we were able to join a peer group where their live and recorded calls were reviewed by the coach and peers."
Jason Denton
Founder & CEO, Reliable Technology Services, Inc
"I love the coaching and call reviews. The feedback from fellow team members has been a game changer. Sometimes it's just a small adjustment that makes all the difference."
Eric
SDR Program Member
"I love the coaching and call reviews. The feedback from fellow team members has been a game changer. Sometimes it's just a small adjustment that makes all the difference."
Eric
SDR Program Member
The numbers behind the program:
Built on Ray's 25+ years in sales leadership, $1B in sales managed across his career, and 5 consecutive years as Expert in Residence at Technology Marketing Toolkit.
~100 active MSP clients
65+ SDRs under direct management
300+ MSP sellers trained and coached
$1M+ in pipeline sourced by OSRs in program
The numbers behind the program:
Built on Ray's 25+ years in sales leadership, $1B in sales managed across his career, and 5 consecutive years as Expert in Residence at Technology Marketing Toolkit.
~100 active MSP clients
65+ SDRs under direct management
300+ MSP sellers trained and coached
$1M+ in pipeline sourced by OSRs in program
FREQUENTLY ASKED QUESTIONS
Do you replace our outside sales rep, or manage the one we already have?
Either one. If you have an OSR, we manage them — install the process, run the weekly reviews, and hold them accountable. If you need to hire one, our Recruiting program handles sourcing, vetting, and placement, and OSR Accelerator builds the system around them. Recruiting and OSR Accelerator are separate engagements.
Whose employee is the OSR?
Yours. Always. The OSR is on your payroll, sells under your brand, and uses your CRM. We're the fractional management layer — we don't lease you a closer, we manage the one you have.
How long until we see results?
A new OSR ramps over 90 days against documented milestones. An existing OSR who's been underperforming usually shows movement in the first 60 days, because the bottleneck is almost never effort — it's the lack of process and management. We'll be honest with you on the Clarity Call about what's realistic for your situation.
What CRM do you work in?
Yours. We're agnostic on platform — we install the process inside whatever CRM you already use. Most of the time, a "broken" CRM isn't broken; it's just not being used. Once we run a real sales motion through it, it becomes an asset instead of a sunk cost.
If you don't have a CRM, or you'd rather start fresh, we have one we can stand up for you — pre-loaded with our pipeline structure and the OSR playbook. That's an optional add-on, not part of the core program.
How is this different from a sales coach or a sales trainer?
A coach gives advice. A trainer runs a workshop. Neither of them manages your rep on a Tuesday afternoon when a deal is stalling. We do. OSR Accelerator is fractional management — weekly meetings, weekly call reviews, weekly pipeline pressure. That's the difference between knowing what to do and actually doing it.
What does it cost?
OSR Accelerator starts at $3,500/month per rep. We'll walk through what's involved for your specific situation on the Clarity Call.
FREQUENTLY ASKED QUESTIONS
Do you replace our outside sales rep, or manage the one we already have?
Either one. If you have an OSR, we manage them — install the process, run the weekly reviews, and hold them accountable. If you need to hire one, our Recruiting program handles sourcing, vetting, and placement, and OSR Accelerator builds the system around them. Recruiting and OSR Accelerator are separate engagements.
Whose employee is the OSR?
Yours. Always. The OSR is on your payroll, sells under your brand, and uses your CRM. We're the fractional management layer — we don't lease you a closer, we manage the one you have.
How long until we see results?
A new OSR ramps over 90 days against documented milestones. An existing OSR who's been underperforming usually shows movement in the first 60 days, because the bottleneck is almost never effort — it's the lack of process and management. We'll be honest with you on the Clarity Call about what's realistic for your situation.
What CRM do you work in?
Yours. We're agnostic on platform — we install the process inside whatever CRM you already use. Most of the time, a "broken" CRM isn't broken; it's just not being used. Once we run a real sales motion through it, it becomes an asset instead of a sunk cost.
If you don't have a CRM, or you'd rather start fresh, we have one we can stand up for you — pre-loaded with our pipeline structure and the OSR playbook. That's an optional add-on, not part of the core program.
How is this different from a sales coach or a sales trainer?
A coach gives advice. A trainer runs a workshop. Neither of them manages your rep on a Tuesday afternoon when a deal is stalling. We do. OSR Accelerator is fractional management — weekly meetings, weekly call reviews, weekly pipeline pressure. That's the difference between knowing what to do and actually doing it.
What does it cost?
OSR Accelerator starts at $3,500/month per rep. We'll walk through what's involved for your specific situation on the Clarity Call.
Ready to get out of the closing seat?
Book a 15-minute Clarity Call. We'll look at your current sales motion, identify what's leaking, and tell you honestly whether OSR Accelerator is the right fit.
No credit card. No pressure. If we're not the right fit, we'll be the first to tell you.
Ready to get out of the closing seat?
Book a 15-minute Clarity Call. We'll look at your current sales motion, identify what's leaking, and tell you honestly whether OSR Accelerator is the right fit.
No credit card. No pressure. If we're not the right fit, we'll be the first to tell you.
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