



Services
Your Sales Rep Is Stuck — Now What?
May 28, 2025

Services
Your Sales Rep Is Stuck — Now What?
May 28, 2025

Services
Your Sales Rep Is Stuck — Now What?
May 28, 2025
It's a Common Problem
It’s a problem every VP of Sales has encountered. Maybe you’re facing it right now.
You’ve got a rep who’s stuck. Maybe more than one. They’re capable, they’re showing up, they’re trying — but they’re not producing.
And with all the demands and responsibilities you're managing, you can't invest the time and attention they need to get over the hump and start delivering on their potential.
To senior management, it's a simple problem with a simple fix: fire the rep and move on.
But you know it’s not that easy.
You’ve already made the investment: onboarding, training, time, reputation.
The rep has potential. They know the product. They want to succeed.
But healthcare sales is complex. Long cycles. Cross-departmental buyers. Executive decision makers. A misstep anywhere can stall the deal.
And if you do let them go? You're back to square one: More recruiter fees, more interviews, more onboarding.
And no guarantee the replacement is better.
Meanwhile, the territory loses momentum, deals go cold, and prospects start getting bounced around. That’s when buyer confidence falters—and sales activity grinds down even further.
You’re already stretched thin. Every hour you spend reviewing this rep’s calls, helping them prep, or troubleshooting their pipeline is time you’re not spending on your stronger performers — or the strategic initiatives that could actually move the business forward.
And while this one rep struggles, the rest of the team feels it. Morale dips. Pipeline coverage thins. You find yourself leaning harder on your top reps to pick up the slack — just to stay on pace.
And that’s the part that really stings. You take pride in building a strong team. You want everyone performing at a high level. But when one piece isn’t working, it creates pressure everywhere else.
On the team. On the number. On you.
There’s a Smarter Way
You don’t need a full reset. You need momentum.
But not just any sales coach can help here. Health tech is different.
It’s complex, crowded, and risk-averse — with long sales cycles, confusing org charts, and multiple stakeholders who all think differently. If your rep doesn’t understand how health plans and health systems actually buy, they’re going to keep spinning their wheels.
That’s where I come in. I work exclusively in health tech—with founders, sales teams, and investors — and I know how to diagnose what’s wrong, fast.
Whether it’s a rep issue, a territory issue, or a sales process mismatch, I help you find the root, and move forward.
How the Program Works
1. Assess First, Decide Second
Before we do anything, we get a clear picture of what’s going on.
I assess the rep’s performance, mindset, and how they’re managing the sales process. I also look at their territory, the positioning, and where deals are stalling.
The goal is to understand if this person can turn it around. And what that would take.
Sometimes the answer is no. And if that’s the case, better to know now.
2. Build a Clear Plan
If the rep has potential, we build a focused 60–90 day plan to get them there.
It’s specific, time-boxed, and aligned with your goals.
The rep knows what’s expected. You know what to look for. And we’ve got a shared framework to measure progress.
It’s not just more “coaching.” It’s structured performance improvement.
3. Coach + Execute
This is where we do the work.
I meet regularly with the rep one-on-one to review sales calls, prep for key meetings, troubleshoot deals, and sharpen their sales approach. We dig into buyer dynamics, decision flows, messaging, and what it really takes to move deals forward in health tech.
Along the way, I bring structure. Templates. Frameworks. Workflows. Exercises pulled from decades of selling into healthcare, coaching founders, running accelerators, and working as an Entrepreneur-in-Residence. All customized to sync with your existing sales process and leadership philosophy. So nothing feels bolted on.
4. Track Progress + Share Feedback
You’ll get regular updates — no chasing, no guesswork.
I keep you in the loop with progress check-ins, quick debriefs, and milestone reviews. You’ll know how the rep is doing, what’s improving, and where the friction still lives.
You stay focused on leading the team. I stay focused on getting this rep moving.
5. Outcome-Based Structure
This isn’t open-ended coaching. It’s a focused, time-boxed engagement with clear expectations. And skin in the game.
The investment depends on the length of the program and the specific performance metrics we agree on up front. And while there’s no guaranteed outcome, the cost of inaction — or of replacing a rep outright — is usually far greater.
Let’s do the math:
Recruiting fees: ~$25,000
Travel and training during ramp-up: $5,000–$10,000
Exec time (5% over 90 days): $8,000
Misc. onboarding costs: $2,000
Total cost to rehire: $40,000–$45,000
That’s not counting the indirect costs: lost pipeline, eroded team morale, and the time it takes to rebuild customer trust.
By comparison, a focused turnaround program gives you the chance to recover the rep — and the revenue — without hitting reset.
Get Your Revenue on Track
If you’re dealing with a stuck rep — or just need an outside perspective to get things moving again — I can help.
Let’s talk.
No pressure, no pitch. Just a quick conversation to see if this kind of engagement makes sense for your team.
It's a Common Problem
It’s a problem every VP of Sales has encountered. Maybe you’re facing it right now.
You’ve got a rep who’s stuck. Maybe more than one. They’re capable, they’re showing up, they’re trying — but they’re not producing.
And with all the demands and responsibilities you're managing, you can't invest the time and attention they need to get over the hump and start delivering on their potential.
To senior management, it's a simple problem with a simple fix: fire the rep and move on.
But you know it’s not that easy.
You’ve already made the investment: onboarding, training, time, reputation.
The rep has potential. They know the product. They want to succeed.
But healthcare sales is complex. Long cycles. Cross-departmental buyers. Executive decision makers. A misstep anywhere can stall the deal.
And if you do let them go? You're back to square one: More recruiter fees, more interviews, more onboarding.
And no guarantee the replacement is better.
Meanwhile, the territory loses momentum, deals go cold, and prospects start getting bounced around. That’s when buyer confidence falters—and sales activity grinds down even further.
You’re already stretched thin. Every hour you spend reviewing this rep’s calls, helping them prep, or troubleshooting their pipeline is time you’re not spending on your stronger performers — or the strategic initiatives that could actually move the business forward.
And while this one rep struggles, the rest of the team feels it. Morale dips. Pipeline coverage thins. You find yourself leaning harder on your top reps to pick up the slack — just to stay on pace.
And that’s the part that really stings. You take pride in building a strong team. You want everyone performing at a high level. But when one piece isn’t working, it creates pressure everywhere else.
On the team. On the number. On you.
There’s a Smarter Way
You don’t need a full reset. You need momentum.
But not just any sales coach can help here. Health tech is different.
It’s complex, crowded, and risk-averse — with long sales cycles, confusing org charts, and multiple stakeholders who all think differently. If your rep doesn’t understand how health plans and health systems actually buy, they’re going to keep spinning their wheels.
That’s where I come in. I work exclusively in health tech—with founders, sales teams, and investors — and I know how to diagnose what’s wrong, fast.
Whether it’s a rep issue, a territory issue, or a sales process mismatch, I help you find the root, and move forward.
How the Program Works
1. Assess First, Decide Second
Before we do anything, we get a clear picture of what’s going on.
I assess the rep’s performance, mindset, and how they’re managing the sales process. I also look at their territory, the positioning, and where deals are stalling.
The goal is to understand if this person can turn it around. And what that would take.
Sometimes the answer is no. And if that’s the case, better to know now.
2. Build a Clear Plan
If the rep has potential, we build a focused 60–90 day plan to get them there.
It’s specific, time-boxed, and aligned with your goals.
The rep knows what’s expected. You know what to look for. And we’ve got a shared framework to measure progress.
It’s not just more “coaching.” It’s structured performance improvement.
3. Coach + Execute
This is where we do the work.
I meet regularly with the rep one-on-one to review sales calls, prep for key meetings, troubleshoot deals, and sharpen their sales approach. We dig into buyer dynamics, decision flows, messaging, and what it really takes to move deals forward in health tech.
Along the way, I bring structure. Templates. Frameworks. Workflows. Exercises pulled from decades of selling into healthcare, coaching founders, running accelerators, and working as an Entrepreneur-in-Residence. All customized to sync with your existing sales process and leadership philosophy. So nothing feels bolted on.
4. Track Progress + Share Feedback
You’ll get regular updates — no chasing, no guesswork.
I keep you in the loop with progress check-ins, quick debriefs, and milestone reviews. You’ll know how the rep is doing, what’s improving, and where the friction still lives.
You stay focused on leading the team. I stay focused on getting this rep moving.
5. Outcome-Based Structure
This isn’t open-ended coaching. It’s a focused, time-boxed engagement with clear expectations. And skin in the game.
The investment depends on the length of the program and the specific performance metrics we agree on up front. And while there’s no guaranteed outcome, the cost of inaction — or of replacing a rep outright — is usually far greater.
Let’s do the math:
Recruiting fees: ~$25,000
Travel and training during ramp-up: $5,000–$10,000
Exec time (5% over 90 days): $8,000
Misc. onboarding costs: $2,000
Total cost to rehire: $40,000–$45,000
That’s not counting the indirect costs: lost pipeline, eroded team morale, and the time it takes to rebuild customer trust.
By comparison, a focused turnaround program gives you the chance to recover the rep — and the revenue — without hitting reset.
Get Your Revenue on Track
If you’re dealing with a stuck rep — or just need an outside perspective to get things moving again — I can help.
Let’s talk.
No pressure, no pitch. Just a quick conversation to see if this kind of engagement makes sense for your team.
It's a Common Problem
It’s a problem every VP of Sales has encountered. Maybe you’re facing it right now.
You’ve got a rep who’s stuck. Maybe more than one. They’re capable, they’re showing up, they’re trying — but they’re not producing.
And with all the demands and responsibilities you're managing, you can't invest the time and attention they need to get over the hump and start delivering on their potential.
To senior management, it's a simple problem with a simple fix: fire the rep and move on.
But you know it’s not that easy.
You’ve already made the investment: onboarding, training, time, reputation.
The rep has potential. They know the product. They want to succeed.
But healthcare sales is complex. Long cycles. Cross-departmental buyers. Executive decision makers. A misstep anywhere can stall the deal.
And if you do let them go? You're back to square one: More recruiter fees, more interviews, more onboarding.
And no guarantee the replacement is better.
Meanwhile, the territory loses momentum, deals go cold, and prospects start getting bounced around. That’s when buyer confidence falters—and sales activity grinds down even further.
You’re already stretched thin. Every hour you spend reviewing this rep’s calls, helping them prep, or troubleshooting their pipeline is time you’re not spending on your stronger performers — or the strategic initiatives that could actually move the business forward.
And while this one rep struggles, the rest of the team feels it. Morale dips. Pipeline coverage thins. You find yourself leaning harder on your top reps to pick up the slack — just to stay on pace.
And that’s the part that really stings. You take pride in building a strong team. You want everyone performing at a high level. But when one piece isn’t working, it creates pressure everywhere else.
On the team. On the number. On you.
There’s a Smarter Way
You don’t need a full reset. You need momentum.
But not just any sales coach can help here. Health tech is different.
It’s complex, crowded, and risk-averse — with long sales cycles, confusing org charts, and multiple stakeholders who all think differently. If your rep doesn’t understand how health plans and health systems actually buy, they’re going to keep spinning their wheels.
That’s where I come in. I work exclusively in health tech—with founders, sales teams, and investors — and I know how to diagnose what’s wrong, fast.
Whether it’s a rep issue, a territory issue, or a sales process mismatch, I help you find the root, and move forward.
How the Program Works
1. Assess First, Decide Second
Before we do anything, we get a clear picture of what’s going on.
I assess the rep’s performance, mindset, and how they’re managing the sales process. I also look at their territory, the positioning, and where deals are stalling.
The goal is to understand if this person can turn it around. And what that would take.
Sometimes the answer is no. And if that’s the case, better to know now.
2. Build a Clear Plan
If the rep has potential, we build a focused 60–90 day plan to get them there.
It’s specific, time-boxed, and aligned with your goals.
The rep knows what’s expected. You know what to look for. And we’ve got a shared framework to measure progress.
It’s not just more “coaching.” It’s structured performance improvement.
3. Coach + Execute
This is where we do the work.
I meet regularly with the rep one-on-one to review sales calls, prep for key meetings, troubleshoot deals, and sharpen their sales approach. We dig into buyer dynamics, decision flows, messaging, and what it really takes to move deals forward in health tech.
Along the way, I bring structure. Templates. Frameworks. Workflows. Exercises pulled from decades of selling into healthcare, coaching founders, running accelerators, and working as an Entrepreneur-in-Residence. All customized to sync with your existing sales process and leadership philosophy. So nothing feels bolted on.
4. Track Progress + Share Feedback
You’ll get regular updates — no chasing, no guesswork.
I keep you in the loop with progress check-ins, quick debriefs, and milestone reviews. You’ll know how the rep is doing, what’s improving, and where the friction still lives.
You stay focused on leading the team. I stay focused on getting this rep moving.
5. Outcome-Based Structure
This isn’t open-ended coaching. It’s a focused, time-boxed engagement with clear expectations. And skin in the game.
The investment depends on the length of the program and the specific performance metrics we agree on up front. And while there’s no guaranteed outcome, the cost of inaction — or of replacing a rep outright — is usually far greater.
Let’s do the math:
Recruiting fees: ~$25,000
Travel and training during ramp-up: $5,000–$10,000
Exec time (5% over 90 days): $8,000
Misc. onboarding costs: $2,000
Total cost to rehire: $40,000–$45,000
That’s not counting the indirect costs: lost pipeline, eroded team morale, and the time it takes to rebuild customer trust.
By comparison, a focused turnaround program gives you the chance to recover the rep — and the revenue — without hitting reset.
Get Your Revenue on Track
If you’re dealing with a stuck rep — or just need an outside perspective to get things moving again — I can help.
Let’s talk.
No pressure, no pitch. Just a quick conversation to see if this kind of engagement makes sense for your team.
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