I hope you enjoy reading this blog post. If you want my team to just do your marketing for you, click here.
I hope you enjoy reading this blog post. If you want my team to just do your marketing for you, click here.
Author: Jeremy Haynes | founder of Megalodon Marketing.
Earnings Disclaimer: You have a .1% probability of hitting million-dollar months according to the US Bureau of Labor Statistics. As stated by law, we can not and do not make any guarantees about your own ability to get results or earn any money with our ideas, information, programs, or strategies. We don’t know you, and besides, your results in life are up to you. We’re here to help by giving you our greatest strategies to move you forward, faster. However, nothing on this page or any of our websites or emails is a promise or guarantee of future earnings. Any financial numbers referenced here, or on any of our sites or emails, are simply estimates or projections or past results, and should not be considered exact, actual, or as a promise of potential earnings – all numbers are illustrative only.
Most coaches are leaving money on the table. Research shows that acquiring a new customer is 5 to 25 times more expensive than retaining an existing one, yet many coaches still operate on transactional models rather than building long-term partnerships.
You close a client, deliver amazing results, they’re thrilled with the transformation… and then they disappear. Maybe they come back six months later for another session or two, but there’s no consistency, no predictability, and honestly? You’re starting over with the sales process every single time.
Meanwhile, your calendar looks like Swiss cheese, your revenue swings wildly from month to month, and you’re constantly hunting for the next client just to keep the lights on.
There’s a better way.
The retainer model isn’t just for agencies and consultants. It’s actually perfect for coaches – maybe even MORE perfect for coaches – because ongoing support is literally what creates lasting transformation.
But here’s what most coaches get wrong: They structure their retainers like they’re selling monthly sessions instead of building a real partnership. And that’s why their retainers don’t stick.
Let me show you how to build a coaching retainer that clients actually want to keep paying for, that protects your profit margins, and that dramatically increases the lifetime value of every relationship.
If your business is already generating $100k+ per month, My Inner Circle is where you break through to the next level. Inside, I’ll help you identify and solve the bottlenecks holding you back so you can scale faster and with more clarity.
Before we get into the solution, let’s talk about why the traditional coaching model is working against you.
When you sell individual sessions or short-term packages, you’re creating a transactional relationship. Client has a problem, you help them solve it, transaction complete. See you next time (maybe).
This seems fine on the surface, but it creates three massive problems:
Problem one: You’re constantly selling. Every month is a scramble to fill your calendar. You can’t plan. You can’t scale. You’re always in feast or famine mode.
Problem two: Your clients get worse results. Real transformation doesn’t happen in 6 sessions over 8 weeks. It happens with consistent support, accountability, and adjustment over time. Studies show that 87% of coaching clients report a positive ROI, with executive coaching delivering returns ranging from 500% to 788% when implemented as ongoing partnerships rather than short-term interventions.
Problem three: You’re capping your earning potential. There’s only so many hours in a week. You hit your ceiling fast, and the only way to grow is to raise rates (which makes sales harder) or burn yourself out taking more clients.
The math just doesn’t work long-term.
A retainer model flips all of this. Instead of selling sessions, you’re selling ongoing partnership. Instead of hunting for clients monthly, you’re building a stable base. Instead of delivering disconnected interventions, you’re creating continuous transformation.
And the economics? Way better for everyone involved.
Here’s where most coaches mess this up right out of the gate.
They think a retainer is just “monthly sessions with a subscription.” So they offer something like “4 sessions per month for $2,000” and call it a retainer.
That’s not a retainer. That’s a package with monthly billing.
A real coaching retainer is structured around ongoing value delivery, not just scheduled sessions. It’s access, support, accountability, and strategic guidance whenever it’s needed – not just during your 60-minute Zoom calls.
Think about it from your client’s perspective. They don’t wake up with problems conveniently timed to your Thursday 2pm slot. They hit obstacles on Monday morning, have breakthrough moments on Saturday, and need guidance when decisions come up – which is rarely on a predictable schedule.
If your retainer is just “we talk twice a month,” you’re missing the entire point of retained support.
The retainer should give them confidence that you’re in their corner consistently, that they can reach out when they need help, and that you’re invested in their success beyond our scheduled calls.
That’s what they’re actually buying. That’s what justifies ongoing payment.
Let me break down the structure that actually converts and retains clients.
Component 1: Scheduled Strategy Sessions
Yes, you still have regular calls. These are your anchors. Usually 2-4 per month depending on your pricing tier.
But these aren’t “coaching sessions” where you just talk about whatever’s on their mind that day. These are strategic planning and review sessions where you’re setting direction, measuring progress, and making adjustments.
Come with an agenda. Review metrics. Set clear action items. Make these sessions feel structured and valuable, not just casual check-ins.
Component 2: Asynchronous Access
This is the game-changer that most coaches skip.
Your clients can reach out between sessions via your preferred channel – Slack, Voxer, email, whatever works for your workflow. You respond within 24 business hours (or whatever timeframe you commit to).
This isn’t about being available 24/7. It’s about removing the friction between “I have a question” and “I get an answer.”
Set clear boundaries about response times and availability. But give them a way to get unstuck without waiting a week for your next scheduled call.
Component 3: Resources and Tools
Part of your retainer should include access to your frameworks, templates, worksheets, or whatever proprietary resources you’ve developed.
Maybe it’s a custom dashboard where you track their metrics. Maybe it’s a resource library. Maybe it’s recorded trainings on common challenges.
This isn’t busywork. This extends your value beyond your time and gives clients tools they can use independently (which actually makes them more successful AND less dependent on you for every little thing).
Component 4: Accountability and Check-ins
Build in regular accountability touchpoints. Weekly check-in forms they submit. Monthly progress reviews. Whatever structure keeps them moving forward even when you’re not actively working together.
This is where transformation actually happens – in the consistent execution between your sessions, not in the sessions themselves.
Component 5: Strategic Adjustments
As you work together longer, you learn their patterns, their strengths, their blind spots. Your guidance becomes more tailored and more valuable over time.
This compounding insight is what makes long-term retainers so powerful. You’re not starting from scratch every engagement. You’re building on deep understanding.
Make sure your retainer structure allows you to adapt and customize your support as the relationship evolves.
Here’s where the margin protection comes in.
Most coaches underprice retainers because they’re thinking about it wrong. They calculate their hourly rate, multiply by estimated hours, and price based on that.
Wrong approach.
Your retainer pricing should be based on the value delivered and transformation created, not hours worked.
If you’re helping a business owner scale from $500K to $1M, your monthly retainer could easily be $5K-10K. The value is massive compared to the cost. Research demonstrates that executive coaching has a 788% return on investment based on factors including increases in productivity and employee retention.
If you’re helping an executive level up in their career, potentially adding hundreds of thousands to their earning potential, $3K-5K per month is a no-brainer investment.
Stop thinking about hours. Start thinking about outcomes.
Here’s a framework that works:
Entry Level Retainer: $1,500-2,500/month
Mid-Level Retainer: $3,500-5,000/month
Premium Retainer: $7,500-15,000/month
Notice how the value scales, but your time commitment doesn’t scale linearly? That’s how you protect margin.
A premium client paying $10K isn’t getting 10x more of your time than an entry-level client paying $2K. They’re getting deeper strategic involvement, faster response times, and more customized support.
Here’s the thing: Most people don’t naturally think about hiring a coach on retainer.
They think about hiring a coach for a specific problem or goal. “I need help with my leadership skills.” “I want to scale my business.” “I’m navigating a career transition.”
Your job is to reframe the conversation from project-based to partnership-based.
Instead of: “I offer a 12-week coaching program to help you achieve X”
Try: “I partner with leaders long-term to help them consistently level up across multiple areas of their business and life. Most clients work with me for 1-2 years because the transformation compounds over time.”
See the difference?
You’re not selling a fixed engagement. You’re selling ongoing evolution.
When you position it this way, the conversation shifts from “Can I afford 12 weeks?” to “Does it make sense to have Jeremy in my corner as I grow?”
Much stronger position.
Here’s exactly how I position retainers in sales conversations:
“Here’s how this works. We don’t just tackle one challenge and then you’re on your own. Real growth is continuous. You’ll face new challenges, new opportunities, new obstacles as you evolve.
My retainer model means you always have strategic support when you need it – not just during scheduled sessions, but whenever critical decisions or challenges come up. Think of me as your always-available strategic advisor, not just a coach you see twice a month.
Most of my clients stay with me for 12-24 months because the value compounds. The longer we work together, the better I understand your unique situation, and the more targeted and effective my guidance becomes.”
That’s the pitch. You’re selling partnership, not sessions.
The first 90 days of a retainer relationship determines whether that client stays for 6 months or 3 years.
Most coaches completely blow this crucial window.
They treat the first month like any other month. Generic sessions, no special attention, no clear wins. And then they wonder why clients churn after 3-4 months.
Here’s how to onboard for retention:
Week 1: Deep Discovery
Go deeper than you normally would in initial sessions. You’re not just understanding their current challenge – you’re understanding their entire situation, their patterns, their history, their goals across multiple timeframes.
Build a comprehensive picture. Document everything. This becomes your roadmap.
Week 2-4: Quick Wins
Intentionally engineer some quick wins in the first month. You want them to see immediate value from the retainer.
This doesn’t mean solving everything right away. It means identifying 2-3 areas where you can create noticeable progress fast.
Month 2: Strategic Planning
Now that you understand them deeply and you’ve built some momentum, create a real strategic plan for the next 6-12 months.
Where are we going? What are the major milestones? What’s the transformation we’re building toward?
This gives them a vision of the journey, not just month-to-month support.
Month 3: Review and Adjust
Check in on the plan. What’s working? What needs adjustment? How are they feeling about the partnership?
This is also when you start to introduce additional resources or support elements that deepen the relationship.
If you nail this 90-day onboarding, your retention rates will skyrocket. Clients who make it past 90 days typically stay 12+ months.
Now let’s talk about the fear most coaches have with retainers: “What if they take advantage and demand all my time?”
Valid concern. Here’s how you prevent it.
Set Clear Boundaries
In your retainer agreement, specify:
Don’t be vague. Clear boundaries protect both of you.
Teach Clients How to Use You
Most clients don’t naturally know how to use retained support well. They either under-utilize (waste of their money) or over-utilize (waste of your time).
Train them explicitly: “Here’s when to reach out between sessions. Here’s how to make our scheduled sessions most valuable. Here’s what I need from you to give you the best support.”
Good clients appreciate this clarity.
Use Async Strategically
Async support doesn’t mean you’re writing essays in response to every message. Often, a voice note or quick video explanation is faster for you and more valuable for them than a lengthy written response.
And sometimes the right answer is: “Great question. Let’s tackle this properly in our session Thursday. In the meantime, here’s what I’d do…”
You’re controlling your time while still being responsive.
Tier Your Availability
Not all retainer clients need the same level of access. Your premium clients get more of you than your entry-level clients. That’s not unfair – that’s business.
Make sure your pricing tiers reflect different levels of access, and don’t feel guilty about it.
The biggest objection to retainers isn’t price – it’s commitment.
“What if I want to cancel? Am I locked in? What if it’s not working?”
Here’s how I handle this:
“I get it. Committing to ongoing coaching feels like a big decision. Here’s how we handle that:
We’ll start with a 3-month initial commitment. That gives us enough time to do real work together and for you to see the value clearly. After that, it’s month-to-month. If at any point you want to pause or stop, just give me 30 days notice.
But here’s what I’ve found: By month 3, you’ll either be completely bought in and we’ll be doing great work together, or it’ll be clear this isn’t the right fit. I’ve never had someone hit month 3 and be unsure. It’s always obvious by then.”
This gives them an out while also framing the decision as low-risk.
You can also offer a trial month or a reduced-rate first month to lower the barrier to entry. Once they experience the value, converting to full retainer is easy.
Now here’s where retainers get really powerful for your business: lifetime value growth.
A client who pays you $3K one time has a lifetime value of $3K.
A client who pays you $3K per month for 18 months has a lifetime value of $54K.
That’s not just more revenue – that’s more predictable revenue, which means you can invest in your business, hire support, and actually plan for growth.
But here’s the key: You need to actively manage for retention and expansion.
Don’t just collect monthly payments and hope clients stick around. Actively work to increase the value you’re delivering and the duration of the relationship.
Here’s how:
Regular Value Reviews
Every 3-6 months, do a formal review of the progress you’ve made together. Document wins, quantify results, reflect on transformation.
This keeps the value visible and fresh in their mind. They’re not just paying a monthly fee – they’re investing in ongoing results.
Identify Expansion Opportunities
As you work together, new opportunities emerge. Maybe they need help with their team, not just themselves. Maybe their business is growing and they need more strategic support.
When you see these opportunities, present expanded retainer options. “Based on where you’re heading, here’s how we could structure more comprehensive support…”
Many of my long-term clients started at $2,500/month and gradually expanded to $7,500/month as their needs grew and the value became undeniable.
Create Exit Friction (The Good Kind)
The longer someone works with you, the more embedded you become in their success. Your frameworks become their operating system. Your guidance becomes essential to their decision-making.
This isn’t about trapping people. It’s about becoming genuinely valuable and integrated into how they work.
When canceling means losing something they genuinely depend on, retention becomes natural.
Let me walk you through how to actually sell retainers, because this is different from selling packages or programs.
Step 1: Qualify Hard
Not everyone is a retainer client. You’re looking for people who:
If someone’s just looking to solve one specific problem and move on, they’re not your retainer client. And that’s okay.
Step 2: Position It Early
Don’t wait until the end of your sales call to mention the retainer structure. Lead with it.
“I work with clients on a retainer basis because real transformation requires ongoing support. Let me explain how that works…”
This filters out people who aren’t interested right from the start.
Step 3: Sell the Transformation, Not the Structure
Focus on what their life looks like 6 months, 12 months, 24 months into this partnership. What changes? What becomes possible? What problems disappear?
The retainer structure is just the vehicle. The destination is what they’re buying.
Step 4: Offer Clear Next Steps
“Based on everything we’ve discussed, I think the mid-tier retainer makes sense for where you’re at. That’s $4,000 per month, we’d start with a 3-month commitment, and I’m confident we can achieve [specific outcomes] in that timeframe. Want to move forward?”
Direct. Clear. Confident.
Step 5: Make Onboarding Seamless
Once they commit, immediately send a welcome packet with:
Remove all friction from getting started.
Here’s the final piece that makes retainers truly powerful: They’re scalable in ways one-off coaching isn’t.
Once you have 10-15 retainer clients at $3-5K per month, you’re at $30-75K in monthly recurring revenue. That’s a real business.
But you can’t take on 50 individual coaching clients. You’d lose your mind.
So here’s how you scale:
Group Retainers
Offer a lower-priced retainer that includes group coaching plus limited individual access. Maybe $1,000/month gets them:
You can support 30-40 people in this model without much more time than supporting 10 individual clients.
Team Retainers
Instead of coaching individuals, coach entire teams or organizations. One $15K retainer can replace three $5K individual retainers, but only requires one set of sessions.
Leverage Delegation
Bring on associate coaches to handle some of the session delivery while you maintain strategic oversight and high-touch support for premium clients.
Your retainer model becomes the foundation for building a real coaching business, not just a solo practice.
If you’re currently doing one-off sessions or fixed programs, switching to retainers might feel like a big shift.
It is. But it’s worth it.
Start by offering retainers alongside your current model. You don’t have to go all-in immediately.
For your next few sales conversations, present the retainer option. See how people respond. Refine your positioning based on the questions and objections you hear.
As you build up retainer clients, you’ll naturally have less availability for one-off work. Let that happen. You’re not closing off opportunities – you’re upgrading your business model.
Within 6-12 months, you can transition to primarily or exclusively retainer-based coaching. Your revenue becomes predictable, your calendar becomes manageable, and your clients get dramatically better results.
That’s the whole point of this model. Better for them, better for you, better business.
Stop selling sessions. Start building partnerships.
This week, do this:
Design your retainer structure. What’s included at each tier? What’s the pricing? What are the boundaries?
Create a simple one-page retainer overview that explains how it works and what clients get.
In your next sales conversation, position yourself as a retained strategic partner, not a session-based coach.
See how it lands. Adjust based on feedback. Keep refining.
The coaching retainer model isn’t complicated. You’re just reframing your value from discrete interventions to ongoing partnership.
But that reframing changes everything – for your margins, for your client relationships, and for the lifetime value of your business.
Your expertise is worth more than hourly fees. Your guidance compounds over time. Your clients need you consistently, not sporadically.
Build a business model that reflects that reality.
The retainer model is how you do it.
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Jeremy Haynes is the founder of Megalodon Marketing. He is considered one of the top digital marketers and has the results to back it up. Jeremy has consistently demonstrated his expertise whether it be through his content advertising “propaganda” strategies that are originated by him, as well as his funnel and direct response marketing strategies. He’s trusted by the biggest names in the industries his agency works in and by over 4,000+ paid students that learn how to become better digital marketers and agency owners through his education products.
Jeremy Haynes is the founder of Megalodon Marketing. He is considered one of the top digital marketers and has the results to back it up. Jeremy has consistently demonstrated his expertise whether it be through his content advertising “propaganda” strategies that are originated by him, as well as his funnel and direct response marketing strategies. He’s trusted by the biggest names in the industries his agency works in and by over 4,000+ paid students that learn how to become better digital marketers and agency owners through his education products.
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