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The “Retire Smarter” Playbook: How to Turn Aging Clients into High-Value Advisory Relationships (on Autopilot)

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Most firms miss the opportunity to turn near-retirement clients into recurring advisory revenue. This step-by-step playbook shows how to identify, market to, and serve this high-value segment — automatically with CountingWorks PRO.

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Webinar Series

The “Retire Smarter” Playbook: How to Turn Aging Clients into High-Value Advisory Relationships (on Autopilot)

You Don’t Need New Clients. You Need to Activate the Right Ones.

The easiest way to grow your firm right now isn’t by spending on ads or chasing new leads — it’s by re-engaging the clients you already have.

Specifically, the ones nearing retirement.

These clients are entering the most tax-sensitive phase of their financial lives. And if you’re only doing their returns, you’re missing out on thousands in potential revenue per client and leaving them vulnerable to avoidable tax mistakes.

That’s where the Retire Smarter Playbook comes in — a fully automated campaign designed to help you turn 55–70-year-old clients into loyal, year-round advisory relationships with zero extra effort.

Step 1: Identify the Opportunity Inside Your Own Database

Every firm has this segment hiding in plain sight.

Your CRM (or client list) already holds the key indicators — birth years, IRAs, Social Security income, 401(k) rollovers, Schedule B dividends.

You can manually filter this data, or if you’re on CountingWorks PRO, MAX automatically tags these clients for you.

MAX uses smart segmentation to find clients who match:

  • Ages 55 to 70
  • Retirement or investment income reported
  • Mentions of “401(k), IRA, pension, or RMD” in past filings
  • Married filing jointly (higher planning opportunity)

That’s your high-value target list — no ads, no cold leads, just warm relationships waiting to be activated.

Step 2: Package the Offer

Clients don’t buy “advisory.” They buy outcomes.

Here’s how to turn complex services into clear, sellable packages that feel approachable and valuable:

Package

Description

Price Range

Duration

Retirement Tax Readiness Review

A quick look at income mix, retirement timeline, and tax exposure. Ideal for clients 1–5 years from retirement.

$300–$750

One-time

Distribution Strategy Plan

Annual review of withdrawals, Roth conversions, RMDs, and charitable strategies.

$1,200–$2,500

Ongoing

Legacy & Gifting Tax Review

Evaluate estate, trust, and gifting opportunities for tax savings.

$500+

One-time or add-on

These can be positioned as standalone engagements, bundled into advisory tiers, or introduced as a low-barrier way to start quarterly planning.

Automatic Playbook that will help you curate content and appeal to your ideal near-retirement client base.

Step 3: Launch the Campaign

Now comes the fun part — letting automation do the heavy lifting.

If you’re a CountingWorks PRO firm, the Retire Smarter Playbook is plug-and-play:

  • MAX identifies eligible clients automatically.
  • It sends three pre-written, branded emails.
  • Your blog and newsletter update with retirement tax strategy content.
  • Engagement letters and proposals are created on demand.
  • Follow-up reminders trigger automatically after 7 days.

You can even personalize the tone and voice (educational, human, or concierge-style) — all without writing a word yourself.

Sample Campaign Flow

Week 1 – Awareness

Email: “Are You Paying More Tax in Retirement Than You Should?”

CTA: Schedule a Retirement Tax Readiness Review

Week 2 – Education

Newsletter or blog auto-publishes: “The 3-Year Window to Optimize Your Social Security and Taxes.”

CTA: Learn more

Week 3 – Proof + Conversion

Email: “How One Simple Roth Conversion Saved $4,000 a Year.”

CTA: Book a personalized Retirement Tax Review

Week 4 – Reminder

MAX automatically triggers a short follow-up or text:

“We’re wrapping up our Retirement Tax Reviews this month. Want to reserve your spot?”

You stay top-of-mind. MAX handles the delivery. Clients take action.

Automatic blog post to educate your clients and promote your expertise

Step 4: Deliver and Delight

Once a client books a session, your intake form (prebuilt in ClientHub) collects details like:

  • Planned retirement age
  • Social Security eligibility dates
  • IRA and 401(k) balances
  • Charitable interests
  • Desired annual income

MAX automatically generates a one-page summary of tax opportunities you can review live or send post-meeting.

You can record a quick voice overview, drop it into the client portal, and mark the task complete — all tracked inside CountingWorks PRO.

What used to take hours now takes minutes — and it feels incredibly high-touch for the client.

Step 5: Renew Automatically

The magic of advisory is retention.

Each “Retirement Tax Readiness Review” turns into a yearly touchpoint, a quarterly planning cadence, and a new revenue stream that compounds over time.

MAX’s renewal workflow auto-generates next year’s proposal, updates the content, and even sends a “How much tax did you save?” recap message to remind clients of the value they’re getting.

It’s recurring revenue on autopilot.

Why This Works

✅ Zero marketing cost: You’re reactivating your existing client base.

✅ Instant credibility: You’re already their trusted advisor.

✅ High perceived value: “Retirement tax strategy” feels elite, not commoditized.

✅ Emotional connection: Clients care deeply about their legacy, not line items.

✅ Automation advantage: You set it up once — MAX runs it every year.

The Big Takeaway

You don’t need a new product. You need a new conversation.

And right now, no conversation is more valuable than “Are you set up to retire tax-smart?”

Firms using CountingWorks PRO can turn this into a done-for-you revenue playbook with literally no manual lift — automated marketing, proposals, intake, and follow-up.

Because when you let automation handle the busywork, you can focus on what you do best:

being the human guide who helps clients retire smarter.

Ready to Activate Your Retire Smarter Campaign?

CountingWorks PRO firms can turn this playbook on inside MAX in minutes — and start converting existing clients into advisory revenue before tax season even begins.

Tactical Tuesday

The “Retire Smarter” Playbook: How to Turn Aging Clients into High-Value Advisory Relationships (on Autopilot)

You Don’t Need New Clients. You Need to Activate the Right Ones.

The easiest way to grow your firm right now isn’t by spending on ads or chasing new leads — it’s by re-engaging the clients you already have.

Specifically, the ones nearing retirement.

These clients are entering the most tax-sensitive phase of their financial lives. And if you’re only doing their returns, you’re missing out on thousands in potential revenue per client and leaving them vulnerable to avoidable tax mistakes.

That’s where the Retire Smarter Playbook comes in — a fully automated campaign designed to help you turn 55–70-year-old clients into loyal, year-round advisory relationships with zero extra effort.

Step 1: Identify the Opportunity Inside Your Own Database

Every firm has this segment hiding in plain sight.

Your CRM (or client list) already holds the key indicators — birth years, IRAs, Social Security income, 401(k) rollovers, Schedule B dividends.

You can manually filter this data, or if you’re on CountingWorks PRO, MAX automatically tags these clients for you.

MAX uses smart segmentation to find clients who match:

  • Ages 55 to 70
  • Retirement or investment income reported
  • Mentions of “401(k), IRA, pension, or RMD” in past filings
  • Married filing jointly (higher planning opportunity)

That’s your high-value target list — no ads, no cold leads, just warm relationships waiting to be activated.

Step 2: Package the Offer

Clients don’t buy “advisory.” They buy outcomes.

Here’s how to turn complex services into clear, sellable packages that feel approachable and valuable:

Package

Description

Price Range

Duration

Retirement Tax Readiness Review

A quick look at income mix, retirement timeline, and tax exposure. Ideal for clients 1–5 years from retirement.

$300–$750

One-time

Distribution Strategy Plan

Annual review of withdrawals, Roth conversions, RMDs, and charitable strategies.

$1,200–$2,500

Ongoing

Legacy & Gifting Tax Review

Evaluate estate, trust, and gifting opportunities for tax savings.

$500+

One-time or add-on

These can be positioned as standalone engagements, bundled into advisory tiers, or introduced as a low-barrier way to start quarterly planning.

Automatic Playbook that will help you curate content and appeal to your ideal near-retirement client base.

Step 3: Launch the Campaign

Now comes the fun part — letting automation do the heavy lifting.

If you’re a CountingWorks PRO firm, the Retire Smarter Playbook is plug-and-play:

  • MAX identifies eligible clients automatically.
  • It sends three pre-written, branded emails.
  • Your blog and newsletter update with retirement tax strategy content.
  • Engagement letters and proposals are created on demand.
  • Follow-up reminders trigger automatically after 7 days.

You can even personalize the tone and voice (educational, human, or concierge-style) — all without writing a word yourself.

Sample Campaign Flow

Week 1 – Awareness

Email: “Are You Paying More Tax in Retirement Than You Should?”

CTA: Schedule a Retirement Tax Readiness Review

Week 2 – Education

Newsletter or blog auto-publishes: “The 3-Year Window to Optimize Your Social Security and Taxes.”

CTA: Learn more

Week 3 – Proof + Conversion

Email: “How One Simple Roth Conversion Saved $4,000 a Year.”

CTA: Book a personalized Retirement Tax Review

Week 4 – Reminder

MAX automatically triggers a short follow-up or text:

“We’re wrapping up our Retirement Tax Reviews this month. Want to reserve your spot?”

You stay top-of-mind. MAX handles the delivery. Clients take action.

Automatic blog post to educate your clients and promote your expertise

Step 4: Deliver and Delight

Once a client books a session, your intake form (prebuilt in ClientHub) collects details like:

  • Planned retirement age
  • Social Security eligibility dates
  • IRA and 401(k) balances
  • Charitable interests
  • Desired annual income

MAX automatically generates a one-page summary of tax opportunities you can review live or send post-meeting.

You can record a quick voice overview, drop it into the client portal, and mark the task complete — all tracked inside CountingWorks PRO.

What used to take hours now takes minutes — and it feels incredibly high-touch for the client.

Step 5: Renew Automatically

The magic of advisory is retention.

Each “Retirement Tax Readiness Review” turns into a yearly touchpoint, a quarterly planning cadence, and a new revenue stream that compounds over time.

MAX’s renewal workflow auto-generates next year’s proposal, updates the content, and even sends a “How much tax did you save?” recap message to remind clients of the value they’re getting.

It’s recurring revenue on autopilot.

Why This Works

✅ Zero marketing cost: You’re reactivating your existing client base.

✅ Instant credibility: You’re already their trusted advisor.

✅ High perceived value: “Retirement tax strategy” feels elite, not commoditized.

✅ Emotional connection: Clients care deeply about their legacy, not line items.

✅ Automation advantage: You set it up once — MAX runs it every year.

The Big Takeaway

You don’t need a new product. You need a new conversation.

And right now, no conversation is more valuable than “Are you set up to retire tax-smart?”

Firms using CountingWorks PRO can turn this into a done-for-you revenue playbook with literally no manual lift — automated marketing, proposals, intake, and follow-up.

Because when you let automation handle the busywork, you can focus on what you do best:

being the human guide who helps clients retire smarter.

Ready to Activate Your Retire Smarter Campaign?

CountingWorks PRO firms can turn this playbook on inside MAX in minutes — and start converting existing clients into advisory revenue before tax season even begins.

Already a Client and Have Questions?

Send Us an Email to help@countingworkspro.com

Or call our team at 1-800-442-2477.

First Time Hearing About Our Product?

Speak To Us and See Our Product In Action
Webinar Series

The “Retire Smarter” Playbook: How to Turn Aging Clients into High-Value Advisory Relationships (on Autopilot)

You Don’t Need New Clients. You Need to Activate the Right Ones.

The easiest way to grow your firm right now isn’t by spending on ads or chasing new leads — it’s by re-engaging the clients you already have.

Specifically, the ones nearing retirement.

These clients are entering the most tax-sensitive phase of their financial lives. And if you’re only doing their returns, you’re missing out on thousands in potential revenue per client and leaving them vulnerable to avoidable tax mistakes.

That’s where the Retire Smarter Playbook comes in — a fully automated campaign designed to help you turn 55–70-year-old clients into loyal, year-round advisory relationships with zero extra effort.

Step 1: Identify the Opportunity Inside Your Own Database

Every firm has this segment hiding in plain sight.

Your CRM (or client list) already holds the key indicators — birth years, IRAs, Social Security income, 401(k) rollovers, Schedule B dividends.

You can manually filter this data, or if you’re on CountingWorks PRO, MAX automatically tags these clients for you.

MAX uses smart segmentation to find clients who match:

  • Ages 55 to 70
  • Retirement or investment income reported
  • Mentions of “401(k), IRA, pension, or RMD” in past filings
  • Married filing jointly (higher planning opportunity)

That’s your high-value target list — no ads, no cold leads, just warm relationships waiting to be activated.

Step 2: Package the Offer

Clients don’t buy “advisory.” They buy outcomes.

Here’s how to turn complex services into clear, sellable packages that feel approachable and valuable:

Package

Description

Price Range

Duration

Retirement Tax Readiness Review

A quick look at income mix, retirement timeline, and tax exposure. Ideal for clients 1–5 years from retirement.

$300–$750

One-time

Distribution Strategy Plan

Annual review of withdrawals, Roth conversions, RMDs, and charitable strategies.

$1,200–$2,500

Ongoing

Legacy & Gifting Tax Review

Evaluate estate, trust, and gifting opportunities for tax savings.

$500+

One-time or add-on

These can be positioned as standalone engagements, bundled into advisory tiers, or introduced as a low-barrier way to start quarterly planning.

Automatic Playbook that will help you curate content and appeal to your ideal near-retirement client base.

Step 3: Launch the Campaign

Now comes the fun part — letting automation do the heavy lifting.

If you’re a CountingWorks PRO firm, the Retire Smarter Playbook is plug-and-play:

  • MAX identifies eligible clients automatically.
  • It sends three pre-written, branded emails.
  • Your blog and newsletter update with retirement tax strategy content.
  • Engagement letters and proposals are created on demand.
  • Follow-up reminders trigger automatically after 7 days.

You can even personalize the tone and voice (educational, human, or concierge-style) — all without writing a word yourself.

Sample Campaign Flow

Week 1 – Awareness

Email: “Are You Paying More Tax in Retirement Than You Should?”

CTA: Schedule a Retirement Tax Readiness Review

Week 2 – Education

Newsletter or blog auto-publishes: “The 3-Year Window to Optimize Your Social Security and Taxes.”

CTA: Learn more

Week 3 – Proof + Conversion

Email: “How One Simple Roth Conversion Saved $4,000 a Year.”

CTA: Book a personalized Retirement Tax Review

Week 4 – Reminder

MAX automatically triggers a short follow-up or text:

“We’re wrapping up our Retirement Tax Reviews this month. Want to reserve your spot?”

You stay top-of-mind. MAX handles the delivery. Clients take action.

Automatic blog post to educate your clients and promote your expertise

Step 4: Deliver and Delight

Once a client books a session, your intake form (prebuilt in ClientHub) collects details like:

  • Planned retirement age
  • Social Security eligibility dates
  • IRA and 401(k) balances
  • Charitable interests
  • Desired annual income

MAX automatically generates a one-page summary of tax opportunities you can review live or send post-meeting.

You can record a quick voice overview, drop it into the client portal, and mark the task complete — all tracked inside CountingWorks PRO.

What used to take hours now takes minutes — and it feels incredibly high-touch for the client.

Step 5: Renew Automatically

The magic of advisory is retention.

Each “Retirement Tax Readiness Review” turns into a yearly touchpoint, a quarterly planning cadence, and a new revenue stream that compounds over time.

MAX’s renewal workflow auto-generates next year’s proposal, updates the content, and even sends a “How much tax did you save?” recap message to remind clients of the value they’re getting.

It’s recurring revenue on autopilot.

Why This Works

✅ Zero marketing cost: You’re reactivating your existing client base.

✅ Instant credibility: You’re already their trusted advisor.

✅ High perceived value: “Retirement tax strategy” feels elite, not commoditized.

✅ Emotional connection: Clients care deeply about their legacy, not line items.

✅ Automation advantage: You set it up once — MAX runs it every year.

The Big Takeaway

You don’t need a new product. You need a new conversation.

And right now, no conversation is more valuable than “Are you set up to retire tax-smart?”

Firms using CountingWorks PRO can turn this into a done-for-you revenue playbook with literally no manual lift — automated marketing, proposals, intake, and follow-up.

Because when you let automation handle the busywork, you can focus on what you do best:

being the human guide who helps clients retire smarter.

Ready to Activate Your Retire Smarter Campaign?

CountingWorks PRO firms can turn this playbook on inside MAX in minutes — and start converting existing clients into advisory revenue before tax season even begins.

Guide

The “Retire Smarter” Playbook: How to Turn Aging Clients into High-Value Advisory Relationships (on Autopilot)

You Don’t Need New Clients. You Need to Activate the Right Ones.

The easiest way to grow your firm right now isn’t by spending on ads or chasing new leads — it’s by re-engaging the clients you already have.

Specifically, the ones nearing retirement.

These clients are entering the most tax-sensitive phase of their financial lives. And if you’re only doing their returns, you’re missing out on thousands in potential revenue per client and leaving them vulnerable to avoidable tax mistakes.

That’s where the Retire Smarter Playbook comes in — a fully automated campaign designed to help you turn 55–70-year-old clients into loyal, year-round advisory relationships with zero extra effort.

Step 1: Identify the Opportunity Inside Your Own Database

Every firm has this segment hiding in plain sight.

Your CRM (or client list) already holds the key indicators — birth years, IRAs, Social Security income, 401(k) rollovers, Schedule B dividends.

You can manually filter this data, or if you’re on CountingWorks PRO, MAX automatically tags these clients for you.

MAX uses smart segmentation to find clients who match:

  • Ages 55 to 70
  • Retirement or investment income reported
  • Mentions of “401(k), IRA, pension, or RMD” in past filings
  • Married filing jointly (higher planning opportunity)

That’s your high-value target list — no ads, no cold leads, just warm relationships waiting to be activated.

Step 2: Package the Offer

Clients don’t buy “advisory.” They buy outcomes.

Here’s how to turn complex services into clear, sellable packages that feel approachable and valuable:

Package

Description

Price Range

Duration

Retirement Tax Readiness Review

A quick look at income mix, retirement timeline, and tax exposure. Ideal for clients 1–5 years from retirement.

$300–$750

One-time

Distribution Strategy Plan

Annual review of withdrawals, Roth conversions, RMDs, and charitable strategies.

$1,200–$2,500

Ongoing

Legacy & Gifting Tax Review

Evaluate estate, trust, and gifting opportunities for tax savings.

$500+

One-time or add-on

These can be positioned as standalone engagements, bundled into advisory tiers, or introduced as a low-barrier way to start quarterly planning.

Automatic Playbook that will help you curate content and appeal to your ideal near-retirement client base.

Step 3: Launch the Campaign

Now comes the fun part — letting automation do the heavy lifting.

If you’re a CountingWorks PRO firm, the Retire Smarter Playbook is plug-and-play:

  • MAX identifies eligible clients automatically.
  • It sends three pre-written, branded emails.
  • Your blog and newsletter update with retirement tax strategy content.
  • Engagement letters and proposals are created on demand.
  • Follow-up reminders trigger automatically after 7 days.

You can even personalize the tone and voice (educational, human, or concierge-style) — all without writing a word yourself.

Sample Campaign Flow

Week 1 – Awareness

Email: “Are You Paying More Tax in Retirement Than You Should?”

CTA: Schedule a Retirement Tax Readiness Review

Week 2 – Education

Newsletter or blog auto-publishes: “The 3-Year Window to Optimize Your Social Security and Taxes.”

CTA: Learn more

Week 3 – Proof + Conversion

Email: “How One Simple Roth Conversion Saved $4,000 a Year.”

CTA: Book a personalized Retirement Tax Review

Week 4 – Reminder

MAX automatically triggers a short follow-up or text:

“We’re wrapping up our Retirement Tax Reviews this month. Want to reserve your spot?”

You stay top-of-mind. MAX handles the delivery. Clients take action.

Automatic blog post to educate your clients and promote your expertise

Step 4: Deliver and Delight

Once a client books a session, your intake form (prebuilt in ClientHub) collects details like:

  • Planned retirement age
  • Social Security eligibility dates
  • IRA and 401(k) balances
  • Charitable interests
  • Desired annual income

MAX automatically generates a one-page summary of tax opportunities you can review live or send post-meeting.

You can record a quick voice overview, drop it into the client portal, and mark the task complete — all tracked inside CountingWorks PRO.

What used to take hours now takes minutes — and it feels incredibly high-touch for the client.

Step 5: Renew Automatically

The magic of advisory is retention.

Each “Retirement Tax Readiness Review” turns into a yearly touchpoint, a quarterly planning cadence, and a new revenue stream that compounds over time.

MAX’s renewal workflow auto-generates next year’s proposal, updates the content, and even sends a “How much tax did you save?” recap message to remind clients of the value they’re getting.

It’s recurring revenue on autopilot.

Why This Works

✅ Zero marketing cost: You’re reactivating your existing client base.

✅ Instant credibility: You’re already their trusted advisor.

✅ High perceived value: “Retirement tax strategy” feels elite, not commoditized.

✅ Emotional connection: Clients care deeply about their legacy, not line items.

✅ Automation advantage: You set it up once — MAX runs it every year.

The Big Takeaway

You don’t need a new product. You need a new conversation.

And right now, no conversation is more valuable than “Are you set up to retire tax-smart?”

Firms using CountingWorks PRO can turn this into a done-for-you revenue playbook with literally no manual lift — automated marketing, proposals, intake, and follow-up.

Because when you let automation handle the busywork, you can focus on what you do best:

being the human guide who helps clients retire smarter.

Ready to Activate Your Retire Smarter Campaign?

CountingWorks PRO firms can turn this playbook on inside MAX in minutes — and start converting existing clients into advisory revenue before tax season even begins.

News & Product Update

The “Retire Smarter” Playbook: How to Turn Aging Clients into High-Value Advisory Relationships (on Autopilot)

October 28, 2025
/
10
min read
Lee Reams
CEO | CountingWorks PRO

You Don’t Need New Clients. You Need to Activate the Right Ones.

The easiest way to grow your firm right now isn’t by spending on ads or chasing new leads — it’s by re-engaging the clients you already have.

Specifically, the ones nearing retirement.

These clients are entering the most tax-sensitive phase of their financial lives. And if you’re only doing their returns, you’re missing out on thousands in potential revenue per client and leaving them vulnerable to avoidable tax mistakes.

That’s where the Retire Smarter Playbook comes in — a fully automated campaign designed to help you turn 55–70-year-old clients into loyal, year-round advisory relationships with zero extra effort.

Step 1: Identify the Opportunity Inside Your Own Database

Every firm has this segment hiding in plain sight.

Your CRM (or client list) already holds the key indicators — birth years, IRAs, Social Security income, 401(k) rollovers, Schedule B dividends.

You can manually filter this data, or if you’re on CountingWorks PRO, MAX automatically tags these clients for you.

MAX uses smart segmentation to find clients who match:

  • Ages 55 to 70
  • Retirement or investment income reported
  • Mentions of “401(k), IRA, pension, or RMD” in past filings
  • Married filing jointly (higher planning opportunity)

That’s your high-value target list — no ads, no cold leads, just warm relationships waiting to be activated.

Step 2: Package the Offer

Clients don’t buy “advisory.” They buy outcomes.

Here’s how to turn complex services into clear, sellable packages that feel approachable and valuable:

Package

Description

Price Range

Duration

Retirement Tax Readiness Review

A quick look at income mix, retirement timeline, and tax exposure. Ideal for clients 1–5 years from retirement.

$300–$750

One-time

Distribution Strategy Plan

Annual review of withdrawals, Roth conversions, RMDs, and charitable strategies.

$1,200–$2,500

Ongoing

Legacy & Gifting Tax Review

Evaluate estate, trust, and gifting opportunities for tax savings.

$500+

One-time or add-on

These can be positioned as standalone engagements, bundled into advisory tiers, or introduced as a low-barrier way to start quarterly planning.

Automatic Playbook that will help you curate content and appeal to your ideal near-retirement client base.

Step 3: Launch the Campaign

Now comes the fun part — letting automation do the heavy lifting.

If you’re a CountingWorks PRO firm, the Retire Smarter Playbook is plug-and-play:

  • MAX identifies eligible clients automatically.
  • It sends three pre-written, branded emails.
  • Your blog and newsletter update with retirement tax strategy content.
  • Engagement letters and proposals are created on demand.
  • Follow-up reminders trigger automatically after 7 days.

You can even personalize the tone and voice (educational, human, or concierge-style) — all without writing a word yourself.

Sample Campaign Flow

Week 1 – Awareness

Email: “Are You Paying More Tax in Retirement Than You Should?”

CTA: Schedule a Retirement Tax Readiness Review

Week 2 – Education

Newsletter or blog auto-publishes: “The 3-Year Window to Optimize Your Social Security and Taxes.”

CTA: Learn more

Week 3 – Proof + Conversion

Email: “How One Simple Roth Conversion Saved $4,000 a Year.”

CTA: Book a personalized Retirement Tax Review

Week 4 – Reminder

MAX automatically triggers a short follow-up or text:

“We’re wrapping up our Retirement Tax Reviews this month. Want to reserve your spot?”

You stay top-of-mind. MAX handles the delivery. Clients take action.

Automatic blog post to educate your clients and promote your expertise

Step 4: Deliver and Delight

Once a client books a session, your intake form (prebuilt in ClientHub) collects details like:

  • Planned retirement age
  • Social Security eligibility dates
  • IRA and 401(k) balances
  • Charitable interests
  • Desired annual income

MAX automatically generates a one-page summary of tax opportunities you can review live or send post-meeting.

You can record a quick voice overview, drop it into the client portal, and mark the task complete — all tracked inside CountingWorks PRO.

What used to take hours now takes minutes — and it feels incredibly high-touch for the client.

Step 5: Renew Automatically

The magic of advisory is retention.

Each “Retirement Tax Readiness Review” turns into a yearly touchpoint, a quarterly planning cadence, and a new revenue stream that compounds over time.

MAX’s renewal workflow auto-generates next year’s proposal, updates the content, and even sends a “How much tax did you save?” recap message to remind clients of the value they’re getting.

It’s recurring revenue on autopilot.

Why This Works

✅ Zero marketing cost: You’re reactivating your existing client base.

✅ Instant credibility: You’re already their trusted advisor.

✅ High perceived value: “Retirement tax strategy” feels elite, not commoditized.

✅ Emotional connection: Clients care deeply about their legacy, not line items.

✅ Automation advantage: You set it up once — MAX runs it every year.

The Big Takeaway

You don’t need a new product. You need a new conversation.

And right now, no conversation is more valuable than “Are you set up to retire tax-smart?”

Firms using CountingWorks PRO can turn this into a done-for-you revenue playbook with literally no manual lift — automated marketing, proposals, intake, and follow-up.

Because when you let automation handle the busywork, you can focus on what you do best:

being the human guide who helps clients retire smarter.

Ready to Activate Your Retire Smarter Campaign?

CountingWorks PRO firms can turn this playbook on inside MAX in minutes — and start converting existing clients into advisory revenue before tax season even begins.

News & Product Update

The “Retire Smarter” Playbook: How to Turn Aging Clients into High-Value Advisory Relationships (on Autopilot)

Thursday, October 30, 2025

October 30, 2025
/
10
min read
Lee Reams
CEO | CountingWorks PRO

You Don’t Need New Clients. You Need to Activate the Right Ones.

The easiest way to grow your firm right now isn’t by spending on ads or chasing new leads — it’s by re-engaging the clients you already have.

Specifically, the ones nearing retirement.

These clients are entering the most tax-sensitive phase of their financial lives. And if you’re only doing their returns, you’re missing out on thousands in potential revenue per client and leaving them vulnerable to avoidable tax mistakes.

That’s where the Retire Smarter Playbook comes in — a fully automated campaign designed to help you turn 55–70-year-old clients into loyal, year-round advisory relationships with zero extra effort.

Step 1: Identify the Opportunity Inside Your Own Database

Every firm has this segment hiding in plain sight.

Your CRM (or client list) already holds the key indicators — birth years, IRAs, Social Security income, 401(k) rollovers, Schedule B dividends.

You can manually filter this data, or if you’re on CountingWorks PRO, MAX automatically tags these clients for you.

MAX uses smart segmentation to find clients who match:

  • Ages 55 to 70
  • Retirement or investment income reported
  • Mentions of “401(k), IRA, pension, or RMD” in past filings
  • Married filing jointly (higher planning opportunity)

That’s your high-value target list — no ads, no cold leads, just warm relationships waiting to be activated.

Step 2: Package the Offer

Clients don’t buy “advisory.” They buy outcomes.

Here’s how to turn complex services into clear, sellable packages that feel approachable and valuable:

Package

Description

Price Range

Duration

Retirement Tax Readiness Review

A quick look at income mix, retirement timeline, and tax exposure. Ideal for clients 1–5 years from retirement.

$300–$750

One-time

Distribution Strategy Plan

Annual review of withdrawals, Roth conversions, RMDs, and charitable strategies.

$1,200–$2,500

Ongoing

Legacy & Gifting Tax Review

Evaluate estate, trust, and gifting opportunities for tax savings.

$500+

One-time or add-on

These can be positioned as standalone engagements, bundled into advisory tiers, or introduced as a low-barrier way to start quarterly planning.

Automatic Playbook that will help you curate content and appeal to your ideal near-retirement client base.

Step 3: Launch the Campaign

Now comes the fun part — letting automation do the heavy lifting.

If you’re a CountingWorks PRO firm, the Retire Smarter Playbook is plug-and-play:

  • MAX identifies eligible clients automatically.
  • It sends three pre-written, branded emails.
  • Your blog and newsletter update with retirement tax strategy content.
  • Engagement letters and proposals are created on demand.
  • Follow-up reminders trigger automatically after 7 days.

You can even personalize the tone and voice (educational, human, or concierge-style) — all without writing a word yourself.

Sample Campaign Flow

Week 1 – Awareness

Email: “Are You Paying More Tax in Retirement Than You Should?”

CTA: Schedule a Retirement Tax Readiness Review

Week 2 – Education

Newsletter or blog auto-publishes: “The 3-Year Window to Optimize Your Social Security and Taxes.”

CTA: Learn more

Week 3 – Proof + Conversion

Email: “How One Simple Roth Conversion Saved $4,000 a Year.”

CTA: Book a personalized Retirement Tax Review

Week 4 – Reminder

MAX automatically triggers a short follow-up or text:

“We’re wrapping up our Retirement Tax Reviews this month. Want to reserve your spot?”

You stay top-of-mind. MAX handles the delivery. Clients take action.

Automatic blog post to educate your clients and promote your expertise

Step 4: Deliver and Delight

Once a client books a session, your intake form (prebuilt in ClientHub) collects details like:

  • Planned retirement age
  • Social Security eligibility dates
  • IRA and 401(k) balances
  • Charitable interests
  • Desired annual income

MAX automatically generates a one-page summary of tax opportunities you can review live or send post-meeting.

You can record a quick voice overview, drop it into the client portal, and mark the task complete — all tracked inside CountingWorks PRO.

What used to take hours now takes minutes — and it feels incredibly high-touch for the client.

Step 5: Renew Automatically

The magic of advisory is retention.

Each “Retirement Tax Readiness Review” turns into a yearly touchpoint, a quarterly planning cadence, and a new revenue stream that compounds over time.

MAX’s renewal workflow auto-generates next year’s proposal, updates the content, and even sends a “How much tax did you save?” recap message to remind clients of the value they’re getting.

It’s recurring revenue on autopilot.

Why This Works

✅ Zero marketing cost: You’re reactivating your existing client base.

✅ Instant credibility: You’re already their trusted advisor.

✅ High perceived value: “Retirement tax strategy” feels elite, not commoditized.

✅ Emotional connection: Clients care deeply about their legacy, not line items.

✅ Automation advantage: You set it up once — MAX runs it every year.

The Big Takeaway

You don’t need a new product. You need a new conversation.

And right now, no conversation is more valuable than “Are you set up to retire tax-smart?”

Firms using CountingWorks PRO can turn this into a done-for-you revenue playbook with literally no manual lift — automated marketing, proposals, intake, and follow-up.

Because when you let automation handle the busywork, you can focus on what you do best:

being the human guide who helps clients retire smarter.

Ready to Activate Your Retire Smarter Campaign?

CountingWorks PRO firms can turn this playbook on inside MAX in minutes — and start converting existing clients into advisory revenue before tax season even begins.

Lee Reams
CEO | CountingWorks PRO

As the founder and CEO of CountingWorks, Inc, Lee is passionate about helping independent tax and accounting professionals compete in the modern age. From time-saving digital onboarding tools, world-class websites, and outbound marketing campaigns, Lee has been developing best-in-class marketing solutions for over twenty years.

Lee Reams
CEO | CountingWorks PRO

As the founder and CEO of CountingWorks, Inc, Lee is passionate about helping independent tax and accounting professionals compete in the modern age. From time-saving digital onboarding tools, world-class websites, and outbound marketing campaigns, Lee has been developing best-in-class marketing solutions for over twenty years.

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Create a year-long tax planning strategy for a freelancer earning $75,000 with multiple 1099 clients.

Below is a personalized, year-long tax planning strategy developed by CountingWorks, Inc., specifically for a freelancer earning $75,000 with multiple 1099 clients....

1. Establish a Robust Recordkeeping System

  • Dedicated Business Accounts: Open a separate business bank account and credit card to clearly define your income and expenses. This step not only simplifies your tax documentation but also aligns with our best-practices at CountingWorks.
  • ...

2. Manage Quarterly Estimated Tax Payments
...

Thank you! This is so helpful.
Gladly! Remember, you can also turn this information into audio and send to your clients directly via ClientHub.