iPlanRx Apollo Sequence Library

Batch 1 of 4 · Peer-to-peer voice · Free Benefits Scorecard offer · Calendly fallback

🎯 Silver Bullit 5-Touch Cadence 100+ Prospects/Week
Sending As →
✓ Emails signed as Ben Madden
Sequence Library: Batch 1 — Superintendent · Owner/CEO Batch 2 — HR Director · Biz Manager/CFO Batch 3 — CESA · Chamber Batch 4 — Associations · Re-Engagement
🗺️

iCHRA State Expansion — Quick Reference

Use these state-specific hooks in Touch 1 subject lines when prospecting outside Wisconsin

Wave States iCHRA Advantage Touch 1 Hook Status
Wave 1 Indiana + Michigan IN: $400/employee tax credit + 18–45% cheaper than group. MI: Competitive market, adjacent to WI "Indiana just made iCHRA cheaper — $400/employee tax credit most owners don't know about" Active Now
Wave 2 Ohio Individual beats group in EVERY county, no exceptions "Ohio is one of few states where iCHRA saves money in literally every county — including yours" Active Now
Wave 3 Georgia + North Carolina GA: 12–57% cheaper than group. NC: Fast-growing, less broker competition "Georgia employers are leaving serious money on the table at renewal time" Start Q3 2026
Wave 4 Kentucky + South Carolina Both states: individual cheaper than group in nearly every county "Kentucky employers are overpaying for group health — the individual market is cheaper in nearly every county" Start Q4 2026
Wave 5 Texas New iCHRA tax credit for small businesses, applications open Jan 2027 "Texas is about to make iCHRA even more valuable — most owners don't know it yet" Pre-position Now
🏫

School District → Superintendent

Lead offer: iPlanRx Benefits Scorecard · Source: iCHRA District Opportunity Calculator v4.4

📊 Scorecard Pre-Pulled 📅 18-Day Cadence 5 Touches

The Offer — Use This Language Consistently

"I pulled a complimentary iPlanRx Benefits Scorecard for [District Name] — it's a one-page look at your current plan's cost position relative to similar Wisconsin districts, where your biggest exposure is, and what a restructured strategy could save. Takes about 20 minutes to walk through on a quick call."

Touch 1 — EmailDay 1
Touch 2 — PhoneDay 3
Touch 3 — EmailDay 7
Touch 4 — PhoneDay 12
Touch 5 — BreakupDay 18
Subject Lines
A
Your District's Benefits Scorecard is Ready — {{contact.District Name}}
B
{{contact.District Name}}: Financial Savings Opportunity Score — {{contact.Opportunity Score}}/18
C
We ran the numbers on {{contact.District Name}}'s health benefits
Email Body
CTAOffer two specific days + Calendly link
Strategic Notes
  • Pull the district in the iCHRA Calculator BEFORE sending — personalize the premium number and plan type from real data
  • "I pulled a Scorecard" signals you already did the work — removes the "I'll think about it" objection before it forms
  • No product pitch in Touch 1 — ever. The Scorecard IS the offer
  • Subject line A works better for high-score districts (14+). Subject line B for mid-tier (10–13)
  • Keep it under 150 words. Superintendents read on phones between meetings
  • Send Tuesday–Thursday, 6:45–7:15 AM or 4:30–5:00 PM
Phone Script — Live Answer
"Hi {{first_name}}, this is Ben Madden with iPlanRx — did I catch you at an okay time? [Pause] Great. I sent you a quick note a couple days ago — I pulled a Benefits Scorecard for {{contact.District Name}} showing where your health plan costs land relative to other Wisconsin districts. It's one page and takes about 20 minutes to walk through. Is there a time this week or next that would work for a quick call?" [If yes — book it right now. Don't let them off the phone without a date] [If no — "No problem at all. I'll send the Calendly link so you can grab a time that works."]
Voicemail Script
"Hi {{first_name}}, Ben Madden with iPlanRx. I emailed a couple days ago — I pulled a Benefits Scorecard for {{contact.District Name}} and wanted to see if a 20-minute call made sense. I'll send that link over so you can grab a time if the numbers look interesting. Talk soon." [Immediately after voicemail — send a one-line email:] "Just left you a voicemail — Scorecard is ready when you are. https://calendly.com/tom-madden/results-pepy-meetings"
Strategic Notes
  • Goal of this call is ONE thing: book the 20-minute call. Nothing else
  • Do not explain iCHRA on this call unless they ask — stay on the Scorecard
  • If they say "send me something" — that's a yes. Send Calendly immediately after hanging up
  • If they say "we're happy with our broker" — "Totally understand. The Scorecard isn't about switching — it's just a benchmark. Most districts find it useful even when they stay put."
  • Best call times: 7:00–8:00 AM, 11:30 AM–12:15 PM, 3:45–4:30 PM
  • Always send the follow-up email within 5 minutes of a voicemail
Subject Lines
A
Re: {{contact.District Name}} — one stat you might find interesting
B
Most WI districts don't know this about their plan
Email Body
CTAOne insight + Calendly link — nothing more
Strategic Notes
  • This email does one job: give them a reason to be curious that they didn't have before
  • The "gap carriers don't show you" framing is a challenger insight — it works because it's true and verifiable
  • Do NOT restate the full offer from Touch 1 — trust they read it. This is an additive nudge, not a repeat pitch
  • Keep it under 100 words — shorter than Touch 1
  • Use the "Re:" prefix in Subject A — it signals continuity and increases open rates
  • {{contact.Above Below}} pulls directly from the Apollo Contact CSV export — no manual fill-in needed
Phone Script — Live Answer
"Hi {{first_name}}, Ben Madden from iPlanRx again — I'll be quick. I've sent a couple notes about the {{contact.District Name}} Scorecard. I don't want to keep bugging you if the timing's just off — but I also don't want to move on if there's something here worth your 20 minutes. Honest question: is health plan cost not a priority right now, or just haven't had a chance to look at it?" [If timing — book a future date] [If not a priority — "Fair enough. Mind if I check back in before your next renewal?"] [If interested — book it now]
Voicemail Script
"Hi {{first_name}}, Ben Madden with iPlanRx. Last voicemail I'll leave for a bit — I have the {{contact.District Name}} Scorecard ready if the timing ever works. Link is in your email. No pressure either way — just didn't want it to go to waste. Take care."
Strategic Notes
  • Touch 4 is your "honest conversation" moment — treating them like a peer, not chasing them
  • The direct question "is this not a priority or just timing?" forces a real answer and often unlocks a stalled conversation
  • "Before your next renewal" keeps the door open on a future trigger date
  • Tone shift here: slightly more direct, slightly less cheerful. Peers are straight with each other
  • If they've opened the emails multiple times (track in Apollo) — reference it: "I can see the Scorecard caught your eye — happy to walk through it whenever"
Subject Lines
A
Closing the loop on {{contact.District Name}}
B
Should I hold the Scorecard or move on?
Email Body
CTALow pressure — leave the door open, don't beg
Strategic Notes
  • Breakup emails get the highest response rate in any sequence — the psychology of finality works
  • "I'll hold the analysis" keeps the Scorecard as a future asset — doesn't throw it away
  • Mention real triggers: renewal date, board pressure, cost increase — these resonate with superintendents specifically
  • Do NOT apologize for reaching out. You offered something valuable. Own that
  • Move to a 90-day re-engagement sequence after this — set a task in Apollo to re-contact before their likely renewal window
  • Add to a "warm nurture" list in Apollo for quarterly district newsletter or market update touches
Sequence Strategy Touch 1 personalizes with real data → Touch 2 calls while momentum is fresh → Touch 3 adds a challenger insight → Touch 4 has the honest peer conversation → Touch 5 creates urgency through finality. Every touch either books the call or keeps the door open for renewal season.
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Small Employer → Owner / CEO

Lead offer: iPlanRx Benefits Scorecard · Hook: cost exposure they don't know about · 50–500 employees, WI-based

💡 Challenger Hook 📅 18-Day Cadence 5 Touches

The Offer — Use This Language Consistently

"Most Wisconsin business owners I talk to are funding their carrier's profit margin and don't know it. I'd like to send you a complimentary iPlanRx Benefits Scorecard — a one-page analysis of where your plan sits on cost, compliance, and employee value. Takes about 20 minutes to walk through, and you'll know pretty quickly if there's anything worth a closer look."

Touch 1 — EmailDay 1
Touch 2 — PhoneDay 3
Touch 3 — EmailDay 7
Touch 4 — PhoneDay 12
Touch 5 — BreakupDay 18
Subject Lines
A
{{company_name}} — are you funding your carrier's profit margin?
B
What your health plan renewal doesn't show you
Email Body
CTA"Worth it?" — one soft question + Calendly link
Strategic Notes
  • The carrier profit margin insight is the hook — it's true, provocative, and owners haven't heard it from their current broker
  • No Scorecard pre-pull for employers — the hook creates curiosity in its place
  • Subject line A is more provocative — use for companies 100+ employees where cost stakes are higher
  • Subject line B is softer — use for smaller companies (50–100 ee) where the owner may be less adversarial toward carriers
  • "Whether there's a better structure worth considering" — positions you as analytical, not salesy
  • Send Tuesday–Thursday, 7:00–8:00 AM or 5:00–5:30 PM
Phone Script — Live Answer
"Hi {{first_name}}, this is Ben Madden with iPlanRx — do you have just a minute? [Pause] I sent you a quick note a couple days ago about your health plan. The short version: most Wisconsin business owners are structured on fully-insured plans that are designed to benefit the carrier more than the employer — and a one-page analysis usually shows pretty quickly whether that's happening with you. I'd like to send that over — takes 20 minutes to walk through together. Is there a time this week that works?" [If yes — book it on the phone. Get a specific day and time] [If "send me something" — "Absolutely. I'll send the Calendly link right now so you can grab a time that works." Send immediately] [If "we're happy with our broker" — "That's great — this isn't about switching brokers. It's just a benchmark so you know where you stand. A lot of owners find that useful even when they stay put."]
Voicemail Script
"Hi {{first_name}}, Ben Madden with iPlanRx. I emailed a couple days ago about your health plan — specifically about whether your current structure is working for you or more for your carrier. I'd love to show you a one-pager that answers that question pretty quickly. Sending you that link now. Talk soon." [Send immediately after:] "Just tried to reach you — link is below whenever you're ready. https://calendly.com/tom-madden/results-pepy-meetings"
Strategic Notes
  • Owners are busy and decisive — get to the point in 15 seconds flat
  • "Working for you or more for your carrier" is the reframe that lands — the challenger insight delivered verbally
  • The "happy with our broker" objection is common — never attack the broker. Position around knowledge, not replacement
  • If they engage at all on the phone — that's a warm lead. Push for a specific day, not "sometime next week"
  • Best call times for business owners: 7:30–8:30 AM, 12:00–1:00 PM
  • Never call Friday afternoon
Subject Lines
A
The number your renewal letter doesn't include
B
Re: {{company_name}} — one more thing worth knowing
Email Body
CTASingle loss ratio insight — Calendly link only
Strategic Notes
  • Loss ratio is a real concept owners can Google — credible and verifiable, which makes the challenger insight land harder
  • "The number your carrier never puts in the renewal letter" — provocative framing that makes them feel like they've been missing something
  • Don't explain loss ratio fully — leave them wanting the answer. The Scorecard fills that gap
  • Under 100 words — this is a pattern interrupt, not a brochure
  • Subject A performs best with analytical owners (manufacturing, professional services). Subject B for relational owners
Phone Script — Live Answer
"Hi {{first_name}}, Ben Madden from iPlanRx — I'll be straight with you. I've reached out a couple times about your health plan and I don't want to be the guy who keeps calling when the answer is no. But I also talk to Wisconsin business owners every week who've been on the same plan structure for years without anyone ever showing them the alternative — and most of them wish someone had shown them sooner. Is health plan cost something that's on your radar right now, or is the timing just off?" [If timing — "When would be a better time? I'll put it in my calendar."] [If not interested — "Fair enough. Mind if I check back before your next renewal?"] [If curious — book it immediately]
Voicemail Script
"Hi {{first_name}}, Ben Madden with iPlanRx. This is my last call for a while — just didn't want to move on without making sure the timing wasn't just off. The Scorecard link is in your email whenever it makes sense. No pressure. Take care."
Strategic Notes
  • "I'll be straight with you" — the peer-to-peer pivot that shifts the entire conversation dynamic
  • The "wish someone had shown them sooner" line uses social proof without naming names — implies a pattern without overpromising
  • The direct question forces a real answer — timing vs. not interested are very different follow-up paths
  • Never apologize for reaching out — you're offering value, not asking for a favor
  • If they say renewal is X months out — put a specific task in Apollo to call back 60 days before that date
Subject Lines
A
Closing the loop — {{company_name}}
B
One last thing before I move on
Email Body
CTAFinality creates response — don't soften it
Strategic Notes
  • Breakup emails routinely get the highest response rate — the psychology of loss is more powerful than any pitch
  • "I'll hold the Scorecard" keeps your asset alive without begging
  • Mention real triggers for owners: renewal coming up, costs jumping, second opinion — actual moments they'll re-engage
  • Do not add any new pitch content here — pure finality
  • Move to 90-day re-engagement in Apollo — tag as "renewal nurture" and set a task 60 days before their likely renewal window
  • Add to quarterly newsletter list — WI employer health cost benchmarks keep you top of mind passively
Sequence Strategy Touch 1 leads with the carrier profit margin insight to create curiosity → Touch 2 calls while the email is fresh → Touch 3 adds the loss ratio hook to deepen the gap → Touch 4 has the honest peer conversation → Touch 5 uses finality to trigger latent interest. Every non-responder goes into a renewal-timed re-engagement sequence.
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CESA Administrator

CESA Executive Directors, Deputy Directors, Benefits Coordinators · District-wide iCHRA adoption

🏫 CESA Track 📅 21-Day Cadence 4 Touches

The Offer — Use This Language Consistently

"Using our proprietary AI analysis tools, we ran a district-by-district Benefits Scorecard across all districts in your CESA — combining public WI DPI data with district-specific health plan data. I have a one-page aggregate summary ready. A CESA-administered iCHRA program could give every district a fixed, predictable cost structure, with your office guiding the rollout rather than each district figuring it out alone. Takes about 20 minutes to walk through."

Touch 1 — EmailDay 0
Touch 2 — PhoneDay 4
Touch 3 — EmailDay 10
Touch 4 — BreakupDay 21
Subject Lines
A
{{cesa_name}} district health benefits — we ran the numbers
B
{{districts_analyzed}} districts, one pattern worth knowing about
Email Body
CTAData-led open + soft question + Calendly link
Strategic Notes
  • Pull {{avg_single_premium}}, {{avg_mkt_gap}}, {{self_funded_count}}, and {{districts_analyzed}} from the CESA PDF report in the iCHRA Calculator before sending
  • The three-bullet data summary signals you already did the work — removes the "I'll look into it myself" objection
  • CESA administrators respond to operational framing: "your office guiding the rollout" positions iCHRA as a CESA service, not a disruption
  • Subject line A works when you know the CESA name is distinctive. Subject line B leads with scale — use when district count is high (10+)
  • Send Tuesday–Thursday, 7:00–8:00 AM or 3:30–4:30 PM
Phone Script — Live Answer
"Hi {{first_name}}, Ben Madden with iPlanRx — I sent you a note earlier this week about the district health benefits analysis we ran for {{cesa_name}}. Do you have just a minute? [Pause] The short version: using our proprietary AI analysis tools, we looked at all {{districts_analyzed}} districts and found an average {{avg_mkt_gap}} gap between what your fully-insured districts are paying and what's available on the ACA marketplace. A CESA-level program could address that across all of them at once rather than district by district. I have a one-page summary ready — takes about 20 minutes to walk through. Is there a time this week or next that works?" [If yes — book it on the phone] [If "send me something" — "Absolutely, sending the Calendly link now."] [If "districts handle their own benefits" — "Totally understand — this is actually designed to make it easier on the districts by having CESA lead the process. Worth at least seeing the data."]
Voicemail Script
"Hi {{first_name}}, Ben Madden with iPlanRx. I emailed earlier this week — using our proprietary AI analysis tools, we ran a district-by-district Benefits Scorecard across {{cesa_name}} combining WI DPI and district-level data, and found some patterns worth a quick conversation. I'll send the Calendly link so you can grab a time if it looks interesting. Talk soon." [Send immediately after voicemail:] "Just tried to reach you — the {{cesa_name}} district analysis is ready when you are. https://calendly.com/tom-madden/results-pepy-meetings"
Strategic Notes
  • CESA administrators are coordinators, not salespeople — frame the call as sharing data, not pitching a product
  • "Rather than district by district" is the key operational hook — it speaks directly to their role as a centralizing resource
  • The "districts handle their own benefits" objection is the most common — have this reframe ready before you dial
  • Best call times: 7:30–8:30 AM, 11:30 AM–12:30 PM, 3:00–4:00 PM
  • Always send the follow-up email within 5 minutes of a voicemail
Subject Lines
A
The {{self_funded_count}} self-funded districts in {{cesa_name}}
B
Re: {{cesa_name}} — the claims risk angle
Email Body
CTAClaims risk hook + CESA rollout framing + Calendly
Strategic Notes
  • Self-funded claims risk is the highest-urgency pain point for district administrators — one bad year can trigger a budget crisis
  • The iCHRA conversion framing here is structural, not sales-y: fixed contribution, employee choice, cost certainty
  • "Easier to roll out when a CESA is leading it" reinforces the administrator's value to their member districts
  • Use Subject A when {{self_funded_count}} is 3 or more — the specificity of the number earns opens
  • Keep it under 120 words — administrators read between meetings, not at their desk
Subject Lines
A
Closing the loop — {{cesa_name}}
B
Should I hold the {{cesa_name}} analysis?
Email Body
CTAFinality — name the real future trigger moments
Strategic Notes
  • Breakup emails get the highest response rate — the psychology of finality consistently unlocks latent interest
  • "Next CESA benefits meeting" and "board questions about cost structure" are real trigger moments for administrators — not generic
  • "I'll hold the aggregate Scorecard" keeps the asset alive without begging — signals ongoing value
  • Do not add any new pitch content — pure finality and warmth
  • Move to 90-day re-engagement in Apollo — tag as "CESA renewal nurture" and set a task before the next likely district renewal window
Sequence Strategy Touch 1 leads with a data-rich district-by-district analysis to establish credibility immediately → Touch 2 calls while the data is fresh and addresses the "districts handle this themselves" objection directly → Touch 3 sharpens the angle to self-funded claims risk — the highest-urgency pain point → Touch 4 uses finality and names CESA-specific trigger moments to unlock latent interest. Shorter cadence (21 days, 4 touches) reflects the longer CESA decision cycle.
🤝

Association

Executive Directors, Membership Directors, Chamber of Commerce leaders · Co-branded member benefit

🤝 Association Track 📅 21-Day Cadence 4 Touches

The Offer — Use This Language Consistently

"We're building association-sponsored iCHRA programs across Wisconsin that give members exclusive iPlanRx pricing and onboarding support, a co-branded benefits resource through the association, and a no-cost Benefits Scorecard to see if iCHRA makes sense for their business. The association pays nothing. Your members get a tangible new benefit. And {{association_name}} gets to be the organization that brought it to them."

Touch 1 — EmailDay 0
Touch 2 — PhoneDay 4
Touch 3 — EmailDay 10
Touch 4 — BreakupDay 21
Subject Lines
A
A member benefit your {{association_name}} members don't have yet
B
{{association_name}} — a new health benefits program worth considering
Email Body
CTAMember value framing + soft question + Calendly link
Strategic Notes
  • "The association pays nothing" removes the #1 objection before it forms — say it early and explicitly
  • Association leaders respond to credit: "{{association_name}} gets to be the organization that brought it to them" is the actual value proposition for them personally
  • The three-bullet member benefit list is scannable — busy EDs read bullets, not paragraphs
  • Subject A is more intriguing for well-run associations proud of their member value. Subject B is more direct for pragmatic leaders
  • Send Tuesday–Thursday, 7:30–8:30 AM or 4:00–5:00 PM
Phone Script — Live Answer
"Hi {{first_name}}, Ben Madden with iPlanRx — I sent you a note earlier this week about a member benefit program for {{association_name}}. Do you have just a minute? [Pause] The short version: we're partnering with Wisconsin associations to offer their members exclusive access to a health benefits solution that most small businesses don't know exists yet. It costs the association nothing, and it gives your members something genuinely useful — especially the ones that are struggling with rising health plan costs. I'd love to show you what a co-branded program looks like for {{association_name}}. Is there a time this week that works?" [If yes — book it on the phone] [If "our members handle their own benefits" — "Exactly — this doesn't change that. It just gives them a better option and a trusted resource through you."] [If "send me something" — "Absolutely, sending the Calendly link now."]
Voicemail Script
"Hi {{first_name}}, Ben Madden with iPlanRx. I emailed earlier this week about a co-branded member benefit program for {{association_name}} — a health benefits solution that costs the association nothing and gives your members exclusive pricing and access. I'll send the Calendly link so you can grab a time if it's worth a look. Talk soon." [Send immediately after voicemail:] "Just tried to reach you — happy to show you what this looks like for {{association_name}} whenever it works. https://calendly.com/tom-madden/results-pepy-meetings"
Strategic Notes
  • Lead with the association's name — it signals this isn't a mass call, it's specific to them
  • "Costs the association nothing" must be in every verbal touchpoint — it's the fastest objection killer
  • The "members handle their own benefits" objection is extremely common — have this reframe memorized before you dial
  • Best call times: 8:00–9:00 AM, 12:00–1:00 PM, 4:00–5:00 PM
  • Always send the follow-up email within 5 minutes of a voicemail
Subject Lines
A
What other Wisconsin associations are doing with this
B
Re: {{association_name}} member benefits — one more angle
Email Body
CTAThree concrete delivery models + Calendly — nothing more
Strategic Notes
  • Concrete delivery models make the abstract feel real — association leaders need to visualize what "co-branded" actually means before they'll commit to a call
  • "You get the credit" closes the paragraph — it's the most important line in the email
  • "None of these require budget or staff time" reinforces zero-cost, zero-lift for the association
  • Subject A uses peer social proof — works well when the association is competitive or status-conscious. Subject B for those who prefer directness
  • Under 100 words of body copy — let the bullet format do the work
Subject Lines
A
Closing the loop — {{association_name}}
B
Should I hold this for {{association_name}}?
Email Body
CTAFinality — name real association trigger moments
Strategic Notes
  • Breakup emails get the highest response rate — finality creates urgency where follow-up couldn't
  • "Renewal season, a member survey, a board discussion about value-adds" — these are the real moments associations re-engage, name them specifically
  • "The program is ready to go whenever {{association_name}} is" keeps the asset alive without begging
  • Do not add any new pitch content — pure finality and warmth
  • Move to 90-day re-engagement in Apollo — tag as "association nurture" and set a task before the next likely membership renewal or annual meeting
Sequence Strategy Touch 1 leads with the zero-cost co-branded member benefit angle — the association pays nothing, members gain something → Touch 2 calls while the email is fresh and has the "members handle their own benefits" reframe ready → Touch 3 makes the abstract concrete with three specific delivery models and reinforces zero lift for the association → Touch 4 uses finality and names real association trigger moments to unlock latent interest.