iPlanRx Apollo Sequence Library

Sequence Library: Batch 1 — Superintendent · Owner/CEO Batch 2 — HR Director · Biz Manager/CFO Batch 3 — CESA · Chamber of Commerce Batch 4 — Associations · Re-Engagement

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Multiplier Tracks — Different Strategy Than Batches 1 & 2

These are partnership conversations, not direct sales pitches. Ben is not selling iCHRA or a Scorecard to CESAs or Chambers — he's opening a discussion about how iPlanRx could become a resource they offer their districts or members. The ask is a 30-minute exploratory call. One CESA relationship = potential access to 20–40 districts. One Chamber relationship = potential access to hundreds of member businesses. Tom should consider leading or co-leading the discovery call for these contacts — the founder-to-executive dynamic carries more weight at this level.

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CESA → Executive Director

12 CESAs in Wisconsin · Each serves 20–40+ school districts · Partnership conversation

🔀 Multiplier Track 📅 21-Day Cadence 4 Touches

CESA 1Milwaukee · Waukesha · Ozaukee · Washington · Racine · Kenosha

CESA 2Dane · Rock · Green · Jefferson · Walworth

CESA 3Grant · Iowa · Lafayette · Richland · Crawford · Vernon

CESA 4La Crosse · Monroe · Trempealeau · Buffalo · Pepin · Pierce

CESA 5Adams · Waushara · Marquette · Columbia · Sauk · Juneau · Wood

CESA 6Fond du Lac · Dodge · Washington · Winnebago · Calumet · Outagamie

CESA 7Brown · Kewaunee · Door · Manitowoc · Sheboygan · Calumet

CESA 8Oconto · Marinette · Florence · Forest · Langlade · Menominee · Shawano

CESA 9Lincoln · Marathon · Portage · Waupaca · Wood · Oneida · Vilas

CESA 10Chippewa · Clark · Eau Claire · Taylor · Jackson

CESA 11Barron · Burnett · Polk · St. Croix · Dunn · Pierce · Washburn

CESA 12Ashland · Bayfield · Douglas · Iron · Price · Rusk · Sawyer · Washburn

The Ask — 30-Minute Exploratory Conversation

"We'd like to have a 30-minute conversation about your role serving Wisconsin school districts and whether there's a fit for iPlanRx to become a resource you offer your districts — something that gives their superintendents and business managers health benefits benchmark data they currently don't have access to, at no cost to the CESA."

Touch 1 — EmailDay 1

Touch 2 — PhoneDay 4

Touch 3 — EmailDay 10

Touch 4 — BreakupDay 21

Subject Lines

A resource for your districts — worth a 30-minute conversation

iPlanRx + [CESA #] — exploring a fit

Email Body

Hi [First Name], I'm Ben Madden with iPlanRx — we work with Wisconsin school districts on health benefits strategy. I'm reaching out because I'd like to have a conversation about your role serving districts in [CESA Region] and whether there's a fit for iPlanRx to become a resource you offer them. Here's the context: most Wisconsin school districts renew their health plan every year without ever seeing a benchmark comparison — what similarly-structured districts are actually paying, where their cost exposure sits, and whether an alternative structure makes sense. That data exists, and we've built tools around it specifically for Wisconsin districts. The question I'd like to explore with you is whether that's something [CESA #] could see value in offering its districts — at no cost to the CESA. Would a 30-minute conversation make sense? [Calendly link] Ben Madden iPlanRx | Green Bay & Madison, WI [phone]

CTA30-minute exploratory call — no commitment implied

Strategic Notes

This is NOT a sales pitch — it's an invitation to explore a partnership. Every word should reflect that
"Your role serving districts" shows you understand what a CESA does — it's not a generic cold email
"At no cost to the CESA" removes the obvious objection before it forms — they're not being asked to pay for anything
"That data exists and we've built tools around it" — subtle credibility signal without overselling. Let the conversation do the rest
Subject line A is warmer and more collaborative. Subject line B is more direct — use when you've done homework on that specific CESA
Tom or Jason should be the sender for CESA outreach — founder/senior title carries more weight with Executive Directors than a prospecting rep
Send Tuesday–Thursday, 7:30–8:30 AM

Phone Script — Live Answer

"Hi [First Name], this is Ben Madden with iPlanRx — do you have just a minute? I sent you a note a few days ago. We work with Wisconsin school districts on health benefits strategy and I wanted to reach out to you specifically because of the role [CESA #] plays with your districts. The short version: most districts in your region are renewing their health plan without a benchmark comparison — we've built that benchmark, and I'd like to explore whether it's something [CESA #] would find useful to offer your districts. No cost to the CESA — just a 30-minute conversation to see if there's a fit. Would that be worth your time?" [If yes — book it. Offer to include Tom on the call: "Would it make sense to include our founder Tom Madden on that call? He leads our district strategy work."] [If "send me more information" — "Happy to. I'll send a brief overview — would it be okay if I followed up with a call after you've had a chance to look at it?"] [If "we already have something like this" — "That's great to hear. I'd be curious to learn more about what you're using — would 20 minutes still make sense just to compare notes?"]

Voicemail Script

"Hi [First Name], Ben Madden with iPlanRx. I emailed a few days ago about a potential resource for your districts around health benefits benchmarking — something we offer at no cost to the CESA. I'd love 30 minutes to explore whether there's a fit. Sending the link now. Talk soon." [Send immediately:] "Just left you a voicemail — happy to find 30 minutes at your convenience. [Calendly link]"

Strategic Notes

Offer to include Tom on the discovery call — Executive Directors respond better to founder-level conversations on partnership discussions
"Compare notes" is a powerful reframe if they claim to have something similar — it keeps the door open without being confrontational
"Send me more information" is a soft yes — follow up with a one-page overview and a specific ask to reconnect after they've read it
Best call times for CESA Executive Directors: 8:00–9:00 AM or 1:00–2:00 PM
CESA Executive Directors serve on various WI education boards — a relationship here can open doors far beyond just their districts

Subject Lines

What Wisconsin districts are paying — [CESA #] region data

Re: iPlanRx + [CESA #] — one more thought

Email Body

Hi [First Name], Following up on my earlier note. One thing that might be worth knowing: we've scored all 413 Wisconsin school districts on health benefits cost efficiency — and for the districts in [CESA #]'s region, the data shows a meaningful range between the most and least cost-efficient districts. That gap represents real dollars in fund balances across your region. And most of those districts have no idea where they stand relative to each other. That's the conversation I'd like to have — whether there's a role for [CESA #] in helping surface that data for your districts. 30 minutes at your convenience. [Calendly link] Ben iPlanRx

CTARegional data angle — positions CESA as the conduit

Strategic Notes

"We've scored all 413 Wisconsin school districts" — this is real and credible. It signals iPlanRx has built something substantive, not just a generic pitch
"Whether there's a role for [CESA #] in helping surface that data" — positions the CESA as a champion for their districts, not a passive referral source
Executive Directors are motivated by serving their districts well — framing this as a district benefit rather than a vendor relationship is the right angle
Subject line A with regional data specificity is strong — it implies you've already done the work for their region
Under 120 words — Executive Directors are busy administrators, not sales prospects

Subject Lines

Closing the loop — [CESA #]

Leaving the door open — iPlanRx + [CESA #]

Email Body

Hi [First Name], I've reached out a few times and haven't heard back — I'll assume the timing isn't right and won't keep following up. I'll leave this here in case it becomes relevant: we work with Wisconsin school districts on health benefits benchmarking and strategy, and we're always open to a conversation about how [CESA #] might play a role in bringing that resource to your districts. If that ever makes sense — a new budget cycle, a district raising the benefits question, or just the right time — my info is below. [Calendly link] Ben Madden iPlanRx | [phone] | [email]

CTAClean exit — no pressure, long re-engagement window

Strategic Notes

CESA Executive Directors are long-term relationship targets — the exit must be respectful and leave no bad taste
"A district raising the benefits question" is a realistic trigger — districts often bring issues to their CESA before going external
Move to a 6-month re-engagement in Apollo — not 90 days. These are senior administrators and over-contacting is relationship-damaging
Add to an annual "WI district benefits benchmark" distribution list — a one-page annual summary of district benefits trends is a legitimate reason to re-engage with zero sales pressure
A warm introduction from any district contact you've already connected with is far more valuable than any cold sequence — always ask district contacts "Is your CESA involved in benefits decisions at all?"

Sequence Strategy Touch 1 frames the conversation as exploring a fit — no pitch, no product → Touch 2 calls and offers Tom on the discovery call to elevate the conversation → Touch 3 introduces the 413-district scoring data to signal real capability → Touch 4 exits cleanly with a long re-engagement window. Every CESA contact goes into a 6-month nurture cycle. One warm introduction from a district contact is worth more than this entire sequence.

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Chamber of Commerce → President / CEO

WI Chambers — each represents dozens to hundreds of member businesses · Member benefit conversation

🔀 Multiplier Track 📅 21-Day Cadence 4 Touches

The Ask — 30-Minute Exploratory Conversation

"We'd like to have a 30-minute conversation about your role serving Wisconsin business owners and whether there's a fit for iPlanRx to become a member benefit your Chamber offers — something that gives your members access to health benefits benchmarking and strategy at no cost to them or to the Chamber."

Touch 1 — EmailDay 1

Touch 2 — PhoneDay 4

Touch 3 — EmailDay 10

Touch 4 — BreakupDay 21

Subject Lines

A member benefit worth a 30-minute conversation

iPlanRx + [Chamber Name] — exploring a fit for your members

Email Body

Hi [First Name], I'm Ben Madden with iPlanRx — we work with Wisconsin business owners on health benefits strategy. I'm reaching out because I'd like to have a conversation about your role at [Chamber Name] and whether there's a fit for iPlanRx to become a resource you offer your members. Here's the context: most Wisconsin business owners are on fully-insured health plans that are designed to benefit the carrier more than the employer — and most of them have never had an independent analysis of whether their plan is cost-competitive. That analysis is what we provide, at no cost to the business owner. The question I'd like to explore with you is whether that's something [Chamber Name] would find value in offering its members — and what that could look like. Would a 30-minute conversation make sense? [Calendly link] Ben Madden iPlanRx | Green Bay & Madison, WI [phone]

CTA30-minute exploratory — "what that could look like" signals flexibility

Strategic Notes

Chamber Presidents hear vendor pitches constantly — the key differentiator is leading with member value, not iPlanRx value
"What that could look like" — signals you're not arriving with a fixed program. You're open to shaping the partnership around what works for their Chamber
"At no cost to the business owner" — removes the most common Chamber objection: "our members don't want to be sold to"
Subject line A is warmer — better for smaller regional Chambers where the President wears many hats
Subject line B is more direct — better for larger metro Chambers (Green Bay, Madison, Milwaukee area) with more structured partnership processes
Tom should lead or co-lead Chamber discovery calls — founder-to-executive conversations carry more weight for partnership discussions
Send Tuesday–Thursday, 8:00–9:00 AM

Phone Script — Live Answer

"Hi [First Name], this is Ben Madden with iPlanRx — do you have just a minute? I sent you a note a few days ago. We work with Wisconsin business owners on health benefits strategy, and I wanted to reach out to you specifically because of what you do for your members at [Chamber Name]. The short version: most Wisconsin business owners have never had an independent look at whether their health plan is cost-competitive — we provide that at no cost to them. And I'd like to explore whether that's something [Chamber Name] would want to make available to its members. No cost to the Chamber. Just a 30-minute conversation to see if there's a fit. Would that make sense?" [If yes — book it. Offer to include Tom: "Would it help to have our founder Tom Madden on that call? He leads our partnership conversations."] [If "we have a benefits vendor already" — "Totally understand — we're not looking to replace anyone. This would be an additional resource for members who want an independent second opinion on their current plan. Different from what a vendor typically offers."] [If "send me information" — "Happy to. I'll send something brief — could we find 20 minutes to talk after you've had a chance to look at it?"]

Voicemail Script

"Hi [First Name], Ben Madden with iPlanRx. I emailed a few days ago about a potential member benefit for [Chamber Name] — specifically around health benefits benchmarking for your members at no cost to them or the Chamber. I'd love 30 minutes to explore whether there's a fit. Sending the link now. Talk soon." [Send immediately:] "Just left you a voicemail — happy to find 30 minutes at your convenience. [Calendly link]"

Strategic Notes

"We're not looking to replace anyone" — critical objection handler for Chambers that have existing broker or benefits vendor relationships
"Independent second opinion" — positions iPlanRx as additive, not competitive with their existing relationships
Always offer to include Tom on the discovery call for Chamber conversations — this elevates the conversation immediately
Best call times: 8:30–10:00 AM, 1:30–3:00 PM
Chambers often have monthly member meetings, newsletters, and events — ask about those channels during the discovery call as potential distribution vehicles

Subject Lines

What [Chamber Name] members are likely paying — and don't know

Re: [Chamber Name] — one more thought on member value

Email Body

Hi [First Name], Circling back on my earlier note. One thing that tends to resonate with Chamber leaders: the majority of small and mid-size Wisconsin businesses are on fully-insured health plans that haven't been independently benchmarked — ever. They renew with the same carrier year after year because that's the path of least resistance. The iPlanRx Benefits Scorecard gives them that independent benchmark for the first time. Most find at least one thing worth a closer look. For a Chamber, that's a tangible member benefit that costs nothing to offer and delivers real value at first contact. Worth 30 minutes to explore? [Calendly link] Ben iPlanRx

CTA"Tangible member benefit that costs nothing to offer" — the Chamber value prop

Strategic Notes

"Tangible member benefit that costs nothing to offer" — this is the core Chamber value prop stated plainly. It answers "what's in it for us" without being asked
"Delivers real value at first contact" — signals that members don't have to commit to anything to get something useful. That's important for Chambers protective of member experience
"Path of least resistance" is a peer insight — Chamber Presidents know this is true of their members and appreciate the honesty
Keep it under 130 words — Chamber Presidents are busy and this email should feel like a quick read, not a sales deck

Subject Lines

Closing the loop — [Chamber Name]

Moving on — but leaving the door open

Email Body

Hi [First Name], I've reached out a few times and haven't heard back — I'll assume the timing isn't right and won't keep following up. If it ever makes sense to explore a member benefit program around health benefits benchmarking — new board year, a member asking about benefits strategy, or just the right time for a new partnership conversation — my info is below. We're building our Wisconsin presence and would value the relationship whenever the timing works. [Calendly link] Ben Madden iPlanRx | [phone] | [email]

CTARespectful exit — names Chamber-specific re-engagement triggers

Strategic Notes

"New board year" is a real Chamber trigger — leadership transitions often bring new appetite for partnerships
"A member asking about benefits strategy" — positions the Chamber President as someone who might proactively reach out when a member need arises
"We're building our Wisconsin presence" — honest, not overselling. It implies you're growing and that early partnerships matter
Move to 6-month re-engagement in Apollo — same as CESAs, over-contacting Chamber Presidents is relationship-damaging
Attend Chamber events in your target markets (Green Bay, Madison, Fox Valley, etc.) — in-person introductions at Chamber events are far more effective than cold email for this contact type
Consider joining 1–2 key Chambers as a member — it gives you instant warm access to the President and legitimacy with the membership

Sequence Strategy Touch 1 leads with member value and flexibility — "what that could look like" signals a partnership, not a vendor pitch → Touch 2 calls, handles the existing vendor objection, and offers Tom on the discovery call → Touch 3 states the Chamber value prop plainly: tangible member benefit, zero cost to offer → Touch 4 exits cleanly with Chamber-specific re-engagement triggers. Chamber Presidents who engage become distribution channels — every discovery call should explore newsletters, member meetings, and co-branded touchpoints.