iPlanRx Apollo Sequence Library

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

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Associations — Highest Multiplier in the System

Wisconsin associations represent concentrated, homogeneous membership — WASB members are all school board members, WMC members are all Wisconsin manufacturers and businesses. One endorsed partnership here reaches a targeted, pre-qualified audience that no amount of cold outreach could replicate. The pitch is identical to Chambers: a member benefit conversation, not a sales call. Tom should lead all Association discovery calls. These relationships take longer to develop but have the highest long-term revenue potential in the entire system.

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Association → Executive Director

WI-based associations serving school districts, employers, and business owners · Member benefit conversation

🔀 Multiplier Track 📅 21-Day Cadence 4 Touches

WASBWI Association of School Boards · School district board members statewide

WASDAWI Association of School District Administrators · District superintendents statewide

WASAWI Association of School Administrators · School principals and administrators

WMCWI Manufacturers & Commerce · Largest WI business association · 3,800+ members

NFIB WisconsinNational Federation of Independent Business · Small business owners statewide

WRAWI Restaurant Association · Hospitality employers across WI

ABC WisconsinAssociated Builders & Contractors · Construction and contracting employers

SHRM WI ChaptersSociety for HR Management · HR Directors and Benefits Managers statewide

WICPAWI Institute of CPAs · CPA firms — strong referral partner potential

WRA (Realtors)WI Realtors Association · Independent agents and small brokerage owners

The Ask — 30-Minute Exploratory Conversation

"We'd like to have a 30-minute conversation about your role serving [association members] and whether there's a fit for iPlanRx to become a resource your association offers its members — health benefits benchmarking and strategy at no cost to members or to the association."

Touch 1 — EmailDay 1

Touch 2 — PhoneDay 4

Touch 3 — EmailDay 10

Touch 4 — BreakupDay 21

Subject Lines

A member benefit worth exploring — iPlanRx + [Association Name]

Health benefits strategy for [Association Name] members — 30 minutes?

Email Body

Hi [First Name], I'm Ben Madden with iPlanRx — we work with Wisconsin [school districts / employers / business owners] on health benefits strategy. I'm reaching out because I'd like to have a conversation about whether iPlanRx could become a resource [Association Name] offers its members. Here's the context: most [members] are renewing their health plan every year without an independent benchmark — what comparable organizations are actually paying, where their cost exposure sits, and whether an alternative structure makes financial sense. We've built that benchmark specifically for Wisconsin, and we provide it at no cost to the member. The question I'd like to explore with you is whether [Association Name] would see value in making that available to your members — and what that partnership could look like. Would a 30-minute conversation make sense? [Calendly link] Ben Madden iPlanRx | Green Bay & Madison, WI [phone]

PersonalizeSwap [members] to match the association — "school districts" for WASB/WASDA, "business owners" for WMC/NFIB, "HR directors" for SHRM

Strategic Notes — By Association Type

WASB / WASDA / WASA: Lead with district fund balance impact and board-level cost visibility. These leaders are deeply familiar with the pressure districts face on benefits costs
WMC / NFIB: Lead with the carrier profit margin insight — business-focused, financially analytical audience. Cost efficiency resonates strongly
WRA / ABC Wisconsin: Lead with workforce retention angle — health benefits as a competitive hiring tool in industries with high turnover
SHRM chapters: Lead with compliance risk and ACA affordability — HR professionals care most about staying compliant and having better data for leadership conversations
WICPA: Position as a referral partner relationship — CPAs advise clients on cost reduction. iPlanRx is a tool they can refer clients to
Tom should be the sender and lead all Association discovery calls — founder-to-executive carries maximum weight here

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 / employers] on health benefits strategy, and I wanted to reach out specifically because of the role [Association Name] plays with your members. The short version: most [members] renew their health plan every year without an independent benchmark comparison — we've built that for Wisconsin, and I'd like to explore whether [Association Name] would see value in making that available to your members. No cost to the association or the members. Just a 30-minute conversation to see if there's a fit. Would that be worth your time?" [If yes — book it. "Would it make sense to include our founder Tom Madden on that call? He leads our partnership work."] [If "we have a benefits partner already" — "Totally understand — we're not looking to replace anyone. This is more of an independent benchmarking resource that complements what members already have. Different from a broker relationship."] [If "send me something" — "Happy to. I'll send a brief overview — could we find 20 minutes 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 [Association Name] around health benefits benchmarking — at no cost to your members or the association. 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

"Independent benchmarking resource that complements what members already have" — this is the critical reframe when they have an existing benefits partner. You're not competing, you're adding a layer of independent analysis
Always offer Tom on the discovery call — association executives respond to founder conversations on partnership discussions
WICPA is a special case — frame the call as exploring a referral relationship, not a member benefit program. CPAs refer clients, they don't endorse products
SHRM chapters often have monthly meetings — ask about presenting at a chapter meeting as an alternative to a one-on-one call
Best call times: 8:30–10:00 AM, 1:00–2:30 PM

Subject Lines

What [Association Name] members are likely leaving on the table

Re: iPlanRx + [Association Name] — one more thought

Email Body

Hi [First Name], Following up on my earlier note. One thing that tends to resonate with association leaders: the members who benefit most from an independent benefits benchmark are often the ones who would never go looking for it on their own. They assume their broker is giving them the full picture — and usually, they're not getting the comparison data that would tell them otherwise. An association endorsement changes that. It gives members a reason to look, a trusted source to turn to, and a tangible benefit that costs nothing to offer. That's the 30-minute conversation I'd like to have. [Calendly link] Ben iPlanRx

CTA"Association endorsement changes that" — the member trust angle

Strategic Notes

"Members who benefit most are the ones who would never go looking" — this is the insight that resonates with association leaders who think about serving their less engaged members
"Association endorsement changes that" — this elevates the association's role from passive to active. They're not just hosting a vendor, they're delivering member value
"Trusted source to turn to" — associations are trusted by their members in a way no vendor ever will be. This email makes that trust transferable
Under 120 words — these are senior executives with full inboxes
Subject line A implies your research shows a gap — even without naming a number, it suggests you have data worth sharing

Subject Lines

Closing the loop — [Association Name]

Leaving the door open — iPlanRx + [Association Name]

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 / employers] on health benefits strategy, and we're always open to a conversation about whether there's a role for [Association Name] in bringing that resource to your members. If the timing ever works — a new board year, a member raising the benefits question, or just the right moment for a new partnership conversation — my info is below. [Calendly link] Ben Madden iPlanRx | [phone] | [email]

CTARespectful clean exit — 6-month re-engagement minimum

Strategic Notes

"New board year" is the strongest association re-engagement trigger — leadership transitions bring new appetite for partnerships across every association type
Move to 6-month re-engagement minimum — association executives have long memories and over-contacting is permanently damaging
Consider attending annual association conferences as exhibitor or attendee — WASB, WASDA, and WMC all hold major annual events where in-person introductions are worth more than 10 cold emails
Nashville iCHRA conference (May 13–14) may surface association partnership opportunities — bring materials
A warm introduction from any member you've already worked with is the single most effective path into any association — always ask clients "Are you involved in any associations where other members might benefit from what we did for you?"

Sequence Strategy Touch 1 is personalized by association type — school district associations get fund balance language, employer associations get carrier profit margin language, HR associations get compliance language → Touch 2 calls and handles the existing partner objection by positioning as additive, not competitive → Touch 3 uses the "members who need it most won't go looking" insight to make the association feel like the catalyst → Touch 4 exits cleanly with a 6-month window. One association endorsement is worth more than 500 cold emails.

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90-Day Re-Engagement — The Passive Revenue Engine

This sequence runs automatically in Apollo for every prospect who completed Batches 1 or 2 without responding. Set the trigger: 60 days before their estimated renewal month. Ben doesn't manage it — Apollo fires it on schedule. It is not a repeat of the original pitch. It leads with a new angle, new data, or a market development. Three touches, lighter cadence, longer gaps. Every non-responder in your system gets a second life when their renewal comes around.

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90-Day Re-Engagement Sequence

All segments · Triggered 60 days before estimated renewal · 3 touches · Do NOT repeat the original pitch

⚙️ Apollo Automated 📅 90-Day Window 3 Touches

Apollo Trigger Setup — By Segment

School Districts

Tag: "district-renewal-nurture" · Set task 60 days before estimated renewal month · Most WI districts renew July 1 — trigger in May

Small Employers

Tag: "employer-renewal-nurture" · Set task 60 days before renewal month noted in Apollo · Default to January 1 if unknown

HR Directors

Tag: "hr-renewal-nurture" · Same trigger as employer — HR Director and Owner/CEO re-engagement often happen together

Business Managers

Tag: "district-renewal-nurture" · Add second trigger in January — WI district budget season starts February

Touch 1 — EmailDay 1 of Re-Eng

Touch 2 — PhoneDay 14

Touch 3 — FinalDay 30

Subject Lines — Districts

Districts

Renewal season — the [District Name] Scorecard is still here

Districts Alt

Before your renewal — one conversation worth having

Subject Lines — Employers

Employers

Before [Company Name]'s next renewal — worth a look?

Employers Alt

New data on WI employer health costs — relevant before your renewal

Email Body — Districts

Hi [First Name], I reached out a few months ago about a Benefits Scorecard for [District Name] — didn't hear back, and I moved on. With renewal season coming up, I wanted to put it back in front of you one more time. The Scorecard is still here, the data is current, and the 20-minute conversation offer still stands. Most districts that engage tell me the timing of our first conversation was just off. If that's the case here, now might be the right window. [Calendly link] Ben iPlanRx

Email Body — Employers

Hi [First Name], I reached out a few months ago about a complimentary Benefits Scorecard for [Company Name] — never heard back, so I moved on. With your renewal likely coming up, I wanted to put it back on your radar. One thing worth knowing: WI employer health costs shifted again this year — the gap between fully-insured plans and alternative structures has widened. If the timing wasn't right before, renewal season is usually when it gets right. Takes 20 minutes. Same offer as before. [Calendly link] Ben iPlanRx

Strategic Notes

"Didn't hear back, and I moved on" — this is the most important phrase in the re-engagement sequence. It acknowledges reality without being passive-aggressive, and it resets the relationship
Do NOT rehash the original pitch — trust they remember it. One new angle per touch is enough
For employers: "the gap has widened" is the new data point — it implies the case for switching has gotten stronger since you last spoke
For districts: "renewal season is usually when it gets right" — normalizes the timing without making them feel bad for not responding earlier
Keep it under 100 words — this is a gentle knock on the door, not a new campaign
This email consistently produces 15–25% response rates from cold non-responders when timed to renewal windows

Phone Script — Live Answer (All Segments)

"Hi [First Name], this is Ben Madden with iPlanRx — I reached out a few months ago about your health plan and never heard back. I'm not going to re-pitch you — just calling because your renewal is likely coming up and I wanted to check if the timing is any better. The offer is the same: a 20-minute call and a one-page Scorecard. No commitment, no sales pressure. Is this a better time?" [If yes — book it immediately] [If "still not interested" — "Totally fair. I won't reach out again unless something changes on your end. Take care."] [If "renewal isn't for a while" — "Good to know — when is it? I'll put a note and reach back out closer to that window."]

Voicemail Script

"Hi [First Name], Ben Madden with iPlanRx — I reached out a few months ago and never connected. With your renewal coming up I wanted to check in one more time. Same offer — 20 minutes, one-page Scorecard, no obligation. Link is in your email if the timing's better now. Take care."

Strategic Notes

"I'm not going to re-pitch you" — this phrase disarms the defensive posture that comes from a second round of outreach. It signals self-awareness and earns a few extra seconds of attention
If they tell you their exact renewal date — this is gold. Update Apollo immediately and set a task 45 days before that date every year going forward
"I won't reach out again unless something changes on your end" — if they say they're still not interested, honor it. This is the professional exit that protects your sender reputation
Best call times for re-engagement: same as original sequence by segment type

Subject Lines

Last touch — [Name/District/Company], the door stays open

Moving on for good — but here if you need us

Email Body

Hi [First Name], This is the last time I'll reach out — I don't want to be the vendor that keeps showing up uninvited. If you ever want an independent look at your health plan costs — renewal coming up, costs jumping, employees pushing back, or just wanting a second opinion — my info is below. The Scorecard offer doesn't expire. Wishing you a good renewal season either way. [Calendly link] Ben Madden iPlanRx | [phone] | [email]

Final"The Scorecard offer doesn't expire" — leaves a permanent open door

Strategic Notes

"I don't want to be the vendor that keeps showing up uninvited" — this level of self-awareness is rare and memorable. It often generates a response of respect even from people who aren't interested
"The Scorecard offer doesn't expire" — this is the lasting hook. It signals you're available on their timeline, not yours
"Wishing you a good renewal season" — genuine, warm, and specific. It leaves a positive final impression
After this touch — move to annual passive nurture only: one email per year with WI district or employer health cost benchmarks. No sales language, just useful data. This keeps iPlanRx top of mind for the moment they're finally ready
This final email is also the most frequently forwarded — prospects sometimes share it with a colleague or board member who then reaches out proactively

Re-Engagement Strategy Touch 1 reintroduces with a new data angle and renewal timing — never repeats the original pitch → Touch 2 calls with radical honesty: "I'm not going to re-pitch you" → Touch 3 is the final graceful exit that leaves a permanent open door. Every non-responder after this moves to annual passive nurture. The renewal trigger makes this sequence work — timing is everything in benefits outreach.

🎯 iPlanRx Apollo Prospecting System — Complete

All 8 sequences built, written, and ready to load into Apollo. This is the full Silver Bullit outreach engine for Wisconsin school districts, small employers, CESAs, Chambers, and Associations — plus a renewal-triggered re-engagement system that runs passively in the background.

Sequences

Total Touches

Market Segments

413

WI Districts Scored

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Re-Engagement