OBB Holdings — internal working doc

Kreilkamp pilot — scope, test pricing, ongoing cost

For Luke · built from the 5/27 sit-down + the Tenstreet research + the incentive-alignment frame · 2026-05-28

The number you owe Tim and Jill. Built to price the test low enough to be an easy yes, and put the real money in a durable fee that only grows when Kreilkamp's driver retention does — so the price negotiates itself and they root for us to win.

1. What we scope to Tim

The pilot is the driver-hiring top-of-funnel automation, three connected pieces running against Kreilkamp's existing Tenstreet ATS:

Missed-call + after-hours rescue. Every inbound recruiting call that isn't answered — nights, weekends, AND business hours (Tim's own scope expansion in the room) — triggers an automatic SMS within minutes opening a mobile-friendly pre-screen. Captures the 30-40% of interested drivers who otherwise call the next carrier on their list (Tenstreet's own data).
SMS pre-screen (compressed). A short, mobile-native pre-qualifying conversation — kept under Jeff's "less than 5 questions" bar so experienced drivers don't self-select out. Captures the FMCSA-aligned fields, routes only judgment-ready candidates to Jeff with qualified / needs-clarification / disqualified flags. The AI never makes a hire/no-hire call.
Calendared callback + recruiter handoff. Qualified drivers get scheduled into the recruiter's queue (the Paradox-style flow Jeff knew from his old shop), results written back onto the Tenstreet record so Jeff sees everything in one place.

Plus: pipeline events push into the Power BI dashboards Kreilkamp already runs — no new dashboard to learn.

⚠️ Week-1 discovery decision Tim's team owns — flag it explicitly in the proposal: Tenstreet has its OWN native SMS texting (dedicated number, two-way, auto-enrolls applicants). Our Twilio layer must either REPLACE Tenstreet's texting or COEXIST with clear handoff rules — otherwise drivers get two threads with split opt-out/TCPA consent. Jeff + Kreilkamp decide this in week 1; we don't build SMS until they do. This is the single thing most likely to derail the pilot if skipped.

The cadence frame (how to talk about success)

Not a one-time burst of 50 drivers. The win is a sustainable drumbeat — ~10 qualified, warm, recruiter-ready leads every 40 days, indefinitely. Against ~70% turnover on a 285-truck fleet needing 150-200 hires/year, that's the difference between Jeff's team forever chasing the next fire and a pipeline that just runs. "You never suffer a driver-hiring bottleneck again" — not "you got a surge this quarter."

2. Test-phase pricing

Price the test to be an easy yes. Per Jill's 401k-advisor steer (low entry → big book → more total) and Tim's small-town-margin instinct ("$18 beer vs $4"), and per the partnership-not-vendor frame: the test is where Tim finds out we're real at low risk. The money is in the durable phase, not here.

Recommended test fee
$18,000–22,000 · 90-day pilot, fixed

Why this band (not the $45-65K ladder you walked in with):

Tim + Jill signaled hard to come in low; managers must buy in, and "a win at too high a price won't stick."
It covers the real build: Tenstreet API activation (~$500 + their monthly), the Twilio/SMS + voice agent build, Power BI integration, and OBB's 3-5 week engineering effort — at a thin-but-not-underwater margin.
It's low enough that the test reads as "let's find out," not "big bet."

Structure the test on milestones, not a lump

$8K at signing — covers week-1 discovery (the texting-seam decision), Tenstreet activation, infrastructure stand-up.
$7K at first proof milestone — first 10 qualified, recruiter-ready leads delivered (your real proof bar, ~day 40).
$5K at cadence-proof milestone — second 10 in the next ~40 days, proving it's a sustainable drumbeat, not a one-off.

(Frame to the CFO as "three payments tied to milestones." Don't telegraph "10 is my proof bar" — let the milestone hit, then surface the ongoing conversation.)

Honest margin note: at $18-22K the test is close to break-even after Tenstreet fees + 3-5 weeks of build (especially if you, not Kyler, carry the engineering). That's intentional — it's the loss-leader for the durable. It only pencils out if the ongoing structure (below) is real and lands. If the durable doesn't materialize, OBB ate the build at cost. That's the bet.

3. Ongoing cost to sustain

This is where the incentive alignment lives — and where the real money is. Per the partnership frame: OBB earns more only when Kreilkamp's pain shrinks.

Structure: small base + retention-tied kicker

Base retainer: $2,500–3,000/mo — covers infrastructure (Twilio + AI model + Tenstreet monthly, passed through or capped), monitoring, threshold-tuning when Jeff wants changes, monthly cadence reporting. Small enough it's not a barrier.
Retention kicker: the alignment lever. A per-driver bonus for every hire who passes a tenure milestone ABOVE Kreilkamp's current baseline. Conservative shape: $500-750 per driver who hits 6-month tenure above the baseline run-rate.
Infra pass-through, capped (Twilio + AI models) so Tim's cost is predictable; anything over the cap, Kreilkamp pays direct.

The math Jill can verify in 5 minutes: each retained driver avoids ~$8-12K of replacement + ramp-loss cost. If we move 6-month retention even 15 points, that's 20-30 fewer lost drivers/year — $200-300K of value Kreilkamp captures, against a kicker that costs them a fraction of it. Our biggest invoice is their best year.

Worked example (illustrative, tighten with their real baseline)

Base: $3K/mo × 12 = $36K/yr
Kicker: if the system drives +20 retained-past-6-months over baseline × $625 = ~$12.5K/yr
Total OBB Y1 ongoing: ~$48K — against $200K+ of value Kreilkamp captures. ~4:1 in their favor.

The kicker grows as retention improves — so OBB's revenue rises only by reducing OBB's own future top-of-funnel demand. Perfect alignment, and the reason Tim roots for us.

One thing to lock before papering the kicker: the baseline definition (6-month retention rate on the last 100 hires, fixed vs. rolling). Jill will run that math harder than anyone — pick a definition that won't be argued in month 14. Push the per-driver number toward the top of the band ($750) once the baseline's known, because the win-share to Kreilkamp is so lopsided.

4. The Tenstreet reality (what gates the build)

Doable-but-gated. Real XML/SOAP API — webhook-on-new-lead + write-back via custom questions/tags. Auth = API key + Company ID + approved Source (not OAuth). Email integrations@tenstreet.com → approval → ~$500 activation + ~$100-200/mo (third-party-reported, confirm).
3-5 week timeline to a working loop. The slip risks are Tenstreet's approval queue + the texting-seam decision — NOT the code. Budget the approval lead time into the quote.
Pre-scope ticket to Tenstreet to confirm: API pricing/whether Kreilkamp's contract includes it, new-lead event granularity, custom-question field IDs, update-by-Subject-ID, and whether the AI fit-score is API-exportable (do NOT promise the fit-score until confirmed).

5. What to put in front of Tim vs. hold

Put in front: the 3-piece scope, the cadence frame, the test fee ($18-22K, milestone-structured), the partnership-not-vendor pitch (the incentive one-pager, reframed for him), the Power BI integration.
Hold for the day-40 milestone conversation: the ongoing retention-kicker structure. Land the test win first, then the durable lands with concrete ROI instead of a hypothetical.
Don't promise: Tenstreet fit-score export; a specific go-live date until Tenstreet activation clears; anything touching financials (security-posture frame holds).
The texting-seam decision goes IN the proposal as a named week-1 discovery item — it's honest, and it inoculates against the thing most likely to break the pilot.