OBB
SHERI (CPA) — DISCOVERY CALL DESIGN
Pre-call email + Zoom agenda + scoped directions
For Luke
Prepared 2026-05-22 · for Zoom next week
Sheri — Discovery Call Design
Pre-call email to set expectations + scope, a 45-minute Zoom agenda built around three scoped service directions, and the diagnostic questions that route her toward the right one.
What you know about Sheri (from prior research in #sheri-cpa): 55, owner-operator CPA firm with ~500 active clients. Friend of Amy's. Not exiting; feeling AI competitive pressure. Stated pains: (1) document chase eats most of her email volume during tax season, (2) hiring qualified CPAs is hard. Stack: Drake (tax) + a Thomson Reuters product (CRM, exact product TBC). Email host: unknown (Petey flagged this — Google vs Microsoft determines integration path).
What we're trying to do with this call: learn enough to scope a 30-day pilot that fits one specific pain — not pitch a generic AI engagement. Anti-bait posture: she's a friend of Amy's, treat the call as discovery, not sales.
The pre-call email Luke sends to Sheri
To: Sheri
From: Luke Olson · OBB Holdings
Subject: Zoom next week — and three quick questions before we talk
Hi Sheri,
Amy mentioned we should connect. I'd love to do a 45-minute Zoom next week — let me know what works between [Day 1] and [Day 2]. I'll send the calendar invite once we pick a time.
Two quick questions before the call, so we don't spend our 45 minutes orienting:
- Email + stack. Drake on the tax side, a Thomson Reuters product on the CRM side — does that sound right? And on email: are you on Microsoft 365 (Outlook) or Google Workspace?
- Document chase. During the January-through-April stretch, roughly what share of your inbound email is chasing documents from clients — "still waiting on your W-2," "haven't received your prior-year return," etc.? A rough percentage is fine.
That's it. Two short answers and I'll come in with a focused proposal of what we could actually build for the firm in a 30-day pilot, not a generic AI pitch.
Talk soon,
Luke
Why two and not three:
- Q1 (stack) resolves Petey's open question (Google vs Microsoft) and confirms which Thomson Reuters product she has. Both materially change the integration playbook.
- Q2 (document-chase share) tells us whether the dominant pain is a 30-min build or a 30-day build. If >30% of inbound, the pain is acute and quantifiable.
- What we left out: a hiring question. Asking by email how many CPAs she's interviewed and hired in 18 months is a recruiter's qualifying question, and a friend-of-Amy referral has not earned the right to ask it before the call. Surface hiring conversationally during the Zoom instead.
Three scoped directions — choose one based on her answers
The call shouldn't pitch all three. Pre-route from her email answers, then walk in with the chosen direction as the working hypothesis. Other two stay in reserve as second-call material.
A
Document-chase concierge
Trigger: she says document chase is >30% of busy-season email volume, OR she names it as the #1 pain unprompted on the call.
OBB stands up a managed document-collection system — likely TaxDome (industry standard, IRS §7216-compliant), or whatever portal her Thomson Reuters product offers if it's adequate. We don't sell the tool; we operate it on her behalf. We set up the templates, configure the automated reminders + escalation cadences, write the client-facing copy in her voice, and run the daily exception queue (clients who don't respond, complicated requests, document-quality issues). She and her staff get a clean queue of "ready to work on" instead of an inbox full of chase.
What a 30-day pilot looks like: we onboard 20-30 of her active clients onto the system, run the full document-collection cycle for an upcoming filing, measure inbox volume reduction + her staff time saved. If it works, we expand to the full ~500-client book and bill monthly.
Pricing posture: floor $1,500/mo (per Relic pricing rubric); typical landing $3,500-$5,000/mo for a 500-client book with active document-collection management.
B
Hiring operations (not technical screening)
Trigger: she explicitly identifies hiring as the #1 pain AND her bottleneck is "I can't find candidates / I don't have time to run a search," not "I need help judging if someone's technically competent."
Important scoping note: OBB does not assess CPA technical competence — Sheri does that, and any pitch otherwise would be dishonest. What OBB can do is run the operational pipeline: post the role on CPA-specific boards (AICPA, Accountingfly, GoingConcern, regional CPA-society boards), respond to inbound applicants within the hour, run a short structured intake call (logistics + interest + salary expectations + start date — not technical assessment), and hand Sheri a small short-list of motivated applicants whose basics check out. The technical interview is hers.
What a 30-day pilot looks like: we run the operational layer of one full hiring cycle for one open role. Measured: number of motivated applicants surfaced, time-from-post-to-short-list, whether Sheri's technical interview pipeline runs cleaner because operational fluff has been handled.
Pricing posture: per-search operational fee $2,500-$4,000 per role. This is below traditional CPA-recruiter rates (20-25% of first-year salary, ~$15-25K) because we are not doing technical screening or guaranteeing fit — we are running the funnel ops a recruiter would, without the recruiter's network advantage.
C
Fractional-COO frame (both pains, broader scope)
Trigger: she names both pains plus a third (e.g., partner-time-on-admin, client churn, capacity planning) AND her stated frustration is "I don't have time to think strategically about the firm."
OBB takes on a broader operational role — document-chase AND hiring AND whatever else surfaces as friction-friction-friction. We essentially become a fractional ops partner for the firm: monthly cadence with her, prioritized backlog of "the next operational thing to fix," and an outside set of hands that doesn't add to her partner-meeting load. This is the highest-value engagement but also requires the most trust — only fits if Sheri is genuinely ready to delegate operationally.
What a 30-day pilot looks like: we pick one high-leverage problem (likely document chase if that's her stated pain) and run it as Direction A, with a weekly 30-min sync where we surface the next 2-3 problems we'd attack in months 2-3.
Pricing posture: $7,500-$12,000/mo retainer. Floor $5K. Luke owns the number.
The §7216 conversation — language Luke needs ready
If Direction A surfaces as the chosen path, Sheri will (correctly) ask within 5 minutes of any concrete discussion: "how does OBB legally touch my clients' tax documents?" IRC §7216 makes unauthorized disclosure of taxpayer return information a misdemeanor (and a civil §6713 penalty). The §7216 obligation runs against Sheri — she's the tax-return preparer; OBB is the downstream recipient. She's the one with criminal exposure if it's botched. OBB drafts; Sheri issues.
There are two clean structural paths under §7216, and Sheri's preference picks one:
- Auxiliary-services arrangement (Treasury Reg §301.7216-2(d)). OBB is engaged as a contractor performing services in connection with return preparation, governed by a confidentiality agreement between Sheri's firm and OBB. No per-client consent required. This is how most outsourced bookkeeping + document-prep vendors operate. Cleanest path for most firms.
- Per-client written consent (Treasury Reg §301.7216-3). If Sheri's clients are sensitive to having a named third party touch their documents, each client signs a consent in the specific format the regulation requires. More friction operationally, more transparency to clients.
Three sentences Luke needs ready when this comes up:
- "§7216 is your obligation as the preparer, not ours — we'd never put your name on a form we drafted without your review. The two ways to structure it are an auxiliary-services arrangement under §301.7216-2(d), or per-client consents under -3 if your clients are sensitive to having OBB named. Most firms our size go with -2(d). Your call."
- "During the 30-day pilot, we test the workflow on a small cohort — 20-30 clients you pick — and whichever consent structure you choose is the first thing we operationalize. No document moves to the OBB side until that's signed off."
- "On the insurance side — what does your firm normally require of a contractor at this scope? We'd rather match your existing spec than guess. If you need a specific endorsement on our coverage, we'll either get it bound before contract or refer you to someone better-built for that level of controls."
What Luke does NOT say: "TaxDome is §7216-compliant." True of the tool, not of any workflow on top of it — the compliance is in the consent process and OBB's data-handling posture, not the software. Also do NOT say "we carry E&O coverage" without checking with Kevin whether OBB has the right policy bound — promising verifiable coverage we don't have is the deal-killer that ends the Amy relationship along with the deal.
Data-handling posture — the 90-second pitch
Adjacent to §7216 — Sheri will ask "where do these documents live? Who at OBB sees them?" Luke's answer:
- Where the documents live: in the client portal (TaxDome or whatever portal her Thomson Reuters product offers) — Sheri's tenant, not OBB's. OBB has scoped access for operational purposes only; primary copies never leave her tenant.
- Who at OBB sees them: a named human operator (Luke can name the person on the call), identified to Sheri up front. Not a rotating team. Logged access.
- Retention + offboarding: if the pilot doesn't continue, OBB's access is revoked within 48 hours of termination and we provide a written attestation of access revocation. Documents stay in Sheri's tenant; OBB does not retain copies.
- What we don't have yet (honest): SOC 2 audit. We're a small operator. If Sheri's firm requires audited controls (some states + larger client contracts do), we tell her up front and refer her to a vendor built for that level. We don't bluff our way past it.
Compliance layers adjacent to §7216 that may apply:
- GLBA Safeguards Rule. Since the 2023 amendments, CPA firms are treated as "financial institutions" under GLBA. The Safeguards Rule requires Sheri's firm to have a written information-security program covering its service providers (OBB). Worth one sentence: "your written ISP will need to cover us — we'll help you scope what that looks like for the OBB engagement."
- State CPA-board rules. Some state boards (TX, CA, NY are stricter) have specific rules on outsourcing client work. One line: "state board rules on outsourcing vary — we'll confirm yours before contract."
The 45-minute Zoom agenda
0:00-0:05
Warm-up + framing
Catch up on the Amy connection (where she and Sheri's friendship is at), then frame: "Amy mentioned the firm is doing well but you're feeling AI pressure. I sent the three questions ahead of time so we can use this call to dig in on what would actually help — not pitch anything generic."
0:05-0:20
Sheri tells her story
Open-ended. "Walk me through what's working at the firm right now, and what's frustrating you." Let her run. Take notes. Listen for what's NOT in her email answers — surprise pains, surprise strengths, who else in the firm matters, what she's already tried.
0:20-0:40
Pressure-test the chosen direction + handle §7216
Walk through the direction you pre-selected based on her email answers. Frame it as "based on what you said, here's the shape of what we could do — does this look right, or am I solving the wrong problem?" If she pushes back, drop the direction and pivot to the alternate. The §7216 conversation typically surfaces here unprompted — have the three sentences ready. The goal is calibration, not closing.
0:40-0:45
Wrap + next step
"If you want to think about it, I'll send a one-page summary of what we discussed by end of week, including the pilot scope and pricing." Don't push the close. Don't quote pricing live. The pilot scope conversation happens on a second 30-min follow-up call once she's had time to react to the written summary. The friend-of-Amy dynamic means relationship trumps the deal if there's a conflict.
Listen-fors during the call
- "I tried TaxDome / Karbon / another platform." → most useful diagnostic in the call. Either she found it didn't fit (we're not selling the tool; we're operating one — different value-prop) OR her firm rejected it for a reason (workflow, client-facing UX, integration with Drake or her Thomson Reuters CRM). Get the specific reason — it's the difference between a sale and a no-sale.
- "I'm not sure about AI in client work." → she's hearing AI = mistakes / hallucinations / compliance risk. Reassure: OBB's posture is human-operated automation, not AI-replaces-staff. Surface §7216 + data-handling posture here — see sections above.
- "My partner / staff would never use that." → adoption-side concern. The 30-day pilot needs an internal champion who is not Sheri. Probe: who in the firm would be the day-to-day touchpoint? If she can't name one, that's the obstacle.
- "How do you bill for this?" → don't quote pricing live (see Wrap). Say: "Pricing depends on which direction we pick and the scope — I'll send the proposal with numbers in the written summary after this call." Don't anchor on a number she can react to in the moment.
- She mentions a specific client by name with affection → she's emotionally invested in client relationships. Position OBB as her staff, not as a layer between her and her clients. She'll reject anything that feels like we're inserting ourselves into her client relationships.
- Exit / retirement / sale. If she mentions it offhand, acknowledge it ("makes sense at this stage") and move on. Do NOT pivot the conversation to "let's make the firm sellable in 3-5 years." That's the predatory-roll-up move, and Sheri will have heard it before from someone less trustworthy. Stay on the operational pain she came to talk about.
Graceful no-sale exit — preserve the Amy relationship
If Sheri is polite but uninterested — or if the diagnostic surfaces that her pains aren't actually OBB-shaped — the call has to end cleanly, with Amy's relationship intact.
Recommended close: "Sheri, this was useful for me even if it doesn't turn into work — I have a better feel for what CPAs your size are actually wrestling with right now. If something changes or you want a second opinion on anything, I'm a Zoom away. And let Amy know I appreciated the connect."
Do not: send a follow-up "just checking in" email a week later if she didn't bite. Trust her to come back if it surfaces. Amy stays comfortable.
What to leave OFF the discovery call
- Pricing. Don't quote numbers. The pricing in the direction cards above is for your reference — quote in writing afterward.
- OBB's own track record. If she asks, be honest: "We're newer than the bigger firms in this space. Our differentiator is that we run the tools, we don't sell them — and Amy can vouch for the work we've done for her." Don't oversell adjacent clients we haven't asked permission to name.
- Technical specifics. If she asks "how does the AI work?" — redirect to "what it does for you," not "what's under the hood." Tax-firm partners don't buy on tech stack; they buy on outcomes.
- Multiple directions. Don't show her all three direction cards above. Pick one, pitch it, hold the other two in reserve. The packet looks chaotic if you walk in with three things you could do.
What we need from Sheri to confirm before the second call
Assuming the discovery call surfaces interest, post-call:
- Sample of her client-facing email voice (forward us a real document-chase email she sent last year, redacted as needed).
- Confirmation of the Thomson Reuters CRM product name (so we can scope the integration option).
- Email-system confirmation (Google Workspace vs Microsoft 365).
- Her availability for a 30-min second call to walk through the formal 30-day pilot scope.
- If Direction B (hiring): the role description she's been trying to fill, and what salary band she's in.
Pricing ownership + decision rights
Per the standard rubric: floor $1,500/mo, typical landing $3,500-$8,500/mo, Luke-review on anything >$10K/mo. Sheri is Amy-introduced (not Ryan-introduced), so this rubric applies cleanly. Luke owns the final number. Kevin and Petey both wanted eyes on this thread (per Petey's 5/20 channel note); loop them in before quoting if there's any ambiguity.
Open before the call: Sheri's answers to the two pre-call questions. If she replies fast, we re-pick the direction to pitch and send Luke a one-line "go with Direction X" message. If she doesn't reply before the Zoom, Luke opens the call with the two questions verbally and routes from there.