APPLETON ADVISORSFRACTIONAL CFO · FINANCIAL OPERATIONS · EXIT READINESS
REF AA-2026-BC-01 · PRIVATE BRIEFING

The finance function Benefit Cloud's growth deserves.

A working brief prepared for your team: what we heard, the 90-day build we'd run, and how the engagement works. Companion to the document and deck already in your inbox.

PREPARED FORBenefit Cloud
PREPARED BYAppleton Advisors
DATEJune 2026
STATUSFor discussion · June 18
§ 01What we heard

Five symptoms, one root cause: nobody owns the finance function.

BOOKS

Bookkeeping without visibility

An outsourced QBO firm categorizes transactions and produces a monthly P&L. No balance sheet, no cash flow cadence, no relationship.

CASH

No line of sight on cash

MRR is known precisely, but cash flow forecasting is guesswork, forcing conservative, ad hoc calls on pay, hiring, and spend.

SPEND

An expense black hole

A single corporate card carries most company spend with limited receipt capture and no budget controls.

TIME

Founder as bottleneck

Billing runs, collections review, and financial oversight all route through the CEO, on top of everything else.

EXIT

An eventual exit in mind

The likely path is acquisition by a strategic. Clean, diligence-ready financials are a strategic asset, not hygiene.

WORKING WELL

The billing engine is an asset

Automated PEPM billing into Stripe with sticky, compounding revenue. The foundation is strong; the visibility layer is what's missing.

§ 02Target state

One toggle is the whole pitch.

Flip the switch to see the same six dimensions before and after the build.

TODAY WITH APPLETON
Six dimensions · current state
Corporate spend
Vendor payments
Books & close
Cash visibility
Owner compensation
Exit readiness
§ 03The plan

A phased 90-day build, then an ongoing strategic cadence.

PHASE 1 · DAYS 1–45

Consolidate the stack

  • Implement Ramp: cards, bill pay, treasury
  • QBO cleanup: a SaaS chart of accounts
  • Expense policy and budget controls
  • Coordinated handoff with your tax firm
PHASE 2 · DAYS 45–90

Build visibility

  • Owned monthly close calendar
  • Three-statement reporting + SaaS metrics
  • Rolling 13-week cash flow forecast
  • Owner compensation framework
PHASE 3 · ONGOING

Strategic finance & exit readiness

  • Budget vs. actual; hiring trigger models
  • Quarterly advisor-grade reporting
  • Diligence-ready data room
  • AR and billing process refinement
§ 04Engagement model

Partner-led, built around what already works, designed to hand off.

Fractional model

A monthly retainer scoped to what the business actually needs. Typically heavier in the first 90 days, then a steady operating cadence. No full-time overhead.

Works with existing pieces

QBO stays as the system of record. Your tax firm stays. Your billing engine stays. We connect them, own the process, and fill the gap between bookkeeping and decisions.

Built to hand off

Everything documented and structured so that when Benefit Cloud is ready for a full-time CFO or controller, the keys hand over cleanly.

§ 05Who you'd work with

Operator experience at both ends of the scale you're traveling.

Roman Hawkins

FOUNDER & MANAGING PARTNER

Business Unit CFO for a privately held fintech with ~$750M in revenue, and fractional CFO for early-stage startups. Hands-on across M&A, ASC 606 revenue recognition, and board-level reporting.

Appleton is built for companies like Benefit Cloud: technical founders with real revenue who need finance infrastructure that matches the quality of their engineering, without the cost of a full-time hire.

$80M+
Capital raised for clients
$5M+
In client savings
10 yr
Avg. partner industry experience
1 day
Response SLA, partner-signed
§ 06Beyond this scope

Six practices, one desk. The engagement expands as you mature.

THIS ENGAGEMENT

Fractional CFO

Forecast and budget ownership, board cadence, capital structure, team coaching.

Capital Formation

Investor model and deck, data room architecture, Q&A war room, term-sheet negotiation.

M&A & Diligence

Sell-side preparation, quality of earnings, target screening, 100-day plans.

Finance & Accounting

Monthly close and controls, audit and 409A prep, payroll, global entities.

Operations Strategy

Unit economics rebuild, pricing and packaging, GTM finance, KPI frameworks.

Board & Investor Relations

Board package design, investor letters, KPI dashboards, IR readiness.

§ 07Next steps

Three steps between today and a scoped proposal.

1

Reconnect

Walk through this brief and answer questions. Tyler welcome.

THU · JUNE 18
2

Short diagnostic

Read-only access to QBO plus a look at current card and bank activity to scope the cleanup precisely.

WEEK OF JUNE 22
3

Scoped proposal

Fixed scope and retainer pricing within a week of the diagnostic.

+1 WEEK
Book the June 18 slot →

Or reply to the email thread · partners@appletonadvisors.ai