Sherman CFO Advisory

Board-ready financials, before a sponsor, lender or buyer asks.

I'm a fractional CFO for PE-backed and founder-owned insurance services, insurtech and fintech companies. I install institutional-grade reporting, forecasting and margin visibility in weeks, not quarters, so leadership, the board and outside capital see the same numbers.

Set up 15 minutes See the diagnostic

Or write to ted@shermancfoadvisory.com

Ted Sherman
Ted Sherman, ChFC, CLUFounder, Sherman CFO Advisory

Who I work with

PE-backed and founder-owned companies with approximately $10M to $75M in revenue: insurance services (TPAs, MGAs/MGUs, benefits administration), plus insurtech and fintech businesses that run on recurring or contract-based revenue. U.S.-based operations.

Signs it's time

This tends to fit when one of these is already true:

  • A recent close that's still missing board-ready financials months after the deal
  • A sale, raise or lender review ahead, and a data room that isn't ready for diligence
  • A finance seat that's empty, overwhelmed, or still run by the founder or a bookkeeper
  • Reporting assembled by hand every month instead of on a fixed cadence

Start here

CFO Readiness / Risk Diagnostic

Fixed scope, defined deliverables, fixed fee.

The entry point for every new engagement, whether insurance services, insurtech or fintech. A fixed-scope review that shows you exactly where your finance function is exposed, before a sponsor, lender or acquirer finds it first.

What it reviews

  • Close and reporting: calendar, controls, board packages
  • KPIs and retention: ARR, NRR, churn, CAC, margin by client
  • Cash and forecast: 13-week visibility, budget integrity
  • Diligence readiness: data room, QoE, working capital
  • Finance team and systems: capacity, gaps, key-person risk

What you get

  • A ranked scorecard of where reporting is exposed
  • A prioritized 90-day action plan
  • A straight recommendation on what to fix first, whether you need me, and at which tier. Or that you don't.

What I typically find

Patterns that show up when a finance function has outgrown its setup. This describes common situations, not any one company.

  • A monthly close that depends on one person's spreadsheets and slips when they are out
  • KPI definitions (churn, NRR, margin by client) that differ between finance, operations and the board deck
  • Margin by client or product that is assumed, not measured, so pricing and renewals are set without it
  • No rolling 13-week cash view, or one that lives only in the founder's head
  • A data room and QoE support that get assembled only after a buyer or lender asks
  • A finance team doing controller work, with no one owning forward-looking analysis

Engagements after the diagnostic

Ongoing work is scoped to what the diagnostic finds. Each tier builds on the one before it.

Financial Operating Foundation

  • Monthly close on a fixed calendar, without adding headcount
  • KPI dashboard your board or sponsor can read in 90 seconds (ARR, NRR, churn, CAC, gross margin)
  • Board packages that answer questions before they're asked
  • Variances caught before they're surprises

Strategic Finance Partner

  • Everything in Foundation
  • 13-week cash forecast that removes guesswork
  • Annual budget built once, defended without rework
  • True margin by client and service line

Transaction Readiness & Integration

  • Everything in Strategic Partner
  • Data room organized well before diligence
  • QoE and working capital prep that surfaces issues early
  • Add-on integration with clean consolidated reporting

How engagements work

  1. Assess

    CFO Readiness / Risk Diagnostic. Pinpoint exactly where your reporting is exposed, before a board, sponsor or acquirer finds it first.

  2. Build

    Stand up dashboards and forecasts so leadership sees clean numbers on a fixed cadence, not in a fire drill.

  3. Run

    I own the monthly cycle: close oversight, board packages and forward-looking guidance, so your finance function runs on schedule every month.

Experience

15+ years as CFO and senior financial executive in PE-backed, recurring-revenue and insurance services businesses, from $12M to $175M in revenue.

  1. Chief Financial Officer

    Nonstop Health, medical benefits administration

    • Recruited by private equity ownership after the sale to build financial leadership and infrastructure for the next phase of growth.
    • Built board-level KPI and retention reporting directly from raw operational data, with ground-up three-statement budgets and forecasts that included sensitivity scenarios.
    • Built client, enrollment and revenue retention models for a recurring, subscription-based revenue base, giving ownership visibility into renewal risk and portfolio health.

  2. TriPlus Services to Davies Insurance & Risk Management

    Nine years, four promotions, one business through its full PE lifecycle

    1. VP of FinanceTriPlus Services, PE-backed insurance TPA
    2. CFOTriPlus Services
    3. CFOTriPlus Services and Disability Management Services, after the Davies acquisitions
    4. CFODavies Life & Health, the combined company
    5. CFO & Head of Strategic InitiativesDavies Insurance & Risk Management, a $175M-revenue, 900-employee division

    Under PE ownership

    • Scaled TriPlus to $25M+ in revenue and about 200 employees, doubling the business.
    • Reduced annual office footprint costs by about $200K through a renegotiated real estate strategy and an updated staffing model.

    Sale and integration

    • Partnered with the CEO, the PE sponsor and an investment banker on the 2020 sale to Davies: contributed to the CIM, participated in management presentations, and helped evaluate offers and negotiate final terms.
    • Supported Davies' M&A team on valuation modeling and diligence for the Disability Management Services acquisition, then led the finance integration that combined it with TriPlus into Davies Life & Health.

    Division level

    • Held business-unit leaders across nine companies accountable to a $7M+ annualized savings target for enterprise margin initiatives.
    • Scaled finance and accounting to 20+ people across multiple locations. Established SOC 1 Type 2 and SOC 2 Type 2 certifications and an ERM (enterprise risk management) framework.

  3. Vice President, Risk & Capital Management Solutions

    Conning, insurance industry consulting

    • Advised C-suites and boards at insurance companies across North America on risk's impact on financial performance and capital position, using proprietary financial and actuarial modeling tools.
    • Responsible for a group of clients that purchased Conning's software for their own internal use, supporting their implementation and calibration, training and ongoing support.

  4. Financial reporting and analysis

    The Hanover Insurance Group, P&C insurance

About Ted Sherman

I've spent 15+ years running finance for PE-backed and founder-owned companies. I started Sherman CFO Advisory for companies that need CFO-level financial leadership and aren't able or ready to commit to a full-time seat.

At Conning, the job was never only building the model. It was making sure the people deciding from it understood what it was telling them. I still work that way.

The thread through every role is the set of metrics recurring-revenue businesses live and die by: retention, renewal risk and cohort economics. It's the discipline PE investors lean on most when underwriting recurring cash flow.

Credentials
Chartered Financial Consultant (ChFC) and Chartered Life Underwriter (CLU), The American College
Education
BBA, Finance, University of Massachusetts Amherst, Isenberg School of Management
Systems
NetSuite, Sage Intacct, Planful, Excel and Google Sheets
Based
Massachusetts, working remotely with U.S. companies

Common questions

Who do you work with?

PE-backed and founder-owned companies with approximately $10M to $75M in revenue and U.S.-based operations: insurance services (TPAs, MGAs/MGUs, benefits administration), plus insurtech and fintech companies with recurring or contract-based revenue.

What does the diagnostic produce?

A ranked scorecard of where your reporting is exposed, a prioritized 90-day action plan, and a straight recommendation on what to fix first, whether you need me, and at which tier. Sometimes the answer is that you don't.

Do I have to keep working with you after the diagnostic?

No. The diagnostic is a fixed-scope engagement with its own deliverables. If the findings point to ongoing work, I'll recommend a tier. If they don't, you still have the plan.

How is this different from hiring a full-time CFO?

Some companies need CFO-level financial leadership but aren't able or ready to commit to a full-time seat. Fractional work covers that gap: the monthly close, board reporting, forecasting and diligence readiness, scoped to what the company needs.

How do you handle confidential information?

I'm glad to sign a mutual NDA before you share anything sensitive. Company financials, sponsor materials and diligence documents are used only for your engagement and are never shared with other clients or used in my marketing. Examples on this site are anonymized.

Let's set up 15 minutes.

Tell me what you can't see in your business today, and I'll tell you where I'd start.

Prefer email? Write to me directly.

Email Ted

ted@shermancfoadvisory.comlinkedin.com/in/tedshermanfinance

Not sure where to start? Tell me what you're seeing.

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What's prompting this? Check all that apply.

Please don't include financial statements or other sensitive documents here. We can set up a secure way to share those after we talk.

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