Fractional CTO · Fractional CFO · Technology & Finance

Senior leadership for technology and finance. From the people who do the work.

Product Advantage LLC is a small, senior practice in Orlando, Florida, co-founded by Justin and Megan VanWinkle. Fractional and interim CTO and CFO, technical and financial due diligence, builds, systems, and advisory for startups, growth-stage companies, PE portfolio companies, and established businesses. No agency layers, no junior rotation.

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How an engagement runsTechnology + finance

Weeks 1–2Assessment. A written plan, risks ranked, priced up front.

Week 3 onBoth seats covered. CTO, CFO, or both. One team, weekly cadence.

QuarterlyBoard-ready update. Roadmap and numbers that agree with each other.

CTO practice

Justin VanWinkle

Fractional and interim CTO. Builder, operator, investor.

CFO practice

Megan VanWinkle

CPA, MBA. Fractional CFO and controller, financial systems.

Also Family investment officeBetterDocketSpectatorOrlando, FL

One practice. Both seats. The people on the call do the work.

Two Practices

Technology and finance, led by the people who do the work

Most companies need senior judgment in both seats long before they can justify two full-time executives. We cover either seat, or both, on a cadence that fits the stage you're at.

CTO · Technology · Led by Justin VanWinkle

Fractional & interim CTO, builds, and advisory

Senior technical leadership without the full-time hire, and the hands to build, rescue, and ship. Fractional and interim CTO, technical due diligence, post-acquisition integration, SaaS MVP development, AI-built app rescue, forward deployed engineering, and engineering team building.

Proof: Hook Security from services company to platform, 200,000+ MAU with a five-person team. BetterDocket and Spectator, shipped and in production.

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CFO · Finance · Led by Megan VanWinkle, CPA, MBA

Fractional & interim CFO, diligence, and systems

Senior finance leadership for companies that need the judgment every week but not the full-time executive. Fractional CFO and controller, interim CFO, financial due diligence, audit readiness, post-acquisition finance integration, and financial systems selection and implementation.

Background: an accounting degree, an MBA, a CPA, and years in finance and accounting at Disney, where Megan is currently a manager in financial systems.

Explore the CFO practice →

How We Work

Four things that are true on every engagement

Whether it's a six-week build, a two-week diligence review, or a twelve-month interim seat, the shape is the same.

Always

Direct access

The person on the call is the person doing the work. No account manager, no junior rotation, no handoff to a bench.

Weeks 1–2

Scoped up front

Every engagement opens with a two-week assessment and a written plan you keep. Retainers and builds are scoped up front. Interim and fractional seats run on a monthly retainer or a day rate.

Technology + finance

One practice, both seats

A CTO and a CFO who already work together. Financial systems, billing, revenue data, and diligence are where the two meet, and they don't fall between two vendors.

First call

Honest about fit

If the right answer is a vendor, a hire, or a dropped feature, we say so on the first call. Sometimes the recommendation is not to hire us.

Who We Work With

Companies whose growth outran the people running it

The common thread is a business where technology or finance is on the critical path and the leadership seat is empty, part-time, or held by someone who would rather be doing their actual job.

Startups and growth-stage companies

Between rounds, between leaders, or ahead of a raise. Senior judgment on a cadence you can afford, and a plan investors can read.

PE portfolio companies and operating partners

Diligence before the deal, interim leadership through a transition, and integration after the close. A resource you can send in, on the technology side or the finance side.

Established businesses

Where the systems multiplied, the spreadsheets took over, and the person who "handles IT" or "does the books" is now making decisions for the whole company.

For Investors & Operating Partners

Both reviews, one team

Technical and financial due diligence from the same practice, on the same timeline, written for the same committee. Then the interim seat or the integration, if the deal needs one. We sit on the investor side too, through our family office and as technical advisor to DeepWork Capital's Fund 3 portfolio.

Before the deal

Technical Due Diligence

Architecture, security, team, delivery, cost, and AI claims. A data-room-ready report in two to three weeks.

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Before the deal

Financial Due Diligence

Quality of revenue, margins, working capital, forecast, books, and systems. Buyer-side or sell-side.

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Transition

Interim CTO

The technology seat covered for a fixed term through a transition, a raise, or a sale.

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Transition

Interim CFO

The finance seat covered for a fixed term through a transition, a raise, a sale, or an audit.

Learn more →

The Team

Two operators, not a consultancy

Both have run the function they now offer fractionally: one inside venture-backed software companies and a Fortune 500 integration, the other inside the finance organization of one of the largest companies in the world.

Co-founder · CTO practice

Justin VanWinkle

Fractional and interim CTO since 2023, CTO at Hook Security, and founder of BetterDocket. Before that: M&A integration lead and principal product manager at IBM, solutions architect for Fortune 500 clients, and a US Air Force crew chief.

Meet Justin →

Co-founder · CFO practice

Megan VanWinkle, CPA, MBA

Accounting undergraduate, MBA, and CPA. Years in finance and accounting at Disney, where she is currently a manager in financial systems. Leads the fractional CFO, controller, diligence, and systems engagements.

Meet Megan →

Investing

We also sit on the other side of the table.

Megan and Justin co-founded and run the VanWinkle Group, a family investment office that invests directly in technology startups and in venture funds such as DeepWork Capital Fund 3. The technical and financial due diligence we do for clients is the same diligence we do before writing a check.

About the Investment Office → Pitch a Company

Direct

Early-stage technology companies

Software, AI, vertical SaaS, and tools for professionals. Founder-first, technically and financially rigorous.

Funds

Limited partner in venture funds

Including DeepWork Capital Fund 3. Access to the broader early-stage ecosystem and co-investment flow.

Contact

Let's talk about what you need.

A product to build, a codebase to rescue, a finance function that needs a lead, a deal that needs diligence, or a decision you're stuck on. Tell us what's going on. You'll get a reply within one business day, honest feedback, and no follow-up sequence if we're not a fit.

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Reply within 24 hoursFrom Justin or Megan, not a sales team.
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Free first call30 minutes. You leave with a recommendation either way.
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Scoped up frontRetainers and builds are scoped up front. Interim and fractional engagements run on a monthly retainer or a day rate.