DMS Strategic Financial Advisory Reclaims More Than 800 Hours a Year with Claude

How a fractional CFO practice turned months-long planning, forecasting, and reconciliation work into hours, with Endsight’s guidance on making Claude a repeatable part of the finance function.

Key Takeaways at a Glance

• Client: DMS Strategic Financial Advisory, a fractional CFO practice serving wine, golf, defense, and technology services companies.

• Problem: Annual planning, supply and demand run-out modeling, and daily reconciliation were rebuilt by hand from exports out of several systems, consuming months and hundreds of hours a year.

• Solution: Claude, working natively in Excel, with recurring analyses saved as reusable skills. Endsight introduced the approach, ran the working sessions on the run-out model, and taught the skills workflow.

• Results: Annual operating plan from three months to about 16 hours; 400+ hours a year removed from run-out modeling; daily cash reconciliation from 75 minutes to 3; executive what-if scenarios answered in the meeting.

• Why it worked: The method captures an expert’s judgment as a repeatable procedure, so every subsequent run takes minutes and the same framework carries to the next company.

Overview

DMS Strategic Financial Advisory provides fractional CFO and project finance services to a portfolio of companies: a multi-unit consumer packaged goods business in the wine industry, an operator of community golf courses, a defense firm, and a managed technology services provider. Founder David Smith does the strategic work a full-time CFO would do, plus the operational projects other CFOs do not have time for.

Challenges

The heaviest of that work was periodic and manual. An annual operating plan for the CPG business, which sells through several distinct channels, took one to three months of gathering departmental inputs, loading them into a planning system, and reconciling twenty spreadsheets whenever an assumption changed. Supply and demand run-out modeling across thousands of SKUs consumed 400 to 500 hours a year of his own time, and more of an assistant’s, with every new sales scenario forcing a rebuild. A daily cash reconciliation for the golf business took an hour and fifteen minutes every morning. And a multi-year cleanup of that company’s books, after several accountants had passed through them, looked like a job only an outside accounting firm could take on.

“This is what every winery struggles with. Their supply and demand.”

David Smith, Founder and Fractional CFO, DMS Strategic Financial Advisory

Solution and Implementation

David’s use of Claude began with Endsight. After watching Endsight’s leadership work through their own executive workflow in Claude, and seeing Endsight automate a payroll accrual reconciliation with it, he decided to try the same approach on his own finance work. Endsight’s AI & Automation team then worked with him in a series of sessions on his supply and demand run-out model: watching the process end to end, having Claude turn weeks of chat iteration into a saved skill with deterministic spreadsheet logic, and teaching him how to save, update, and reuse skills so the work becomes repeatable.

From there the method was his own. Pull the source data out of the systems where it lives, whether a general ledger, a planning tool, an inventory report, or a bank export. Give it to Claude with a plain-English description of the analysis. Iterate until the output ties out. Save the procedure as a skill so the next run takes minutes instead of days. Because Claude works natively in Excel, the deliverables are the same workbooks the executives already use, now with features David could describe but had never known how to build, such as a toggle between best-case, worst-case, and most-likely demand plans.

Results

The 2027 annual operating plan for the CPG business, normally a three-month effort, was built bottom-up from general ledger data in about 16 hours. More important is what happens after the first draft. When an executive asks what closing a facility or removing a business unit would do to the numbers, David now models the scenario during the meeting rather than a week later. In one thirty-minute budget review, three such scenarios were run and resolved on the spot. A five-year financial model built from ten years of history, the kind of work behind a valuation, is now a one-day project instead of four weeks.

The supply and demand run-out model, once a 400-to-500-hour annual burden, now runs a single product in minutes and the whole portfolio on demand, with a saved skill that updates the full model whenever new inventory or demand numbers arrive. David estimates the change is worth about half a headcount across himself and his assistant.

The daily cash reconciliation dropped from 75 minutes to 3 minutes. Run every morning as a skill, that is roughly 438 hours a year returned on one routine task. The bank-to-ledger cleanup that would have gone to an outside firm is now an iterative project he works month by month.

It has also already surfaced process problems in other places the business did not know it had including an unintended discount created by a price ceiling on a subscription club.

“I’m not a computer programmer. But I now am an Excel computer programmer, because I ask it in English to do something I know can be done in Excel, and it does it in a minute.”

David Smith, Founder and Fractional CFO, DMS Strategic Financial Advisory

The same frameworks are being carried to other companies in the portfolio, and the operating plan model will be re-run monthly as actuals post, so the time savings compound rather than repeat once.

Conclusion

None of this required custom software or a data platform project. It required a finance leader willing to describe his work in plain English, a partner to show him how to make the result repeatable, and a model capable of handling the volume of data a real business produces. The frameworks DMS built are now standing assets, re-run monthly and carried from one company to the next, and the time they return goes back into the strategic work a CFO is actually hired for.

About DMS Strategic Financial Advisory

DMS Strategic Financial Advisory provides fractional CFO services and project-based finance work to companies that need executive-level financial leadership without a full-time hire. Founded four years ago by David Smith, the practice serves clients in consumer packaged goods, hospitality, defense, and technology services, covering planning, forecasting, valuation, reconciliation, and the operational finance projects in-house teams do not have time to take on.

About Endsight

Endsight is a Napa-based managed service provider and Claude Partner Network member serving small and mid-sized businesses in Northern California and beyond. Our AI & Automation practice helps clients choose a platform, deploy it as a governed business system, train their teams, and then build the skills, connectors, and automations that turn general-purpose AI into leverage on the work that matters most.