AI Office Hours Recording - Q4 2026 with David Smith

Skip to content

Overview

November 3rd, 2026

David Smith of DMS Strategic Financial Advisory serves as fractional CFO for a portfolio of companies. In one case, he put off a board presentation until the weekend before it was due. He sat down with Claude on Saturday and had it done that day.

That’s just one example. Working with Endsight’s AI & Automation team, David reclaimed more than 800 hours a year across two workflows. His daily cash reconciliation went from 75 minutes to 3. He got there without custom software, using plain English and saved Claude skills.

If you spend more of your week gathering numbers than thinking about them, you’re not alone. Many teams pull reports by hand from one system after another. In this session, David sat down with Brian Tirado, Jason Clause, and Michelle Brezenski for an open conversation, not a demo. Then we opened the floor to questions from attendees.

What we covered:

Introduction
AI update with Brian Tirado: What had changed in AI over the previous quarter, and what went into Endsight’s Claude certification.
A conversation with David Smith, CFO:
- How he put together a full board presentation in one day
- How saved skills turn a one-time analysis into a repeatable process
- Running what-if scenarios live, in the meeting
- Where his finance experience still makes the call
- Why clean, repeatable data is what makes AI answers trustworthy
Resources: Endsight’s AI Office Hours and Cybersecurity Office Hours series, plus a podcast from Endsight’s founder.
Audience Q&A: About 20 minutes of questions from attendees.

Michelle Brezenski

Manager, Development @ Endsight

With over 20 years of IT experience and 17 years at Endsight, Michelle is a seasoned professional who has worked in different capacities within the company. Since 2014, she has led Endsight's development department's efforts and is passionate about data-driven decision making and leveraging technology to solve business problems. Michelle holds multiple certificates from Microsoft, most of which focus on database management.

zoom-jclause

Jason Clause

Director of Marketing @ Endsight

Jason has spent more than 20 years helping businesses apply technology to transform how they work, and the past several years presenting on what that looks like in practice. He's a hands-on operator familiar with Copilot, ChatGPT, Claude, and Google Gemini, with working experience in advanced prompting, skill development, and MCP development. He builds daily in each of Claude's core products: Chat, Cowork, Claude Code, and Claude Design. Jason has a bachelor's degree in Public Relations from Kent State University and is a Microsoft Certified Professional.

Brian Tirado

Brian Tirado

Director of AI & Automation @ Endsight

Brian leads Endsight's AI and Automation practice, where he helps small and mid-sized organizations move from experimenting with AI to using it in daily work. He guides clients through platform selection, rollout, security and governance, user adoption, and the practical question of which workflows are worth automating first. He stays hands-on on both sides of the work, building alongside Endsight's internal AI team and delivering integrations, custom skills, and automations inside client environments.

Endsight-bug-inverse-transparent-blue-circle-600

David Smith

CFO @ Endsight

David entered the wine industry in the early 2000s, where he has held key financial and IT leadership roles. He began at Trinchero Family Estates, overseeing finance, accounting, and IT for vineyard and wine operations. He later served as CFO at Starmont/Merryvale, Far Niente/Nickel & Nickel, and Foley Family Wines, managing IT systems alongside his financial responsibilities. In recent years, David has worked as a fractional CFO and consultant, helping businesses across various industries with system upgrades, transformations, and process reengineering.