I Don't Report on the Business. I Run Inside It.

Scott Hess is a CFO with 20+ years of experience building finance functions that actually run the business — not just scorecard it. He's worked across DTC, ecommerce, SaaS, and PE-backed brands from $10M to $300M, and his operating scope has almost always extended well beyond finance. Marketing analytics, supply chain strategy, organizational design, technology implementation — if it moves the business, it's in scope.

Before founding Main Street IQ, Scott served as CFO at Watch Gang, a $40M subscription ecommerce brand where he held full operating responsibility across finance, HR, legal, and logistics. He embedded directly in the marketing team to connect spend decisions to CAC and LTV — and when the team understood what their discounting strategy was actually doing to customer profitability, they changed their behavior. CAC dropped 5%, retention climbed 7%, and the company posted its first two profitable years. He also cut the month-end close cycle by 40% and grew ARR 22% while reducing OPEX 12%.

Before that, he was CFO and VP of Operations at Haberdash, a luxury omnichannel menswear retailer, where he redesigned the sales compensation structure around gross profit instead of top-line revenue — a quiet fix that drove sales up 23% while cutting comp expense 9%. He also pushed the CEO to migrate to Shopify, made the business case, led the build, and watched ecommerce revenue grow 30%.

He spent 12 years at Northern Trust building the institutional finance foundation — large-scale modeling, M&A due diligence, ERP implementation — that underpins every client engagement today. He's also a Navy veteran and holds an MBA from Pepperdine's Graziadio School of Business.

Main Street IQ was built on one core belief: finance teams at growing companies are almost always a version or two behind the business they're supposed to support. The RAID Framework is how Scott fixes that — without adding headcount, without slowing things down, and without handing you a deck full of recommendations you have to figure out yourself.

He works with a small number of clients at a time. That's intentional.