Jon
Eberly

That quote comes from the fund's lead investment in Trellis Corporation, a cross-channel ecommerce advertising platform. It is the kind of statement that sounds obvious until you realize most VCs can't say it with personal conviction — they've never had to run a digital campaign for a financial services client at U.S. Bank's scale. Eberly has.

Before Clock Four, Eberly worked at Agency.com in roles spanning VP, Client Partner, and Technology Director — a range that suggests someone who refused to specialize too early. He was also Partner and Director of Sandbox Interactive at Sandbox Studio. These aren't filler lines on a resume; they're the period when he was learning what clients actually need from a digital partner, before he went and built one.

Sentiero's filter is blunt: if the AI is removable, the company doesn't qualify. The fund targets seed-stage software companies where machine intelligence is a structural component of the product — not a feature layer, not a marketing claim, not a chatbot bolted to a legacy workflow. The managing partner, David Evans, articulates the screen this way: "We want artificial intelligence to be a core pillar of the product — a pillar that really generates value."

This matters in 2024 and beyond because the market is flooded with companies that added "AI-powered" to their homepage after ChatGPT launched. Sentiero has been making this distinction since 2021 — before the hype made it necessary to explain. The fund's inaugural investment, Data Sentinel, was a $250,000 check into a $2.9 million round led by Brightspark Ventures. That kind of capital discipline — writing small, early, deliberate checks — reflects an investor who knows how far the first dollar has to stretch.

The portfolio now spans 18 active companies across sectors including security, ecommerce, legal tech, HR, and aerospace. Two have already exited (Sumatra, Skintelligent). The target range is up to $500,000 per company, with a planned initial portfolio of 10 investments — already exceeded.

Behind the fund is an advisory board of 20+ investor-entrepreneurs covering 30+ industries, roughly 75% based in the Dallas-Fort Worth corridor. They review potential investments before final due diligence and provide the portfolio companies with operating expertise and client connections. It is a model that treats the fund's network as a product.

The agency story is the part that matters most for understanding what Jon Eberly actually brings to a founder's cap table. Clock Four launched in San Francisco in 2006 — the year Twitter launched and the iPhone didn't yet exist — into a market where "digital agency" still required explanation.

Over 12 years, Eberly built it into a firm known for customer experience strategy, brand activation, lifecycle marketing, and digital ecosystem development. The client list — U.S. Bank, Juniper Networks, Veritas Technologies — reflects the firm's gravitational pull toward financial services and enterprise technology, sectors that reward rigor over cleverness.

It had offices in both San Francisco and New Jersey. It employed 50 people. It was never venture-backed. That last fact deserves a pause. Growing a professional services business to that scale on its own revenue is not a rounding error — it requires sustained sales discipline, margin management, and client retention over years. The skills are different from building a software product, but the underlying mindset — find real problems, solve them better than the alternative, keep clients long enough to compound — transfers directly.

When Hero Digital acquired the company in late 2018, it was the firm's fourth add-on acquisition. Clock Four was positioned as a strategic expansion of Hero's capabilities in consumer financial services and B2B technology. Eberly stayed on as Executive Vice President — a signal that the acquisition was about talent and relationships, not just revenue.

He is also reported to have had multiple self-funded exits before Clock Four, including work in digital imaging. The details are sparse — Eberly doesn't broadcast his earlier wins — but the pattern suggests someone who has been building and selling technology-adjacent businesses since before digital agencies were a category.

The Sentiero portfolio reads like a tour of the places where AI is doing unglamorous, high-value work — not generating images or writing copy, but automating compliance, testing software, managing ecommerce, and making aerospace systems smarter.

Eberly serves on the boards of the SF YMCA and EF Fund, a thread of civic engagement that runs parallel to his professional life. He is also a Board Advisor at Metrical, Inc., an ecommerce intelligence company, and Principal at Adportas, Inc., his boutique executive consulting practice that operates alongside his Sentiero work.

He sails. It's the kind of hobby that tells you something about a person's relationship with uncertainty — you can't negotiate with wind and current, only read them and commit to a line. The same disposition shows up in how he describes investment decisions: not about finding certainty, but about finding the right conditions to move.

His Twitter handle remains @clockfourjon, years after selling the company. It's a small thing, but it's specific: a man who made his name in one chapter doesn't try to erase it when the next one starts. That kind of consistency tends to compound.

His education at the University of Virginia was in the mold of a liberal arts foundation — no specific degree detail is documented publicly — before he entered the early years of the digital economy through agency.com, one of the pioneering digital consultancies of the late 1990s and early 2000s. That cohort of digital natives, forged in the first dot-com cycle, developed a particular kind of toughness. They built through a crash, then built again.