An internal promotion during a leadership handoff
Crumbl, the dessert franchise known for its weekly rotating cookie menu, promoted Jacob Moncur to Chief Technology Officer on July 8, 2026. Moncur has run engineering as Vice President since 2020, through the years when Crumbl grew to nearly 1,200 locations across all 50 states, Canada, and Puerto Rico. He replaces Bryce Redd, who moves to a Senior Advisor and Board seat during the transition. The move lands inside a larger shakeup: on May 11 co-founders Jason McGowan and Sawyer Hemsley announced they would step back from day-to-day leadership while the company searches for successors, with all three founders staying on the board.
The founders left little doubt about the choice. McGowan and Hemsley said 'Jake has been a cornerstone of how we have built and scaled this company, and there is no one better positioned to lead our technology forward.' Redd, the outgoing CTO, added that he had 'full confidence in his vision and leadership.' Moncur, for his part, said he was 'proud of the foundation this team has built and energized by what we get to build next.' The language is deliberate. A company midway through a founder handoff wants to signal that the technology roadmap is not up for renegotiation.
The digital stack is the growth engine at 1,200 stores
Crumbl is a technology operation wearing a bakery's branding. Moncur built the company's earliest mobile ordering apps and led its launch on Apple Vision Pro, where Crumbl was among the first food and beverage brands live on day one. For a franchise that markets a new cookie lineup every week, the app is the storefront, the loyalty engine, and the demand-forecasting input all at once. The weekly menu drop is a coordinated digital event across roughly 1,200 locations, and the systems that handle ordering, inventory, and franchisee operations are what make that cadence possible at national scale.
That is why the CTO seat is load-bearing here. A dessert chain expanding this fast lives or dies on the reliability of its ordering and point-of-sale infrastructure during peak demand, and on the data it collects to plan production and reduce waste. Promoting the person who built that stack keeps institutional knowledge in the building at exactly the moment when a botched platform migration or an outage during a launch would be most damaging. For franchise operators, the technology group is the connective tissue between corporate and hundreds of independent owners, and continuity there protects the whole system.
Continuity over an outside search
The decision to promote from within, rather than run an outside search, is the part worth studying. Crumbl had reason to look externally: a founder transition often comes with pressure to bring in seasoned public-company operators, and a new CEO frequently wants their own lieutenants. Crumbl instead chose the person who already understood the codebase, the franchisee relationships, and the operational quirks of a weekly product cycle. That is a bet on execution speed over a fresh outside perspective, and it removes one large variable from an already crowded transition, which is a sensible way to reduce risk when several senior seats are moving at once.
The tradeoff is real. An internal promotion can entrench existing technical debt and existing assumptions, and a first-time CTO carries execution risk that a proven external hire might not. Crumbl hedged by keeping Redd close as an advisor and board member, which gives Moncur a direct line to the person who held the seat before him. That structure, an insider promotion with the predecessor retained for continuity, is a repeatable pattern for any operator that values roadmap stability during a leadership change. It works only when the predecessor genuinely cedes authority rather than shadow-running the function from the board.
Why founder transitions put tech leadership at risk
Founder transitions are where technology roadmaps quietly break. Founders often carry product vision in their heads, make architecture calls by instinct, and hold relationships that no org chart captures. When they step back, the risk is drift: a stalled roadmap, a wave of departures, or a new leader who rips up working systems to make a mark. Crumbl is trying to firewall its technology function from that turbulence by locking in a known quantity before the CEO search concludes. Sequencing the CTO decision ahead of the CEO hire is itself a signal about what the board wants protected first.
The board's composition reinforces the point. McGowan, Hemsley, and Redd all remain directors, so the founders retain influence over strategy even as they exit operations. For Moncur, that is a support structure and a constraint at once. He inherits deep context and goodwill, and he also answers to the people who built what he now owns. Whether that produces continuity or gridlock depends on how much room the board gives him to change direction. Enterprises watching their own founder-led vendors should ask the same question before renewing a multi-year contract through a leadership transition, because roadmap risk on the vendor side becomes roadmap risk on yours.
What retail and franchise operators should take from it
There is a build-versus-buy lesson buried in the Vision Pro detail. Crumbl chose to build novel digital experiences in-house rather than wait for a platform vendor to package them, and being first on a new device is a marketing asset as much as a technical one. That posture only works with a technology leader who can move fast and owns the roadmap. Moncur's promotion preserves that in-house building capability. For operators weighing whether to staff a real engineering team or outsource to agencies and off-the-shelf commerce platforms, Crumbl is a data point for keeping the capability inside the walls.
The caution is that in-house building is expensive and only pays off when digital is genuinely core to the business. For Crumbl, where the app is the primary customer relationship and the weekly drop is a digital event, the investment is defensible. For a retailer whose customers mostly walk in and pay at a terminal, the same spend would be hard to justify. The general rule holds: match the depth of your technology bench to how much of your revenue and differentiation actually runs through software. Crumbl has decided that number is high, and it staffed the CTO seat accordingly.
