Howard Migdal and the last few dollars before dinner

The last few dollars can ruin dinner before anyone has cooked it. A customer chooses the food, admires the order, reaches checkout and discovers that convenience has brought several friends, all expecting payment. Howard Migdal has spent much of his working life getting people to order meals online. In 2026, his argument for winning more of those orders became unusually easy to understand: Grubhub would absorb delivery and service fees on restaurant orders over $50.

George Clooney helped announce the policy in Grubhub’s first national Super Bowl commercial, directed by Yorgos Lanthimos. The famous face supplied the spectacle. Migdal supplied the business proposition. Customers might order more often, and buy more food, if the final bill stopped giving them reasons to reconsider. For a delivery executive, an abandoned basket is a particularly dispiriting still life.

That bet makes a useful introduction to Migdal, a Detroit native and Michigan State graduate whose career has crossed the Canadian border in both directions. He helped start GrubCanada in 2008, years before taking charge of Grubhub. Along the way came an acquisition, hotel bookings, Canadian delivery operations and the problem that follows any marketplace into adulthood: persuading all the people who make it work to keep showing up.

A Canadian beginning, with a familiar name

GrubCanada was founded by Migdal and Ross Lipson. Its resemblance to Grubhub was more than alphabetical; the Canadian venture was patterned after the American service. The opportunity was concrete. Restaurants had meals to sell. Customers wanted to order them online. A business that connected the two could become useful without owning a dining room or writing a menu.

The founders also tried a route with rather better lighting than the average sales meeting. They appeared on CBC’s Dragons’ Den, accepting an offer of $200,000 for half the company from Brett Wilson. The deal was never completed. Television furnished an offer, rather than the ending. In October 2011, Just-Eat Canada acquired the business, adding more than 200 neighbourhood restaurants in Ontario and British Columbia to its network.

There is something instructive about that early sequence. A televised handshake makes a satisfying scene; an acquisition changes where someone works on Monday. Migdal’s subsequent career would be built inside the operational world that follows the pitch. The restaurant signs up, the customer places an order, and the promise made by the platform becomes somebody’s immediate responsibility.

The hotel-room detour

Food was not his only lesson in matching spare capacity with a willing buyer. By 2015, Migdal was regional director of HotelTonight Canada. The service offered another version of a familiar marketplace question: how do you put something available in front of someone ready to buy it, at the right moment?

Describing HotelTonight’s GeoRates feature, he explained how hotels could target offers by location. A Toronto property could reach someone searching from Vancouver if its booking history suggested that connection was useful. He also acknowledged the uneasy relationship hotels could have with online travel agencies, including pricing restrictions and the pressure to maintain visibility on those platforms.

The detour belongs in his story because it shows the merchant’s side of the screen. A booking platform offers access to customers, while also influencing the terms on which businesses compete for them. Later, at a food marketplace, similar tensions would surround who owns the customer relationship, what a sale costs, and whether visibility produces business worth having.

Four years inside the machinery

Migdal joined SkipTheDishes in 2018 and held managing director and chief operating officer roles before becoming CEO in November 2022. Kevin Edwards was retiring. The promotion came after more than four years spent on operational and strategic initiatives, giving Migdal a running start on the company’s workings rather than a grand entrance from outside.

A small example of his commercial thinking appeared in 2020 with Skip Rewards. Customers earned points on orders and could redeem them for discounts. Migdal described the possibility of using additional incentives to encourage people to try something new, including products introduced by restaurant partners. The everyday purchase could become the beginning of the next purchase.

Rewards are hardly exotic. Their significance here is continuity. Years before Grubhub’s latest fee policy, Migdal was discussing ways to give customers a financial reason to return and merchants a reason to participate. In a business full of apps competing for the same dinner, remembering yesterday’s customer has a certain practical charm.

Back to the company that inspired the idea

On March 13, 2023, Just Eat Takeaway.com announced Migdal as Grubhub’s new CEO and its executive vice president for North America. Adam DeWitt, who had spent eleven years at Grubhub, would stay through May 1 to support the transition. Steve Puchala became interim CEO at SkipTheDishes, reporting to Migdal.

It was an unusual return journey: the co-founder of a Canadian business modelled on Grubhub now led Grubhub itself. The appointment also placed him in charge of an established brand facing forceful competition. History could explain how the company reached the customer’s phone. It could do less to determine which icon the customer tapped tonight.

Migdal put the obligation plainly in 2024: “customers’ expectations are very high.” That is a rather bracing sentence for a company marking its twentieth anniversary. An anniversary invites a business to admire its past; customers generally prefer to know when their food will arrive. His task was to make the older company useful enough to choose again.

His public introduction to Chicago included an August 2023 conversation with Jack Lavin at the Chicagoland Chamber of Commerce. Afterwards, Migdal described himself as a new resident and pointed to Grubhub’s work with The Hatchery Chicago and its Serving the City programme. The company’s national business had a local address, and he was beginning to speak about the responsibilities that came with it.

A shorter route to the customer

Amazon supplied a different kind of address. In May 2024, the relationship between the companies expanded to include Grubhub ordering within Amazon’s website and shopping app, while Grubhub+ became an ongoing Prime benefit. Migdal celebrated the chance for restaurant partners to reach tens of millions more consumers.

The logic was distribution. A delivery company can persuade people to download its app, or it can also appear in a place they already visit. The Amazon arrangement gave Migdal a way to pursue the latter. It placed restaurant ordering beside an existing shopping habit, reducing the distance between thinking about dinner and arranging for it.

By June 2026, further integrations included Eater, Beli, Alexa+ and Bilt. These approached the ordering decision from different directions: restaurant recommendations, friends’ rankings, voice requests and rewards. Seen together, they suggest a company trying to catch demand at the moment it forms. A recommendation is more commercially interesting when dinner can follow it home.

The price of changing course

Partnership announcements tell only part of a CEO’s story. In June 2023, shortly after Migdal’s appointment, Grubhub announced roughly 400 corporate job cuts, about 15 percent of its workforce. His message described costs that had risen faster than the business. The strategic reset had an immediate human cost.

Then ownership changed. Wonder announced a deal for Grubhub in November 2024 at an enterprise value of $650 million, including $500 million in senior notes and $150 million in cash. The acquisition closed in January 2025. Migdal remained CEO as Grubhub became part of Marc Lore’s broader food business.

On February 28, Migdal told employees that approximately 500 positions would be eliminated as the businesses integrated. He described reducing management layers, removing duplicated work and putting leaders closer to operations. Employees affected would receive severance and outplacement support. Those details belong beside the growth plans. A simpler organisation chart can represent a very complicated day for the people removed from it.

There was also a reckoning over the company’s conduct. In December 2024, Grubhub agreed to pay $25 million to settle federal and Illinois charges concerning delivery pricing, driver earnings claims and restaurant listings without consent. The settlement required operational changes. These were charges against the companies, rather than a personal finding against Migdal, but addressing them formed part of the institution he led.

Dinner beyond the delivery bag

The 2026 fee policy brought his attention back to the customer’s bill. Grubhub said it would absorb the delivery and service fees itself on qualifying restaurant orders over $50. Taxes and certain government-mandated charges could still apply. The distinction matters: a simple promise has to survive the checkout where customers test it.

“Grubhub fully absorbs those fees, not our restaurant partners.”

Howard Migdal, February 2026

His stated expectation was that customers would put some savings into additional food and return more frequently. That is a commercial hypothesis, with results to be earned over time. The policy gives a family ordering together a reason to consider Grubhub, while giving the company a clear proposition to advertise.

By September 2026, the next experiment involved eating at the restaurant. Grubhub was testing The Drop with selected users in Chicago and New York, using technology from Claim, the rewards business acquired by Wonder. Customers linked a card, chose from personalised weekly offers and could earn Grubhub credits for subsequent pickup or delivery.

The path had lengthened from the original online order to a cycle of discovery, dining and return visits. Yet the question running through Migdal’s career remained recognisable. What makes a customer choose a restaurant, and what makes that choice worth repeating? After GrubCanada, hotel rooms, Canadian operations and Chicago, he is still working on the transaction. Dinner gives him another chance tomorrow.