Caesars Bets on Flex Parlays and Bet Insurance as Sportsbook Rivalry Heats Up

Sportsbooks must look beyond simply adding more betting markets to keep users engaged as bettor habits shift, according to Dominic Hammond, senior vice-president of sports at Caesars Digital.

Beyond More Markets: Retention over Volume

“For me, content will always be king,” said Hammond. “We’re constantly adding new markets… [and] we always perform very well.”

However, as the sports betting landscape matures, Caesars recognizes that market volume alone isn’t enough. What customers want now, beyond what they can bet, is ways to protect those wagers when unpredictability strikes.

Flex Parlays and Injury Protection

With the start of the NFL season, Caesars Digital rolled out a series of features designed to address bettor fatigue. Flex Parlays allow bettors to miss one or more legs of an eligible parlay and still receive a reduced payout.

“[With Flex Parlay], we know customers want to have fun,” Hammond said. “Losing parlays over and over again isn’t great. You want to give customers a sense of getting a win… We all remember the time when we missed the parlay by one.”

Concurrently, Caesars expanded its Injury Protection feature, which refunds qualifying bets—including player props—if a key athlete is ruled out early due to injury.

“Injury Protection was a big one… We heard it from our customers,” Hammond noted. “Customers are saying, ‘Give me as many options as you can, and give me multiple ways to protect this bet.’ Sometimes we don’t like it, but we respond. A lot of us are bettors ourselves—what do we want to build? What excites us?”

Gamification and Market Depth

Caesars also launched Squad Builder, a free-to-play in-app game where users build a seven-player roster throughout the week tied to player props, competing for a $50,000 weekly jackpot.

Proprietary technology allows Caesars to roll out these complex tools seamlessly. While the technology was tested during major summer tournaments—where Caesars offered ten times as many markets as the 2022 Qatar World Cup—the NFL remains the ultimate proving ground.

Facing Down Prediction Markets and Rivals

The product push comes as regulated sportsbooks face new pressure from the rise of prediction markets.

“We know they have a formidable offering, and they are spending a lot of money,” Hammond said. “Fundamentally, we view their product as sports betting… We know we can take parlays in a completely different direction with things like Flex, plus Caesars Rewards and loyalty programs that prediction markets don’t have.”

Competitors are reacting quickly. BetMGM introduced BetDefense to refund first-quarter injury losses, while Fanatics expanded its Fair Play protection across both its sportsbook and prediction market arms, issuing refunds as FanCash.

Ultimately, the NFL season remains the premier stage for operators to test these engagement bets. “We are constantly innovating,” Hammond said, “but there’s no getting around the NFL being the biggest platform… where we have the biggest reason to shout in the market.”