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Sportsbook operators are preparing for another NFL season with one high-profile operator facing increased pressure to improve its standing.

The NFL season has traditionally served as the time of year when operators roll out their latest technology upgrades, as well as improved promotional offerings to capture returning players.

In past years, promotional efforts have been more pronounced as operators offered significant bonuses to attract players, and although those efforts have since been curtailed somewhat since many of the largest operators have chased profitability, the beginning of a new season has continued to serve as a high point for customer acquisition.

“This is the most busy time of year for us typically from a customer acquisition perspective, I guess the Super Bowl, but the whole NFL, kind of NBA, that whole fall timeframe is usually the biggest overall period,” said DraftKings CEO Jason Robins during a company earnings call earlier this month. “And, really, I see no reason to think that that's going to slow down.”

“Obviously, we're going to be very closely monitoring the data and if we see any changes, we'll adjust our spend and adjust our approach. But right now, I think, if anything, you'd expect it to build, because we're in really the least busy time of year and we're still seeing very strong customer acquisition. So, I don't know why that would slow down going into the busiest time of year," he said. 

In addition to improving betting technology and attempting to strengthen parlay offerings, market leaders FanDuel and DraftKings have pursued partnerships that provide increased viewership for NFL games, with DraftKings featuring new “Bet and Watch” options within the platform, and FanDuel offering a three-week free trial of the NFL Sunday Ticket package which allows viewers to watch any out-of-market games.

“We had so many other great things that we were trying to get done last year, and I think to do it in a sort of haphazard way wasn't our style,” Robins said. “We want to do it right, so we really wanted to make sure it wasn't just some kind of hack together integration of a video feed."

“If somebody tries it, we want them to say this is great, and come back, we get one shot at a first impression.”

While the market leaders are focused on retaining their strong performance, Penn Entertainment’s ESPN BET may be the operator with the most riding on improving its standing, amid concerns from investors about the company’s online performance to date compared with the significant financial investment the company has made in digital offerings, first with its Barstool Sportsbook offering, and now its partnership with the Disney-owned "Worldwide Leader in Sports".

Penn CEO Jay Snowden said the company does not intend to be overly aggressive in service of pursuing customers, instead relying on converting players in their existing databases and technological improvements.

“We’ll do some spending around that, but again, that’s all built into our guidance for the rest of the year,” Snowden said. “And remember, we have a digital database of almost 4 million and a lot of those digital customers only bet on football.”

“So, there’s a huge reactivation opportunity for us and we think with the much-improved product that we have and all of the new features … we feel like we have an opportunity to drive better engagement, deeper loyalty and retention and monetization as we move forward.”

One area of improvement Penn is strongly pursuing is improving its parlay offerings, which have been a major strength for DraftKings, and especially FanDuel.

“FanDuel has been in a class of their own from a hold rate perspective because their parlay percentage is best in class,” Snowden said, referring to the metric measuring the percentage of handle comprising parlays.

“And what we’re seeing already, keeping in mind that our parlay offering is going to be significantly better at the start of football season than it’s ever been.”

Snowden pointed to data in Illinois where the company has performed strongly with parlay percentage despite a product that still needs improvement.

“For us to be sort of sitting at a number two position in terms of parlay as a percentage of handle when our parlay offering hasn’t been as competitive as it’s about to be at the start of football, we think there’s a lot of opportunity for us to continue to close the gap between us and FanDuel in terms of parlays as a percentage of handle, and with that will come an improved hold percentage.

“I’m not saying that we’re going to get to FanDuel and not going to give you a time frame, but clearly there’s a big opportunity for us to continue to close that gap over time as we improve the experience for those that like to bet on parlays and overall just bet inside the app,” he added.