Knowledge bank: DraftKings' CCO on applying learnings from finance to igaming

It’s International Women’s Day (8 March) and DraftKings offices around the world would normally be a hive of activity. But that’s not been the case since 2020, as the Boston-headquartered operator has declared it a global company holiday for all employees for the second year running. And it’s a cause for celebration that remains front and centre of the company’s ethos. Just last year, the firm pledged to donate up to $350,000 to non-profit organisations across the US to support female-owned small businesses and entrepreneurs.

This year, DraftKings has a variety of efforts taking place throughout the month and year-round in collaboration with the business’ inclusion, equity and belonging team, women’s business resource group, corporate social responsibility department and the benefits team to support females within the company and give back to organisations that empower women.

In honour of Women’s History Month, DraftKings invited Valerie Gordon, a TV producer and engaging speaker, to hold a ‘Commander-in-She: Communicating with Confidence’ workshop for employees to learn to communicate with confidence and influence.

The emphasis that has been placed on International Women’s Day is something that DraftKings’ chief compliance officer (CCO) Jennifer Aguiar is immensely proud of, especially being one of two females on the leadership team, alongside Stephanie Sherman who was promoted to CMO in January 2022. Having two women at C-level means a variety of diverse opinions and different outlooks are being brought to the table.

“From my perspective, being on the team, I’ve always been very vocal anyway, so I tend to not hold back. I think having both me and Steph there, it gives the entire team a bit of a different direction and makes them think differently. And neither one of us is shy to bring up those conversations,” she tells EGR Intel.

The US sports betting giant has a dedicated inclusion, equity and belonging team that focuses on diversity and inclusion within the organisation. DraftKings employees continue to undertake training in this area across all levels of the business as well as partake in recruiting and speaking initiatives at various schools to encourage diverse hiring.

“It’s fascinating to be part of that and see the different approaches and different ways to operate. When I look back, historically, not necessarily at Draft-Kings, but in general, people tend to kind of surround themselves with all the same type of people. And I think that just doesn’t work. That’s where we really tried to focus on bringing different folks in to get different perspectives. And that helps us drive forward,” says Aguiar.

While the online gambling sector is traditionally male-dominated, DraftKings’ CCO doesn’t see that as an obstacle for women’s career development and growth within the sector. “I don’t think about whether it’s a male-dominated industry or not. If it’s something I’m interested in, I’m going to push forward,” she asserts.

At DraftKings, there are a myriad of opportunities for women to excel within the business, whether your passion is sports or marketing. “If you’re interested in something, go for it. I don’t know exactly what the industry can do, except for being out there and visible and have job descriptions that wouldn’t necessarily turn a woman away.”

For Aguiar, who joined DraftKings back in 2016 when it was purely a daily fantasy sports (DFS) company, her career path has seen her promoted from head of compliance and risk to VP, compliance and risk in 2018, and then move into her current CCO position in February 2021. Having worked in financial services for 20 years before joining DraftKings, Aguiar has seen a great deal of overlap between the banking and online gambling worlds.

“It was a pleasant surprise that there were so many similarities. Both verticals are really dealing with people’s money. The actual gaming regulations are different, but a lot of the foundational things like privacy, anti-money laundering, etc., crossover to both types of companies. So, it actually was a lot easier to make that transition by having that background,” she explains.

That trend has continued today as a number of Aguiar’s own team members also hail from a financial services background. “So, that tends to be an area where we focus on hiring because of the similarities.”

Having worked for the likes of Citizens Bank and LendingClub in the past, Aguiar was able to bring a great deal of enterprise risk and compliance knowledge to the US sports betting and igaming operator. “I was able to take the best pieces of their programmes and build the programme that was right for Draft-Kings. So that was super helpful because I was able to have the experience in multiple different organisations. That allowed me to kind of pick and choose and get the best programme in place for DraftKings,” she remarks.

Get with the programme

When Aguiar joined the operator in 2016, she was tasked with building out its compliance programme, drawing on the experience she had gained in the financial sector. “I think that set us up for the expansion into different verticals. It was obviously a lot less complicated when it was just DFS, but it was still complicated enough because of each of the states having their own sets of regulations.

“When PASPA was overturned [in May 2018] and we started getting into sports betting and igaming, it was just a matter of folding the processes into what we already had. So, it actually wasn’t as complicated because we already had the infrastructure in place to be able to take on those new verticals,” she adds.

While the compliance programme was devised when DraftKings was a DFS-only company with nearly 300 staff members onboard, it has since evolved and been modified to now be commensurate to a public, larger international organisation boasting over 3,500 employees.

In her current role as CCO, Aguiar’s team is also in charge of devising an enterprise risk programme. Since assuming the C-level position, her team has quadrupled in size over the last few years, with an expanded focus to cover areas such as responsible gaming, player protection, anti-money laundering, privacy and investigations. Aguiar says the growth of the team and its expanded remit has been “fantastic because it really ties into the culture of compliance that we have”.

Working in compliance means there’s no chance of Groundhog Day. Aguiar tells EGR Intel: “What’s the topic of the week? Is there a fire drill to deal with? It’s always something different, which is why I love it. Since I joined compliance, whether it be financial services or here, I think that’s one of the best things about it – no day is ever the same.”

Championing compliance

When Aguiar’s appointment as CCO was announced in February 2021, DraftKings CEO Jason Robins applauded her for creating “a culture of compliance”, which he has been fully supportive of throughout. As part of the compliance training programme, every year – except during Covid – Robins has featured in a video talking about the importance of compliance and risk management.

Having Robins speak in the video “really set the tone from the top”, explains Aguiar, and the compliance team is fully engaged with all parts of the business. She adds: “We’re always out and working with everybody, one of the best things that we have is we’re touching every part of the company. It’s really shown that we do have a culture where people are reaching out to us constantly. I think that shows it’s actually been received well.”

The compliance team meets quarterly with other departments to present training and licensing metrics.  Photo by Darren McCollester/Getty Images for DraftKings

The Nasdaq-listed operator also has a compliance committee led by the CCO, and in addition to that the compliance team meets quarterly with other departments in the business to present training and licensing metrics as well as sharing information.

With legislation varying on a state-by-state basis, regulation is a constantly evolving beast for the compliance team to deal with. As presented during Draft-Kings’ Investor Day 2022 on 3 March, the operator is live in 17 US states for online sports betting and five for igaming. With New York and Louisiana being the most recent states it has entered and Ontario next on the horizon, it has been a busy time for the firm. But Aguiar attributes the success of new market entries to its platform’s adaptability to change.

“We have a saying here that every state/jurisdiction is a snowflake because they all have their own regulatory requirements. And we have a platform that can handle different state requirements. So, that made it a lot easier to be flexible and nimble in order to adapt to the different requirements.”

The last two years have also seen the operator enhance its use of technology for compliance. “There’s been some start-up companies that have put out technology that I wish I’d had years ago, to be honest with you. We’ve been partnering with several of those companies on different areas,” reveals the CCO.

One of those agreements includes working with one entity on regulatory change management, which is a “game changer” for DraftKings. “Because of all the regulations, when they change or when new ones come out, we’re partnering with a company that helps us through that process. So we don’t have to do Google spreadsheets anymore.”

By using new technology and tools that are launched, the operator has been able to enhance its capabilities in the privacy and licensing space. In addition, it is utilising a risk and compliance GRC tool to track risks, controls and tests.

Peer review

While the US is still in its infancy when it comes to regulated online gambling compared to Europe, compliance is becoming much more prominent in the country. Aguiar points to the importance of learning from established jurisdictions like the UK, and that US regulation may well change in the future depending on what’s happening in Europe.

“We’re in the early stages but I think the best thing about it is we get the learnings from what we see in the UK and other jurisdictions in Europe. It allows us to get ahead of that, we can see what’s coming.”

She also adds that following the acquisition of SBTech in 2020, there is significant experience and institutional knowledge that the supplier was able to bring to DraftKings. Aguiar particularly highlights the UK as an international jurisdiction DraftKings follows with interest on the gaming side. “The UK is an area that we always look at. They tend to be a leader in a lot of this. When they make changes, there’s other jurisdictions that follow. So that’s really one that I do keep a pulse on.”

As for other markets, the US sports betting, DFS and igaming operator is also involved with other organisations to keep abreast of new developments. From an anti-money laundering standpoint, Aguiar is part of the American Gaming Association (AGA) AML consortium. The company also has a relationship with the international membership organisation for anti-financial crime, ACAMS, and the International Association of Privacy Professionals.

“We have a lot of folks certified in anti-money laundering. So, there’s a constant wave of information that’s provided, which is fantastic, and that allows us to adjust accordingly,” she adds.

And when it comes to responsible gambling (RG), DraftKings has a growing RG team that works directly with the AGA. Christine Thurmond joined as the firm’s first director of RG in February 2020, coming from the Massachusetts Council on Compulsive Gambling. “She’s involved on a day-to-day basis, not just with the AGA but with a lot of the other different agencies to stay ahead of everything there,” explains Aguiar.

With ever-changing regulation to contend with, it’s clear that DraftKings’ compliance team is constantly being kept on its toes. But having the full backing and support from the top of the organisation means the culture of compliance is a strong message that is heard and welcomed across all levels of the workforce.

Coupled with two strong female leaders at executive level and International Women’s Day marked as a company holiday already, it looks like this year’s #BreakTheBias theme is already a reality.

Inspiring others to fulfil their dreams, Aguiar urges women to “make your own destiny”.