Full-Time

Lead Site Reliability Engineer

Posted on 8/20/2026

DraftKings

DraftKings

5,001-10,000 employees

Online platform for fantasy sports betting

Compensation Overview

$148k - $185k/yr

+ Bonus + Equity

Boston, MA, USA

In Person

Bachelor's

Category
DevOps & Infrastructure (1)
Required Skills
Datadog
Kubernetes
Distributed Systems
Data Visualization
AWS
Observability

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Requirements
  • A Bachelor's Degree in Computer Science or a related field, or equivalent relevant education, experience, and training.
  • At least 7 years of experience in Site Reliability Engineering, including hands-on experience defining and operationalizing Service Level Objectives, Service Level Indicators, and error budgets at scale.
  • Deep experience with observability platforms such as Datadog, including building dashboards, monitors, and reporting from metrics and logging pipelines.
  • Experience connecting infrastructure-level reliability objectives to application or platform-level outcomes and evaluating how technical dependencies affect end-user experience.
  • Strong knowledge of distributed systems and the failure modes that can make reliability measurement complex, with the ability to assess what technical signals truly represent.
  • Proven ability to influence across engineering teams, translate reliability concepts for technical and non-technical audiences, and drive alignment without direct authority.
  • Excellent written and verbal communication skills, including experience developing and presenting reliability reporting to Senior Managers, Directors, and cross-functional stakeholders.
  • Working knowledge of cloud and infrastructure environments such as Amazon Web Services, Kubernetes, and on-premise systems, with the technical depth to partner effectively with the teams operating them.
Responsibilities
  • Lead and mature the Service Level Objective development process across Infrastructure Engineering, establishing clear frameworks and standards for setting meaningful reliability targets.
  • Partner with engineering teams to design and implement Service Level Objectives, beginning with the critical user journeys each service supports and translating them into measurable indicators, targets, and error budget policies.
  • Review and refine existing reliability objectives to keep them aligned with changing customer impact, technical dependencies, and business priorities.
  • Connect infrastructure reliability targets to the application and platform experiences they support, making dependencies and their impact on end-user experience clear and measurable.
  • Build reporting processes and tooling that provide a clear view of reliability across critical components, translating technical signals into actionable insights for Senior Managers and Directors.
  • Influence reliability practices across teams through technical guidance, design reviews, mentoring, and collaboration with engineering partners.
  • Help teams distinguish meaningful service degradation from true downtime by applying thoughtful measurement strategies to complex distributed systems.

DraftKings runs an online gaming and entertainment platform that includes daily fantasy sports, sports betting, online casino games, and a marketplace for digital collectibles. Users participate in cash-prize fantasy contests or place bets on events, and the platform handles bets, winnings, and digital-asset transfers within a regulated environment to ensure fairness. The company differentiates itself by offering a broad mix of services—fantasy sports, real-money betting, casino games, and NFTs—on a single platform with strong regulatory compliance. Its goal is to provide a complete, legally compliant entertainment and gaming experience that appeals to sports fans, gamblers, and digital collectors while growing revenue across contests, bets, casino games, and NFT trading.

Company Size

5,001-10,000

Company Stage

IPO

Headquarters

Boston, Massachusetts

Founded

2012

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Simplify Jobs

Simplify's Take

What believers are saying

  • DraftKings Predictions reached 600,000 customers, with volume rising from $2.3 billion to $11 billion.
  • July 2026 World Cup betting lifted DraftKings' New York gross revenue to $72.9 million.
  • DraftKings secured a $600 million term loan B and $750 million revolver for flexibility.

What critics are saying

  • August 2026 lawsuits allege DraftKings Predictions is an illegal unlicensed sportsbook.
  • Q2 2026 revenue fell 5% to $1.44 billion, with ARPMUP down 13%.
  • Prediction markets invite CFTC, state-regulator, and class-action battles that can cripple expansion.

What makes DraftKings unique

  • DraftKings' 2026 super app unifies Sportsbook, Casino, DFS, Jackpocket, and Predictions.
  • Shared poker launched July 8, 2026 across Michigan, Pennsylvania, and New Jersey.
  • DraftKings maintains U.S. sportsbook leadership, posting $661.5 million New York handle in July 2026.

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Benefits

Performance Bonus

Company Equity

Growth & Insights and Company News

Headcount

6 month growth

-1%

1 year growth

0%

2 year growth

0%
GamblingNews.uk
Aug 20th, 2026
Kenneth Dart's Candle Lake acquires 5.8% stake in DraftKings for $691M as gambling portfolio expands

Kenneth Dart has acquired a 5.8% stake in DraftKings through his Candle Lake Investment vehicle, according to an SEC filing released on 14 August. The position comprises 28,581,386 shares valued at approximately $691 million. DraftKings' share price has fallen more than 46% over the past year to just over $24 per share, pressured by increased competition and disappointing financial results. Despite this, 22 of 25 analysts rate the stock as a buy. Dart's gambling portfolio now includes roughly 30% stakes in Flutter Entertainment and Evolution, plus a 0.6% holding in Hacksaw Gaming. His Flutter investment has lost $4.2 billion in value since his initial $7.62 billion stake. Earlier this month, Candle Lake submitted a formal takeover bid for Evolution after crossing the 30% ownership threshold.

InterGame Ltd
Aug 19th, 2026
Novig: Early prediction markets volume topped rivals.

Novig: Early prediction markets volume topped rivals. Operator says its opening trading volume beat the early figures posted by Kalshi, Polymarket, DraftKings and Underdog. August 19, 2026 Industry News Novig says its opening week's sports event contracts trading volume was higher than that reported by prediction market rivals Kalshi, Polymarket, DraftKings and Underdog. The company told CNBC it generated over US$125m in sports event contract trades in its first week, claiming from its own calculations that this figure topped the early figures reported by its competitors. Novig went live with its prediction markets platform in June following Commodity Futures Trading Commission (CFTC) approval. The company claims to offer a differentiated model in which customers trade against one another. Novig to take advantage of busy sports calendar. Writing on LinkedIn, Novig CEO and co-founder Jacob Fortinsky said: " August is one of the slowest months on the sports calendar. And in its first week, Novig did $125M+ in trading volume. "That's especially meaningful when you consider InterGame Ltd is a 21+ platform, and intentionally not capturing the entire market. "We're just getting started. September is around the corner, the sports calendar is about to explode and we're gearing up for what's next." CNBC reported that parlays accounted for a third of Novig's opening sports trading volume, with baseball the most popular sport. "Our highest-volume day since launching nationwide...was $26.3m in trading volume," Fortinsky told the outlet. Novig went live having secured over $105m in capital following a Series B funding round worth $75m that closed in February. Confirmation of its opening volume comes as prediction markets continue to be locked in legal battles with state actors across the US over their regulatory status.

MarketScreener
Aug 17th, 2026
DraftKings launches $600M term loan B and upsizes credit facility to $750M

DraftKings has launched syndication for a $600 million term loan B facility and a new $750 million revolving credit facility maturing in 2031. The company intends to use proceeds from the term loan to repurchase a portion of its convertible notes due 2028 and for general corporate purposes. The new revolving facility will replace DraftKings' existing $500 million revolving credit facility maturing in 2029. The company expects the new facility to remain substantially undrawn at closing. It will be used to enhance liquidity and provide additional financial flexibility. Both transactions are subject to market and other conditions. DraftKings operates sports betting and iGaming services across multiple US states and Canadian provinces.

PYMNTS
Aug 13th, 2026
DraftKings shows rewards in dollars to simplify redemption.

DraftKings shows rewards in dollars to simplify redemption. By PYMNTS | August 12, 2026 DraftKings has rolled out a new rewards currency called Crown Cash that powers the company's loyalty program, DraftKings Rewards, and makes it easier to view and use rewards across eligible DraftKings experiences, the digital sports and gaming company said in a Wednesday (Aug. 12) press release. Crown Cash is now available to eligible customers across DraftKings Casino, Sportsbook, Daily Fantasy Sports, Jackpocket and Golden Nugget Online Gaming. The currency will expand to DraftKings Predictions and other offerings, according to the release. With Crown Cash, customers can see the value they have earned in dollars and use it to place eligible wagers on DraftKings Sportsbook, play games on DraftKings Casino and Golden Nugget Online Gaming, and participate in other experiences, the release said. The rollout of Crown Cash supports DraftKings' super app strategy to create a unified platform, per the release. DraftKings also announced Wednesday that it revamped the DraftKings Rewards loyalty program, adding Casino Weekly Bonus Back, Birthday Bonus and Crown Cash Boosts. "By pairing flexibility with personalized benefits and unforgettable experiences, we're delivering a loyalty program that recognizes customers in meaningful ways," DraftKings Chief Customer Officer Shawn Henley said in the release. "DraftKings Rewards and Crown Cash make it easier for customers to see and use the rewards they've earned across our platforms, bringing greater consistency and connection across DraftKings." PYMNTS reported Friday (Aug. 7) that DraftKings is positioning itself not simply as a sportsbook operator, but as a nationwide sports commerce platform capable of acquiring, engaging and monetizing customers across multiple products. When reporting the company's second-quarter earnings in a press release, DraftKings Co-Founder and CEO Jason Robins said the company's core business grew across handle, users and engagement. "Our super app is now live nationwide, and Predictions is already growing faster than we anticipated," Robins said during the call. DraftKings entered prediction markets in December with the launch of DraftKings Predictions, a standalone app and web products. The PYMNTS Intelligence report "Embedded Offers: The Billion-Dollar Opportunity Inside Recent Consumer Spending" found that when offers, rewards and discounts are embedded into the customer journey, they can shape what consumers buy, where they choose to shop and the methods they use to pay.

Yahoo Finance
Aug 10th, 2026
DraftKings validates Kalshi's prediction market while trying to capture it, says dual investor

Joel Shulman, founder of ERShares and portfolio manager of the XOVR ETF, says DraftKings is both validating Kalshi's prediction markets business and attempting to capture it. Shulman, who holds stakes in both companies, called the validation "the more important signal". DraftKings recently reported revenue of $1.44 billion, down 5% and missing estimates, though adjusted earnings per share beat expectations. The company disclosed that roughly 600,000 customers have engaged with its predictions product, with annualised volume growing from $2.3 billion in April to $11 billion in July. Shulman noted DraftKings increased sales and marketing spending by 38% to $323 million, whilst average revenue per payer fell 13%. He suggested this indicates a competitive response rather than a temporary shift.