Lead Site Reliability Engineer

Posted 4 Days Ago
Be an Early Applicant
Boston, MA, USA
Hybrid
148K-185K Annually
Senior level
Consumer Web • Gaming • Mobile • News + Entertainment • Software
Jackpocket gives lottery fans an easy, secure way to order lottery tickets from their phone.
The Role
Leads reliability practices across Infrastructure Engineering by defining Service Level Objectives, Service Level Indicators, error budgets, observability standards, and reporting. Partners with engineering teams to connect infrastructure reliability to application and platform outcomes, analyzes distributed-system failure modes, builds Datadog dashboards and monitoring, and influences reliability strategy through technical guidance, mentoring, and executive communication.
Summary Generated by Built In

At DraftKings, AI is becoming an integral part of both our present and future, powering how work gets done today, guiding smarter decisions, and sparking bold ideas. It’s transforming how we enhance customer experiences, streamline operations, and unlock new possibilities. Our teams are energized by innovation and readily embrace emerging technology. We’re not waiting for the future to arrive. We’re shaping it, one bold step at a time. To those who see AI as a driver of progress, come build the future together.

The Crown Is Yours

As a Lead Site Reliability Engineer, you’ll set the reliability standard across our Infrastructure Engineering organization. You’ll define how we measure reliability for critical services, partnering with engineering teams to build and refine Service Level Objectives that connect infrastructure performance to the experiences our platforms support. You’ll turn complex telemetry into clear, actionable insights that help teams and senior leaders make better decisions about reliability, risk, and priorities. As an individual contributor, you’ll lead through technical expertise and influence, shaping a consistent reliability practice across the organization.

What you’ll do as a Lead Site Reliability Engineer
  • 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.

What you’ll bring
  • 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.

Join Our Team

We’re a publicly traded (NASDAQ: DKNG) technology company headquartered in Boston. As a regulated gaming company, you may be required to obtain a gaming license issued by the appropriate state agency as a condition of employment. Don’t worry, we’ll guide you through the process if this is relevant to your role.

The US base salary range for this full-time position is 148,000.00 USD - 185,000.00 USD, plus bonus, equity, and benefits as applicable. Our ranges are determined by role, level, and location. The compensation information displayed on each job posting reflects the range for new hire pay rates for the position across all US locations. Within the range, individual pay is determined by work location and additional factors, including job-related skills, experience, and relevant education or training. Your recruiter can share more about the specific pay range and how that was determined during the hiring process. It is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.

Skills Required

  • Bachelor's degree in Computer Science or a related field, or equivalent education, experience, and training.
  • At least 7 years of Site Reliability Engineering experience.
  • Hands-on experience defining and operationalizing Service Level Objectives, Service Level Indicators, and error budgets at scale.
  • Deep experience with Datadog, including dashboards, monitors, and reporting from metrics and logging pipelines.
  • Experience connecting infrastructure-level reliability objectives to application or platform outcomes.
  • Strong knowledge of distributed systems and complex reliability measurement failure modes.
  • Ability to influence across engineering teams and drive alignment without direct authority.
  • Excellent written and verbal communication skills, including presenting reliability reporting to senior stakeholders.
  • Working knowledge of Amazon Web Services, Kubernetes, and on-premise systems.
  • May be required to obtain a gaming license issued by the appropriate state agency.
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The Company
HQ: New York, NY
330 Employees
Year Founded: 2013

What We Do

Jackpocket is creating a more convenient, fun, and responsible way to take part in the lottery. The first licensed third-party lottery app in the United States, Jackpocket offers players a secure way to order official state lottery tickets, such as Powerball, Mega Millions, and more. Lottery players use Jackpocket to place ticket orders for their favorite games, check lottery results, join lottery pools with other Jackpocket players, and turn on Autoplay so they never miss a drawing. Jackpocket is available in Arizona, Arkansas, Colorado, Idaho, Maine, Massachusetts, Minnesota, Montana, Nebraska, New Hampshire, New Jersey, New Mexico, New York, Ohio, Oregon, Texas, Washington, D.C., and West Virginia with many new markets on the horizon.

Why Work With Us

Our dedicated team of superhumans (and an adorable office pup or two) are making waves in an $80 billion industry. We believe transparency, teamwork, and a healthy dose of daily fun are key to creating Worktopia. Jackpocketeers are supportive, forward-thinking, and truly enjoy spending time together. Come join us for the long haul!

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