Senior Site Reliability Engineer - Chicago - BetterUp

Description

Let's face it, a company whose mission is human transformation better have some fresh thinking about the employer/employee relationship. We do. We can't cram it all in here, but you'll start noticing it from the first interview. Even our candidate experience is different. And when you get an offer from us (and accept it), you get way more than a paycheck. You get a personal BetterUp Coach, a development plan, a trained and coached manager, the most amazing team you've ever met (yes, each with their own personal BetterUp Coach), and most importantly, work that matters. This makes for a remarkably focused and fulfilling work experience. Frankly, it's not for everyone. But for people with fire in their belly, it's a game‑changing, career‑defining, soul‑lifting move. Join us and we promise you the most intense and fulfilling years of your career, doing life‑changing work in a fun, inventive, soulful culture. If that sounds exciting—and the job description below feels like a fit—we really should start talking.

We are a hybrid company with a focus on in‑person collaboration when necessary. Employees are expected to be available to work from one of our office hubs at least two days per week, or eight days per month. Our US hub locations include: Austin, TX; Chicago, IL; New York City, NY; San Francisco, CA; and the Washington, DC metro area. If this is a role based in Europe, our Europe hub locations are London, UK and Amsterdam, NL. Please ensure you can realistically commit to this structure before applying.

What You'll Do

• Leverage AI‑powered tools and automation to transform how we monitor, troubleshoot, and maintain production systems
• Build and operate cloud infrastructure on AWS, using Terraform to codify and version‑control our entire environment
• Manage and scale Kubernetes clusters that power BetterUp's platform, ensuring high availability and performance
• Design intelligent alerting and observability systems
• Collaborate with engineering teams to embed reliability into the development lifecycle, shifting left on operational concerns
• Automate incident response workflows and build self‑healing infrastructure
• Experiment with and adopt emerging AI tools for log analysis, anomaly detection, and predictive maintenance
• Drive continuous improvement through data‑driven retrospectives and reliability metrics

If you have some or all of the following, please apply

• 4+ years of experience in SRE or infrastructure roles
• Genuine excitement about AI tooling: you're already using copilots, AI assistants, or LLM-based tools in your workflow and are excited to push your skillset further in this area
• Deep experience with AWS
• Hands‑on Kubernetes experience: deploying, scaling, debugging, and securing clusters
• Strong Terraform skills with experience managing complex, multi‑environment infrastructure
• Familiarity with modern observability stacks (Datadog, Prometheus, OpenTelemetry)
• Strong debugging instincts and comfort navigating distributed systems
• Clear communication skills - you can explain a production incident to engineers and executives alike
• A builder's mindset: you see manual processes as opportunities for automation

AI at BetterUp

Our team thrives at the intersection of human expertise and AI capability. As an AI‑forward company, adaptation and continuous learning are part of our daily work. We're looking for teammates who are excited to evolve alongside technology – people who experiment boldly, share their discoveries openly, and help define best practices for AI‑augmented work. These professionals thoughtfully integrate AI into their work to deliver exceptional results while maintaining the human judgment and creativity that drives real innovation. During our interview process, you'll have opportunities to showcase how you harness AI to learn, iterate, and amplify your impact.

Benefits

• Access to BetterUp coaching; one for you and one for a friend or family member
• A competitive compensation plan with opportunity for advancement
• Medical, dental, and vision insurance
• Flexible paid time off
• Per year:
  • All federal/statutory holidays observed
  • 4 BetterUp Inner Workdays )
  • 5 Volunteer Days to give back
  • Learning and Development stipend
  • Company wide Summer & Winter breaks
• Year‑round charitable contribution of your choice on behalf of BetterUp
• 401(k) self contribution

We are dedicated to building diverse teams that fuel an authentic workplace and sense of belonging for each and every employee. We know applying for a job can be intimidating, please don't hesitate to reach out — we encourage everyone interested in joining us to apply.

BetterUp Inc. provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, national origin, disability, genetics, gender, sexual orientation, age, marital status, veteran status. In addition to federal law requirements, BetterUp Inc. complies with applicable state and local laws governing nondiscrimination in employment in every location in which the company has facilities. This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation, and training.

The base salary range for the role is as follows:

• New York and San Francisco: $164,000 - $205,000
• Austin and Arlington (D.C. Area): $147,600 - $184,500

Protecting your privacy and treating your personal information with care is very important to us, and central to the entire BetterUp family. By submitting your application, you acknowledge that your personal information will be processed in accordance with our Applicant Privacy Notice. If you have any questions about the privacy of your personal information or your rights with regards to your personal information, please reach out to