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Senior Site Reliability Engineer

Since 2018, Wisp has been on a mission to put healthcare back in patients’ hands. We connect patients with hassle-free sexual + reproductive care online, with discreet and convenient treatment that saves them time, money, and stress. Our goal is to empower everyone to make the decisions about their health that are right for them. We’ve scaled quickly, serving patients across the nation and becoming part of the WELL Health family—and now we want you.

We are a growing, fully-remote team in the United States looking for collaborators who are committed to our mission, passionate about results, eager to build something amazing, and excited to have high levels of ownership, accountability, and personal growth.

Who We’re Looking For

We are currently looking for a Senior Site Reliability Engineer to join our Engineering team at Wisp. This person will be the primary engineer responsible for ensuring that Wisp’s systems are available to serve the patient experience. You will bring a passion for solving complex problems and constantly looking for areas of improvement.

What You’ll Do

  • Use infrastructure as code practices (Terraform, Terragrunt, etc.), to build, launch, and maintain AWS infrastructure solutions that are resilient, secure, and transparent

  • Oversee and optimize Kubernetes environments with an emphasis on security hardening and efficient load distribution

  • Enable engineering teams by being the champion of CI/CD best practices and owning the workflows, migrations, and rollbacks of software delivery at Wisp

  • Manage all traffic ingress for Wisp’s ecosystem including edge caching, application load balancing, and proxy configurations (Nginx, Envoy)

  • Establish comprehensive observability solutions that deliver actionable insights to both engineering teams and key business stakeholders

  • Collaborate with security and software engineers to implement best practices for system reliability, performance, and security across our infrastructure

This Role Could Be A Good Fit For You If…

  • Demonstrated proficiency with 5+ years of experience in Python, Go, or Shell scripting

  • Deep understanding of networking fundamentals spanning TCP/IP, firewalls, routing, DNS, and load balancing

  • Proven ability to implement key SRE principles including monitoring systems, performance optimization, and automation workflows

  • Comprehensive expertise in container orchestration technologies including Docker, Buildpack, and/or Kubernetes

  • Self-directed professional capable of working autonomously, identifying potential issues, and implementing effective solutions with minimal oversight

  • Exceptional interpersonal skills with a track record of clear communication and productive collaboration across technical and non-technical teams

Visa sponsorship or transfer is not available for this position at present. Must be authorized to work in the country this requisition states.

Wisp is an equal-opportunity employer. We are proud to foster a workplace free from discrimination. We strongly believe that diversity of experience, perspectives, and background will lead to a better environment for our employees and a better product for our users and patients.

If you are committed to collaborative problem solving, creating high-quality and user-centric products, and want to make waves in sexual and reproductive healthcare, join us!

What You Should Know About Senior Site Reliability Engineer, Wisp

Wisp is on a mission to put healthcare back in patients’ hands, and we’re looking for a Senior Site Reliability Engineer to help us do just that! If you’re someone who thrives on solving complex problems and is passionate about building resilient and secure systems, you're going to love this role. At Wisp, our fully-remote team is dedicated to making sexual and reproductive care as convenient and stress-free as possible. In this position, you will be the primary engineer ensuring that our systems are always up and running to enhance the patient experience. You will utilize infrastructure as code practices, oversee Kubernetes environments, and champion CI/CD best practices as you optimize our infrastructure. This role is perfect if you have at least 5 years of experience with Python, Go, or Shell scripting and a strong grasp of networking fundamentals. Your expertise with container orchestration technologies like Docker or Kubernetes will be invaluable. You'll have the opportunity to collaborate with talented engineers and contribute to projects that make a real difference in people’s lives. Join Wisp and take ownership of your work while being part of a diverse team committed to delivering exceptional healthcare services!

Frequently Asked Questions (FAQs) for Senior Site Reliability Engineer Role at Wisp
What are the main responsibilities of a Senior Site Reliability Engineer at Wisp?

As a Senior Site Reliability Engineer at Wisp, your primary responsibility will be to ensure that our systems are reliably available to serve patients. You'll build and maintain AWS infrastructure using tools like Terraform and Terragrunt, optimize Kubernetes environments, manage traffic ingress, and establish observability solutions. Your role also involves championing CI/CD best practices and collaborating closely with security and software engineers to enhance system reliability and performance.

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What qualifications are required for the Senior Site Reliability Engineer position at Wisp?

The ideal candidate for the Senior Site Reliability Engineer role at Wisp should have at least 5 years of professional experience in software engineering or site reliability engineering. Proficiency in Python, Go, or Shell scripting is essential, along with a deep understanding of networking fundamentals such as TCP/IP, firewalls, and load balancing. Expertise in container orchestration technologies like Kubernetes is also necessary to excel in this role.

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How does Wisp support professional development for a Senior Site Reliability Engineer?

Wisp encourages continuous professional growth by providing opportunities for skill enhancement, ownership in projects, and collaboration with cross-functional teams. As a Senior Site Reliability Engineer, you’ll work closely with other tech experts, learn new technologies, and be part of an environment that values innovation and improvement. We believe that fostering a culture of ownership leads not only to personal growth but also to a better product for our users.

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What are the technical skills needed for the Senior Site Reliability Engineer role at Wisp?

To succeed as a Senior Site Reliability Engineer at Wisp, you should have strong technical skills in scripting languages such as Python, Go, or Shell. Additionally, a deep knowledge of networking fundamentals, performance optimization, and automation workflows is crucial. Familiarity with container orchestration technologies like Docker and Kubernetes, as well as infrastructure as code practices, are also essential for this role.

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What is the team culture like for the Senior Site Reliability Engineer at Wisp?

The team culture at Wisp is collaborative and inclusive, promoting a healthy work-life balance while ensuring that everyone’s voice matters. We encourage open communication between technical and non-technical teams to foster creativity and innovation. As a Senior Site Reliability Engineer, you’ll have the chance to bring your ideas to the table and work on projects that have a meaningful impact on healthcare delivery.

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Common Interview Questions for Senior Site Reliability Engineer
Can you explain your experience with AWS infrastructure?

Absolutely! When discussing your AWS experience, elaborate on the specific services you've worked with, highlight projects where you’ve implemented infrastructure using tools like Terraform or CloudFormation, and discuss the outcomes. Mention any challenges you faced and how you overcame them, emphasizing your problem-solving skills.

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What is your approach to ensuring the reliability of a system?

When answering, focus on the key principles of Site Reliability Engineering. Discuss how you would implement monitoring systems, use chaos engineering to identify weaknesses, establish SLAs, and ensure thorough documentation. Provide examples of how you've maintained uptime and performance in past roles.

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How do you handle incidents and outages?

In your response, outline a structured incident response process—from detection to resolution. Share any incidents you've managed in the past, how you communicated during the event, and the ways you conducted post-mortems to prevent future occurrences. This demonstrates your analytical and team collaboration skills.

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What CI/CD tools have you worked with and how did you implement them?

Discuss the specific CI/CD tools you’ve used, like Jenkins or GitLab CI, and explain how you implemented these systems within your workflows. Focus on how you automated testing and deployment processes, improving efficiency and minimizing errors in production.

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Describe your experience with container orchestration tools like Kubernetes.

Detail your hands-on experience with Kubernetes. Talk about deploying, scaling, and managing applications with it. You may also want to mention any specific challenges you've faced while working with Kubernetes and how you resolved them, showcasing your technical know-how and resilience.

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How do you prioritize tasks when managing multiple projects?

In answering this question, highlight your ability to assess project urgency and importance. Discuss using tools or methodologies like Agile or Kanban, and explain how you allocate resources or delegate tasks among team members to ensure timely delivery while maintaining quality.

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Can you give an example of a time you improved a system’s performance?

Share a specific instance where you identified a performance issue, the steps you took to analyze it, and the improvements implemented. Make sure to highlight quantifiable results, such as reduced load times or increased system availability, demonstrating both your analytical skills and impact on the project.

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What strategies do you employ for monitoring system performance?

Outline your approach to implementing monitoring solutions, using tools like Prometheus or Grafana. Discuss metrics you prioritize, alerts you set up, and how you use collected data to make informed decisions. This showcases your proactive approach and commitment to system reliability.

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How do you ensure security in your infrastructure?

Explain the best practices you follow for securing infrastructure, including regular audits, monitoring access controls, and employing encryption standards. Discuss how you collaborate with other teams to implement security measures, emphasizing your attention to detail in protecting sensitive data.

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Why do you want to work for Wisp as a Senior Site Reliability Engineer?

Share your alignment with Wisp's mission to empower patients in healthcare. Discuss how the role resonates with your career goals and values. Mention any specific projects or technologies at Wisp that attract you, demonstrating your knowledge and enthusiasm for the position.

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Rise from Within
Diversity of Opinions
Work/Life Harmony
Growth & Learning
Transparent & Candid
Medical Insurance
Paid Time-Off
Maternity Leave
Mental Health Resources
Equity
Child Care stipend
Paternity Leave
WFH Reimbursements
Flex-Friendly
Dental Insurance
Vision Insurance
Life insurance
Health Savings Account (HSA)
Flexible Spending Account (FSA)
401K Matching
Military leave

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Full-time, remote
DATE POSTED
April 16, 2025

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