Software Engineer, DevOps

We provide savings on insurance premiums for commercial businesses that are leveraging modern technology on their worksites.

While we began with commercial construction, we're expanding into adjacent sectors, including Energy, Agriculture, and Real Estate.

To date, Shepherd has raised over $20M from leading investors, including:

• Y Combinator – W21 cohort

• Susa Ventures – lead our Pre-Seed round

• Spark Capital - lead our Seed round

• Costanoa Ventures + Intact Ventures – lead our Series A round

• And several more.

We're a team of technologists and insurance enthusiasts, bridging the two worlds together. Check out our team page to meet some of us!

About You

We're looking for a talented DevOps/SysOps engineer who's passionate about what we're building and ready to do the best work of their career. You thrive on ownership, drive results, and care deeply about both technical excellence and platform reliability.

You would be our dream candidate if...

• You take end-to-end ownership of our infrastructure and systems, from initial architecture through ongoing maintenance and optimization.

• You enjoy automating everything, from building CI/CD pipelines to managing deployments, while maintaining high-quality standards.

• You are passionate about platform health and are skilled at implementing monitoring, logging, and alerting systems to ensure high availability and performance.

• You are not afraid of ambiguity, and it may even excite you to solve complex, multi-faceted problems.

• You care about others' growth and enjoy collaborating with and mentoring other engineers—you've led or been a major contributor on significant infrastructure projects.

• You have strong opinions, weakly held—you advocate for your ideas but adapt when presented with better solutions.

• You communicate technical concepts clearly to both technical and non-technical stakeholders.

• You care deeply about security and continuously evaluate and improve the security posture of our infrastructure and applications.

About the Role

As a Senior DevOps/SysOps Engineer, you will be a key member of our engineering team, leading major initiatives and owning a large area of our cloud platform. You will drive the technical decisions for your domain and play an integral role in building our engineering culture.

You will:

• Lead major initiatives to architect, build, and manage scalable, reliable, and secure cloud infrastructure.

• Contribute to product strategy and architectural decisions for the platform, not just implementation.

• Work across the stack and collaborate closely with software development teams to troubleshoot production issues and improve application performance.

• Balance innovation with pragmatic delivery—staying current with emerging tech while championing operational excellence and best practices.

Qualifications

• Experience: 5+ years of experience in a DevOps, SysOps, or Site Reliability Engineering (SRE) role.

• Cloud Proficiency: Deep expertise with at least one major cloud provider (AWS, GCP, or Azure).

• IaC: Proven experience with Terraform, CloudFormation, or similar IaC tools.

• Containerization: Strong knowledge of container orchestration platforms, particularly Docker and Kubernetes.

• CI/CD: Hands-on experience with CI/CD tools like Jenkins, GitLab CI, GitHub Actions, or CircleCI.

• Scripting: Proficiency in scripting languages such as Python or Bash.

• Monitoring: Experience with monitoring and observability tools like Prometheus, Grafana, Datadog, or New Relic.

Bonus Points

• Experience with serverless architectures (AWS Lambda, Google Cloud Functions).

• Knowledge of modern security frameworks and tools.

• Strong understanding of networking principles and Linux system administration.

• A passion for automating repetitive tasks and a mindset of continuous improvement.

• Excellent communication and collaboration skills.

🏥 Premium Healthcare
100% contribution to top-tier health, dental, and vision

🏖️ Unlimited PTO
Flexibility to take the time off, recharge, and perform

🥗 Daily lunches, dinners, and snacks
We work together, and enjoy meals together too

🖥️ SF, NYC, or Dallas-Fort Worth Offices
Premium office spaces on both coasts with daily lunches provided

📚 Professional Development
Access to premium coaching, including leadership development

🏦 401(k) Plan
Competitive 401(k) plan offered

🐶 Dog-friendly office
Plenty of dogs to play with and make friends with in the SF office