Lead Infrastructure Engineer

• We're seeking a Lead Infrastructure Engineer to join our founding team. This isn’t just a job- it’s a chance to architect and scale the foundation of an AI-native legal platform from the ground up.

• You’ll work directly with the founding team to design and own the infrastructure that powers Shepherd — ensuring our systems are secure, reliable, and built to handle sensitive legal workflows at scale. This role sits at the core of everything we do: from AI pipelines and data systems to application performance and security.

• As an early member of the team, you’ll have full ownership over Shepherd’s infrastructure, DevOps practices, and security posture- building the systems, standards, and tooling that enable rapid product development without compromising trust.

• This is a rare opportunity to define the infrastructure backbone of a category-defining company operating at the intersection of AI, legal services, and regulated data.

• Design, build, and manage Shepherd’s cloud infrastructure (AWS, GCP, or similar)

• Own deployment pipelines, CI/CD systems, and developer infrastructure

• Architect scalable, high-availability systems to support a growing AI-native application

• Build and manage infrastructure for AI workloads (LLMs, embeddings, vector databases, RAG pipelines)

• Establish best practices for monitoring, logging, alerting, and incident response

• Implement and maintain strong security and compliance standards (SOC 2 readiness, data encryption, access controls)

• Ensure reliable handling of sensitive and privileged legal data

• Optimize system performance, cost efficiency, and scalability

• Collaborate closely with engineering and product teams to support rapid iteration and deployment

• Evaluate and integrate new infrastructure tools and technologies as the platform evolves

• Lead infrastructure strategy and help hire and mentor future infrastructure and DevOps engineers

• 6–10+ years of experience in infrastructure, DevOps, or platform engineering roles

• Strong experience with cloud platforms (AWS, GCP, or Azure) and modern infrastructure tooling

• Expertise in CI/CD, containerization (Docker), and orchestration (Kubernetes or similar)

• Experience building and scaling production systems with high reliability and uptime requirements

• Strong understanding of security best practices, including IAM, encryption, and network security

• Experience with monitoring and observability tools (e.g., Datadog, Prometheus, Grafana)

• Ability to design systems for scalability, fault tolerance, and performance

• Comfortable operating as a technical leader and making high-impact decisions

• Experience supporting AI/ML infrastructure (LLMs, vector databases, distributed workloads)

• Familiarity with compliance frameworks such as SOC 2, GDPR, or similar

• Experience in regulated industries (legal, fintech, healthcare, etc.)

• Background as an early or founding engineer in a startup environment

• Experience building internal developer platforms or tooling

• Owner mindset- You take full responsibility for Shepherd’s infrastructure and reliability

• Security-first thinking- You design systems with trust, privacy, and compliance at the core

• Systems thinker- You build for scale, resilience, and long-term evolution

• Builder mentality- You move quickly while maintaining high standards

• Collaborative- You partner closely with product and engineering teams

• Adaptable- You’re comfortable evolving architecture as the company grows

• Competitive compensation: $150,000 – $165,000 base salary

• Meaningful equity: Early-stage ownership with significant upside

• Direct impact: Own and define Shepherd’s infrastructure, security, and scalability from day one

• Cutting-edge systems: Work on AI-native infrastructure and modern cloud architectures

• Professional growth: Opportunity to build and lead the infrastructure function as the company scales

• Mission-driven work: Help democratize access to high-quality legal services for startups

We believe ambitious outcomes are possible. We explore unconventional ideas, test them rigorously, and act on the data- learning fast without distraction or comparison.

Mediocrity has consequences. We set the highest standard in our execution, judgement, and how we show up everyday- because excellence compounds.

Speed and urgency are habits that when modeled consistently and scaled through automation, become contagious across the team, the product, and our customers.

Legal work runs on trust, not features. We earn trust by being responsive, transparent, and accountable to our customers- particularly when it’s uncomfortable.

We pair high standards with empathy and ambition with humanity. Respect and integrity are NOT separate from winning- they are how we win.

We are an equal opportunity employer and are committed to building a diverse and inclusive workplace. We do not discriminate on the basis of race, color, religion, gender, gender identity or expression, sexual orientation, national origin, age, disability, veteran status, or any other legally protected characteristic.