Founding Engineer at Venture-Backed, AI-Native Law Firm

About Us

Shepherd is the hybrid law firm for startups, combining AI-powered technology with experienced attorney oversight to deliver faster, more affordable, and transparent legal services. Built for early-stage companies from pre-seed through Series B, Shepherd provides fixed-cost pricing and glass-box transparency- eliminating the unpredictability of traditional billable hours. The firm's contextual AI learns each client's business, risk appetite, and deal preferences, enabling personalized legal solutions at a fraction of BigLaw costs. Unlike pure technology platforms, Shepherd clients work directly with dedicated attorneys who provide strategic guidance and relationship-driven counsel. Shepherd is building the future of legal services- where efficiency increases client value, not just law firm margins.

The Opportunity

We’re looking for a Founding Engineer / Head of Engineering to own the technical vision and build the core product from the ground up. This is a true founding team–level role: you’ll architect the AI engine, shape the product’s data and workflow systems, and lead the technical execution that powers the first AI-native law firm for startups.

As Founding Engineer / Head of Engineering, you’ll partner closely with the CEO and CLO to turn complex legal workflows into scalable, automated systems- blending LLMs, structured data, and human-in-the-loop validation into a seamless, modern startup experience.

This is a 0→1 product build, a leadership role, and an opportunity to define the technical foundations of a category-defining company.

What You’ll Do

Technical Leadership

• Architect the end-to-end technology stack for the Shepherd platform (LLM infrastructure, workflow engine, database design, API integrations (Slack, Docusign, ect).

• Establish engineering best practices, technical roadmap, and long-term architecture decisions.

• Build the foundation for a secure, compliant system that meets startup and enterprise legal standards.

• Own the evaluation, fine-tuning, and deployment of LLMs for contract analysis, summarization, redlining, and risk scoring.

Product & AI Development

• Build our core features:

  • AI contract review and redlines

  • Build and expand a context-aware AI

  • Smart drafting and document automation

  • Workflow automation (intake, tasking, approvals)

  • Legal hub for requests, docs, alerts, and lawyer interaction

• Design human-in-the-loop systems that blend AI speed with attorney validation.

• Translate ambiguous legal workflows into clean, reliable, repeatable technical systems.

• Work directly with early customers to validate and iterate on features in real time.

Security, Compliance & Infrastructure

• Set up infrastructure that meets SOC-2 and privacy standards.

• Implement secure document storage, access controls, role-based permissions, and audit trails.

• Ensure ethical, compliant, and trustworthy use of AI models across the platform.

Team & Culture

• Hire and lead a world-class engineering team as we scale (frontend, backend, ML/AI).

• Build a culture of velocity, quality, and ownership.

• Act as a technical co-founder who can communicate clearly with investors, partners, and customers.

Who You Are

• 6–12+ years of experience as a full-stack engineer or technical founder (AI/ML or workflow-heavy SaaS strongly preferred).

• Deep experience building production AI systems (LLM fine-tuning, embeddings, RAG, evaluation).

• Strong product instincts with a bias toward shipping quickly and iterating.

• Experience designing secure, scalable architectures for B2B or workflow products.

• Comfortable in ambiguity: able to turn undefined problems into structured, elegant solutions.

• Entrepreneurial DNA- you want to build, own, and scale something from the ground up.

• Bonus: experience with legal tech, fintech, compliance systems, or other highly regulated verticals.

Why Join Us

• Ground-Floor Equity: Ground-floor opportunity to build a generational company redefining legal infrastructure.

• Category Creation: Help build the first AI-native hybrid law firm + SaaS platform for startups.

• Technical Challenge: Blend LLMs, data, automation, and legal reasoning into one seamless workflow engine.

• Massive Market: Startups and SMBs spend $25B+ per year on legal- and the shift toward automation is accelerating.

• Mission-Driven Team: Work alongside founders building a more accessible, modern, and scalable legal system.

Compensation

• Equity: Significant founding team equity stake

• Cash: 140k-160k base to start, increasing with each subsequent funding round