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
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