Vice President, AI

Location: Seattle, Washington; Seattle, Washington

Department: Engineering

Work Mode: Hybrid

About the Role

Docusign brings agreements to life, powering over 1.5 million customers and a billion people across 180 countries with the #1 platform in e-signature and contract lifecycle management (CLM). Our Intelligent Agreement Management (IAM) platform unleashes business-critical data trapped in documents, accelerating business and simplifying lives. As Vice President, AI in Engineering, you'll lead our GenAI transformation, driving innovation in AI-powered e-signatures, agentic workflows, and agreement automation to dominate the IAM market. We're seeking a visionary, product-minded AI leader with deep technical expertise and proven large-scale leadership. You've shipped an AI-first product to PMF ($5M+ ARR or NPS >40) and scaled teams of 100+ elite engineers, including Distinguished Engineers. Reporting to the GVP, Engineering, you'll build and inspire a world-class GenAI org, owning the 0→1 incubation and 1→n scaling of features like intelligent extraction, automated negotiation agents, and compliant RAG pipelines. Stay hands-on—prototyping LLMs, architecting MLOps, and guiding foundation model strategies—while fostering a culture of ruthless impact, speed, and experimentation. Collaborate with Product, Security, Legal, and partners to embed AI governance, optimizing for enterprise-grade security, cost, and performance in regulated workflows. Represent DocuSign externally via keynotes and OSS, attracting top AI talent to our innovation-driven culture. This hybrid role (minimum 2 days/week in-office) demands a leader who thrives in B2B SaaS, distills AI complexity for all audiences, and pivots fearlessly to win market leadership. Join us to make agreements AI-native and the world more agreeable.

Key Responsibilities

• Lead and grow a 100+ person GenAI organization of engineers and researchers, setting a high technical bar while fostering speed, experimentation, and accountability
• Drive the 0→1 and 1→n journey for GenAI features and agentic workflows central to DocuSign's Intelligent Agreement Management (IAM) strategy
• Translate technical AI breakthroughs into market-winning products for e-signature, CLM, and agreement automation
• Establish measurable PMF metrics, conduct fast-paced market experiments, and pivot strategies ruthlessly without ego
• Stay technically sharp by reviewing code, guiding architecture, and prototyping with modern LLM stacks
• Guide teams on foundation model selection, fine-tuning, retrieval pipelines (RAG), and robust governance including security, compliance, and risk controls
• Collaborate cross-functionally with Security, Legal, Product, and vendor partners to optimize for cost, performance, and enterprise compliance
• Represent DocuSign’s AI leadership internally and externally through keynotes, open-source contributions, and industry partnerships
• Attract, inspire, and challenge world-class AI talent to innovate in intelligent agreement management
• Influence product leaders to prioritize AI-driven features that unleash business-critical data from agreements

Required Qualifications

• 12+ years of experience in production software engineering, with 7+ years focused on ML and AI systems
• 10+ years of engineering leadership, including scaling and leading large, high-performing teams of 100+ engineers
• Proven track record as a founder, early technical leader, or principal engineer on an AI-first product achieving PMF (sustained growth, $5M+ ARR, or NPS >40)
• Deep expertise in modern LLM architectures, RAG, orchestration frameworks, and MLOps
• Fluency in at least two of: Python, Go, Rust, TypeScript, with hands-on MLOps experience
• Ability to distill complex AI concepts for technical and executive audiences
• Experience driving AI products from 0→1 incubation to market leadership in B2B environments

Preferred Qualifications

• Published contributor to AI research, open-source projects, or community forums
• Prior experience in B2B SaaS, workflow automation, or e-signature platforms
• Proven success scaling an AI team from incubation to significant organizational scope while maintaining technical credibility
• Advanced degree (Master’s/PhD) in Computer Science, Electrical Engineering, or equivalent experience
• Experience with agentic AI workflows and governance in regulated industries

Required Skills

• Leadership of large-scale engineering teams (100+)
• AI product development from 0→1 to PMF
• Modern LLM architectures and fine-tuning
• Retrieval-Augmented Generation (RAG)
• AI orchestration frameworks
• MLOps and production AI deployment
• Python, Go, Rust, or TypeScript programming
• Technical architecture design and code review
• Cross-functional collaboration with Legal/Security
• PMF metrics and market experimentation
• Talent attraction and team scaling
• AI governance, security, and compliance
• Public speaking and thought leadership
• Distilling complex AI for executives
• Agentic workflows and automation
• B2B SaaS product strategy

Benefits

• Competitive base salary with bonus eligibility based on company performance
• Restricted Stock Units (RSUs) as part of total compensation
• Paid Time Off including earned time off and company holidays
• Paid Parental Leave up to six months for birth, adoption, or foster care
• Comprehensive health benefits plans with 100% employer-paid options from day one
• Retirement plans with potential employer contributions
• Learning and Development programs including coaching, online courses, and education reimbursements
• Compassionate Care Leave for life-changing events

DocuSign is an Equal Opportunity Employer.