AI Transformation Director

Docusign • San Francisco, CA

15h • Hybrid

About The Position

As the AI Transformation Director, you will launch and scale AI agents and lead pilots. This is a senior activation role for someone who possesses deep strategic knowledge in GTM operations alongside expert-level fluency in modern LLMs, agentic orchestration, multi-agent governance, and enterprise systems integration. You will partner directly with C-suite and VP leaders across revenue and technology to drive operational velocity, superior SaaS unit economics, and sustainable competitive advantage.

Requirements

• Basic Experience in SaaS Sales operations, including designing sales compensation structures, managing quota allocation, and optimizing territory models in large-scale enterprise environments
• 15+ years of leadership and program delivery experience within Go-To-Market operations, Revenue Operations, and GTM strategy in enterprise SaaS environments
• 6+ years of specialized leadership in applied AI, machine learning automation, and operationalizing LLM agent applications
• Experience designing and scaling multi-workstream AI transformation roadmaps across complex, global GTM motions (Sales, CS, Marketing, Digital, CPQ, Billing)
• Experience with AI system architecture: multi-agent frameworks (LangGraph, AutoGen, CrewAI), LLM orchestration, RAG systems, vector DBs, and modern GTM data platforms (Snowflake, Reverse ETL, CDPs)
• Experience with core SaaS financial metrics (ARR, NRR, LTV, CAC payback, pipeline velocity)
• Experience presenting to, influencing, and aligning C-suite leadership on disruptive strategy, build vs. buy decisions, and technology investments
• Bachelor's Degree in Computer Science, Data Science, Engineering, or related technical/quantitative field

Nice To Haves

• Master's Degree / MBA in Data Science, Computer Science, or Management Information Systems
• Recognized industry thought leadership in AI for Revenue Operations, AI GTM Systems, or Agentic AI Workflows
• Expertise in leading build vs. buy evaluations for enterprise AI tools and negotiating key technology partnerships
• Track record of successfully executing multi-million dollar AI/digital transformation portfolios that deliver measurable financial ROI

Responsibilities

• Apply deep expertise in SaaS sales models, compensation design, quota setting, and territory optimization to integrate these domain-specific business rules into the logic of autonomous AI agents to ensure alignment with financial and operational objectives
• Focus on launching pilots, and globally scaling up pilots, drive rep enablement, track friction, and manage culture shift
• Own the end-to-end lifecycle of complex AI agent program rollout-from conceptualization and development to pilot design, rollout governance, rep enablement, friction tracking, and global scaling, and establish rigorous readiness gates and iteration frameworks
• Define target populations, pilot/control cohorts, sequencing, and rollout approach
• Track adoption by cohort and identify where performance is off track, provide RCA and action plan
• Mobilize FLMs, Enablement, Product, or Ops when adoption needs correction
• Determine when to iterate, scale, pause, or transition into run-the-business ownership
• Connect AI transformation directly to enterprise financial levers, maximizing LTV, shortening CAC payback periods, accelerating pipeline velocity, and lowering cost-to-serve
• Integrate SaaS sales models, compensation design, quota setting, and territory optimization rules into the logic of autonomous AI agents to ensure financial and operational alignment
• Serve as a trusted advisor to the CRO, CMO, CTO, and VP of Transformation, aligning AI capabilities with core growth metrics and driving change management across global revenue teams, and create the GVP/senior-leader cadence needed to drive accountability and adoption
• Establish enterprise-grade standards for Responsible AI, model drift monitoring, hallucination prevention, data security, and auditability across all automated revenue motions
• Connect AI transformation directly to enterprise financial levers, designing frameworks that maximize LTV, shorten CAC payback periods, accelerate funnel velocity, and lower cost-to-serve
• Define global patterns, reusable agent architectures, Agentic UI (AGUI) standards, and governance protocols to ensure rapid, secure scaling across all global GTM regions
• Direct cross-functional pods (Engineering, Applied AI, RevOps, Product, Data Platform) in deploying production-grade agentic platforms, custom RAG integrations, and autonomous action engines
• Establish enterprise-grade standards for Responsible AI, model drift monitoring, hallucination prevention, data security, and auditability across all automated revenue motions
• Evaluate continuously emerging market trends in LLM orchestration, multi-agent frameworks (LangGraph, AutoGen, CrewAI), and sales intelligence to keep the GTM tech stack at the market forefront
• Lead change management visions across global revenue teams, driving organizational readiness, culture shifts, and sustained adoption of autonomous AI systems
• Lead the end-to-end lifecycle of complex AI agent programs, from conceptualization and development to deployment and performance monitoring, and establish rigorous program management frameworks to oversee agent interdependencies, lifecycle governance, and integration, ensuring that autonomous systems consistently deliver reliable, high-value outcomes aligned with enterprise business goals
• Focus on designing and launching pilots, and globally scaling up pilots that pass the gate, drive rep enablement, track friction, and manage culture shift

Benefits

• Bonus: Sales personnel are eligible for variable incentive pay dependent on their achievement of pre-established sales goals. Non-Sales roles are eligible for a company bonus plan, which is calculated as a percentage of eligible wages and dependent on company performance.
• Stock: This role is eligible to receive Restricted Stock Units (RSUs).
• Paid Time Off: earned time off, as well as paid company holidays based on region
• Paid Parental Leave: take up to six months off with your child after birth, adoption or foster care placement
• Full Health Benefits Plans: options for 100% employer paid and minimum employee contribution health plans from day one of employment
• Retirement Plans: select retirement and pension programs with potential for employer contributions
• Learning and Development: options for coaching, online courses and education reimbursements
• Compassionate Care Leave: paid time off following the loss of a loved one and other life-changing events

What This Job Offers

• Job Type: Full-time
• Career Level: Senior