GTM Analytics & AI Measurement Director

Docusign • San Francisco, CA

4h • Hybrid

About The Position

Docusign is seeking a GTM Analytics & AI Measurement Director to determine whether, where, and to what extent AI is improving the go-to-market organization. The role will establish measurement frameworks for GTM AI initiatives, from setting baselines and designing evaluations before launch to quantifying incremental impact on pipeline, win rates, sales cycle, retention, and productivity after rollout. It will use controlled experiments, holdout designs, and causal inference to distinguish AI-driven impact from other factors affecting GTM performance.

The director will partner with AI Product, RevOps, Data Engineering, and IT teams to ensure new AI tools are instrumented from day one, and will work with GTM leaders to translate findings into decisions to scale, improve, or retire initiatives. Beyond AI measurement, the position will lead development of analytic products that inform GTM decisions, using experimental and causal rigor. This is an individual contributor role reporting to the VP of Growth Strategy & Operations.

The position is hybrid, with a weekly in-office expectation of at least two days per week. The role is eligible for a company bonus plan and Restricted Stock Units. Benefits include paid time off and holidays, paid parental leave, health plans, retirement and pension programs, learning and development options, education reimbursements, and compassionate care leave.

Requirements

• 15+ years of experience in data science, analytics, or quantitative strategy, including 5+ years in B2B SaaS go-to-market.
• 12+ years of experience and a Master's degree and equivalent experience.
• Experience with experimental design and causal inference, including A/B testing, difference-in-differences, synthetic control, and uplift modeling.
• Experience with SQL and Python (pandas, statsmodels, scikit-learn, or similar), and Snowflake or a similar cloud data warehouse.
• Experience with GTM metrics including pipeline, conversion, win rate, sales cycle, NRR, churn, CAC payback, and LTV.
• Experience with LLM-based systems and evaluation methods, including output quality, failure modes, and LLM-as-judge.
• Experience translating complex analysis into clear recommendations for executive audiences.

Nice To Haves

• Advanced degree (MS or PhD) in Statistics, Economics, Data Science, Operations Research, or a related quantitative field.
• Experience measuring the impact of AI, automation, or sales productivity tools in a GTM organization, from pre-launch baseline through post-rollout ROI readout.
• Hands-on experience with uplift modeling, heterogeneous treatment effects, or causal ML tools such as EconML, DoWhy, or CausalML.
• Experience evaluating LLM-based systems, including output quality scoring, LLM-as-judge frameworks, and linking model quality to business outcomes.
• Working knowledge of agent frameworks and AI workflows such as LangGraph, CrewAI, AutoGen, or Azure AI Foundry, and prompt design.
• Familiarity with GTM data sources such as Salesforce, Gong or other conversation intelligence platforms, Clari, and product usage telemetry.
• Experience building executive-facing scorecards and dashboards using tools such as Tableau, Looker, or Sigma that tie adoption metrics to revenue outcomes.
• Background in forecasting or investment sizing models used to prioritize a roadmap or allocate budget.
• Track record of influencing senior leaders, including CROs, CFOs, and GTM VPs, to scale, change, or stop programs based on analytical findings.
• Comfort working in a fast-moving environment that values speed and experimentation while maintaining a high bar for statistical rigor.

Responsibilities

• Build core data and analytical products to serve GTM motions in partnership with internal IT teams.
• Own the measurement strategy for GTM AI initiatives, defining success, establishing pre-launch baselines, and setting KPI hierarchies from adoption to productivity to revenue outcomes.
• Design rigorous evaluations of AI deployments, including A/B tests, staged rollouts with holdout groups, and quasi-experimental methods when randomization is not feasible.
• Quantify the incremental impact and ROI of individual AI tools and the overall AI portfolio, separating AI-driven lift from seasonality, territory changes, pricing, and other confounders.
• Build and maintain an impact scorecard for GTM leadership tracking adoption, usage depth, productivity gains, and revenue attribution across Sales, Customer Success, Marketing, and Partner teams.
• Develop forecasting and sizing models to estimate the value of proposed AI initiatives and help prioritize the roadmap based on expected business impact.
• Make data-driven recommendations to scale, iterate on, or sunset AI initiatives, and present findings and trade-offs to the CRO, CFO, and GTM leadership.
• Ensure data instrumentation is incorporated from day one by partnering with AI Product, Data Engineering, IT, and RevOps teams.

Benefits

• Company bonus plan for non-sales roles, calculated as a percentage of eligible wages and dependent on company performance.
• Restricted Stock Units (RSUs).
• Paid time off and paid company holidays based on region.
• Up to six months of paid parental leave after birth, adoption, or foster care placement.
• Health benefit plans, including options that are 100% employer paid and plans with minimum employee contributions, available from day one.
• Retirement and pension programs, with potential employer contributions.
• Learning and development options, including coaching, online courses, and education reimbursements.
• Paid compassionate care leave following the loss of a loved one and other life-changing events.

What This Job Offers

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