GTM Analytics & AI Measurement Director

Docusign is seeking a GTM Analytics & AI Measurement Director to assess whether and how AI initiatives improve go-to-market performance. The role will build measurement frameworks and analytical products, quantify impact and ROI, and advise leaders on investment and implementation decisions.

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: define what success looks like, establish pre-launch baselines, and set the KPI hierarchy from adoption to productivity to revenue outcomes (pipeline, win rate, cycle time, ACV, retention)
• Design rigorous evaluations for AI deployments, including A/B tests, staged rollouts with holdout groups, and quasi-experimental methods (difference-in-differences, synthetic control, propensity matching) where randomization isn't feasible
• Quantify the incremental impact and ROI of individual AI tools and of 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 that tracks adoption, usage depth, productivity gains, and revenue attribution across Sales, CS, Marketing, and Partner teams
• Develop forecasting and sizing models to estimate the value of proposed AI initiatives before investment, 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

Skills

• 15+ years of experience in data science, analytics, or quantitative strategy, with 5+ years in B2B SaaS GTM
• 12+ years of experience and a Master's degree and equivalent experience
• Experience with experimental design and causal inference (A/B testing, diff-in-diff, synthetic control, uplift modeling)
• Experience with SQL and Python (pandas, statsmodels, scikit-learn or similar); experience with Snowflake or similar cloud data warehouses
• Experience with GTM metrics: pipeline, conversion, win rate, sales cycle, NRR, churn, CAC payback, LTV
• Experience with LLM-based systems and how to evaluate them (output quality, failure modes, LLM-as-judge)
• Experience turning complex analysis into clear recommendations for executive audiences
• 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, ideally from pre-launch baseline through post-rollout ROI readout
• Hands-on experience with uplift modeling, heterogeneous treatment effects, or causal ML (e.g., EconML, DoWhy, 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 (e.g., LangGraph, CrewAI, AutoGen, Azure AI Foundry) and prompt design, enough to partner credibly with AI builders and design the right instrumentation
• 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 (e.g., Tableau, Looker, 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 (CRO, CFO, 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 holding a high bar for statistical rigor

Benefits

• Non-Sales roles are eligible for a company bonus plan, which is calculated as a percentage of eligible wages and dependent on company performance.
• 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
• Hybrid: Employee divides their time between in-office and remote work. Access to an office location is required. (Frequency: Minimum 2 days per week; may vary by team but will be weekly in-office expectation)

Company Overview

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