Senior Director, Head of Data Analytics & Insights

PayPal•San Jose, CA

About The Position

Define and champion the enterprise-wide analytics vision and strategy. Influence executive leadership on leveraging analytics for business transformation. Oversee governance, compliance, and scalability of analytics solutions. Drive cross-functional alignment to embed analytics into organizational culture. Measure and communicate the business impact of analytics initiatives at the executive level. Establish a new operating model for insight consumption, one that includes proactive anomaly detection, narrative-driven reporting, and natural language insights delivered directly into tools like Slack and email. Lead the transformation of our analytics operating model from static dashboards to a layered system of trusted data, shared metrics, and intelligent insight delivery. Build and enforce a dashboard hierarchy (single → double → triple click) that ties every metric to strategic OKRs and downstream actionability. Help guide the rationalization of dashboards and reporting assets to promote clarity and efficient insight consumption Elevate our OKR reporting practice, initially through refined scripting, source alignment, and PowerPoint automation, while architecting the shift to dynamic BI delivery (e.g., Looker Pulse, Salesforce CRMA, ReactJS, Slack-native reporting, AI-generated voiceovers). Experience contributing to data governance practices and supporting consistent metric definitions to ensure accuracy and reliability of core business reporting. Embed insights into the flow of work by partnering with LLM engineers and platform leads to drive Slack, email, and executive summary integrations. Oversee three key pillars: Merchant and Commercial Analytics: responsible for end-to-end analysis of transaction activity, payment volumes, revenue, and margin across segments, channels, and products, delivering insight into business performance, partner impact, and monetization levers that drive growth and profitability. Pipeline and Forecast Management: responsible for accurate pipeline and forecast aggregation from multiple data sources and platforms. Provide data backed insights on conversion trends, productivity and other KPIs. Build analytics models to enhance accuracy of forecasts for New Sales and Portfolio performance. Partner cross-functionally with Sales, channel, compensation, business ops, finance, data science and engineering, and AI platform teams to influence tool adoption and insight accessibility. Be a cultural driver for how we use data: shifting the organization away from “pulling dashboards” to “being alerted when it matters.”

Requirements

12+ years relevant experience and a Bachelor's degree OR Any equivalent combination of education and experience.
Ability to serve as a strategic thought partner to senior Global Markets leadership, providing clear, data-driven guidance that informs decision-making
15+ years of experience in business analytics, data strategy, or data transformation roles, with a proven ability to lead through ambiguity.
Familiarity with the Google Analytics product suite (GCP, Looker Studio Pro / Looker Core, Tableau, BQ, etc.) as well as integrations with various LLMs or other productivity tools (i.e. Slack, Teams, etc.) and how they support semantic modeling, real-time dashboards, and narrative reporting.
Familiarity with Salesforce (ideally) or other CRM systems and how to make these CRM systems work well within a broader data environment (e.g., connecting Salesforce to GCP)
Strong executive communication and storytelling skills, you can translate noise into clarity for stakeholders at every level.
Experience leading diverse multi-functional teams across product analytics, GTM/commercial analytics, and infrastructure liaison roles that span across time zones.
Demonstrated ability to evolve how insights are consumed—from manual PowerPoint decks to live dashboards, Slack alerts, and AI-generated summaries.
Comfortable collaborating with LLM engineers, data scientists, and platform teams, even if not building models directly.
High operational rigor: you bring structure and focus to dashboard sprawl, redundant queries, and fuzzy stakeholder asks.

Nice To Haves

Experience leading analytics or reporting teams in fintech, payments, or enterprise-scale SaaS environments.
Familiarity with OKR methodologies and executive-level reporting cycles.
Exposure to AI-enhanced BI tools such as Looker Core, Looker Studio Pro, with GPT integration.
Experience working with distributed analytics teams, including offshore (e.g., India) collaboration models.

Responsibilities

Define and champion the enterprise-wide analytics vision and strategy.
Influence executive leadership on leveraging analytics for business transformation.
Oversee governance, compliance, and scalability of analytics solutions.
Drive cross-functional alignment to embed analytics into organizational culture.
Measure and communicate the business impact of analytics initiatives at the executive level.
Establish a new operating model for insight consumption
Lead the transformation of our analytics operating model from static dashboards to a layered system of trusted data, shared metrics, and intelligent insight delivery.
Build and enforce a dashboard hierarchy (single → double → triple click) that ties every metric to strategic OKRs and downstream actionability.
Help guide the rationalization of dashboards and reporting assets to promote clarity and efficient insight consumption
Elevate our OKR reporting practice
Experience contributing to data governance practices and supporting consistent metric definitions to ensure accuracy and reliability of core business reporting.
Embed insights into the flow of work by partnering with LLM engineers and platform leads to drive Slack, email, and executive summary integrations.
Oversee three key pillars: Merchant and Commercial Analytics
Pipeline and Forecast Management
Partner cross-functionally with Sales, channel, compensation, business ops, finance, data science and engineering, and AI platform teams to influence tool adoption and insight accessibility.
Be a cultural driver for how we use data: shifting the organization away from “pulling dashboards” to “being alerted when it matters.”