Director, Head of Analytics & Transformation, SMB (San Jose)

The Company

PayPal has been revolutionizing commerce globally for more than 25 years. Creating innovative experiences that make moving money, selling, and shopping simple, personalized, and secure, PayPal empowers consumers and businesses in approximately 200 markets to join and thrive in the global economy.

We operate a global, two-sided network at scale that connects hundreds of millions of merchants and consumers. We help merchants and consumers connect, transact, and complete payments, whether they are online or in person. PayPal is more than a connection to third-party payment networks. We provide proprietary payment solutions accepted by merchants that enable the completion of payments on our platform on behalf of our customers.

We offer our customers the flexibility to use their accounts to purchase and receive payments for goods and services, as well as the ability to transfer and withdraw funds. We enable consumers to exchange funds more safely with merchants using a variety of funding sources, which may include a bank account, a PayPal or Venmo account balance, PayPal and Venmo branded credit products, a credit card, a debit card, certain cryptocurrencies, or other stored value products such as gift cards, and eligible credit card rewards. Our PayPal, Venmo, and Xoom products also make it safer and simpler for friends and family to transfer funds to each other. We offer merchants an end-to-end payments solution that provides authorization and settlement capabilities, as well as instant access to funds and payouts. We also help merchants connect with their customers, process exchanges and returns, and manage risk. We enable consumers to engage in cross-border shopping and merchants to extend their global reach while reducing the complexity and friction involved in enabling cross-border trade.

Our beliefs are the foundation for how we conduct business every day. We live each day guided by our core values of Inclusion, Innovation, Collaboration, and Wellness. Together, our values ensure that we work together as one global team with our customers at the center of everything we do and they push us to ensure we take care of ourselves, each other, and our communities.

Job Summary:

At PayPal, we are reinventing the way data and insights power the business decisions that drive growth for millions of small and medium-sized businesses (SMBs). Were seeking a Director, Head of Analytics & Transformation to lead a multi-year evolution of our analytics function within the SMB divisionfrom fragmented dashboards and manual reporting to a future where insights are automated, intelligent, and embedded directly into how decisions are made.

This is not a traditional analytics leadership role. You will both lay out the future vision of the analytics operating model while managing and standardizing the day to day operations of a large analytics team.

Establish a new operating model for insight consumptionone that includes proactive anomaly detection, narrative-driven reporting, and natural language insights delivered directly into tools like Slack and email.

Lead the SMB analytics team composed of analytics and data science professionals structured across several podsensuring that stakeholders like product managers and commercial leads, all the way up to business heads at the EVP level have access to high-quality, actionable insights that reflect the true state of the business.

Oversee and deliver executive-grade OKR tracking and reporting in the short term, supporting high-visibility business rhythms with precision and speed. Understanding the business is just as important as your technical chops.

Job Description:

What Youll Own

• 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.

• Elevate our OKR reporting practice initially through refined scripting, source alignment, and PowerPoint automationwhile architecting the long-term shift to dynamic BI delivery (e.g., Looker Pulse, Slack-native reporting, AI-generated voiceovers).

• 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:

• Product Analytics: responsible for defining and owning core product funnels (acquisition, activation, retention); partnering closely with Product and Engineering to identify drop-off drivers, design rigorous experimentation frameworks, and generate data-backed insights that inform roadmap prioritization, optimize conversion, and deepen understanding of user behavior across segments and journey

• Commercial Analytics : responsible for end-to-end analysis of transaction activity, payment volumes, revenue, and margin across segments, channels, and productsdelivering insight into business performance, partner impact, and monetization levers that drive growth and profitability .

• Data & Analytics Enablement: Senior-level liaison into PayPals broader data infrastructure, tooling, and governance ecosystem.

• Partner cross-functionally with business ops, finance, data 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.

What Were Looking For

• 10+ years of experience in business analytics, data strategy, or data transformation roles, with a proven ability to lead through ambiguity.

• F amiliarity with the Google Analytics product suite (GCP, Looker Studio Pro / Looker Core, 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.

• Strong executive communication and storytelling skills you can translate noise into clarity for stakeholders at every level.

• Experience leading multi-functional teams across product analytics, GTM/commercial analytics, and infrastructure liaison roles .

• Demonstrated ability to evolve how insights are consumedfrom 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.

Preferred Qualification:

Preferred Qualifications

• 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.

Why This Role Matters

This is a chance to fundamentally change how data drives decisions at one of the most impactful financial technology companies in the world. Youll own both the vision and the execution path : from todays reporting environment to tomorrows intelligent, contextual, and automated analytics experience.

If youre a builder, operator, and storyteller with strong data science underpinning, whos excited by the challenge of scaling and modernizing a full stack data and analytics function in a global enterprise wed love to hear from you.

Subsidiary:

PayPal

Travel Percent:

0

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PayPal is committed to fair and equitable compensation practices.

Actual Compensation is based on various factors including but not limited to work location, and relevant skills and experience.

The total compensation for this practice may include an annual performance bonus (or other incentive compensation, as applicable), equity, and medical, dental, vision, and other benefits. For more information, visit .

The US national annual pay range for this role is $137,500 to $236,500

PayPal does not charge candidates any fees for courses, applications, resume reviews, interviews, background checks, or onboarding. Any such request is a red flag and likely part of a scam. To learn more about how to identify and avoid recruitment fraud please visit .

For the majority of employees, PayPal's balanced hybrid work model offers 3 days in the office for effective in-person collaboration and 2 days at your choice of either the PayPal office or your home workspace, ensuring that you equally have the benefits and conveniences of both locations.

Our Benefits:

At PayPal, were committed to building an equitable and inclusive global economy. And we cant do this without our most important assetyou. Thats why we offer benefits to help you thrive in every stage of life. We champion your financial, physical, and mental health by offering valuable benefits and resources to help you care for the whol]]> <