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About the Role

This role operates at the enterprise level, partnering closely with senior leaders to strengthen how the company plans, decides, and executes. The focus is on translating strategy into effective operating mechanisms, improving decision quality and follow-through, and creating visibility across priorities, tradeoffs, and outcomes. This is not a people leadership, program management, or functional ownership role; instead, the role enables leaders to operate more effectively at scale through influence, structure, and clarity.

Responsibilities

Translate annual and multi-year strategic priorities into clear operating plans, milestones, and review cadences.
Structure executive and leadership discussions, including OKR and priority-setting forums.
Own and continuously improve the company’s enterprise operating rhythm, including executive planning sessions, leadership offsites, All Hands, and business reviews.
Maintain enterprise-level visibility into critical initiatives, dependencies, risks, and outcomes.
Design and maintain KPI frameworks, dashboards, and reporting mechanisms.
Develop executive-ready insights, recommendations, and materials for senior leadership.
Contribute to competitive and market analyses.
Use AI tools to produce first-pass drafts of executive materials and rapid competitive scans.
Build simple, repeatable prompt/agent workflows to standardize outputs and reduce cycle time for exec cadence.

Requirements

Proven ability to operate independently in highly ambiguous environments with limited precedent.
Demonstrated experience partnering directly with senior executives and influencing outcomes without formal authority.
Strong executive presence with the ability to adapt communication style and persuade diverse stakeholders.
Experience shaping enterprise operating models, planning processes, or decision frameworks.
Highly analytical, with the ability to synthesize complex information into clear, executive-ready insights.
Motivated by improving how an organization runs rather than owning a single function or team.
Experience utilizing generative AI tools (e.g., Claude, ChatGPT, Bard) for content creation and workflow automation in a professional setting.

Skills

Generative AI tools (e.g., Claude, ChatGPT, Bard)
AI prompt libraries/“skills” and lightweight agent workflows
Disciplined AI usage: no sensitive data leakage, validates key claims, and cites/links sources

Location

San Mateo, California

Work Type

Full-time

Experience Level

7+ years of experience in Strategy & Operations, Business Operations, Consulting, Corporate Strategy, or a Chief of Staff-adjacent role; 8–10+ years preferred.

Education Level

Bachelor's Degree required

Salary/Compensations

USD $72,090.00 - $123,876.00 annually

Benefits

Discretionary bonus
Health insurance
Vision insurance
Dental insurance
401k matching
PTO
Volunteer Time Off (VTO)

About the Company

Rakuten International is a division of Rakuten Group, Inc., a Japanese global technology leader in services that empower individuals, communities, businesses and society.
Headquartered in San Mateo, California with more than 4,000 employees worldwide, the Rakuten International business portfolio includes market leaders in e-commerce, digital marketing, advertising, communications and entertainment.
We create products and services that provide exceptional value by aligning members and the businesses that want to engage them in a shared community.
Rakuten is the most rewarding way to shop, giving millions of members Cash Back when they buy from their favorite brands.
As a leading shopping platform, Rakuten partners with thousands of top brands across apparel, beauty and wellness, grocery, travel, on-demand services, subscriptions, and dining, helping members save on everyday purchases.
Since 1999, Rakuten members have earned more than $4.6 billion in Cash Back, making it the largest Cash Back platform of its kind.
Learn more at Rakuten.com.

Equal Opportunity

Rakuten provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type. Rakuten considers applicants for employment without regard to race, color, religion, age, sex, national origin, disability status, genetic information, protected veteran status, sexual orientation, gender, gender identity or expression, or any other characteristic protected by federal, state, provincial or local laws.