Insights & Operations (Multiple: People & Foundation Focus)

About Gusto

Gusto is a modern, online people platform that helps small businesses take care of their teams. On top of full-service payroll, Gusto offers health insurance, 401(k)s, expert HR, and team management tools. Today, Gusto offices in Denver, San Francisco, and New York serve more than 400,000 businesses nationwide.

Our mission is to create a world where work empowers a better life, and it starts right here at Gusto. That’s why we’re committed to building a collaborative and inclusive workplace, both physically and virtually. Learn more about our Total Rewards philosophy.

About the Role:

We are seeking two versatile Insights & Operations Partners (Gusto’s BizOps/Chief of Staff function) with a passion for company building and problem-solving. These roles are critical to driving operational excellence, strategic initiatives, and cross-functional collaboration across key organizational pillars. We are looking for adaptable individuals with strong leadership, analytical, and communication skills to join our dynamic team. Prior experience in People-related functions, cross-functional program management, or strategic communications is a plus.

Current Openings - Apply to Shape Either Path:

• Chief of Staff, People Team: Partner directly with the future Chief People Officer and their leadership team to manage operations, strategic priorities, and cross-functional people initiatives. This role will collaborate closely with People team directors and cross-organizational partners to identify, develop, and implement impactful people strategies with a business-builder mindset.
• Foundation Insights and Operations: Collaborate with leadership across People, Finance, Legal & Compliance, and IT to enhance employee productivity, inspiration, and company-wide progress. This role will spearhead internal communications (All Hands, newsletters), drive change management, and contribute to company-wide planning and program management, requiring comfort in navigating strategic and employee-level perspectives.

Here’s what you’ll do day-to-day:

• Strategic and Operational Support: Provide high-level support to leadership, managing day-to-day operations, complex project management, and strategic planning.
• Cross-functional Program Management: Own and drive a portfolio of high-impact, cross-functional initiatives, partnering with teams like Engineering, Product, Design, and GTM.
• Compelling Communication & Content Creation: Develop clear and influential communication materials, including presentations, meeting facilitation, and status updates, tailored to diverse audiences.
• Build Cross-functional Partnerships: Cultivate strong relationships with stakeholders across various departments to ensure seamless collaboration and alignment on company-wide objectives.
• Drive Process Improvement: Identify and implement opportunities to optimize team processes and workflows, increasing efficiency and overall effectiveness.

This is a unique opportunity to significantly contribute to Gusto's growth and impact. You will be empowered by Gusto’s Deputy Chief of Staff, joining a world-class Insights and Operations team that balances strategic thinking, operational rigor, and impactful special projects. This role is envisioned as a 24-month stepping stone, offering strong potential for rotation into new challenges or operational leadership.

We’re looking for a builder and a force multiplier who thrives in ambiguity and excels at connecting disparate pieces. Does this sound like you? Read on!

Here’s what we're looking for:

• 5+ years of experience in bizops, consulting, and/or program management, preferably in a high-growth technology startup environment or a related field demonstrating cross-functional impact.
• Particularly for the Chief of Staff role, strong preference for 2+ years in an HR function or Internal Comms
• Exceptional organizational skills with the ability to manage multiple priorities and deadlines in a fast-paced environment.
• Proficiency in project management methodologies and tools.
• A passion for operational excellence and a desire to make a significant impact across Gusto’s teams and employee experience.
• Excellent written and verbal communication and interpersonal skills, with the ability to influence stakeholders at all levels.
• Ability to navigate ambiguity and switch between strategic and tactical thinking seamlessly.
• Strong problem-solving and analytical skills, with the ability to quickly learn new domains.
• Deep empathy and a commitment to understanding and improving the employee experience.
• Grit, hustle, and the ability to flex into problems at all altitudes and across different functional areas.
• The ability to manage complex projects, maintain clear communication flow, and connect strategic vision to operational execution.
• A deep passion for helping others and building a thriving company culture.