Gusto is hiring a

Principal Technical Program Manager, Data

Toronto, Canada
Remote

 


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 300,000 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 Team:

The mission of our Data Team is to create a trusted data ecosystem that fuels innovation. We have projects underway and on our roadmap that touch upon each part of this mission: improving trust in our data through proactive data governance and a significant overhaul of our data warehouse; improving our data ecosystem through enhancing and potentially migrating to more effective data tools; and fueling innovation by building net-new data capabilities that unlock performance and customer experiences such as near real-time data processing. 

Our Data Team comprises ~80+ data practitioners with skills in data platform engineering, analytics engineering, data analysis and reporting, decision science, machine learning, ML Ops, and GenAI. This Technical Program Manager role would add a critical skill set in data product development, enabling our team to build more proactive data solutions to drive our business and create great customer experiences. 

About the Role:

As a Principal Technical Program Manager in the Data organization, you will lead high-impact, cross-functional programs that drive the strategic vision of Gusto’s Data initiatives. In this role, you will collaborate with key business and technical stakeholders to plan, execute, and deliver programs that optimize data systems and governance, advance Gusto analytics maturation and data product capabilities, and expedite the ability for Gusto leadership to make data-informed decisions. You will not only lead programs but also help shape data strategy, ready the organization for technical change, and ensure alignment across multiple cross-functional teams.

As a critical partner to senior leadership, you will leverage both your technical expertise and program management acumen to influence decisions that support the data needs of the entire organization. You will work cross-functionally with data practitioners, product managers, and business leaders across the organization to ensure data programs are executed with precision and clarity. Your ability to manage complexity, balance technical depth with business outcomes, and foster cross-team collaboration will set you apart as a leader in this role.

By joining the Data Leadership team, you will play a key role in the overall data strategy at Gusto, leading efforts that impact data architecture, engineering efficiency, and product delivery. You will focus on bringing organizational rigor to large-scale data initiatives, while supporting teams in solving complex challenges with clear roadmaps, priorities, and strategic guidance.

Here’s What You’ll Do Day-to-Day:

  • Lead and drive complex, cross-functional data programs by developing and managing detailed program roadmaps, project plans, and timelines, ensuring alignment between data teams, product and engineering partners, and business stakeholders.
  • Partner with the Head of Data and senior leadership to define the data strategy, align on priorities, and report on progress across the organization.
  • Oversee the implementation of critical data initiatives such as Amplitude re-implementation, optimizing CDP platforms like Tealium, and improving tracking across web and mobile applications.
  • Collaborate with product managers, data engineers, and analysts to deliver high-quality, scalable data assets that meet organizational and customer needs.
  • Establish and continuously improve operational procedures to enhance team productivity, streamline communication, and drive program success.
  • Serve as a thought partner for executives, providing strategic insights and recommendations for data programs, including resource allocation, risk management, and technical considerations.
  • Design and implement frameworks that ensure readiness for data-driven changes across the business, building scalable solutions to prepare teams for regular data updates and launches.
  • Build strong relationships with engineering, product, and business stakeholders to ensure seamless delivery of data programs that have wide-reaching impacts.
  • Help build Data’s brand within Gusto by creating company-wide communication mechanisms around the work we do
  • Potential opportunity to lead a small team of TPMs in the future.

Minimum Requirements:

  • 8+ years of experience in technical program management at software companies with demonstrated success leading large-scale, cross-functional programs.
  • Deep experience with data engineering processes, architecture, and workflows, including a strong understanding of data platforms, cloud infrastructures, and ETL pipelines.
  • Expertise in Agile methodologies, with a solid background in managing scrum teams, product backlogs, and roadmaps using JIRA or similar tools.
  • Proven ability to communicate effectively across both technical and non-technical audiences, including executive leadership.
  • Strong analytical, problem-solving, and systems-thinking skills with the ability to evaluate complex issues and propose data-driven solutions.

Nice to have:

  • Extensive experience implementing tracking solutions for web and mobile apps, as well as familiarity with customer data platforms (e.g., Tealium, Amplitude).
  • 3-5 years of experience managing and mentoring teams, with a proven ability to lead and develop individual contributors.
  • Proficiency in SQL, with hands-on experience in querying databases like Redshift, Snowflake, or similar platforms.

This role is ideal for a highly strategic, technically adept leader who can navigate the intersection of data, product, and business needs to drive organizational success.

At Gusto, we strive to provide rewards that empower employees to achieve their financial and personal goals. We offer competitive compensation packages with a strong emphasis on equity-based compensation (ownership in Gusto). To learn more about Gusto’s compensation philosophy and benefits offerings, please view our Total Rewards Approach page.

Our cash compensation amount for this role is targeted at $170,000-$210,000/year in Denver, Chicago, and Atlanta, $184,000/year - $228,000 in Los Angeles, and $199,000-$247,000/year for Seattle, San Francisco and New York. Final offer amounts are determined by multiple factors including candidate experience and expertise and may vary from the amounts listed above.


Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees who are based in those locations will be expected to work from the office on designated days approximately 2-3 days per week (or more depending on role). The same office expectations apply to all Symmetry roles, Gusto's subsidiary, whose physical office is in Scottsdale.

Note: The San Francisco office expectations encompass both the San Francisco and San Jose metro areas. 

When approved to work from a location other than a Gusto office, a secure, reliable, and consistent internet connection is required.


Our customers come from all walks of life and so do we. We hire great people from a wide variety of backgrounds, not just because it's the right thing to do, but because it makes our company stronger. If you share our values and our enthusiasm for small businesses, you will find a home at Gusto. 

Gusto is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex (including pregnancy, childbirth, or related medical conditions), marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity or expression, sexual orientation, or other applicable legally protected characteristic. Gusto considers qualified applicants with criminal histories, consistent with applicable federal, state and local law. Gusto is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. We want to see our candidates perform to the best of their ability. If you require a medical or religious accommodation at any time throughout your candidate journey, please fill out this form and a member of our team will get in touch with you.

Gusto takes security and protection of your personal information very seriously. Please review our Fraudulent Activity Disclaimer.

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