Principal Product Manager, Reporting

By the Numbers:

• Named #1 best software for small business of 2024 by G2
• 2,700+ employees in the United States, Canada, Mexico, and Turkiye and growing
• Over $500M in annual revenue
• The SMB market is large (and growing!) with huge opportunities for Gusto to make an incredible impact for SMBs
• There are 6.2M employers in the US, 98% have fewer than 100 employees (1)
• 550,000 new businesses are created each year in the US (1)

What Product Management is like at Gusto:

• We’re looking for high-autonomy, entrepreneurial Product Managers to come build high-impact solutions for small businesses and their employees. We believe in high-ownership Product Managers who operate like business owners - owning an entire roadmap end to end, and shaping the product from strategy setting through the nitty gritty execution details.
• Our Product team is lean, which means you’ll have a high degree of impact and ownership.
• We’re here to serve small and medium businesses. Gusto has a strong mission-driven culture, and we care deeply about lifting up these business owners.

About the Team:

The Reporting team sits within the Core Experience organization and owns one of the most important experiences in the product: giving small business owners clear visibility into data about their payroll, benefits, and spend.

We're at an inflection point. The back-end infrastructure that makes AI-native reporting possible is taking shape and our next chapter is delivering those capabilities to customers in ways that are genuinely useful: fixing the basics, enabling AI-powered answers, and building a reporting experience that meets customers where they are. This PM will drive that work.

Here’s what you’ll do day-to-day:

• Drive the strategy and roadmap end-to-end. In close collaboration with your key partners in engineering, design and data, you'll set the strategic direction for Reporting and own the roadmap across all surfaces (web, mobile, and embedded experiences).
• Define the vision. You'll anchor the team and stakeholders around a clear, compelling vision for how traditional reports and AI-driven answers work together over time—one that connects to Gusto's broader AI transformation and gives everyone a coherent picture of where we're going.
• Ship customer-facing value every cycle. You'll hold yourself and the team accountable for delivering real improvements that customers notice and use, balancing fixing the basics and with bigger, future swings.
• Partner with other product teams on real use cases. You'll work hand-in-hand with app teams like Pay and Benefits to deliver reporting capabilities end-to-end through real customer journeys, proving the infrastructure works and surfacing what needs to get better.
• Drive the data infrastructure forward. You'll bring rigor and clear prioritization to the ongoing data migration work, making sure back-end progress translates into customer-facing capability on a timeline that matters.
• Set up and track the right metrics. You'll define leading indicators for reporting quality and customer satisfaction, use data to drive continuous improvement, and communicate progress honestly to stakeholders.
• Raise the bar on collaboration. You'll work closely with engineering, design, and data partners to build a team that operates with speed and quality. You'll treat partner product teams as customers, giving them a clear path forward, answering their questions, and making it easy for them to build on what you've created.

Here’s what we're looking for:

• Customer obsession. You understand how small businesses use data to make decisions—questions they're actually trying to answer. You stay close to customers through direct research and indirect feedback loops (CX, support tickets, usage data), and you use what you learn to sharpen your priorities constantly.
• Real AI fluency. You use AI tools in your own daily work for synthesis, ideation, analysis and prototyping ideas. You've built AI-powered product features or worked closely enough on them that you understand what good looks. You have a genuine point of view on what AI-native reporting means and where it's going.
• Bias toward shipping. The Reporting team has strong foundations and the job now is to deliver. You set short, clear milestones. You move fast on near-term customer improvements while keeping the longer-term vision clear. You use staged rollouts and learning plans as a matter of course. You don't let platform work crowd out customer-facing progress because you hold both at once, and you know when to push and when to sequence.
• Technical fluency in data. You're comfortable in conversations about data infrastructure: pipelines, data models, APIs, trade-offs between migration approaches. You don't need to write the SQL, but you understand what the engineers are building and why it matters for customers. You've worked on data products where back-end complexity is real and the front-end has to make it feel simple.
• Cross-functional partnership. Reporting sits at the intersection of almost every team at Gusto because App teams depend on our platform to surface data to their customers. You treat partner teams as one of your most important customer groups—you understand their needs, you give them a clear path forward, and you make it easy to build on what you've created.
• Clear, direct communication. You can tell a simple, compelling story about a complex system. You give stakeholders honest, specific progress updates. You escalate when something is off track and you come with a plan. You make it easy for people at any level to understand where Reporting is going and why it matters.
• Strategic clarity. You hold the near-term and long-term at the same time without letting one crowd out the other. You build a multi-year vision that connects to Gusto's AI transformation, and you sequence the work so that every cycle delivers meaningful customer value on the path to that vision. You know when to go narrow and when to open up scope, and you make that call quickly.

The experience we're looking for:

• 8+ years of hands-on product management experience
• At least some of that time spent on data products, analytics tools, reporting platforms, or infrastructure products where internal or external customers were a primary consideration
• Demonstrated track record of shipping customer-facing improvements at pace—things customers notice and use
• Experience with AI-powered product features or data experiences: building them, scoping them, evaluating them, or working closely enough on them that you understand the operational reality
• Strong cross-functional collaboration skills with engineering, design, and data partners
• Experience in environments where back-end platform maturity and front-end customer experience have to be balanced and advanced simultaneously

If you don't think you meet all of the criteria a