Principal Product Operations Manager, Benefits

About the role

Gusto is seeking a strategic leader to establish the operational foundation for a new benefits product. You will bridge the gap between product development and customer service by using data, human judgment, and AI tools to drive business strategy.

Key facts

What you'll do

• Collaborate with Engineering, Design, Product Management, and Customer Experience teams to integrate service strategy into the product lifecycle.
• Act as a primary point of contact for internal and external feedback to ensure service requirements influence company-wide decisions.
• Manage product launches by coordinating between product and support teams to ensure operational readiness.
• Provide actionable recommendations based on qualitative and quantitative data to refine service and product roadmaps.
• Lead cross-functional initiatives to improve service capabilities.
• Use AI tools to prototype service solutions, monitor launch performance, and automate operational workflows.
• Build AI fluency within the team to accelerate data synthesis and reduce manual tasks.

Requirements

• 10+ years of professional experience in business operations, strategy, product operations, or consulting at high-growth startups.
• Background in scaling service models for SaaS products, including managing product betas and new product incubation.
• Ability to navigate ambiguity and make decisions with incomplete information.
• Experience influencing senior leadership across Product and Customer Experience departments.
• Strong data literacy with the ability to translate complex signals into business strategy.
• Demonstrated AI fluency, including using AI to identify automation opportunities and synthesize data.
• Excellent communication skills for both technical and non-technical stakeholders.

Nice to have

• Experience prototyping with AI tools such as Claude, Cursor, or Codex.
• Background in service design or service blueprinting.
• Experience in the benefits, health insurance, or PEO sectors.
• Experience incubating new products within regulated industries.

Skills & tools

• AI-assisted analysis and synthesis
• Service design and blueprinting
• Cross-functional stakeholder management
• Data-driven strategy and roadmapping

Practical notes

• Compensation: $167,000 to $217,000 per year for New York.
• Hybrid work: Employees are expected to work from the office 2-3 days per week.
• Benefits: Includes base pay and equity in the form of RSUs.
• AI expectation: All employees are expected to actively use and grow their fluency in AI tools relevant to their role.