At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff , payroll, health insurance, 401(k)s, and HR , so owners can focus on their craft and their customers.

With teams in Denver, San Francisco, and New York, we support more than 400,000 small businesses nationwide and are building a workplace that reflects the people we serve. All full-time employees receive competitive base pay, benefits, and equity (RSUs) , because everyone who helps build Gusto should share in its success. Offer amounts are determined by role, level, and location. Learn more about our Total Rewards philosophy.

AI is a fundamental part of how work gets done at Gusto. We expect all team members to actively engage with AI tools relevant to their role and grow their fluency as the technology evolves. AI experience requirements vary by role and will be assessed during the interview process.

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:

• Our Product team is lean, which means you’ll have a high degree of impact and ownership. We believe in smaller, empowered teams that move quickly with less overhead. You’ll move fast by pairing sharp product judgment with fluency in AI tools , automating what slows teams down and amplifying what makes them creative and high-performing.
• We’re boundaryless builders. Lines between roles are intentionally blurred, and our PMs do whatever it takes to deliver outcomes. You’ll prototype, automate, design, and ship , using AI as your co-builder to turn problems into durable solutions that deliver customer value with urgency and care.
• 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 , building technology for an AI-first world that gives them the superpowers to run and grow their businesses with confidence.
• We’re comfortable with change. Our environment moves fast, and PMs here thrive in ambiguity , blending curiosity, experimentation, and AI-native craft to shape how products (and work itself) are built at Gusto.

About the Team:

Gusto operates a scaled, full-suite benefits brokerage and is building a Professional Employer Organization (PEO) offering to serve more complex small businesses with a bundled solution for HR, payroll, benefits, and compliance. Our existing brokerage business is among the largest in the US serving the SMB market, and our PEO bet is one of our most strategic new initiatives, with FY26 focused on developing the foundation and FY27 aimed at launching a differentiated, scalable customer experience.

We're looking for a Product Manager to lead the transformation of Gusto's benefits administration platform, the product that powers benefits for tens of thousands of SMBs and their employees. This role owns what happens after benefit selections are made: implementing plans with carriers, fulfilling enrollments, and giving customers visibility into the status of their benefits. It is a broad scope, encompassing agentic workflows, customer-facing experiences, internal tooling, and carrier integrations.

Here’s what you’ll do day-to-day:

• Ownership: Lead long-term strategy. This includes driving research, defining customer and market positioning, shaping product direction, and identifying the investments and internal capabilities required for success. You’ll translate this strategy into actionable guidance that informs company-wide planning and execution.
• North Star: Focus the organization on what matters most. Identify the highest-leverage investments and decisions across functions that will unlock long-term success, reduce ambiguity, and ensure that Gusto is building toward a cohesive and differentiated Benefits & PEO offering.
• Collaborate: Partner across Product, Engineering, Compliance, Legal, CX, Marketing, Sales, and Operations to uncover insights, validate assumptions, and build alignment. You’ll help create shared understanding and ensure cross-functional teams are set up to deliver.
• Accelerate Execution: Step into the highest-priority gaps that stand in the way of success. Whether it’s clarifying requirements, kicking off strategic initiatives, or embedding with a team to drive execution, you’ll help move the work forward by creating clarity, building momentum, and enabling others to succeed.

Here’s what we're looking for:

• 8+ years of product management experience, ideally with additional professional experience in roles that involved leading large, complex, and cross-functional initiatives
• A systems thinker with experience in AI-driven workflows, operations platforms, and process transformation. Benefits experience is a plus, but not a requirement.
• Strong strategic thinking and the ability to connect work across customer needs, product design, internal operations, pricing, and go-to-market
• Excellent communication and storytelling skills, with a talent for making complexity understandable and actionable
• A bias towards action, comfort operating without a clear playbook, and a desire to drive meaningful progress on long-term company priorities

If you don't think you meet all of the criteria above but still are interested in the job, please apply. Nobody checks every box, and we're looking for someone excited to join the team.

Our cash compensation amount for this role is $179,000/yr to $224,000/yr in Denver & most major metro locations, and $210,000/yr to $263,000/yr for San Francisco, Seattle & New York. Final offer amounts are determined by multiple factors including candidate location, experience and expertise and may vary from the amounts listed above.

Where do PMs at Gusto work? We have offices in Denver, San Francisco, and New York and have remote team members across the US and Canada. Our open roles will specify on the careers page and in the job description where the position is eligible for work. (1) Business Applications with Planned Wages (www.census.gov)

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. This includes non-office days for hybrid employees.

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.

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Location

San Francisco

Employment Type

Full time

Department

Finance

Compensation

• $216K – $240K • Offers Equity

The base pay offered may vary depending on multiple individualized factors, including market location, job-related knowledge, skills, and experience. If the role is non-exempt, overtime pay will be provided consistent with applicable laws. In addition to the salary range listed above, total compensation also includes generous equity, performance-related bonus(es) for eligible employees, and the following benefits.

Benefits

• Medical, dental, and vision insurance for you and your family, with employer contributions to Health Savings Accounts

• Pre-tax accounts for Health FSA, Dependent Care FSA, and commuter expenses (parking and transit)

• 401(k) retirement plan with employer match

• Paid parental leave (up to 24 weeks for birth parents and 20 weeks for non-birthing parents), plus paid medical and caregiver leave (up to 8 weeks)

• Paid time off: flexible PTO for exempt employees and up to 15 days annually for non-exempt employees

• 13+ paid company holidays, and multiple paid coordinated company office closures throughout the year for focus and recharge, plus paid sick or safe time (1 hour per 30 hours worked, or more, as required by applicable state or local law)

• Mental health and wellness support

• Employer-paid basic life and disability coverage

• Annual learning and development stipend to fuel your professional growth

• Daily meals in our offices, and meal delivery credits as eligible

• Relocation support for eligible employees

• Additional taxable fringe benefits, such as charitable donation matching and wellness stipends, may also be provided.

About the Team

The Internal Controls function sits within the broader Finance Risk Management (FRM) organization and plays a key role in strengthening the integrity, scalability, and reliability of OpenAI’s finance-critical operations.

Our team designs and governs the Internal Controls over Financial Reporting (ICFR) framework that supports accurate, transparent financial results. We focus on business-process controls across areas like Order-to-Cash, Compute, Data, Global Financial Close, Accounting Operations, Real Estate and AI infrastructure-related spend. We work closely with Product, GTM, Corporate Finance, Legal, BizOps, Strategic Finance, Accounting, Finance Platforms and Compliance to ensure processes are well-designed, well-documented, and audit-ready.

FRM, as the broader function, leads OpenAI’s financial risk posture—spanning governance over internal controls, third-party risk, audit readiness, and financial systems oversight. Together, we provide the foundation of trust that enables OpenAI to operate at global scale.

About the Role

We’re seeking a Senior Manager, Financial Risk Management to shape and scale the readiness frameworks and ways of working that underpin OpenAI’s SOX/ICFR program and broader FRM priorities. This is a highly cross-functional role for someone who can translate ambiguity into clear standards, expectations, and decision paths—so workstream owners can move quickly and consistently.

You’ll be a core partner to Finance, Systems, and operational leaders—aligning stakeholders, driving remediation progress, and turning complex, multi-team efforts into crisp leadership updates and decision asks. Success in this role requires strong judgment, clear communication, and the ability to drive outcomes through influence.

This role is based in San Francisco, CA. We use a hybrid work model of 3 days in the office per week and offer relocation assistance to new employees.

In this role, you will:

• Build and scale the ICFR readiness framework (standards, playbooks, governance, and review cadences) that ensures business-process controls stay consistent, auditable, and scalable as OpenAI grows.

• Lead process/controls design for key finance and spend domains for your assigned pillars (e.g. Revenue, Compute, Financial Close, Accounting Operations), translating complex workflows into clear risks, controls, and ownership models.

• Drive risk assessments and control rationalization (what matters most, where to automate, where to simplify), using data and business context to focus effort on highest-impact reporting risks.

• Run targeted assessments for new/changed areas and translate them into clear expectations, owners, and timelines.

• Provide governance and oversight of the Big 4 provider’s execution of RCMs, narratives, and end-to-end process documentation, ensuring that all documentation is accurate, up-to-date, and fully prepared for testing—clearly articulating evidence requirements and system dependencies.

• Oversee issue management and remediation for your process areas, ensuring deficiencies are root-caused, fixed at the system or process level, and sustainably closed.

• Serve as primary liaison for audits and internal stakeholders for your domains—anticipating requests, aligning on PBC expectations, and communicating control health, risks, and progress through clear metrics and reporting.

• Partner with workstream leads and co-sourced teams to ensure outputs are consistent, high-quality, and leadership-ready.

You might thrive in this role if you have:

• Bachelor’s or Master’s degree in Accounting, Finance, Business Administration, or a related field; CPA, CA, CISA or equivalent strongly preferred.

• 10+ years of experience in financial risk management, internal audit, or financial process transformation, preferably in high-growth, technology-enabled or product-driven env

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PM - Finance Transformation

Location

San Francisco

Employment Type

Full time

Department

Finance

Compensation

• $216K – $240K • Offers Equity

The base pay offered may vary depending on multiple individualized factors, including market location, job-related knowledge, skills, and experience. If the role is non-exempt, overtime pay will be provided consistent with applicable laws. In addition to the salary range listed above, total compensation also includes generous equity, performance-related bonus(es) for eligible employees, and the following benefits.

• Medical, dental, and vision insurance for you and your family, with employer contributions to Health Savings Accounts

• Pre-tax accounts for Health FSA, Dependent Care FSA, and commuter expenses (parking and transit)

• 401(k) retirement plan with employer match

• Paid parental leave (up to 24 weeks for birth parents and 20 weeks for non-birthing parents), plus paid medical and caregiver leave (up to 8 weeks)

• Paid time off: flexible PTO for exempt employees and up to 15 days annually for non-exempt employees

• 13+ paid company holidays, and multiple paid coordinated company office closures throughout the year for focus and recharge, plus paid sick or safe time (1 hour per 30 hours worked, or more, as required by applicable state or local law)

• Mental health and wellness support

• Employer-paid basic life and disability coverage

• Annual learning and development stipend to fuel your professional growth

• Daily meals in our offices, and meal delivery credits as eligible

• Relocation support for eligible employees

• Additional taxable fringe benefits, such as charitable donation matching and wellness stipends, may also be provided.

More details about our benefits are available to candidates during the hiring process.

This role is at-will and OpenAI reserves the right to modify base pay and other compensation components at any time based on individual performance, team or company results, or market conditions.

About the Team

The Finance Transformation team at OpenAI partners closely with Finance, Engineering, Product, and GTM to rethink and scale core business processes as the company grows. Our work sits at the intersection of process design, systems architecture, and operating model evolution—turning fragmented, manual workflows into scalable, repeatable, and well-controlled platforms.

We operate as embedded partners to finance, accounting and operations teams, with real influence over priorities and roadmap. The team focuses on building durable foundations across finance-critical domains such as Record-to-Report, Order-to-Cash, Procure-to-Pay, and Supply Chain—enabling speed, accuracy, and insight as OpenAI continues to evolve.

About the Role

As a PM on the Finance Transformation team, you will lead complex, cross-functional initiatives to redesign and scale core finance and business processes. This role is not traditional project management or intake coordination. Instead, you will operate as a process expert and transformation lead, owning problem definition, future-state design, and end-to-end delivery in close partnership with AI and application engineers.

You’ll work across Finance, Accounting, GTM, Infra, Data and Engineering to align on outcomes, shape technical priorities, and ensure solutions are built for scale, auditability, and long-term sustainability. Success in this role comes from deep understanding of how processes actually work, comfort operating in ambiguity, and the ability to translate business complexity into clear, system-enabled solutions.

This role is based in San Francisco, CA. We use a hybrid work model of 3 days/week in the office and offer relocation assistance.

In this role, you will:

• Lead end-to-end transformation initiatives across core finance and business processes, from current-state assessment through future-state design and scaled adoption.

• Act as a process expert and problem framer, deeply understanding existing workflows to identify root causes, translate business needs into clear requirements, and influence process owners to adopt future-state, leading practices.

• Identify opportunities to leverage automation and AI to improve accuracy, efficiency, and decision-making across finance processes.

• Partner closely with AI and application engineers to design system-native solutions rather than manual workarounds or downstream fixes.

• Redesign operating models, workflows, and controls to enable consistent, repeatable execution as the company scales globally.

• Drive cross-functional alignment across Finance, Accounting, GTM, and Infra; balancing speed, control, and flexibility.

• Define success metrics and outcomes (cycle time, error rates, automation coverage, close impact) and use them to guide delivery and prioritization.

• Lead UAT, change management, and rollout planning to ensure solutions are adopted and sustained in real operations.

You might thrive in this role if you have:

• 8+ years of experience in product management, process transformation, or finance process-owner roles in complex, scaled environments.

• Deep understanding of how finance and operational processes actually run (e.g., O2C, P2P, supply chain, core accounting), even if you’ve not owned every domain directly.

• Experience partnering closely with engineering teams and influencing technical priorities without owning direct reports.

• A strong process mindset—you enjoy untangling ambiguity, identifying root causes, and designing future-state workflows that scale.

• Comfort operating across business and technical contexts, with the ability to translate between stakeholders.

• A bias toward durable, system-enabled solutions over manual processes or one-off fixes.

• Strong written and verbal communication skills, especially in cross-functional settings.

• Experience leading complex initiatives

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