Senior Manager, Accounting

About the Company

Gladly builds customer experience AI designed to help businesses reduce costs while creating stronger customer relationships. The platform is used by leading customer-focused brands and is built to support one continuous conversation across channels, combining automation with human interaction to deliver highly personal and scalable service.

The company has powered hundreds of millions of customer conversations globally and has driven substantial cost savings and customer satisfaction gains for its clients.

The Team

You will join a seasoned leadership group supported by major investors. Reporting to senior finance leadership, you will take full ownership of the accounting function and lead a compact team of two accountants. The environment emphasizes accountability, ongoing process improvement, and collaboration with FP&A, Sales, and Legal.

The Opportunity

Gladly is hiring a hands-on Senior Manager of Accounting to lead the full accounting operation for a fast-growing AI and SaaS business. The role combines technical accounting depth with day-to-day operational ownership, including financial close, payroll, compliance, and control design. You will help scale the finance function while ensuring proper accounting treatment for complex revenue models and new business structures.

This position calls for someone who can both shape strategy and handle execution directly. The ideal person is comfortable working in ambiguity, solving complex accounting questions, and acting as a reliable partner across the business.

What You’ll Do

• Oversee the full monthly, quarterly, and annual close process and ensure timely financial statements prepared in line with US GAAP.
• Manage core accounting areas such as the chart of accounts, general ledger, and fixed assets.
• Lead revenue recognition for subscription and usage-based SaaS offerings under ASC 606, including deferred revenue, contract changes, and commission capitalization.
• Act as the internal resource for technical accounting analysis on emerging business models, including AI licensing and outcome-based pricing.
• Process bi-weekly payroll directly in ADP and manage accounts payable, expenses, and accounts receivable/collections to support cash flow and burn management.
• Coordinate the annual audit and tax preparation while serving as the main contact for external auditors.
• Build, document, and maintain internal controls, accounting policies, and SOX-like readiness.
• Serve as a power user for NetSuite and help improve accounting systems and workflows.
• Lead, coach, and support a team of two accountants, including a senior accountant and a revenue accountant.
• Work closely with FP&A on budgeting and forecasting and with Sales and Legal on deal and contract structure.
• Support fundraising and mergers and acquisitions from an accounting standpoint.

What We’re Looking For

• At least 8 years of accounting experience, including 3 or more years in a people management or supervisory role.
• Strong practical experience with NetSuite on a day-to-day basis.
• Direct payroll processing experience in ADP or an equivalent platform; this role requires having run payroll personally.
• Deep knowledge of US GAAP and proven ASC 606 experience for recurring and usage-based SaaS revenue.
• Ability to conduct technical accounting research, support audits, and strengthen internal control frameworks.
• A player-coach mindset with the ability to balance hands-on execution and strategic leadership.
• Comfort with fast-moving, uncertain environments and a resourceful, high-EQ working style.
• Bachelor’s degree in Accounting, Finance, or a related discipline.
• Active CPA preferred; Big 4 experience is considered a strong plus.
• Must be based in the United States and open to a remote work setup.

Why Join Gladly?

• Competitive pay, equity participation, and stock options.
• Comprehensive benefits package.
• Paid time off, parental leave, and home office support.
• Fully remote work with occasional in-person team gatherings.
• Room for professional development in an inclusive workplace.
• A culture that encourages daily use of AI tools and values transparency, collaboration, and strong team chemistry.

Pay Transparency

The base salary range for this role is $156,000 to $184,000. Gladly notes that the opening is for a Senior Manager title, with openness to Director level for the right candidate. Total cash compensation may vary based on level, skills, experience, and location. Eligible employees may also participate in the company’s equity incentive plan. Commission and annual bonus opportunities may apply only to roles that qualify under the company’s plans.

Additional Information

Gladly encourages candidates to apply even if they do not meet every requirement. The company values different perspectives and experiences and emphasizes an inclusive environment where people can do strong work together.