Director of Accounting

About Gladly Uniquely powered by Customer AI, Gladly is the only CX platform that puts the customer—not tickets—at the center of every conversation. Trusted by the world’s most customer‑centric brands, including Crate & Barrel, Ulta Beauty, and Tumi, Gladly delivers radically efficient and radically personal experiences. Gladly was built for B2C leaders who refuse to compromise on operational efficiency or experience. With Gladly, every conversation feels uniquely tailored and instantly responsive, emotionally intelligent and operationally precise, deeply personal and effortlessly scalable. At the heart of our simply powerful platform is Gladly Customer AI—uniquely designed to maintain a single, continuous conversation across all channels while striking the perfect balance of technology and human connection. Learn more at

The Team You will be joining an experienced leadership team backed by top‑tier investors, including Greylock, NEA, and GGV. Reporting directly to the CFO, you will lead a small, high‑performing team of accounting professionals. This team acts as the financial backbone of the organization, fostering a culture of ownership, continuous improvement, and collaboration with cross‑functional partners in FP&A, Sales, and Legal.

The Opportunity We are seeking a highly motivated and hands‑on Director of Accounting to lead our entire accounting function. As the core financial leader for our high‑growth AI+SaaS company, you will be responsible for scaling our financial operations and ensuring technical accounting compliance (ASC 606). We’re looking for someone with a passion for building efficient processes from the ground up, the curiosity to solve complex technical accounting issues, and the initiative to thrive in a fast‑paced environment. This is a critical leadership role that requires both deep technical expertise and the ability to serve as a trusted sounding board for Gladiators across the organization.

What You’ll Do

Financial Reporting & Close:

Own the end‑to‑end month‑end, quarter‑end, and year‑end close processes, ensuring timely and accurate preparation of financial statements in accordance with U.S. GAAP. Manage the chart of accounts, general ledger, and fixed assets.

SaaS Revenue & Technical Accounting:

Lead complex revenue recognition under ASC 606 for subscription and usage‑based models, including deferred revenue, contract modifications, and commission capitalization. Serve as the internal expert for technical accounting research for new business models (e.g., AI licensing and outcome‑based pricing).

Operational Management:

Oversee daily operational accounting activities, including accounts payable (AP), expense management, and payroll processing. Drive accounts receivable (AR) and collections management to optimize cash flow and meet critical burn‑ratio targets.

Compliance, Audit, and Systems:

Coordinate annual financial audits and tax preparation, serving as the primary liaison with external auditors. Design and maintain internal controls (SOX‑like readiness) and accounting policies to ensure data integrity as the company scales.

Leadership & Collaboration:

Directly manage and mentor the accounting team while partnering closely with FP&A on budgeting and forecasting. Collaborate with Sales and Legal teams to ensure proper contract structure and revenue recognition.

What We’re Looking For

Experience:

10+ years of accounting experience, with at least 3 years in a management or supervisory capacity.

Education:

Bachelor’s degree in Accounting, Finance, or a related field.

Industry Expertise:

Prior accounting leadership experience in a technology or SaaS company that has scaled past $50M in revenue.

Technical Skills:

Deep knowledge of U.S. GAAP with verifiable experience in ASC 606 (Revenue Recognition) as applied to recurring revenue/SaaS business models. Proven expertise with NetSuite and familiarity with financial reporting tools is required.

Professional Background:

Previous experience at a Big 4 public accounting firm (Audit or Advisory) is highly desirable, and an active CPA license is preferred.

Personal Characteristics:

You are a team player with a strong work ethic who leads by example. You possess a high IQ and EQ, allowing you to relate to all levels of the organization and translate complex accounting issues into clear business language.

Exceptional problem‑solving and communication skills, with a collaborative mindset.

The ability to navigate ambiguity and manage multiple priorities effectively.

A willingness to learn and contribute to a fast‑paced team fueled by underdog grit and a shared passion for excellence.

Salary for this role $187,000 - $220,000 USD

The cash compensation above includes base salary, and is not reflective of potential commission for employees in eligible roles, or annual bonus targets under Gladly’s bonus plan for eligible roles. In addition to cash compensation, all Gladly employees are eligible to participate in Gladly’s equity incentive plan to receive stock options per the terms of the agreement. Individual compensation packages are based on a few different factors unique to each candidate, including their career level, skills, experience, specific geographic location qualifications and other job‑related reasons.

Why Join Gladly?

Competitive salaries, stock options, and comprehensive benefits

Generous paid time off, parental leave, and home office stipends

A fully remote work environment with opportunities for in‑person team gatherings

A strong commitment to professional growth and an inclusive workplace where diverse perspectives thrive

At Gladly, we believe in challenging the status quo, celebrating grit, and striving for excellence. We thrive as a team by embracing transparency, collaboration, and a customer‑first mindset. If this role excites you but you don’t meet every qualification, we still encourage you to apply. Diverse perspectives and experiences are the cornerstone of our success.

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