About the role
About Gladly
For business leaders who want to get AI right, Gladly is the only customer experience AI that delivers the cost savings they need AND the customer devotion that drives lasting business value. With over a decade of singular CX focus and trusted by the world's most customer-centric brands including Crate & Barrel, Breeze Airways, and Ulta Beauty, Gladly was designed for devotion, not deflection: purpose-built to engage customers and turn every conversation into lasting relationship equity. The result is experiences that are radically personal and effortlessly scalable, emotionally intelligent and operationally efficient.
At the heart of our simply powerful platform, Gladly maintains one continuous conversation across all channels while striking the perfect balance of AI and human connection. With 450M+ conversations powered globally, $510M+ cumulative cost savings delivered for customers, and a 65% increase in CSAT, this is a team where your work has real impact at scale. Learn more at www.gladly.ai.
The Team
You will be joining an experienced leadership team backed by top-tier investors, including Greylock, NEA, and GGV. Reporting to the Director of Accounting, you will own the revenue and billing cycle end to end. This is an individual contributor role, you own the function rather than a team.
Our accounting 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, Sales Operations, Customer Success, and Legal.
The Opportunity
We are seeking a hands-on Revenue Accountant to own the full revenue cycle at a high-growth AI+SaaS company, from the moment a contract is signed through invoicing, recognition, and cash collection.
This is a role for someone who wants their fingerprints on the process, not just the output. You will inherit a growing book of subscription and usage-based contracts and a billing system in Tabs that is live but not yet fully dialed in. There is real work ahead to tighten the configuration, close the gaps between Tabs and NetSuite, and help shape how revenue operations should run as we scale. If you are energized by cleaning up a schedule, automating a manual close step, and being the person everyone trusts on how a deal should be billed and recognized, you will do the best work of your career here.
You will also be one of the few people in Finance who talks directly to customers. How you handle a billing question shapes how a customer experiences Gladly, and we take that seriously.
What You’ll Do
Customer invoicing & billing: Own the end-to-end billing cycle for subscription, usage-based, and outcome-based contracts. Issue timely, accurate invoices, tie every invoice to the signed order form, and manage billing schedules through upgrades, mid-term changes, renewals, credits, and true-ups.
Revenue reporting & recognition: Maintain revenue and deferred revenue schedules under ASC 606 across recurring and consumption-based models. Own the month-end close journal entries for revenue, AR, and related accounts, and prepare monthly reconciliations, roll-forward, and variance analysis, delivering clean , close-ready reporting on a predictable cadence.
Revenue treatment support: Support the review of new and modified contracts for proper revenue treatment, including standalone selling price allocation, contract modifications, and variable consideration. Document conclusions and partner cross-functionally with Sales on questions that come up, including for newer models like AI licensing and outcome-based pricing.
Commission capitalization & amortization: Own the commission accrual and payout cycle in partnership with FP&A, Sales, and People Ops. Capitalize and amortize commissions and other costs to obtain a contract under ASC 340-40, and maintain the supporting schedules.
Accounts receivable & collections: Serve as the primary contact for accounts receivable matters. Manage the accurate daily recording of cash receipts and application of payments, drive AR aging and collections to hit DSO, cash, and burn ratio targets, and run the collections cadence. Deliver weekly, monthly and ad hoc AR reporting and key metrics to management, escalate at-risk balances with Sales and Customer Success, and maintain the allowance for credit losses.
Customer & cross-functional support: Serve as the front line for billing and invoicing questions from customers and internal teams, resolving them with the same care our customers expect from the rest of Gladly. Partner with Sales, Deal Desk, and Legal during contract review so deals are structured cleanly, and support FP&A with revenue and billings inputs for forecasting.
Systems & process improvement: Help improve the quote-to-cash flow across NetSuite and Tabs, replacing manual work with repeatable, documented processes. Maintain internal controls and audit-ready support, and serve as a key revenue contact for external auditors.
What we’re looking for
Experience: 5+ years in revenue accounting, billing, or order-to-cash roles, including ownership of a monthly revenue close.
Education: Bachelor's degree in Accounting, Finance, or a related field.
Industry expertise: Revenue accounting experience at a technology or SaaS company with recurring and usage-based revenue streams.
Technical skills: Working knowledge of ASC 606 as applied to subscription and usage-based revenue models, including deferred revenue, contract modifications, and variable consideration. Familiarity with ASC 340-40 for commission capitalization and amortization is a plus.
Systems: NetSuite proficiency is required, including familiarity with the Advanced Revenue Management module. Hands-on experience with a dedicated billing platform is required, ideally Tabs, or a comparable system such as Zuora, Ordway, Maxio, or Stripe Billing. Advanced Excel and Google Sheets skills, including pivot tables, lookups, and high-volume reconciliation.
Professional background: A CPA license is preferred but not required.
Personal characteristics: You have real drive and curiosity, you're comfortable owning a function independently, and you're eager to learn and figure things out even when you don't have the answer yet.
Exceptional problem-solving and communication skills, with a collaborative mindset.
The ability to navigate ambiguity, manage competing deadlines, and hold a close timeline without sacrificing accuracy.
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: $110,000 - $125,000 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's 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?
Gladly is redefining customer experience AI; we're designed for devotion, not deflection. We put people at the center of everything we build, from our platform to our culture. When you join us, you'll enjoy:
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
A company where AI is not a buzzword. We build AI products and we expect our team to use AI tools daily
We're a team that believes in transparency, collaboration, and the idea that the best work happens when talented people genuinely enjoy working together. Top talent, good vibes, no politics. If this role excites you but you don't meet every qualification, we still encourage you to apply. The perspectives and experiences you bring matter more than checking every box.