[Hiring] Senior Accountant @Roundtrip

Role Description

As Senior Accountant you'll run the month-end close, prepare our financial reports, apply revenue recognition to our customer contracts, and keep our books accurate and audit-ready. You'll also be the main finance contact for our business customers, so you'll spend real time working directly with health system and payer finance teams.

This is a small-team role, and you'll do a bit of everything:

• Walk a customer through an invoice question.
• Document a revenue policy.
• Tighten up the close checklist.
• Work through a stack of vendor bills.

You'll report directly to our CEO and serve as their primary finance partner. As we grow, we expect this role to grow with us toward planning, analysis, and strategy, and we plan to add support for tactical work like routine collections follow-up so you can spend more time on higher-value work.

You won't be starting from scratch. You'll inherit established systems, processes, and tools that let you be effective from day one. We also have a strong culture of innovation, so there's plenty of room to make things better. If you see a way to add efficiency, customize a workflow, or bring AI into how finance gets done, we want you to run with it.

To be candid, this isn't a role for someone who prefers to follow a process exactly as written. It's built for someone who notices friction, gets frustrated by inefficiency, and feels driven to make the work smooth, predictable, and reproducible.

This role is ideal for someone who:

• Takes pride in clean, accurate books and wants to own the whole cycle, not just one piece of it.
• Enjoys variety: customer calls in the morning, revenue schedules in the afternoon.
• Rolls up their sleeves without being asked, including on work that isn't glamorous.
• Wants to grow from hands-on accounting into a more strategic finance role over time.
• Is genuinely bothered by inefficiency and feels driven to fix it, often with automation and AI.
• Is comfortable in a healthcare tech or B2B services environment (or eager to learn it).

Qualifications

• Progressive responsibility across accounting roles, including ownership of the month-end close.
• Bachelor's degree in Accounting, Finance, or a related field.
• Hands-on revenue recognition experience under ASC 606, ideally with usage-based, B2B, or services contracts.
• Ability to produce accurate GAAP financial statements independently.
• Proficiency in QuickBooks Online and strong spreadsheet skills.
• Clear, confident written and verbal communication with customers and executives.
• Comfort with shifting priorities and a willingness to pitch in wherever the team needs it.
• A drive to make processes smooth, predictable, and reproducible: when something takes too long or breaks too often, you fix the root cause instead of working around it.
• A track record of improving a finance process, such as shortening the close, automating a manual task, or standardizing a workflow.
• Curiosity about AI and automation, and a willingness to experiment with new tools.
• Self-directed and reliable in a fully remote environment, with authorization to work in the US.

Requirements

• Oversee AP, vendor payments, and employee expense reports.
• Ensure that automated journal entries for payroll and benefits are accurate and associated expenses are properly posted.
• Keep transaction coding in QuickBooks Online accurate and consistent.
• Support budgeting, forecasting, and cash flow planning with the CEO, taking on more ownership over time.
• Coordinate with outside advisors on income tax, sales and use tax, and 1099 filings.
• Strengthen internal controls, policies, and documentation as we scale.
• Improve our established tools and workflows through automation, customization, and AI.

Benefits

• Comprehensive Medical, Dental, and Vision Coverage: Roundtrip offers competitive benefits designed to meet a variety of needs. We cover 100% of the employees’ premium for our base medical plan, with buy-up options and family coverage available at an additional cost.
• 401(k): Roundtrip matches employee contributions up to 3% and all employer contributions are 100% vested from day one.
• Flexible, Unlimited Time Off: We trust our team to take the time they need, for rest, vacation, or personal matters. Minimum of 10 days off per year required, 11 paid company holidays observed annually and Paid Parental Leave.
• Flexible Fridays: We reserve Friday afternoons (after 12pm ET) for focused work and flexibility by limiting internal meetings, helping you close the week at your own pace.
• Lifestyle Benefits: Twice yearly credits to Fringe, an online marketplace of hundreds of well-being and lifestyle services including Uber Eats, DoorDash, Airbnb, coffee subscriptions, and more.