Roundtrip Senior Accountant Remote, MD · Remote, PA · Remote, VA · Remote, FL · Remote, CO · Remote, CA · Remote · Full time Company website

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Founded in 2016, Roundtrip is committed to removing transportation barriers and revolutionizing healthcare access. With a passion for patient care, we harness cutting-edge technology to provide unrivaled scheduling and coordination of non-emergency medical transportation. Our clients include some of the most prestigious healthcare providers and forward-thinking Medicare Advantage health plans, all benefiting from our innovative SaaS platform and Navigation Center services. By leveraging our solution, our clients have successfully reduced patient no-shows, expedited the patient discharge process, improved patient and staff satisfaction, and decreased healthcare expenditures on patient rides.

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. One day you might walk a customer through an invoice question. The next, you might document a revenue policy, tighten up the close checklist, or 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)

What You’ll Do:  

Month-End Close and Financial Reporting 

• Own the month-end close from start to finish, including reconciliations, accruals, journal entries, and supporting schedules 
• Prepare monthly GAAP financial statements (income statement, balance sheet, and cash flow) with variance commentary for the CEO 
• Prepare financial inputs for board reporting, investor updates, and audit or lender requests 
• Maintain and improve a close calendar and checklist that make each close faster and more repeatable 

Revenue Recognition 

• Apply ASC 606 to our customer contracts, leveraging internal tooling to facilitate recognition schedules and automated recognition 
• Maintain revenue schedules, deferred revenue, and unbilled receivables 
• Review new and amended customer contracts for billing and revenue impact before they're signed 
• Document revenue policies and accounting positions so they hold up to audit review 

Billing and Customer Accounts 

• Own the monthly billing cycle: reconcile usage and contract data, prepare customer invoices, and get them finalized and sent within the first few days of the month 
• Serve as the main finance contact for customers, resolving billing questions and disputes through to completion 
• Manage AR aging and collections, working with customers to keep balances current (with added support for routine follow-up as we grow) 
• Partner with our Customer Success and Sales teams on pricing, contract terms, and new customer setup 

Accounts Payable, Payroll, and Bookkeeping 

• Oversee AP, vendor payments, and employee expense reports 
• Ensure that automated journal entries for payroll and benefits automated journal entries are accurate and associated expenses are properly posted  
• Keep transaction coding in QuickBooks Online accurate and consistent 

Planning, Controls, and Process 

• 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 

What You’ll have:  

• 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 

Nice to haves: 

• Experience supporting audits or financial reporting at a startup or small company 
• Familiarity with billing platforms, AP automation, or FP&A tools 
• Hands-on experience using AI tools or automation in accounting workflows

Logistics: 

• Reports to: CEO 
• Location: Fully Remote (occasional travel up to about 10%)- As a remote-first company, we collaborate in real time each day through Slack and Microsoft Teams, with twice-yearly in-person gatherings to bring the team together. This role is open to candidates across the U.S., with core collaboration hours from 10:00 AM to 4:00 PM ET.  Please note all work must be performed within the United States. Candidates must be authorized to work for any employer without requiring visa sponsorship. We are unable to provide or assume sponsorship for employment visas at this time. 

What We Offer: 

• Compensation & Equity: The salary range for this role is $80,000-95,000, depending on experience and level of independence, along with stock option grants that give employees the opportunity to share in the company’s success through ownership. 
• 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. 

What happens next:  

Our team will carefully review all applications. Due to the high volume of interest, we’re unable to contact every applicant individually. If your experience aligns with what we’re looking for, a member of our team will reach out to move you into the interview process.  

We know there are a lot of scammers out there, so please note that all legitimate communications related to open opportunities will exclusively come from “@roundtriphealth.com” emails addresses. We will also never ask you to download any kind of software as a part of the interview process.  

Employment Eligibility & Equal Opportunity Statement:  

At Roundtrip we are not only focused on our mission but also hold ourselves to high standards when it comes to our team. Being part of the Roundtrip team isn't just about showing up and doing your job, it's about living our values every day: Lead with Empathy, Own the Outcome, Innovate Responsibility, Embrace Evolution and Partner for Impact.  

Diversity & Inclusion is more than an initiative at Roundtrip. Our team is committed to creating a diverse environment and is proud to be an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, veteran status, or other protected class. If, due to a disability, you need accommodation during the interview or application process, please email [email protected].