Controller

POSITION: Controller

LOCATION: Rocky Hill, CT (Hybrid)

REPORTS TO: Chief Executive Officer

About Plum Dental Group (“Plum”)

Plum is a high-growth Dental Partnership Organization (DPO) with 30+ practices across Rhode Island and Connecticut, 400+ employees, and more than 100,000 patients. As a DPO, we manage all the administrative functions of our practices — marketing, facilities, technology, HR, insurance, accounting, billing, and more — so our dentists can focus on caring for patients.

A few things make Plum different:

• An active acquisition strategy. We acquire 4–6 practices a year and integrate them onto a common operating platform.
• A private equity playbook, without the private equity. Our CEO has spent his career in private equity and runs Plum with that same rigor: clear metrics, tight financial discipline, and a focus on building long-term value. Yet there is no outside capital in the business — Plum is owned entirely by its founders. You get PE-level standards without a PE sponsor’s short clock.
• A real investment in AI. Plum is heavily invested in AI and uses it across the business to scale. We want people who are excited to use these tools in their own work.

The Opportunity

We are hiring a Controller to lead finance and accounting as our longtime CFO retires. This is the most senior finance and accounting role at Plum, and it reports directly to the CEO.

You will own the function end to end: controls, the monthly close, the annual audit, and tax. With 4–6 acquisitions a year, you will also help diligence and integrate new practices, and learn how a rollup is built and financed along the way.

You will work closely with the CEO every day, with no layers in between, and partner with the COO and our operations, RCM, and HR teams. As the company grows, so does this role — you can take on as much responsibility as you can handle.

Duties and Responsibilities

• Financial Controls
  • Design, maintain, and enforce internal controls across all practices and corporate functions
  • Set accounting policies and procedures that scale as new practices join
  • Safeguard company assets and ensure accurate, timely financial records
• Monthly Close and Reporting
  • Own the month-end close from start to finish, on a consistent and timely schedule
  • Review journal entries, reconciliations, accruals, and revenue recognition
  • Manage multi-entity accounting, intercompany activity, and consolidations
  • Deliver accurate monthly financial statements and management reporting to the CEO
  • Build and maintain KPI dashboards that track practice and company performance
• Budgeting and Forecasting
  • Lead the annual budget process with the CEO and operations leaders
  • Prepare rolling forecasts and variance analysis, and explain what is driving results
• Cash and Treasury
  • Manage cash flow, cash forecasting, and banking relationships
  • Oversee debt reporting and ensure compliance with lender covenants
• Transactional Accounting
  • Oversee accounts payable, payroll accounting, and expense management
  • Partner with the billing team to reconcile patient and insurance collections to the books
  • Maintain fixed asset, depreciation, and lease accounting
• Annual Audit
  • Lead the annual financial audit and serve as the main point of contact for outside auditors
  • Prepare audit schedules and support, and resolve audit findings
• Tax and Compliance
  • Partner with our outside tax accountants to prepare and file all required federal, state, and local taxes
  • Oversee payroll, sales and use, property, and other tax filings and compliance
  • Support business insurance renewals and other regulatory reporting
• Acquisitions
  • Support financial diligence on target practices
  • Integrate acquired practices onto Plum’s accounting platform, chart of accounts, and controls
• Cross-Functional Partnership
  • Work closely with the COO and operations team on practice performance, budgets, and operational decisions
  • Partner with revenue cycle management (RCM) on billing, collections, and accurate revenue reporting
  • Work with HR on payroll, benefits, and compensation
  • Give leaders across the company the financial information they need to run their areas
• Team Leadership and Systems
  • Lead, grow, and develop the finance and accounting team of four direct reports
  • Build the team and processes the company will need at twice its current size
  • Improve finance systems and lead automation and AI initiatives within finance and across the business

Requirements

• CPA required
• Bachelor’s degree in Accounting or a related field
• 10+ years of accounting experience, including at least 4 years at a Big Four or similar public accounting firm
• At least 2 years of healthcare accounting experience; multi-site healthcare preferred
• Strong managerial experience, with a track record of managing, growing, and developing a team
• Deep knowledge of GAAP, internal controls, month-end close, and audit
• Experience working with outside tax advisors on multi-entity and multi-state filings
• Experience with QuickBooks and advanced Excel skills
• Willingness to embrace technology and AI to solve problems and increase efficiency
• Strong communication skills and the ability to work with all levels of the company
• Sense of humor, ambition, confidence, humility, empathy, and team player

A plus:

• Experience with acquisitions, including diligence and post-close integration
• Experience in a multi-site or rollup business

Compensation

• Competitive salary, annual bonus, and equity, based on background and experience
  • The ceiling is high at Plum. Compensation can grow considerably as you take on more responsibility.
• Health and retirement benefits

Location and Work Arrangement

Plum’s corporate headquarters is in Warwick, Rhode Island, and we have a satellite office in Rocky Hill, Connecticut. This role is based in our Rocky Hill, CT office .

The position is hybrid. Expect to be on-site more often early on, while you learn the business and build relationships with the team. Remote flexibility grows over time.