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.