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Managing Director, Accounting Services (Start Up)

Oak Services Group, Inc., Marlborough, MA, United States


Managing Director (Accounting Services Start up) Company:

Oak Services Group, Inc. Location:

Hybrid Build and Lead a New Accounting & Finance Practice

Do you want to build and grow an accounting or finance practice—but with the support of a team rather than the risk of going solo? Are you interested in a leadership role with equity participation, helping shape a new managed services and fractional accounting firm? Oak Services Group is launching a new managed services accounting company and is seeking an experienced Managing Director / Senior Accounting Manager to lead our Finance & Accounting Services line of business. This is a rare opportunity to join a startup venture at launch, help build the organization from the ground up, and play a key role in the company’s long‑term growth. Position Overview

This is a senior leadership role responsible for overseeing Oak Services Group’s accounting and finance teams, managing client relationships, and serving as the firm’s technical accounting leader. In the early stages of the company, the Managing Director will also operate in a hands‑on capacity, performing direct accounting work while building and scaling the team. Over time, as the organization grows, the role will evolve toward a more strategic leadership position, with expanded focus on business development, client growth, and organizational leadership. Key Responsibilities

Client Leadership & Advisory Serve as the primary client lead for accounting and finance services Ensure clients receive accurate financial reporting and strategic financial insights Maintain strong client relationships and manage complex client situations professionally Accounting & Technical Leadership Act as the accounting subject matter expert for internal teams Maintain integrity and accuracy of financial records across multiple client organizations Ensure strong internal controls and compliance with accounting standards Process Development & Operations Design and implement scalable accounting processes and procedures Implement accrual processes to improve in‑period reporting accuracy Develop KPIs and perform FP&A analysis Provide real‑time insights into financial performance Support clients in spending management and operational efficiency Startup Leadership Contribute to building the organization during the early startup phase Wear multiple hats and take ownership of critical initiatives Help recruit, mentor, and build the accounting team over time Qualifications

Education & Credentials

Bachelor’s degree in Accounting or Finance CPA strongly preferred Additional credentials such as MBA, CFA, or CMA are a plus Master’s degree preferred but not required Experience

8+ years of progressive accounting experience Experience in public accounting and/or industry leadership roles Background in Big Four or similar accounting firms is highly valued Experience in senior roles such as: Controller CFO Senior Finance Leader Technical Expertise

Strong experience in areas such as: U.S. GAAP Internal controls and compliance Multi‑industry accounting environments Implementing scalable accounting systems FP&A and KPI development Tools & Systems

Advanced proficiency in Excel Experience with QuickBooks and NetSuite preferred Leadership Skills

Strong communication and presentation skills Ability to present to Boards, Audit Committees, and executive leadership Collaborative leadership style with cross‑functional teams High integrity and strong commitment to confidentiality and ethics What Makes the Ideal Candidate

The right candidate will demonstrate: Ability to thrive in a startup environment Willingness to roll up their sleeves and execute A bias for action and strong ownership mentality Passion for helping build and grow a new organization Compensation & Equity

Startup Phase (First 1–2 Years)

Modest performance bonus Equity participation Structured OTE growth plan tied to company revenue milestones Long‑Term Expected Compensation

Significant upside tied to company growth and success This role is designed for a senior candidate who understands the risks and rewards associated with joining an early‑stage startup. Oak Services Group offers:

Medical, dental, and vision insurance Long‑term disability coverage Group life insurance Planned 401(k) plan (to be introduced once eligible) Remote‑first, cloud‑based work environment Occasional in‑person meetings for clients or team events Why Join Oak Services Group

Founder‑led startup funded by a successful entrepreneur Not dependent on outside venture capital expectations Supported by a well‑established Board of Advisors with strong ties to the local business community Collaborative and professional fractional/managed services culture No “up‑or‑out” structure common in large accounting firms About Oak Services Group

Oak Services Group, Inc. is a startup managed services firm specializing in fractional accounting, controllership, and CFO services. We are building a team of experienced professionals who want to deliver high‑quality financial leadership to growing companies. For many roles, we are also open to part‑time or flexible W2 employment arrangements, reflecting our commitment to flexible working relationships. Oak Services Group is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, veteran status, or disability.

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