This is a remote position.
About the Opportunity
The Head of Operations will be responsible for three things: owning the full accounting delivery organization, leading the integration of acquired firms, and driving the operational infrastructure that holds everything together as the company scales. This is not only an operations-focused position. It requires someone who can be the visible authority through hard transitions, earn trust across every level of the organization, and carry all three pillars simultaneously.
Our client is a venture-backed technology company executing an aggressive roll-up strategy in the accounting services space. This is an organization that moves fast, invests in its people, and is building something genuinely differentiated in a fragmented industry. This is a ground-floor leadership opportunity with direct access to the Founder and a clear, intentional path to becoming COO as the organization grows.
You will serve as the diagnostic engine between the accounting practice and the internal product team — not selecting tools, but identifying the problems worth solving and driving the feedback loop that shapes what gets built. CPAs leading business units report directly into this role.
Responsibilities
Delivery & Organizational Leadership
Own the full delivery organization, with CPAs leading business units reporting directly into this role
Ensure that all accountants across acquired firms are performing to standard — work is completed accurately, on time, and at the quality level clients expect
Actively monitor client responsiveness and delivery timelines across the portfolio
Assess the quality of CAS and tax work at the engagement level, with the ability to identify and address gaps directly
Be the visible authority and decision-maker through transitions — not a support function, but the operational leader the organization runs through
Integration & Change Management
Lead the human side of firm integration — bringing staff through transitions in tools, processes, and operating models with clarity and buy-in
Build and manage onboarding and training programs that allow acquired staff to ramp quickly and perform consistently
Own the hiring and development of replacement or backfill talent as the portfolio grows
Drive change because it makes the work better, and bring people along in the process
Operational Excellence & Scale
Drive process improvement across the practice — identifying inefficiencies, standardizing workflows, and maintaining operational performance through multiple concurrent acquisitions
Act as the primary diagnostic voice for the product team: your job is not to select software — it is to identify the problems worth solving. The internal team will build and iterate on the tools that address what you surface
Own the feedback loop between the accounting practice and the product team — continuously translating field reality into product direction and ensuring that what gets built actually gets adopted
Requirements
Significant experience in accounting services delivery in an operational leadership capacity, with senior practitioners having reported directly to you
Demonstrated ability to assess the quality of CAS and tax work at the engagement level in a public accounting environment
Track record of leading and developing accounting teams, including hiring and building training programs
Comfortable operating in a technology-forward environment and engaging substantively with product teams on workflow and tooling decisions
Prior exposure to M&A, firm integration, or multi-entity operations
Highly organized with the ability to manage complexity across multiple firms and workstreams simultaneously
Resilient and adaptable in a fast-moving startup environment — someone who earns trust at every level and leads through change with authority and clarity
Degree in accounting or relevant field
CPA preferred, not required
Benefits
$250,000 – $350,000 year one cash compensation plus equity in this VC-backed accounting firm roll-up
Comprehensive and negotiable benefits package
Fully remote work arrangement
Similar Jobs
What you need to know about the Boston Tech Scene
Key Facts About Boston Tech
- Number of Tech Workers: 269,000; 9.4% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: Thermo Fisher Scientific, Toast, Klaviyo, HubSpot, DraftKings
- Key Industries: Artificial intelligence, biotechnology, robotics, software, aerospace
- Funding Landscape: $15.7 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Summit Partners, Volition Capital, Bain Capital Ventures, MassVentures, Highland Capital Partners
- Research Centers and Universities: MIT, Harvard University, Boston College, Tufts University, Boston University, Northeastern University, Smithsonian Astrophysical Observatory, National Bureau of Economic Research, Broad Institute, Lowell Center for Space Science & Technology, National Emerging Infectious Diseases Laboratories
