About Mashpee Advisors
Mashpee Advisors is a privately held multi-entity operating and investment platform overseeing several profitable businesses across complementary markets. The firm focuses on disciplined growth, operational excellence, and strategic capital allocation across operating companies and related assets.
We are entering a phase of expansion that includes acquisitions, product expansion, and strategic asset ownership initiatives.
Position Overview
Mashpee Advisors is seeking a hands-on, strategic Chief Financial Officer to oversee financial leadership across multiple operating entities and affiliated assets.
This role serves as principal financial strategist responsible for capital allocation, enterprise-level P&L performance, acquisition evaluation and execution (including both operating businesses and select real estate assets), and building scalable financial infrastructure to support long-term growth.
Key Responsibilities
Business Acquisitions & Capital Allocation
- Lead financial modeling and evaluation of acquisition opportunities
- Structure and negotiate transaction terms (cash, debt, seller notes, earnouts)
- Coordinate financial due diligence processes
- Oversee post-close financial integration
- Develop ROI and return-on-capital frameworks
- Establish underwriting standards and capital deployment discipline
Real Estate & Asset Strategy
- Evaluate acquisition of owner-occupied and investment real estate
- Model leaseback structures and entity separation strategies
- Coordinate financing for commercial real estate transactions
- Optimize capital structure between operating entities and property holdings
- Support tax-efficient asset ownership planning in coordination with external advisors
Multi-Entity Financial Leadership
- – Oversee accounting, AP/AR, and monthly close across entities
– Supervise finance team (currently 2 direct reports)
– Consolidate financial reporting across operating companies and asset entities
– Implement KPI dashboards and forward-looking forecasting processes
Debt & Banking Relationships
- Lead lender negotiations for both operating and real estate financing
- Manage leverage capacity and covenant compliance
- Prepare lender-ready reporting packages
- Maintain proactive communication with banking partners
Required Qualifications
- 10+ years in senior financial leadership roles
- Demonstrated buy-side M&A execution experience in lower middle market businesses
- Direct involvement structuring and closing business acquisitions
- Experience evaluating and financing commercial real estate transactions
- Strong financial modeling and capital structuring capability
- Experience operating in multi-entity or holding company environments
Preferred Experience
- Acquisition-driven growth environments
- Experience with sale-leasebacks or owner-occupied real estate structuring
- Direct commercial lender negotiation experience
- CPA, MBA, or equivalent background
Compensation
Competitive base salary plus performance-based bonus tied directly to consolidated P&L performance.
Bonus structure includes:
- EBITDA growth targets
- Cash flow conversion metrics
- Acquisition integration performance
Location: Boston, MA
The role includes meaningful decision authority within defined capital allocation guardrails.]
Apply
Email your CV with Cover letter to info@mashpeeadvisors.com