Job Description

Job Title: Chief Financial Officer

Location : Headquarters; Foxboro, MA

Reports To : Chief Executive Officer

Employment Type : Full-time, Exempt; Bonus & Equity eligible

About ConnectPay

ConnectPay is a rapidly growing, tech-enabled payroll service company specializing in delivering tailored payroll, tax, and HR solutions to meet the unique and expanding needs of small and medium-sized businesses (SMBs) - the largest employment segment in the U.S. With a proven track record of +30% ten year CAGR, our growth is driven organically through high client retention, partnership referral channels, and over 35 successfully integrated acquisitions.

At ConnectPay, our employees are our greatest asset, and every individual in the company carries upside equity. We foster a supportive, collaborative environment that values innovative thinking and professional growth. Our team is empowered with the resources, tools, and autonomy they need to drive success for our clients, themselves, and our community of referral partners. Every role contributes to building a streamlined, reliable payroll experience for our clients while upholding our core values of teamwork, simplify, helpfulness, learn and teach, and security.

Job Summary

As CFO, you will be a strategic financial leader, shaping ConnectPay’s long-term vision while ensuring financial strength and operational efficiency through profitable revenue growth. Reporting directly to the CEO, you will drive the company’s financial strategy, leveraging data-driven insights to optimize profitability, scale our recurring revenue model, and support sustainable and predictable growth. You will play a critical role in capital allocation, investment planning, and risk management, striking a balance between financial discipline and innovation to drive expansion.

Beyond financial leadership, you will be a key partner to the executive team, collaborating across departments to align financial strategy with business growth and profitability. You will oversee financial planning & analysis (FP&A), Accounting, Investor and lender relationships, treasury, People (HR), cap table, financial reporting, and unit economic analysis. At the same time, ensuring transparency and accountability in financial operations and audits.

Key Responsibilities

Financial & Business Strategy

• Partner with C-Suite to develop and execute a financial strategy that supports sustainable growth, software investments, and ROI optimization.
• Lead financial planning and analysis (FP&A), budgeting, and forecasting.
• Translate complex financial data into actionable insights and strategic recommendations.
• Prepare and present financial reports to the board and investors
• Build and maintain robust financial models to support scenario planning, resource allocation, and ROI-driven decision-making.
• Empower cross-functional leaders with financial insights, data analytics, and performance metrics to drive sound decision-making and a performance-driven culture.
• Provide executive sponsorship for periodic executive and company-wide meetings, fostering collaboration, alignment, and morale across the organization.
• Develop scalable financial models for our 100% recurring revenue business, striking a balance between growth, cash flow, and profitability.
• Provide executive sponsorship for periodic executive and company-wide meetings, fostering collaboration, alignment, and morale across the organization.

Revenue & Profitability Optimization

• Partner with sales and business development teams to drive net new revenue and optimize existing revenue streams.
• Manage and model pipeline and Quota to attainment levels and KPI’s.
• Support leaders in optimizing commission plan structures, SPIFFs, incentives, Revenue share program, etc.
• Lead pricing strategy development for small business clients, revenue share models, embedded software solutions, and partner channels.
• Understanding and appropriately timing and planning for the staffing ramps required to maintain the company's objectives.

Accounting & Compliance

• Oversee all accounting operations including general ledger, accounts payable, payroll, and tax compliance.
• Ensure timely and accurate preparation of monthly, quarterly, and annual financial statements.
• Maintain compliance with GAAP and implement strong internal controls.
• Manage external audits, tax filings, K1 distributions, and relationships with auditors, Investors, and the Board.

Operational & Financial Efficiency

• Deliver accurate, timely financial reports, dashboards, and KPI assessments, including consolidated P&L analysis, to support decision-making for executives and investors.
• Ensure compliance, financial transparency, and investor readiness through rigorous financial controls and reporting.
• M&A due diligence and support integration in partnership with cross-functional leaders
• Provide strategic oversight of People operations and HR initiatives, including talent acquisition, onboarding, performance management, compensation and benefits, compliance, and employee development; collaborate with HR leadership to implement policies and programs that foster a performance-driven, compliant, and engaging work environment aligned with company values and long-term goals.

Leadership & Culture

• Develop and lead a high-performing Finance and People team, fostering a culture of accountability and innovation.
• Collaborate across departments to ensure financial strategy supports ConnectPay’s mission, values, and client-first approach.

Qualifications:

• 10+ years of leadership experience in finance, preferably in a high-growth SaaS, fintech, or tech-enabled Service company. Payroll industry experience is ideal, but not required
• Successful track record of scaling lower-middle-market SaaS/Tech-enabled service businesses.
• The ideal candidate brings a demonstrated track record of building and scaling businesses while taking full ownership of outcomes. They operate effectively in dynamic environments and thrive in ambiguous situations. Equally adept at high-level strategy and hands-on problem solving, they approach challenges with an agile and scrappy mindset. They can delve into the details while maintaining a strong strategic perspective. They possess excellent communication skills, an authentic executive presence, consistently prioritize team success, and foster a collaborative, mission-driven culture that aligns with business goals
• Ideally, have experience with the oversight of HR and legal functions, including contracts.
• Strong leadership skills, committed to building and developing high-performing teams.
• Bachelor’s Degree required; MBA preferred.

CP Payroll believes in fair and equitable pay. A reasonable estimate of this role's hiring base salary range is $220,000 - $275,000. The salary offered may be outside of this range depending on a variety of factors, including but not limited to a candidate’s education, training, experience, location, and internal equity. In addition to base salary, all CP Payroll team members receive equity and participate in either an annual bonus plan, based on company and individual performance, or a role-based sales incentive plan.

This role is eligible for an annual bonus with a target of 30% of base salary, based on company and individual performance.

At CP Payroll, we are proud to offer a comprehensive team member benefits package, including 401(k) with company contributions, group medical, dental, and vision coverage, life insurance, short and long-term disability insurance, and flexible spending accounts.

CP Payroll is an equal opportunity employer. We are committed to a work environment free from discrimination and harassment. All employment decisions are made without regard to race, color, religion, gender, sexual orientation, gender identity or expression, national origin, age, disability, marital status, veteran status, or any other protected characteristic under applicable law.

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