Merger & Acquisition Director

Location: Foxboro

Description

Job Summary

Connect Pay is seeking a strategic, relationship-driven leader to build our Mergers & Acquisitions function. As M&A, Director, you will play a central role in shaping and executing Connect Pay's inorganic growth strategy. This position is ideal for a highly motivated professional with proven experience sourcing, evaluating, and executing transactions-particularly within the small-to-mid-sized business (SMB) or founder-led space.

You'll own the full deal lifecycle-from identifying opportunities and building relationships with target companies, to driving due diligence, structuring deals, and facilitating smooth integrations. This is a high-impact, high-visibility role with significant interaction across the executive team, including the CEO, CFO, and President. You will also mentor junior M&A team members and work closely with external advisors to advance Connect Pay's long-term growth goals.

The current President, M&A is planning for retirement and will remain actively involved over the next 12 months to mentor and support your transition. This is a rare opportunity for hands-on knowledge transfer and development, with the expectation that you will fully assume leadership of the function within 6-12 months of hire and transition to report directly to the CEO.

Key Responsibilities

M&A Strategy & Pipeline Development

• Lead the development and evolution of Connect Pay's M&A strategy in alignment with corporate objectives and market dynamics.
• Build and maintain a robust acquisition pipeline across current and adjacent markets, focusing on high-quality small to medium-sized businesses (SMBs) within the payroll and human capital management (HCM) space.
• Proactive sources deals through direct outreach, networking, referrals, and strategic partnerships.

Relationship Management & Deal Sourcing

• Cultivate relationships with business owners, founders, CPAs, brokers, and other key influencers.

• Represent Connect Pay at industry events, conferences, and trade shows to increase visibility and uncover new opportunities.

Deal Execution

• Manage end-to-end transaction execution-including due diligence, financial modeling, valuation, negotiations, and deal structuring.

• Lead cross-functional deal teams, ensuring alignment across finance, legal, operations, and executive leadership.

• Prepare and present deal recommendations to the executive team and board.

Team Leadership & Operational Excellence

• Supervise and mentor M&A Associates and Analysts, fostering development and accountability.

• Maintain CRM discipline and manage pipeline reporting, deal metrics, and KPIs.

• Design scalable frameworks to evaluate, prioritize, and integrate acquisition opportunities efficiently.

Qualifications

• Bachelor's degree required; MBA or equivalent advanced degree preferred.

• 5-8 years of relevant experience in M&A, corporate development, investment banking, private equity, or similar fields.

• Demonstrated success leading SMB or founder-led transactions from sourcing to close.

• Strong financial modeling and analytical skills with a deep understanding of deal mechanics.

• Exceptional relationship-building and communication abilities.

• Highly organized, resourceful, and comfortable working cross-functionally in a dynamic, growth-stage environment.

• High degree of discretion, emotional intelligence, and executive presence.

Why Join Connect Pay?

We are a client-obsessed, fast-growing company on a mission to simplify payroll and HR for America's small businesses. You'll have a direct hand in shaping our future through strategic expansion-working side-by-side with an engaged leadership team and making a meaningful impact on our company and the clients we serve.

CP Payroll believes in fair and equitable pay. A reasonable estimate of this role's hiring base salary range is $160,000 - $200,000 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…