Director of Alternative Investments (Hiring Immediately)

Director of Alternative Investments

Investment Controllership

Full-Time/Boston, MA or Springfield, MA

The Opportunity

Reporting to MassMutual’s Head of Alternative Investments, the Director of Alternative Investments will be a key leader and representative for the investment accounting, reporting, governance, and control processes supporting MassMutual’s commercial mortgage loan and real estate portfolios. The position will lead a team of MassMutual employees focused on ensuring the accurate, timely completion of monthly, quarterly, and annual accounting close cycles for these asset classes, including oversight of accounting services and reporting deliverables prepared by third-party administrators and service providers. As a Director in the Controllers Organization of Corporate Finance, you will join us as we continue our progress toward becoming best-in-class financial stewards for MassMutual. We are forward-thinking and seek others who will leverage curiosity, business acumen, and initiative to strengthen our processes and outcomes. You will lead the team that manages and executes investment accounting, analysis, financial reporting support, control execution, and process improvement for commercial mortgage loans and real estate investments. This includes governance and oversight of financial transactions, statutory and GAAP accounting requirements, regulatory reporting schedules, management reporting, audit support, and key initiatives including technology, ledger, and operating model transformation. You will thrive in a dynamic and agile accounting environment focused on both disciplined execution and continuous improvement, while partnering collaboratively across Investments, Financial Reporting, Accounting Policy, Tax, Capital Management, business unit controllers, auditors, vendors, and other stakeholders.

The Team

The Investment Controllership team is a high-profile team in the Controllers organization, comprised of accountants who oversee our various asset classes and investment activity. The team continues to grow in support of our growing level of assets, key initiatives and special projects. Our team has high business acumen and is driven to provide timely and accurate financial information to our customers. We pride ourselves on working with agility and being a reliable source of information in the organization. We strive to continuously improve by working together as team to make each other and our processes better. Our culture thrives on inquisitive approaches to our work to help identify issues with specificity and demonstrate high levels of accountability to make things right.

The Impact

• Lead the team responsible for ensuring the accurate and timely completion of monthly, quarterly, and annual accounting close cycles for commercial mortgage loans and real estate investments through effective planning, monitoring, review, and problem solving.
• Oversee accounting information and reporting deliverables prepared by third-party administrators and service providers, including financial statements, footnote schedules, regulatory reports, management reports, and other investment accounting outputs.
• Review and analyze financial results, trends, and key drivers for the commercial mortgage loan and real estate portfolios, using strong business acumen and communication skills to develop clear commentary for senior management and financial reporting stakeholders.
• Participate in the creation, analysis, and presentation of monthly and quarterly financial analysis reporting to senior management, including explanations of portfolio performance and its impact on financial results.
• Develop, document, and assure adherence to an internal control framework that supports accurate and timely financial reporting for commercial mortgage loans and real estate. Monitor the control environment, including activities performed by vendors, and recommend improvements to strengthen governance, consistency, and accountability.
• Lead process improvement, automation, and operating model initiatives focused on increasing efficiency, reducing manual risk, improving transparency, and adding business value across the commercial mortgage loan and real estate accounting processes.
• Support annual regulatory financial statement audit requests, participate in auditor discussions, and serve as a key point of contact for audit matters related to commercial mortgage loans and real estate.
• Effectively collaborate with Accounting Policy, the Chief Investment Office, Tax, Financial Reporting, Capital Management, business unit controllers, third-party administrators, and external auditors to resolve complex accounting, reporting, and operational matters.
• Lead or support the implementation of new statutory and GAAP investment accounting requirements and determine the accounting process for new commercial mortgage loan and real estate investments, investment structures, and related transactions.
• Actively participate in the implementation of the Company’s new ledger and related investment accounting technology initiatives, with a focus on future-state reporting, data quality, controls, and target operating model design.
• Manage priorities effectively in a dynamic environment, balancing close execution, reporting deadlines, audit support, project delivery, and continuous improvement activities.
• Lead, develop, and motivate a team that is inspired, engaged, and accountable, while creating opportunities for team members to learn, grow, and contribute to better business outcomes.

The Minimum Qualifications

• Bachelor’s Degree
• 8+ years of relevant accounting, financial reporting, controllership, or investment accounting experience, with direct or related exposure to commercial mortgage loans, real estate, structured finance or private assets
• 1+ years of experience leading teams in a deliverable-oriented environment.
• 4+ years of experience overseeing monthly, quarterly, and annual close processes, financial reporting deliverables, controls, audits, or third-party service provider outputs.

The Ideal Qualifications

• Experience in insurance company investment accounting, including GAAP and statutory accounting for commercial mortgage loans, real estate, or other investment asset classes.
• CPA or progress toward CPA preferred.
• Knowledge of STAT and GAAP accounting requirements, regulatory reporting, financial statement support, and investment-related disclosures.
• Strong analytical skills, including the ability to analyze financial data sets, identify trends, and tell the story of the data in a clear and concise manner.
• Proven ability to complete high-quality work efficiently, manage multiple priorities, and lead through ambiguity in a dynamic and agile environment.
• Experience building and maintaining strong working relationships across cross-functional groups, senior leaders, auditors, and third-party administrators or vendors.
• Excellent verbal and written communication skills with the ability to express ideas in an organized and persuasive manner to leadership, staff, third parties, and other stakeholders.
• Experience identifying internal control issues, developing remediation plans, and implementing process improvements that strengthen the overall control environment.
• Preferred experience working in a Lean Six Sigma, continuous improvement, or root cause problem-solving environment.
• Ability to partner with and influence business leaders and peers in investment process redesign, reporting improvements, and target operating model transformation.
• Experience using investment data and information to analyze and communicate the implications of investment accounting, reporting, and ERP or subledger tools such as Aladin, SAP, Hyperion, NetSuite, or other investment accounting platforms.

What You Can Expect at MassMutual

MassMutual offers the opportunity to do meaningful work within a purpose-driven organization that values long-term impact over short-term outcomes. In this role, you can expect:

• Clear areas of ownership and accountability, with work that connects directly to company and customer outcomes

• A collaborative environment where perspectives are welcomed

• Access to learning, development, and internal networks that support continuous growth and skill-building over time

• Employee-led communities and forums that foster connection, learning, and inclusion across the organization

• A culture grounded in integrity, responsibility, and stewardship—supported by a company with a strong legacy and a future-focused mindset

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MassMutual is an equal employment opportunity employer. We welcome all persons to apply.

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