Mutual Opportunities
Director of Alternative Investments
Boston, Massachusetts; Springfield, Massachusetts
Thank you to our employees for voting us one of the top places to work in Massachusetts for seven consecutive years!
Overview
Finance and Accounting is at MassMutual’s core, and our team is ushering in an era of growth. We are looking for bold ideas, creative solutions, and comfort embracing change. We strive to build a diverse team and leverage different points of view to optimize processes and build strong relationships.
Our team is motivated by challenging work that delivers substantial impact in a culture of accountability and collaboration. We treat policyowners and customers fairly and prioritize financial stability. Being part of a mutual company means that our teams can think long-term, and employees can dive deep into the complex structure of products and the organization.
Our finance teams are experts in their field and thrive in fast-paced environments. They balance the needs of the business and invest in the long term, while always putting the customer first. They align their work with our live mutual philosophy and strive to always make the right choice for our policyowners. We are building a team that truly embodies ‘together we move forward.’
“At MassMutual, finance is the heartbeat of our company. Maintaining financial strength and stability and earning trust are key to how we operate. And as a mutual life insurance company, we don’t have shareholders. This means that our finance team can think long-term when choosing the best paths to fulfill our purpose: helping people to secure their futures and protect the ones they love. We’re looking for dedicated, skilled, creative finance professionals to join us in tackling complex challenges. Here, you’ll have the opportunity to grow your career in a place that values your ideas and invites you to challenge the status quo.”
Job Description
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-focusedmindset
#LI-CR1
MassMutual is an equal employment opportunity employer. We welcome all persons to apply.If you need an accommodation to complete the application process, please contact us and share the specifics of the assistance you need.
California residents: For detailed information about your rights under the California Consumer Privacy Act (CCPA), please visit our California Consumer Privacy Act Disclosures page.
MassMutual will accept applications on an ongoing basis until such time as a candidate has been offered employment. The job description includes the main duties of this position, which may evolve over time. You may be required to perform other duties not listed.
It is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment.
Salary Range: $137,800-$180,800
Hiring Process
Explore
Explore our open jobs by clicking 'search jobs' to find a position that aligns with your experience and skills. You may also consider joining our Talent Network.
Apply
Click the “apply” button on that job posting to complete and submit your application. Your application will be reviewed by a recruiter, which, due to the volume of applications received, may take some time as we carefully consider each application.
Screen
After your application has been reviewed, if you meet the qualifications for the role, a recruiter will reach out to you to start a conversation.
Interview
If you are invited for an interview, you will be scheduled to meet with the hiring manager and hiring team.
Offer
If you are extended an offer to join MassMutual and accept, your start will be contingent upon a satisfactory background check.
Hire
If you accept the offer, we will be so excited to welcome you to the MassMutual community!
If you need an accommodation to complete the application process, please contact us and share the specifics of the assistance you need.
By the numbers*
- 85% of employee respondents say they are proud to work at MassMutual
-
90
% of employee respondents say the work they do at MassMutual is meaningful - 85% of employee respondents say they feel encouraged to come up with new and better ways of doing things
*Source: 2025 MassMutual employee engagement survey
Award-Winning Culture
MassMutual is guided by a single purpose: We help people secure their future and protect the ones they love. As a company operated for the benefit of our members and participating policyowners, we are defined by mutuality and our vision to provide financial well-being for all Americans. It’s more than our company structure — it’s our way of life. We are a company of people protecting people. Our company exists because people are willing to share risk and resources and rely on each other when it counts.
We strive to build a thriving community where everyone is valued, included, and feels that they belong.
At MassMutual, we Live Mutual.
How We Work
MassMutual’s flexible workplace approach combines the importance of connecting in person and the flexibility of working remotely. Our hybrid model puts collaboration first with employees coming in at least three days per week to our spectacular campus settings and also enjoying the flexibility of remote Fridays, company-wide remote weeks, and a bank of flexible remote weeks to use throughout the year.
Benefits for the whole you (and your loved ones)
There’s more to your life than your job and there’s more to your aspirations than a paycheck. We take a holistic view of compensation and benefits that provides the flexibility to create a healthy balance in your life for work, family, and community. We offer the benefits you’d expect, like medical, dental, 401(k), and generous vacation time, but we also offer ones you might not expect, like three paid days for volunteering, a $1,250 annual Well-Being Wallet, and up to 320 hours of caregiver leave.
Explore some of our offerings below. Benefit details can be found here.
Why MassMutual?
Candy
Marketing Consultant
Atsam
Head of Advisor/Client Experience & Business Excellence
Erica
Head of Procurement
where we work
Springfield Office
1295 State Street, Springfield, MA
Boston Office
10 Fan Pier Blvd, Boston, MA
New York Office
2 Park Ave,
New York, NY
Virtual
New Job Openings
Sign up for job alerts
Don’t see the right role today? Sign up for job alerts and we’ll notify you when new opportunities that match your interests become available.
Job recruiter fraud is a scam by impostors posing as recruiters or representatives of a company promoting fake job opportunities to job seekers.
MassMutual will never ask job candidates to pay any kind of fee, make cash or check advancements, cash checks or make an investment in any product or service or provide information such as credit card numbers or banking PIN numbers as part of our hiring process.
If you are contacted by anyone asking for information outlined above, it is likely fraudulent. If you have any concerns about the veracity of a request, please contact us to verify its legitimacy.
Share This Job