Head of AI Strategy

MassMutual•Boston, MA

About The Position

The Team The Research & Development (R&D) team within the Enterprise Technology Experience (ETX) organization is responsible for developing and deploying automation, AI (traditional, generative, and agentic), and other emerging technologies and trends (e.g., health and wellness offerings) to deliver transformative impact to MassMutual customers, financial professionals, and employees. Given all of MassMutual’s technical delivery capabilities within these emerging technology domains sit within R&D, the team has recently been in “growth mode” with a particular focus on building out our technical talent in generative and agentic AI and our strategy and transformation talent as part of a newly established “Strategy & Partnerships” team. The recently established Strategy & Partnerships team within R&D is responsible for partnering with the most senior leaders across MassMutual to develop a holistic strategy for deploying our R&D capabilities toward the most impactful business outcomes and strategic priorities across the enterprise. To that end, the Strategy & Partnerships team is responsible for: 1) Partnering with our Executive Leadership Team (ELT) and other senior business stakeholders to identify opportunities to deliver transformative, step-change impact on MassMutual’s strategic business priorities through the deployment of emerging technologies such as AI 2) Bringing together and leading cross-functional teams composed of business, technology, and control function partners to execute against these opportunities 3) Working with the R&D Leadership Team and a cross-functional group of senior leaders across MassMutual to: Define the transformation approach and best practices that cross-functional teams will leverage to deliver impact at-scale across MassMutual through the deployment of AI and other emerging technologies Partner with stakeholders and senior leaders within Human Resources, Communications, and Corporate Finance to ensure a rigorous approach to change management, communications, and impact tracking is taken 4) Providing regular updates to our Board of Directors, CEO and Executive Leadership Team, and other senior stakeholders on the progress of our program and efforts The Strategy & Partnerships team is comprised of a team of Product Owners that are aligned to MassMutual business areas and a central Program Leadership office which is responsible for defining the overall transformation approach and strategy in collaboration with the broader R&D leadership team. The Head of AI Strategy would lead the Program Leadership office and report into the Head of R&D Strategy & Partnerships. Culturally, we look for individuals with a strong inclination for learning and from a variety of backgrounds who challenge each other openly, regardless of level or role on the team. We operate using a top-down, hypothesis-driven problem-solving approach grounded in strong conceptual thinking / problem structuring skills and deep data analysis. We embrace diversity in all of its forms, require respect, expect consistent delivery of high quality products and look to have fun. The Impact MassMutual, and our industry at-large, are at a pivotal time as emerging technology such as generative and agentic AI are fundamentally transforming how we operate and deliver value to our customers, financial professionals, and employees. This role offers the opportunity to play a central role in that transformation and to shape how MassMutual leverages AI and other emerging technologies to deliver on its key business outcomes and strategy at the highest levels. As the Head of AI Strategy, you will be at the center of defining the overall transformation approach and strategy for our cross-enterprise efforts and be partnering day-to-day with the Head of R&D Strategy & Partnerships, the broader R&D Leadership Team, and other senior stakeholders across the business and technology teams to deliver impact at-scale through the deployment of AI (and broader emerging technologies). If we are successful, we will not only be transforming MassMutual, we will also be transforming and setting an example for the rest of our industry.

Requirements

4+ years of experience at a top-tier strategy consulting firm (must be highly rated) including experience leading substantive portions of project teams OR 10+ years of experience driving strategy setting, operating model redesign, and technology-focused frontline transformation within financial services including substantial people leadership experience
Bachelor’s Degree from leading college or university
Proven track record of developing teams of direct reports through coaching and mentorship
Ability to work collaboratively in a team as well as cross-functionally to create an inclusive environment with people at all levels of an organization
Ability to quickly break down problems in a structured manner, analyze complex data, prioritize analyses, and quickly discern what is most important to draw out insights and implications
Ability to analyze complex financial, industry, and technology trend data and draw out insights and implications that demonstrate “next level thinking” which go beyond surface-level observations
Ability to create simple, powerful, and data-driven communications and effectively use creative storytelling to influence senior leaders and help their decision-making
Outstanding communication skills with a demonstrated ability to build enduring, trust based and high-impact relationships with clients and other colleagues

Nice To Haves

Bachelor’s degree from leading college or university in Investment/Business or an analytical field such as Economics, Mathematics, Engineering, or Computer Science
Experience within the life insurance or broader financial services industry
Experience with emerging technologies and trends such as AI, quantum computing, blockchain / tokenization, longevity revolution / health and wellness trends
Experience working in an agile work environment
Resilient and adaptable approach to getting the work done and skilled in applying judgment to balance process compliance with achievement of business objectives
Strong organizational skills and detail oriented
Outcome oriented with the ability to dynamically switch between drilling down into process details and pulling up to understand the big picture as needed
Ability to communicate objectives, plans, status and results clearly
Strong leadership skills and ability to influence without authority

Responsibilities

Work alongside experienced strategy and transformation leaders to define and continuously refine our transformation approach and strategy for delivering on the highest impact, most strategically important cross-enterprise efforts that leverage AI and other emerging technologies
Lead a team of AI Strategy Associate(s) and be accountable for content creation (i.e., slide decks, bespoke analyses, etc.) for meetings with our Board of Directors, Executive Leadership Team, and other senior stakeholders to update them on program progress and/or answer strategic questions related to our efforts
Bring structure to ambiguous problems and take action to solve them
Demonstrate strong people leadership skills and business intuition in leading a team to perform research on technology, competitive, market, and consumer trends and conducting financial analysis necessary to inform decision-making, using quantitative and qualitative approaches
Synthesize complex information to create compelling and influential narratives with clear takeaways and recommendations
Create client-facing deliverables that are simple, powerful, and data-driven
Communicate in a structured manner with conviction, clarity, and a bias for action
Work collaboratively with a diverse team to come up with the best solution and move MassMutual leaders to action
Establish trust-based relationships with senior MassMutual stakeholders and business partners to better serve their lines of business, functions, and the enterprise as a whole
Foster intellectual curiosity and creative thinking in stakeholders, business partners, colleagues, and your team
Navigate ambiguity to resolve problems and deliver results which likely have significant enterprise-wide impact, beyond the R&D and/or ETX organizations
Further develop your individual and team leadership style, leveraging your own passions, strengths, and personal values

Benefits

At MassMutual, we focus on ensuring fair equitable pay, by providing competitive salaries, along with incentive and bonus opportunities for all employees.
Your total compensation package includes either a bonus target or in a sales-focused role a Variable Incentive Compensation component.
We help people secure their future and protect the ones they love.
As a company owned by our policyowners, we are defined by mutuality and our vision to put customers first.
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.
At MassMutual, we Live Mutual.
At MassMutual, we focus on ensuring fair, equitable pay by providing competitive salaries, along with incentive and bonus opportunities for all employees.
Your total compensation package includes either a bonus target or in a sales-focused role a Variable Incentive Compensation component.
For more information about our extensive benefits offerings please check out our Total Rewards at a Glance.