SVP, Head of Retirement Fiduciary Services

Location: Remote or Hybrid, traveling to Wakefield MA once per month.

The Purpose of Your Role:

The SVP, Head of Retirement Fiduciary Services is the senior business leader for Sentinel Pension Advisors (SPA) and is accountable for advancing Retirement’s vision, mission, strategy, growth, and day‑to‑day execution of SPA’s fiduciary advisory business.

This role is responsible for evolving an outcomes-focused retirement advisory platform that delivers disciplined, consistent fiduciary governance and materially improves participant participation, savings rates, and investment outcomes. It positions the retirement plan as a strategic business lever for employers while simplifying sponsor decision-making through clear recommendations, actionable insights, and confident guidance.

What you'll bring to Sentinel:

You are a dynamic enterprise leader with deep retirement plan and fiduciary expertise, strong technical credibility, and exceptional people leadership. You bring a disciplined, data-driven operating approach, a history of building and scaling advisory teams, and strategic execution that advances Sentinel’s vision for outcomes-focused retirement fiduciary services.

You will work in close partnership with the Head of Retirement and other senior leaders to shape and execute the strategy for Sentinel Pension Advisors, aligning fiduciary governance, plan design, and investment consulting with the broader Retirement and Benefits agenda. You will collaborate frequently with Operations, Technology, Compliance, Sales, and Marketing to enhance our advisory platform, elevate the client experience and drive stronger participant outcomes, and strengthen Sentinel’s position as a leading institutional retirement partner.

What you’ll be responsible for:

You will:

• Think and execute with a strategic, enterprise mindset and a focus on long‑term value creation.
• Be a change agent who can see the future state, build a plan, sequence priorities, and bring people along through clear communication and disciplined execution.
• Operate comfortably at multiple altitudes:
  • In the details of fiduciary frameworks, ERISA standards, and plan strategy.
  • In high‑stakes client and prospect conversations with CEOs, CFOs, HR/Benefits leaders, and investment committees.
  • In enterprise‑level discussions with Sentinel leadership, shaping SPA’s role in the broader firm.
• Demonstrate uncompromising integrity and judgment on fiduciary, regulatory, and ethical matters.
• Exhibit strong communication skills, written and verbal, with the ability to translate technical concepts into business outcomes.
• Model a collaborative, low‑ego approach that strengthens the broader Retirement organization.
• Provide overall leadership, strategy execution, and day‑to‑day management of Fiduciary & Retirement Advisory Services, including plan advisors, CIO, financial wellness educators, and the investment analyst team.
• Assume executive responsibility for select key client relationships
• Ensure transparency and stewardship over key performance indicators (growth, retention, profitability, service quality and participant outcomes).
• Represent Retirement Fiduciary Services in internal forums, steering groups, and cross‑functional initiatives and act as a visible culture carrier and advocate for Sentinel’s values and the Retirement’s Vision and Mission.

Core Competencies:

• Demonstrated senior leadership with strong strategic thinking, sound judgment, and the ability to inspire and align teams around a clear vision.
• Deep expertise in institutional retirement plans, fiduciary governance, plan design, investment consulting, and the integration of recordkeeping/TPA with advisory services.
• Proven track record of driving growth, profitability, operational excellence, and cultural change within an advisory or consulting business.
• Highly organized, analytical, and detail-oriented; a self-starter who is collaborative, results-driven, and effective in managing complexity and ambiguity.
• Demonstrated ability to challenge the status quo constructively, clarify priorities, build teams, drive accountability, and remove obstacles to performance.

Strategic Leadership & Business Direction:

• Provide clear strategic direction for Retirement Fiduciary Services, evolving SPA into a forward-looking, business-aligned, outcomes-oriented advisory platform with differentiated value.
• Set and communicate priorities for the advisory business, emphasizing robust plan governance and consultative influence that shapes client strategy.
• Drive transparency into business unit financials and lead improvements in revenue growth, profitability, and scalability.
• Strengthen RPS/SPA collaboration through clear roles, handoffs, and shared success metrics so every interaction advances participation, savings, and outcomes.
• Lead, develop, and coach a high-performing team, establishing clear expectations, KPIs, and disciplined performance management and development practices.
• Foster a culture aligned with Sentinel’s values and ensure ongoing technical, consultative, and relationship-management development across the advisory organization.

Fiduciary Governance & Regulatory Oversight:

• Serve as a senior subject matter expert on fiduciary governance and retirement plan best practices, providing guidance internally and externally.
• Ensure high‑quality, consistent fiduciary review processes across plan advisors, including IPS design/adherence, committee governance, meeting documentation, and action follow‑up.
• Oversee legal and regulatory compliance within Fiduciary Advisory Services, in close coordination with Compliance.
• Stay current on ERISA, DOL/IRS guidance, and litigation trends and translate them into pragmatic guidance and training for clients and internal teams.

Operational Excellence & Cross‑Functional Collaboration:

• Drive process improvement and standardization across advisory workflows to ensure consistency, scalability, and high‑quality client deliverables.
• Identify and proactively remove obstacles that impair the team’s ability to focus on the highest priorities, especially those tied to participant outcomes and sponsor decision‑making.
• Partner closely with Operations and Technology to streamline implementation, administration, and ongoing service, making it easier for sponsors to manage their plans.
• Collaborate with internal client and participant‑facing teams to ensure cohesive participant engagement strategies, including financial wellness and My Financial Journey.
• Act as a senior connector across departments, fostering strong communication, shared goals, and aligned execution.

Client Engagement:

• Redefine engagement with business owners and leadership teams (CEO, CFO, HR/Benefits) by:
  • Connecting retirement plan decisions directly to revenue growth, talent attraction/retention, workforce health, and P&L impact.
  • Framing the cost of inertia (e.g., higher payroll, benefits, medical costs; delayed retirements; talent bottlenecks) versus the impact of targeted changes.
  • Translating technical concepts (auto‑enrollment, re‑enrollment, managed accounts, etc.) into plain‑language business outcomes.
• Serve as an executive sponsor for key client and intermediary relationships, ensuring high client satisfaction.

About you:

You are a strategic thinker who is just as comfortable shaping long‑term direction as you are rolling up your sleeves and spending meaningful time with wholesalers and advisors. You are a confident communicator and engaging speaker , able to simplify complex topics and influence stakeholders at all levels.

You thrive as a highly collaborative partner , working closely with internal teams to ensure tight alignment between what is promised in the sales process and what is ultimately delivered.

You are resilient, adaptable, and growth‑oriented , energized by change in the retirement and benefits landscape, and you have a proven track record of turning challenges into opportunities for clients, partners, and your organization.

What you need to have:

• Bachelor’s degree required
• Relevant industry licenses and designations required or obtained within a defined timeframe (e.g., FINRA Series 65/66, and one or more advanced credentials such as CFA, CPFA, AIFA, QPA, QKA or similar).
• 15+ years of progressive experience in retirement plan advisory, institutional consulting, or related financial services, including significant leadership responsibility.
• Direct experience overseeing or working closely with investment teams (CIO/analysts) and plan advisor/client‑facing teams.
• Demonstrated success leading in a business‑unit environment (e.g., advisory integrated with recordkeeping, TPA, and/or wealth management) strongly preferred.
• Directly manages the Chief Investment Officer, investment analyst team, plan advisor team and financial wellness educators. along with other leadership roles as assigned.
• Responsible for overall performance management, development, and succession planning within Retirement Fiduciary Services.
• Office‑based role with hybrid flexibility; primary location Wakefield, MA (or other agreed‑upon office location).
• Up to 35% travel may be required to visit clients, prospects, and Sentinel offices.
• Remote work arrangements may be considered in alignment with company policy.
• Salary Range: $170,000 - $240,000

At Sentinel, compensation is calibrated by experience and to your geographic location to reflect local market conditions; the posted salary range may vary based on where you live.

What you’ll be part of:
Joining our company means becoming part of something special. We're driven by a mission to excel in our industry and within our team, supported by people who truly care about our organization.

Sentinel was recognized by The Boston Globe as a Top Place to Work in 2020, 2023, and 2025. The firm also earned the Top Workplaces USA Award from Energage through 2021-2026.

At Sentinel, we welcome people from diverse experiences, backgrounds, and perspectives – and we wouldn’t have it any other way. So even if you don’t meet every single requirement, please consider applying if you like what you see. Our priority is to find talented individuals who enrich our team culture, contribute with enthusiasm, and are passionate about what they do.

Sentinel is an equal opportunity employer and welcomes everyone to our team. If you need reasonable adjustments at any point in the application or interview process, please let us know.

Some of our Benefits:

• PTO (vacation, sick, personal time bank)
• FTO (Flexible time off for vacation, sick, and personal time) after 2 years of service
• 12 Paid Holidays (10 stated and 2 floating holidays)
• 2 Community Volunteer Days
• 5 Summer Half Days
• Medical, Dental, Vision
• Life Insurance
• LTD & STD
• Retirement Plan with 4% Employer Match
• Parental Leave

See What We Stand For:  

Who we are:
Sentinel Group proudly serves nearly 5,000 clients throughout the U.S. For 35+ years, we’ve remained devoted to positively impacting the lives of our people, our clients and our communities. With a 9-year average associate tenure among our 265 professionals, our team’s commitment to excellent service has positioned Sentinel as the only provider who makes benefits EASY: easy for your people; easy for your business; and easy for you.

Our ultimate goal is to help companies and their employees prepare for their future health, wealth and retirement needs. Whether it’s through retirement plans, group health insurance, reimbursement accounts or financial planning, we engineer simple solutions and continuously strive to make them better. Our in-house experts – and their commitment to excellence – define who we are.

Sentinel is also one of the largest employee benefits firms in Massachusetts (Boston Business Journal) and was named a 2022 Retirement Plan Adviser of the Year in the Mentorship category (PLANADVISER Magazine).