Remote Chief Operating Officer Insurance Jobs in Boston, MA

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

The Purpose of Your Role

The SVP, Retirement Fiduciary Services is a senior leader within Sentinel Pension Advisors (SPA) who works closely with the Head of Retirement to shape the direction of the business while leading the execution of our business plan, strategic priorities, and growth initiatives across the business.

You will be responsible for building and leading a strong team, creating the conditions for people to do their best work, and ensuring the business operates with clear priorities, accountability, and strong client service.

With responsibility for leading and managing SPA’s ERISA 3(21) and 3(38) advisory business, you will drive the performance, discipline, and coordination needed to grow the business, expand capacity, and deliver stronger outcomes for clients, participants, and the business.

What you’ll bring to Sentinel Group

You are a strong senior leader with deep retirement plan and fiduciary expertise, sound operating judgment, strong investment acumen and a proven ability to execute strategy through people, process, and accountability. You bring a disciplined, data-driven operating approach, a history of building strong partnerships across teams, and a relentless focus on responsiveness, relationships, and participant outcomes.

What you’ll be responsible for

• Partner closely with the Head of Retirement, SVP, Retirement Plan Services, COO, CIO to help translate the vision, mission, and strategy for our Retirement Fiduciary Advisory Services into actionable business and operating plans.
• Execute against strategic priorities with discipline, transparency, and accountability, ensuring alignment between long-term direction and day-to-day operations.
• Serve as a senior leader for Fiduciary & Retirement Advisory Services, supporting the performance, consistency, and scalability of the advisory business.
• Lead with a relentless focus on building strong relationships internally and externally, improving responsiveness, and delivering better participant outcomes.
• Help establish and monitor key performance indicators related to growth, retention, service quality, profitability, operational effectiveness, and participant results.
• Foster a culture of accountability, collaboration, responsiveness, and continuous improvement across the advisory organization.
• Work comfortably at multiple altitudes:
  • In the details of fiduciary frameworks, ERISA standards, and plan strategy.
  • In important client and prospect conversations with CEOs, CFOs, HR/Benefits leaders, and investment committees.
  • In cross-functional and senior leadership discussions focused on execution, alignment, and business performance.
• Demonstrate strong judgment, integrity, and credibility on fiduciary, regulatory, and business matters.
• Translate technical concepts into practical, actionable business guidance for clients, colleagues, and partners.
• Model a collaborative, low-ego approach that strengthens the broader Retirement organization.

Strategic Execution & Operating Leadership

• Create urgency for growth by challenging the status quo and paint a better future.
• Clarify priorities so effort is focused on what drives results.
• Build and develop a team that can execute, grow, and scale beyond individuals.
• Create accountability through clear ownership, expectations, and follow-through.
• Remove obstacles so our teammates can perform at their best.
• Ensure visibility into business performance and operating metrics, using KPIs and data to guide decisions, improve execution, and address gaps proactively.
• Drive operational discipline and consistency across the advisory team, ensuring that commitments are met and standards remain high.
• Support financial stewardship by helping improve scalability, resource alignment, and business performance in partnership with senior leadership.

Leadership, Team Development & Culture

• Lead, develop, and coach a high-performing team, establishing clear expectations, accountability, and disciplined performance management practices.
• Foster a culture of service excellence, relationship ownership, responsiveness, and continuous improvement.
• Promote alignment across advisory, retirement plan services, investments, operations, compliance, technology, and participant-facing teams.
• Lead by example, helping teams navigate change with resilience, clarity, and a solutions-oriented mindset.

Fiduciary Governance & Advisory Excellence

• Serve as a senior subject matter expert on fiduciary governance, retirement plan best practices, and institutional advisory excellence.
• Strong investment acumen, including the ability to assess retirement plan investment considerations, support fiduciary oversight, and engage credibly in investment-related discussions with clients and stakeholders.
• Ensure high-quality and consistent fiduciary review processes across plan advisors, including IPS design and adherence, committee governance, meeting documentation, and follow-up actions.
• Partner with Compliance and other internal stakeholders to maintain strong regulatory and risk management practices.
• Stay current on ERISA, DOL/IRS guidance, and relevant litigation trends, helping translate changes into practical guidance for internal teams and clients.
• Reinforce an advisory model that simplifies sponsor decision-making through clear recommendations, sound governance, and actionable insights.

Operational Excellence & Cross-Functional Collaboration

• Drive process improvement and standardization across advisory workflows to improve consistency, scalability, and service quality.
• Partner closely with Operations and Technology to streamline implementation, administration, and ongoing service delivery.
• Help ensure that internal handoffs, communication, and service models support a seamless client experience.
• Collaborate with client-facing and participant-facing teams to strengthen engagement strategies and improve participant outcomes.
• Act as a senior connector across departments, building strong relationships, shared goals, and aligned execution.

Client Relationship & Participant Outcome Focus

• Help redefine how the advisory organization engages with business owners and leadership teams by connecting retirement plan decisions to business outcomes, workforce readiness, and employee financial wellbeing.
• Support key client and intermediary relationships as a senior leader, helping ensure high satisfaction, confidence, and trust.
• Promote a consultative approach that combines technical excellence with responsiveness and strong relationship management.
• Keep a clear and consistent focus on improving participant engagement, savings behavior, and retirement readiness.
• Ensure the advisory team brings urgency, follow-through, and practical problem-solving to every client interaction.

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.
• 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: https://www.sentinelgroup.com/About-Us/Join-Our-Team

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).

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