Executive Assistant to the CEO – Boston, MA | Healthcare Leadership Support

Executive Assistant to the CEO

📍 Location: Boston, Massachusetts (Onsite)
💼 Employment Type: Full-Time
🏥 Industry: Healthcare / Hospital System

💰 Compensation & Benefits

• Salary Range: $100,000 – $130,000

• Full benefits package included

• No relocation assistance

• No visa sponsorship available

🚀 Overview

A leading healthcare organization is seeking an experienced Executive Assistant to the CEO to provide high-level administrative and operational support to executive leadership.

This role requires a polished, highly organized professional who thrives in a fast-paced executive environment and has prior experience directly supporting a CEO or senior C-suite leader. The ideal candidate will possess exceptional communication skills, strong MS Teams proficiency, and the ability to manage multiple priorities with discretion and professionalism.

⚠️ This is a fully onsite role — candidates must be able to work onsite 5 days per week.

🔧 Key Responsibilities

Executive Support

• Provide high-level administrative support to the CEO and senior leadership team

• Manage calendars, meetings, and executive scheduling priorities

• Coordinate travel arrangements and process expense reimbursements

• Draft and prepare:

• Correspondence

• Reports

• Presentations

• Meeting materials

• Press releases

• Attend meetings and prepare/distribute meeting minutes

Communication & Coordination

• Serve as the primary point of contact for the executive office

• Triage calls and communications from:

• Internal departments

• Donors

• Media contacts

• Advocacy groups

• External stakeholders

• Maintain professionalism and diplomacy in all communications

Research & Administrative Projects

• Assist with:

• Research grant applications

• Grant reporting tracking

• Policy and funding research

• Conduct web research on:

• Federal funding trends

• Industry opportunities

• Relevant healthcare initiatives

• Identify and distribute articles and information relevant to leadership priorities

Organization & Operations

• Maintain highly organized workflows and executive priorities

• Coordinate office supplies and administrative logistics

• Ensure deadlines, schedules, and deliverables remain on track

• Support cross-functional coordination across departments and leadership teams

✅ Required Qualifications

• Bachelor’s Degree required

• Equivalent experience/training may be considered

• 3–5 years of progressive executive administrative experience

• Prior experience supporting:

• CEO preferred

• Other C-suite executives acceptable

• Advanced proficiency with:

• Microsoft Teams

• Microsoft Word

• Excel

• PowerPoint

• Outlook

• Excellent organizational, communication, and multitasking abilities

⭐ Preferred Qualifications

• Experience within:

• Large hospital systems

• Healthcare organizations

• Complex enterprise environments

• Experience with:

• Project management

• Data management

• Policy research

• Non-profit fundraising support

🛠️ Core Skills

✔ Executive Support
✔ CEO Support
✔ MS Teams
✔ Calendar Management
✔ Travel Coordination
✔ Meeting Coordination
✔ Presentation Preparation
✔ Project Coordination
✔ Executive Communication
✔ Administrative Operations
✔ Microsoft Office Suite
✔ Stakeholder Management
✔ Multitasking & Prioritization

🎯 Ideal Candidate

• Experienced Executive Assistant who has directly supported a CEO or senior executive leadership team

• Highly organized and able to manage competing priorities independently

• Professional, polished, and confident interacting with senior stakeholders

• Strong communicator with exceptional attention to detail

• Comfortable working in a fast-paced healthcare or large enterprise environment

• Able to maintain confidentiality and professionalism at all times

⚠️ Important Notes

• Fully onsite position — no remote or hybrid flexibility

• Candidates must be advanced MS Teams users

• Preference for candidates from larger healthcare systems or enterprise organizations

• No visa sponsorship available

📝 Screening Questions

1. Are you willing to work onsite 5 days per week?

2. Are you an advanced user of MS Teams?

3. Have you previously supported a CEO or other C-suite executive?

🌟 Why Join

• Opportunity to support executive leadership at a respected healthcare organization

• High-visibility role with direct exposure to senior leadership initiatives

• Collaborative and mission-driven culture

• Strong organizational values focused on community impact, innovation, and inclusion

• Excellent opportunity for experienced executive assistants seeking long-term growth in healthcare leadership support

Director of Benefits – Houston, TX | Healthcare Total Rewards Leadership

Director, Benefits
Houston, Texas | Hybrid | Full-Time

This is a high-profile leadership opportunity for an experienced Total Rewards professional to shape and lead enterprise-wide benefits strategy within a large, complex healthcare environment. Combining strategic leadership, operational oversight, compliance expertise, and workforce engagement, this role offers the chance to directly influence employee experience, organisational performance, and long-term talent retention.

Designed for a senior benefits leader with deep healthcare experience, this position provides significant executive exposure and the opportunity to lead transformative initiatives across health and welfare, retirement, wellbeing, and total rewards programs.

The Opportunity

Reporting into executive Total Rewards leadership, you will oversee the design, implementation, governance, and optimisation of comprehensive employee benefits programs across a large healthcare system.

You will:

• Lead enterprise-wide benefits strategy, administration, and compliance initiatives

• Design and implement competitive, cost-effective benefit programs aligned with organisational goals

• Oversee health and welfare plans, retirement programs, wellness initiatives, and voluntary benefits

• Manage relationships with consultants, brokers, actuaries, trustees, and third-party vendors

• Ensure compliance with ERISA, HIPAA, COBRA, FMLA, IRS, DOL, and healthcare reform regulations

• Partner with Compensation, HRIS, and executive HR leadership to deliver integrated Total Rewards strategies

• Drive process improvements, automation, and system enhancements across benefits operations

• Develop metrics and reporting frameworks to evaluate ROI and program effectiveness

• Lead, mentor, and develop a high-performing Benefits team

• Support enterprise transformation initiatives focused on employee engagement and workforce strategy

Compensation & Benefits

• Salary: $160,000 – $200,000

• Annual Bonus: 20–30% performance-based bonus potential

• Schedule: Full-Time | Hybrid Work Environment

• Location: Houston, Texas

• Relocation Assistance: Not provided, but candidates must be willing to relocate to Houston

• Visa Sponsorship: Not available

Comprehensive Executive-Level Benefits Package Includes:

• Medical, Dental, and Vision Insurance

• Life Insurance

• Retirement Programs

• Paid Time Off

• Additional wellbeing, leadership development, and employee support programs

What Makes This Role Stand Out

• Opportunity to lead Benefits strategy within a highly respected healthcare organisation

• Significant executive visibility and enterprise-level influence

• Broad scope across retirement, health & welfare, wellness, and compliance initiatives

• Ability to shape and modernise Total Rewards strategy within a complex healthcare environment

• Strong collaborative culture focused on innovation, employee wellbeing, and operational excellence

• Opportunity to make a measurable impact on workforce engagement and retention

Candidate Profile

Essential Requirements:

• 10+ years of experience managing Benefits operations and implementation within healthcare or complex enterprise environments

• Strong healthcare industry Benefits experience required

• Deep expertise in plan design, evaluation, compliance, and administration across:

• Health & Welfare Plans

• Pension Plans

• 401(k) and 403(b) Programs

• Life & Disability Benefits

• Voluntary Benefits Programs

• Strong understanding of ERISA, COBRA, HIPAA, FMLA, and healthcare reform regulations

• Prior HRIS systems experience

• Bachelor’s degree in Business, HR Management, or related discipline

Preferred Qualifications:

• Master’s degree preferred

• CEBS, CBP, or other HR/Benefits certifications highly desirable

• Experience with wellness strategy development and implementation

• Proven leadership and change management capability

• Strong vendor management, negotiation, and stakeholder engagement skills

What Success Looks Like

The successful candidate will bring a combination of strategic vision, operational discipline, and leadership maturity, with the ability to balance employee experience, compliance, cost management, and organisational growth within a dynamic healthcare environment.

This is an outstanding opportunity for a Benefits leader seeking a role that offers executive influence, enterprise-wide impact, and long-term career growth within a highly respected and mission-driven organisation.

Director of Benefits – Total Rewards, Compliance & HR Leadership (Healthcare)

Director of Benefits

📍 Location: Houston, Texas (Onsite/Hybrid)
💼 Employment Type: Full-Time
📈 Seniority Level: Director
🕒 Experience Required: 10+ years
🎓 Education: Bachelor’s Degree required (Master’s preferred)
💰 Salary: $160,000 – $200,000
🌎 Visa Sponsorship: Not available

🚀 Overview

A leading healthcare organization is seeking a Director of Benefits to lead the strategy, design, and delivery of enterprise-wide benefits programs.

This role is responsible for building and managing competitive, compliant, and cost-effective total rewards offerings, while leading a high-performing team and partnering across HR, finance, and executive leadership.

🔧 Key Responsibilities

Benefits Strategy & Program Leadership

• Design, implement, and manage comprehensive benefits programs, including:

• Health & welfare plans

• Retirement plans (401k, 403b, pension, non-qualified)

• Life, disability, and voluntary benefits

• Develop programs that attract, retain, and engage top talent

• Drive continuous improvement of benefits offerings and service delivery

Compliance & Governance

• Ensure full compliance with:

• ERISA, IRS, DOL regulations

• COBRA, HIPAA, FMLA, healthcare reform laws

• Oversee plan governance, reporting, and regulatory requirements

• Maintain audit readiness and risk mitigation processes

Vendor & Stakeholder Management

• Manage relationships with:

• Brokers

• Consultants

• Actuaries

• Third-party administrators

• Evaluate vendor performance and negotiate contracts

• Partner with internal stakeholders across:

• HR

• Finance

• HRIS

• Executive leadership

Total Rewards Integration

• Collaborate with Compensation and HRIS leadership to deliver a cohesive Total Rewards strategy

• Align benefits programs with organizational goals and workforce strategy

Operations & Systems

• Oversee benefits administration and HRIS integration

• Drive automation and system enhancements to improve employee experience and efficiency

• Act as escalation point for complex benefits issues

Analytics & Performance

• Develop and track KPIs and ROI metrics for benefits programs

• Use data-driven insights to optimize cost, utilization, and engagement

Leadership & Team Development

• Lead, mentor, and develop a team of benefits professionals

• Foster a culture of accountability, collaboration, and continuous improvement

• Support professional growth and capability building across the team

✅ Required Qualifications

• Bachelor’s degree in:

• Business

• Human Resources

• Or related field

• 10+ years of experience in:

• Benefits strategy, design, and administration

• Large, complex or multi-site organizations

• Strong experience across:

• Health & welfare plans

• Retirement programs

• Compliance and regulatory frameworks

⭐ Preferred Qualifications

• Master’s degree (MBA, HR, or related)

• Professional certifications such as:

• CEBS (Certified Employee Benefits Specialist)

• CBP (Certified Benefits Professional)

🧠 Key Skills

• Strong leadership and team management capability

• Deep knowledge of benefits compliance and regulations

• Excellent stakeholder management and communication skills

• Strong analytical, problem-solving, and decision-making ability

• Experience with HRIS systems and benefits platforms

🎯 Ideal Candidate

• Strategic leader with deep benefits expertise in healthcare or complex environments

• Proven ability to balance cost management with employee experience

• Strong operator who can drive both strategy and execution

• Experienced in managing vendors, compliance, and large-scale program