Top 27 Director of technology Jobs in Vermont

Director IT Agile Practice Management - Medicare
CVS Health —Vermont
- $144,200 - $288,400 a year
- Full-time
- Remote
- 3 years
- Bachelor's degree
- Continuous improvement
- Health insurance
- Dental insurance
Executive Director, AI Infrastructure & Platform Engineering
CVS Health —Vermont
- $175,100 - $334,750 a year
- Full-time
- Remote
- Computer Science
- HIPAA
- Recruiting
- Health insurance
- Dental insurance
Director Business Management & Data Products – Growth Analytics
CVS Health —Montpelier, VT
- $144,200 - $288,400 a year
- Full-time
- Finance
- Bachelor's degree
- Continuous improvement
- Health insurance
- Dental insurance
Director, Advanced Analytics & Governance
National Life Insurance Company —Montpelier, VT
- $135,000 - $198,000 a year
- Hybrid work
- Azure
- Computer Science
- HIPAA
- Benefits from day one
- Life insurance
Director of Web and Digital Communications
Middlebury College —Middlebury, VT
- $108,971 - $126,963 a year
- Full-time
- Computer Science
- Marketing
- Office
- Dental insurance
- Tuition reimbursement
Quick Apply
4d
Director, Portfolio Management
National Life Insurance Company —Montpelier, VT
- $127,500 - $187,000 a year
- Hybrid work
- 11+ years
- Office
- Analysis skills
- Adoption assistance
- Benefits from day one
Lead Director - Network and Data Center Engineering
CVS Health —Montpelier, VT
- $144,200 - $288,400 a year
- Full-time
- HIPAA
- High school diploma or GED
- Bachelor's degree
- Health insurance
- Dental insurance
Director, Enterprise Application Development (OnBase)
National Life Insurance Company —Montpelier, VT
- $136,875 - $200,750 a year
- Hybrid work
- Computer Science
- System design
- Office
- Benefits from day one
- Life insurance
Director of Enterprise Systems & Digital Transformation
Mack Molding —Arlington, VT
- From $110,000 a year
- Full-time
- Oracle
- Computer Science
- 8 years
Quick Apply
Lead Director - Software Development Engineering
CVS Health —Montpelier, VT
- $144,200 - $288,400 a year
- Full-time
- Research
- High school diploma or GED
- Bachelor's degree
- Health insurance
- Dental insurance
Lead Director, Software Engineering
CVS Health —Montpelier, VT
- $144,200 - $288,400 a year
- Full-time
- Computer Science
- System design
- HIPAA
- Health insurance
- Dental insurance
Director, Gear Analytics
Vail Resorts Corporate —Vermont
- $145,000 - $175,000 a year
- Full-time
- 18 years or older
- Office
- 8 years
- Health insurance
- Dental insurance
Quick Apply
Innovation Program Director
State of Vermont - Department of Environmental Conservation —Montpelier, VT
- $37.80 - $59.62 an hour
- Multiple hires
- Office
- Microsoft Office
- Master's degree
- Wellness program
- Paid holidays
2d
Senior Director Quantum Technology Solutions
GLOBALFOUNDRIES —Essex Junction, VT
- $198,000 - $333,000 a year
- Full-time
- 11+ years
- English
- Doctor of Philosophy
Associate Director, Life & Annuity Product Systems
National Life Insurance Company —Montpelier, VT
- $105,000 - $154,000 a year
- Hybrid work
- Computer Science
- System design
- 11+ years
- Benefits from day one
- Life insurance
Director, Data Science Operations
Kemper Insurance —Montpelier, VT
- $160,555 - $226,500 a year
- Email
- Remote
- Computer Science
- Java
- SQL
- Health insurance
- Dental insurance
Quick Apply
10d
Oracle Fusion Field Service Implementation Director
PRICE WATERHOUSE COOPERS —Montpelier, VT
- $155,000 - $410,000 a year
- Oracle
- Marketing
- Finance
- Paid holidays
- Health insurance
12d
CDP Strategy & Digital Personalization- Director
PRICE WATERHOUSE COOPERS —Montpelier, VT
- $122,500 - $504,500 a year
- Sales
- 8 years
- High school diploma or GED
- Paid holidays
- Health insurance
11d
Oracle Cloud CPQ Implementation Director
PRICE WATERHOUSE COOPERS —Montpelier, VT
- $155,000 - $410,000 a year
- Oracle
- Computer Science
- Marketing
- Paid holidays
- Health insurance
3d
Associate Director, Actuarial Systems & Innovation
National Life Insurance Company —Montpelier, VT
- $114,375 - $167,750 a year
- Hybrid work
- Computer Science
- Office
- Finance
- Benefits from day one
- Life insurance

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Director IT Agile Practice Management - Medicare

CVS Health -
Vermont

Apply Now

Job Details

Full-time
$144,200 - $288,400 a year

Benefits

Health insurance
Dental insurance
Paid time off
Vision insurance

Qualifications

Jira
Medicare
Coaching
Managing IT teams
Technology management
Continuous improvement
Mentoring
Scrum
IT governance planning
Leading team collaboration initiatives
IT portfolio management
Digital project management boards
Budgeting
Defect tracking tools
Cross-functional team management
Healthcare IT
Project risk management
Team motivation (leadership skill)
Project stakeholder communication
Stakeholder relationship building
Cross-functional communication
Organizational budget management
Agile planning
Senior leadership
Stakeholder management

Full Job Description

We’re building a world of health around every individual — shaping a more connected, convenient and compassionate health experience. At CVS Health®, you’ll be surrounded by passionate colleagues who care deeply, innovate with purpose, hold ourselves accountable and prioritize safety and quality in everything we do. Join us and be part of something bigger – helping to simplify health care one person, one family and one community at a time.

Position Summary

We are seeking an accomplished IT leader to serve as Director, Agile Delivery Practice. This is a high-impact leadership position responsible for overseeing a diverse, strategically important portfolio of technology initiatives and ensuring the highest standards of delivery, governance, and organizational alignment.

In this role, you will lead and support multiple, concurrent programs totaling 633,000+ hours of work and representing $44M+ of annual investment. You will be responsible for connecting business strategy to execution, creating structure and predictability in how work gets done, and ensuring that program outcomes translate into tangible value for the enterprise. Success in this role requires a rare combination of portfolio thinking, hands-on program delivery expertise, and strong stakeholder leadership across technology and business partners.

Required Qualifications

10+ years of experience leading Program Managers, Agile/Scrum teams, and cross-functional technology teams, delivering strategic initiatives and business-critical programs at scale.
10+ years of proven success managing IT portfolios and complex, multi-year technology programs within large, matrixed organizations, including oversight of budgets exceeding $20M.
8+ years of experience balancing strategic portfolio management with hands-on program leadership, adapting to business needs while driving successful program execution and outcomes.
6+ years of experience designing, implementing, and continuously improving program and portfolio governance frameworks, enhancing visibility, prioritization, risk management, and delivery performance.
5+ years of experience supporting Medicare programs, with a strong understanding of healthcare operations, regulatory requirements, and delivery within a complex healthcare environment.
5+ years of experience utilizing portfolio management and product delivery toolsets, including Rally, JIRA, roadmap planning, initiative management, and financial tracking solutions, with a commitment to continuously expanding expertise in emerging tools and practices.
3+ years of experience leading and developing high-performing teams, including direct management of 10+ employees, with a proven ability to coach, mentor, and foster an engaged, results-oriented culture.
3+ years of experience demonstrating strong communication skills and executive presence, with the ability to influence and build alignment across all levels of the organization, including senior executives and cross-functional stakeholders.
3+ years of experience establishing and maintaining high standards for quality, accountability, and stakeholder engagement, with a demonstrated ability to drive results through teams and cross-functional partnerships.
3+ years of experience successfully operating in complex and ambiguous environments, connecting priorities across multiple initiatives and driving clarity, alignment, and execution among diverse stakeholders.

Preferred Qualifications

Agile (e.g., SM, RTE, SPC), PMP, or equivalent certifications preferred.
Experience leading or supporting application modernization initiatives, including the migration of applications and services from on-premises environments to cloud-based platforms.

Education

Bachelor’s degree or equivalent experience required.

Pay Range

The typical pay range for this role is:

$144,200.00 - $288,400.00

This pay range represents the base hourly rate or base annual full-time salary for all positions in the job grade within which this position falls. The actual base salary offer will depend on a variety of factors including experience, education, geography and other relevant factors. This position is eligible for a CVS Health bonus, commission or short-term incentive program in addition to the base pay range listed above. This position also includes an award target in the company’s equity award program.

Our people fuel our future. Our teams reflect the customers, patients, members and communities we serve and we are committed to fostering a workplace where every colleague feels valued and that they belong.

Great benefits for great people

We take pride in offering a comprehensive and competitive mix of pay and benefits that reflects our commitment to our colleagues and their families.

This full‑time position is eligible for a comprehensive benefits package designed to support the physical, emotional, and financial well‑being of colleagues and their families. The benefits for this position include medical, dental, and vision coverage, paid time off, retirement savings options, wellness programs, and other resources, based on eligibility.

Additional details about available benefits are provided during the application process and on Benefits Moments.

We anticipate the application window for this opening will close on: 07/31/2026

Qualified applicants with arrest or conviction records will be considered for employment in accordance with all federal, state and local laws.

Apply Now

Refine Your Search

director of technology jobs in vermont

Director IT Agile Practice Management - Medicare

Executive Director, AI Infrastructure & Platform Engineering

Director Business Management & Data Products – Growth Analytics

Director, Advanced Analytics & Governance

Director of Web and Digital Communications

Director, Portfolio Management

Lead Director - Network and Data Center Engineering

Director, Enterprise Application Development (OnBase)

Director of Enterprise Systems & Digital Transformation

Lead Director - Software Development Engineering

Lead Director, Software Engineering

Director, Gear Analytics

Innovation Program Director

Senior Director Quantum Technology Solutions

Associate Director, Life & Annuity Product Systems

Director, Data Science Operations

Oracle Fusion Field Service Implementation Director

CDP Strategy & Digital Personalization- Director

Oracle Cloud CPQ Implementation Director

Associate Director, Actuarial Systems & Innovation

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