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Director Of Strategic Initiatives Jobs in Springfield, MA

Cigna

Strategic Planning Senior Director

Bloomfield, CT · On-site

... enterprise initiatives. This individual will work at the intersection of strategy, finance ... The Senior Director serves as a trusted advisor to executive leadership and champions an enterprise ...

The Hartford

Director, Strategy Insights

Hartford, CT · Hybrid

$143K - $214K/yr

Dir Strategic Initiatives - NS06AE We're determined to make a difference and are proud to be an ... This role will be dedicated to one or more of the aforementioned organizations. This role serves as ...

The Hartford

Director, Strategy Insights

Hartford, CT · Hybrid

Dir Strategic Initiatives - NS06AE We're determined to make a difference and are proud to be an ... This role will be dedicated to one or more of the aforementioned organizations. This role serves as ...

Green Key Resources

Head of Strategy

West Hartford, CT · On-site

This is a highly strategic Director-level individual contributor role with significant visibility ... Lead Health and Wellness initiatives across North America while ensuring compliance with applicable ...

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Director Of Strategic Initiatives information

See Springfield, MA salary details

$49.3K

$125.2K

$203.3K

How much do director of strategic initiatives jobs pay per year?

As of Sep 7, 2026, the average yearly pay for director of strategic initiatives in Springfield, MA is $125,194.00, according to ZipRecruiter salary data. Most workers in this role earn between $94,700.00 and $155,500.00 per year, depending on experience, location, and employer.

What does a director of strategic initiatives do?

A director of strategic initiatives is a high-level management position within a company charged with brainstorming both short-term and long-term milestones and goals. It is imperative that the organization’s initiatives are in line with its visions whether it’s a one-time project or the cultivation of partnerships. Responsibilities may include proposals, reporting, budgeting, or program development. You’ll oversee a team of individuals. This position requires strong leadership skills along with excellent verbal and oral communication. It is crucial to be able to engage your staff and allow them to take ownership of the company’s mission. The successful job candidate can cultivate these business relationships easily.

What does a director of strategic initiatives do?

A Director of Strategic Initiatives is responsible for identifying, developing, and implementing key projects that align with an organization’s long-term goals. They work closely with senior leadership to drive change, oversee cross-functional teams, and ensure that strategic priorities are executed effectively. Their role often involves analyzing market trends, managing complex projects, and communicating progress to stakeholders. Ultimately, they help organizations adapt and thrive in a competitive environment by guiding critical business initiatives.

How does a director of strategic initiatives typically collaborate with other departments to drive organizational change?

A Director of Strategic Initiatives works closely with leaders across multiple departments, such as operations, finance, marketing, and human resources, to align and implement cross-functional projects. They often facilitate communication between teams, establish clear project goals, and monitor progress to ensure strategic objectives are met. This role requires strong relationship-building skills, as successful collaboration depends on gaining buy-in from key stakeholders and managing competing priorities. Regular meetings, workshops, and updates are common methods for maintaining alignment and momentum.

What are the key skills and qualifications needed to thrive as a director of strategic initiatives, and why are they important?

To thrive as a Director of Strategic Initiatives, you need strong leadership, project management, and analytical skills, typically backed by an advanced degree in business or a related field. Familiarity with strategy frameworks, data analysis tools, and project management systems like Asana or Microsoft Project is often required. Exceptional communication, influence, and cross-functional collaboration abilities set top performers apart in this role. These skills are critical for successfully driving organizational change, aligning stakeholders, and achieving long-term strategic goals.

What is the difference between Director Of Strategic Initiatives vs Business Development Manager?

AspectDirector Of Strategic InitiativesBusiness Development Manager
Primary FocusStrategic projects and long-term growth initiativesIdentifying new business opportunities and partnerships
Required CredentialsBachelor's or Master's in Business, Management, or related fields; experience in strategic planningBachelor's in Business, Marketing, or related fields; sales or marketing experience
Work EnvironmentCorporate strategy teams, cross-departmental projectsSales teams, client-facing roles, market research
Industry UsageCommon in large corporations and strategic planning units

The Director Of Strategic Initiatives focuses on leading strategic projects and long-term growth plans within an organization, often working across departments. In contrast, a Business Development Manager concentrates on identifying and securing new business opportunities and partnerships. While both roles require strategic thinking, the Director Of Strategic Initiatives typically handles broader, organization-wide initiatives, whereas the Business Development Manager is more client and sales-oriented.

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What cities near Springfield, MA are hiring for Director Of Strategic Initiatives jobs?

Cities near Springfield, MA with the most Director Of Strategic Initiatives job openings:

Director Of Strategic Initiatives jobs near you
Infographic showing various Director Of Strategic Initiatives job openings in Springfield, MA as of August 2026, with employment types broken down into 1% As Needed, 85% Full Time, 10% Part Time, and 4% Contract. Highlights an 87% Physical, 4% Hybrid, and 9% Remote job distribution, with an average salary of $125,194 per year, or $60.2 per hour.

Senior Director, Strategic Initiatives & Organizational Change Management

The Travelers Indemnity Company

Hartford, CT • On-site

$126K - $208K/yr

Full-time

Medical, Life, Retirement, PTO

Re-posted 10 days ago

Key responsibilities

  • Partner with leaders to drive strategic planning and ensure alignment across AI and emerging technology initiatives.

  • Implement and embed organizational change management frameworks to support AI and ET adoption and manage change impacts.

  • Provide strategic leadership, mentor team members, and collaborate with stakeholders to communicate and execute AI and ET initiatives.

Job description

Who Are We?
Taking care of our customers, our communities and each other. That's the Travelers Promise. By honoring this commitment, we have maintained our reputation as one of the best property casualty insurers in the industry for over 170 years. Join us to discover a culture that is rooted in innovation and thrives on collaboration. Imagine loving what you do and where you do it.
Job Category
Technology
Compensation Overview
The annual base salary range provided for this position is a nationwide market range and represents a broad range of salaries for this role across the country. The actual salary for this position will be determined by a number of factors, including the scope, complexity and location of the role; the skills, education, training, credentials and experience of the candidate; and other conditions of employment. As part of our comprehensive compensation and benefits program, employees are also eligible for performance-based cash incentive awards.
Salary Range
$126,500.00 - $208,700.00
Target Openings
1
What Is the Opportunity?
The Senior Director, Strategic Initiatives & Organizational Change Management is a key leadership role responsible for driving holistic strategic planning and enterprise-wide change management within the AI & Emerging Technology organization with lens on stakeholders and business outcomes. This role partners with the value stream leaders and business units to develop and refine AI and ET strategies, manage the people side of technology-driven change, and ensure successful adoption of new capabilities. The individual in this role brings deep expertise in both OCM methodologies and strategic planning, serving as a thought leader who builds organizational capability, accelerates AI readiness, and translates emerging technology vision into actionable execution.What Will You Do?
Strategy & Planning
  • Partner with leaders across the AI & ET organization and multiple lines of business to drive holistic strategic planning, ensuring alignment and integration across AI capability development and broader strategy & business planning activities.
  • Lead macro business analysis, strategy development and refinement, articulation of future AI and emerging technology capability needs, and assessment of conceptual ideas that feed into strategic execution.
  • Establish an engagement model with value stream leaders to drive more robust planning, initiative prioritization, resource planning, and strategic roadmap development in support of AI and ET priorities.
  • Build out management information reporting and planning functions to inform departmental planning, strategic decision making, and demonstrate organizational impact and value delivery.

OCM Thought Leadership & Change Adoption
  • Act as a subject matter expert in OCM, providing strategic guidance to business leaders navigating the organizational and cultural shifts associated with AI and emerging technology adoption.
  • Implement and embed the Travelers OCM framework consistently across the organization, ensuring AI and ET-driven changes are effectively managed and business goals are met.
  • Work closely with stakeholders at all levels to assess change impacts, manage expectations, and develop tailored strategies that prepare the organization for successful AI transformation.
  • Proactively identify risks to change initiatives and develop mitigation strategies that account for the unique dynamics of emerging technology implementation.
  • Champion responsible and human-centered approaches to AI adoption, helping employees and leaders build confidence and capability alongside new technologies.
  • Collaborate with business leaders to translate AI and ET strategic vision into actionable, engaging learning programs that build enterprise-wide AI fluency and change readiness.
  • Design and deliver learning experiences that address both the technical and behavioral dimensions of working in an AI-enabled organization.

Team Development & Stakeholder Engagement
  • Provide strong strategic leadership and execution focus, leading with a diverse and inclusive mindset and proactively engaging team members to reach their full potential.
  • Mentor and coach OCM and strategy professionals, fostering leadership, skill development, and knowledge sharing across the team.
  • Collaborate with senior leaders to ensure AI and ET initiatives are communicated effectively, with messaging that is clear, compelling, and tailored to diverse audiences.
  • Actively participate in the OCM Community of Practice to foster knowledge sharing, collaboration, and enterprise capability building with a lens on AI and emerging technology.
What Will Our Ideal Candidate Have?
  • Bachelor's degree in a related field.
  • 7 years of project management experience.
  • 2 years of experience managing others and/or project teams.
  • Strong organization and communication skills.
  • Demonstrated experience developing multi-year technology strategies and roadmaps.
  • Experience working with advanced project-management methodologies and Agile principles.
  • Experience in developing strong, trusted partnerships with senior executives and constituent partners.
  • Ability to lead and inspire team members to achieve optimal results in a highly collaborative and matrixed organization.
  • Systemic thinker with strategic planning expertise, readily sees patterns and connections in a complicated environment.
  • Demonstrated ability to put strategic plans into action.
  • Strong facilitation and conflict resolution skillset.
  • Experience managing multiple complex projects simultaneously.
  • Strong analytical and problem-solving skills.
  • Deep understanding and appreciation for business, business intelligence/analytics, and technology components of program/portfolio management.

What is a Must Have?
  • Bachelor's Degree and 7 years of related experience or equivalent in education and work experience

What Is in It for You?
  • Health Insurance: Employees and their eligible family members - including spouses, domestic partners, and children - are eligible for coverage from the first day of employment.
  • Retirement: Travelers matches your 401(k) contributions dollar-for-dollar up to your first 5% of eligible pay, subject to an annual maximum. If you have student loan debt, you can enroll in the Paying it Forward Savings Program. When you make a payment toward your student loan, Travelers will make an annual contribution into your 401(k) account. You are also eligible for a Pension Plan that is 100% funded by Travelers.
  • Paid Time Off: Start your career at Travelers with a minimum of 20 days Paid Time Off annually, plus nine paid company Holidays.
  • Wellness Program: The Travelers wellness program is comprised of tools, discounts and resources that empower you to achieve your wellness goals and caregiving needs. In addition, our mental health program provides access to free professional counseling services, health coaching and other resources to support your daily life needs.
  • Volunteer Encouragement: We have a deep commitment to the communities we serve and encourage our employees to get involved. Travelers has a Matching Gift and Volunteer Rewards program that enables you to give back to the charity of your choice.

Employment Practices
Travelers is an equal opportunity employer. We value the unique abilities and talents each individual brings to our organization and recognize that we benefit in numerous ways from our differences.
In accordance with local law, candidates seeking employment in Colorado are not required to disclose dates of attendance at or graduation from educational institutions.
If you are a candidate and have specific questions regarding the physical requirements of this role, please send us an email so we may assist you.
Travelers reserves the right to fill this position at a level above or below the level included in this posting.
To learn more about our comprehensive benefit programs please visit http://careers.travelers.com/life-at-travelers/benefits/.

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