Director Of Strategic Initiatives Jobs
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The City of Crisfield is seeking an experienced, collaborative, and results-oriented professional to serve as its Director of Grants & Strategic Initiatives. This leadership position will lead the City's Department of Grants & Strategic Initiatives and play a key role in advancing the priorities established by the Mayor and City Council through strategic planning, external funding, project implementation, partnership development, and organizational leadership.
This is an exceptional opportunity to help shape the City's future by leading initiatives that strengthen infrastructure, housing, economic development, community resilience, and overall quality of life while building a sustainable framework for long-term success.
Primary Responsibilities
The Director will provide leadership for the Department of Grants & Strategic Initiatives and will:
· Lead, manage, and develop the Department of Grants & Strategic Initiatives.
· Establish departmental priorities, annual work plans, performance expectations, and operational goals.
· Develop funding strategies that align with the City's strategic priorities.
· Identify, pursue, and oversee federal, state, regional, foundation, and private grant opportunities.
· Manage the City's grant portfolio from funding opportunity through project closeout.
· Ensure grant compliance, financial accountability, reporting, reimbursements, and successful grant administration.
· Coordinate implementation of strategic initiatives and grant-funded projects across City departments.
· Work collaboratively with elected officials, City leadership, staff, consultants, engineers, contractors, funding agencies, and community partners.
· Build and maintain productive partnerships with businesses, nonprofit organizations, educational institutions, regional organizations, and government agencies.
· Monitor project schedules, budgets, deliverables, and performance measures to ensure successful implementation.
· Prepare reports, presentations, and recommendations for City leadership and elected officials.
· Represent the City at meetings, conferences, and intergovernmental forums.
· Promote innovation, continuous improvement, accountability, and professional development within the department.
· Implement systems, processes, and best practices that improve organizational effectiveness and service delivery.
This position serves as a key member of the City's leadership team and helps transform strategic priorities into funded projects and measurable community outcomes.
Minimum Qualifications
· Bachelor's degree in Public Administration, Business Administration, Finance, Project Management, Planning, Economic Development, or a closely related field.
· Five (5) years of progressively responsible experience in grant administration, public administration, project management, strategic planning, economic development, community development, or a related field.
· Supervisory or management experience preferred.
· Demonstrated ability to manage multiple projects, build collaborative partnerships, and communicate effectively with diverse stakeholders.
· Valid driver's license.
Why Join the City of Crisfield?
The Director of Grants & Strategic Initiatives will have the opportunity to establish and lead a department dedicated to implementing the City's vision and securing resources that support long-term community success. This position offers meaningful leadership responsibilities, broad collaboration with public and private partners, and the opportunity to make a lasting impact through strategic planning, external funding, and successful project delivery.
Application Information
This is a full-time salaried position. The salary range is $75K – 85K. Commensurate with qualifications and experience. As a full-time employee, you will be expected to work 40 hours per week, and your anticipated work hours will follow those of City Hall. You will be granted compensatory time off, in the event of after-hours work. As a full-time employee you are eligible to participate in the City’s employee benefits program, including medical and paid leave in accordance with the City’s Personnel Policy.
To Apply: Submit a cover letter and résumé by August 14, 2026, to vswift@crisfieldcityhall.com
The City of Crisfield is an Equal Opportunity Employer.
Pay: $75,000.00 - $85,000.00 per year
Benefits:
- Health insurance
- Paid time off
- Retirement plan
Work Location: In person
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Find JobsDirector Of Strategic Initiatives Job Market
Who's Hiring
Top Industries Hiring
- Education
- Renewable Energy
- Technology & Software
- Healthcare & Medical Services
- Manufacturing
What Employers Look For
The qualifications that appear most often in director of strategic initiatives jobs.
- 7 or more years of experience in strategy, operations, or program management roles
- Proven ability to lead cross-functional initiatives from design through execution
- Experience presenting to executive leadership and board-level stakeholders
- Proficiency with project management tools such as Asana, Smartsheet, or similar platforms
- MBA or equivalent advanced degree in business, public policy, or a related field
- Familiarity with change management frameworks and organizational design principles
Tips for Your Director Of Strategic Initiatives Job Search
Reframe your resume around outcomes
Director of strategic initiatives roles attract candidates who can show measurable change, not just responsibilities held. Quantify initiative scope, timeline compression, or revenue impact on every bullet. Hiring panels at this level dismiss resumes that list duties without results.
Target openings tied to transformation cycles
Organizations post these roles most often during mergers, leadership transitions, or major growth phases. Filter for postings from companies that recently announced a restructure or new strategic plan, because those roles have real mandates and faster hiring cycles.
Apply early to roles that fit
Migrate Mate lists director of strategic initiatives openings from across the United States in one place, so you can find roles that match and apply directly to each listing.
Tailor your materials to the reporting line
A director of strategic initiatives reporting to the CEO needs different framing than one reporting to a division VP. Study the org chart context in the posting and align your cover letter language to the priorities of whoever you'd report to directly.
Prepare a portfolio of initiative blueprints
Interviewers at this level will ask you to walk through how you've built something from zero. Come with two or three documented examples, including your scoping process, stakeholder map, and how you handled a pivot mid-execution.
Negotiate scope before you negotiate compensation
These roles often carry ambiguous authority over budget and headcount. Before accepting an offer, clarify your decision-making mandate in writing. Scope creep without authority is the most common reason directors of strategic initiatives leave within the first year.
Director Of Strategic Initiatives Jobs: Frequently Asked Questions
Which companies are hiring the most director of strategic initiativess?
The companies hiring the most director of strategic initiativess right now include Nexamp, JPMorganChase, and Pacific Gas and Electric, with the largest share of openings in New York, California, and Texas, based on current listings on Migrate Mate as of August 2026. Healthcare systems, technology companies, and large nonprofit organizations consistently account for a significant portion of these postings.
How many director of strategic initiatives jobs are remote?
About 67% of director of strategic initiatives openings are fully remote or hybrid as of August 2026, reflecting the cross-functional and travel-heavy nature of the role. Sub-areas focused on digital transformation or technology strategy tend to offer the most remote flexibility, while roles tied to operational or facilities-intensive sectors more often require on-site presence.
How do you become a director of strategic initiatives?
Start by building a foundation in strategy consulting, business operations, or program management, where you develop skills in scoping complex problems and driving cross-functional work. Move into roles with increasing initiative ownership, seek exposure to executive decision-making processes, and build a documented portfolio of initiatives you led from concept through measurable outcome. An advanced degree, while not always required, strengthens candidacy.
Can I get hired as a director of strategic initiatives with limited experience?
Getting hired at the director level without deep experience is difficult, but candidates who have led high-visibility projects in adjacent roles, such as chief of staff, strategy analyst, or senior program manager, can make a credible case. Emphasizing initiative ownership, stakeholder influence, and executive exposure matters more than years of tenure in a formal director title.
What does the director of strategic initiatives interview process look like?
The process typically begins with a recruiter screen, followed by a structured interview with the hiring executive covering strategic thinking and past initiative examples. Later rounds often include a case study or presentation in which you are asked to outline an approach to a real organizational challenge. Final conversations frequently involve cross-functional stakeholders whose buy-in you would need on the job.
Where can I find and apply to director of strategic initiatives jobs?
You can find and apply to director of strategic initiatives jobs on Migrate Mate, which lists current openings from employers across the United States. Search the listings to find roles that match your background and apply directly to each one that fits.
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