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Vice President, Business Operations & Strategy

Location: Cleveland, OH

Reports To: President & CEO

Employment Type: Full-Time

MyCity Transportation is seeking an experienced, highly analytical, and entrepreneurial leader to serve as Vice President of Business Operations & Strategy. This is a high-impact executive support role for a leader who can connect finance, contracts, pricing, analytics, compliance, project management, business intelligence, and strategic planning into one disciplined operating system for growth.

MyCity Transportation is a rapidly growing transportation management and mobility services company specializing in transit operations, paratransit, microtransit, mobility management, transportation consulting, and public-sector transportation partnerships. We are seeking an experienced, highly analytical, and entrepreneurial leader to serve as Vice President of Business Operations & Strategy. This position serves as the President & CEO's primary business partner and will play a key role in driving financial performance, strategic growth, organizational efficiency, contract administration, business intelligence, proposal pricing, and corporate initiatives. This is a unique opportunity for an ambitious professional seeking broad executive-level responsibility and the ability to directly influence company growth and profitability.

The Vice President of Business Operations & Strategy is responsible for overseeing corporate business operations, financial management, strategic planning, contract administration, performance analytics, compliance initiatives, special projects, and business development support. The successful candidate will combine strong financial acumen, project management expertise, business intelligence capabilities, and strategic thinking to support executive decision-making across all areas of the organization.

Financial Leadership

• Lead annual budgeting and forecasting processes
• Monitor monthly financial performance
• Prepare executive financial reports and dashboards
• Analyze actual versus budget performance
• Monitor divisional profitability and margins
• Develop financial models supporting operational decisions
• Assist with cash flow planning and capital allocation decisions
• Identify risks and opportunities affecting financial performance

Proposal Pricing & Business Development

• Develop and maintain pricing models for transportation contracts
• Support proposal development and RFP responses
• Analyze operational data for staffing, scheduling, fleet utilization, and service delivery assumptions
• Evaluate contract profitability and risk
• Assist in developing financial narratives for proposals
• Conduct market research and competitive analysis
• Support strategic growth initiatives and acquisitions

Strategic Planning

• Support development and execution of corporate strategic plans
• Lead special projects assigned by executive leadership
• Conduct business research and operational analysis
• Develop recommendations that improve profitability and efficiency
• Track key performance indicators and strategic objectives

Contract Administration

• Maintain and organize all corporate contracts
• Track renewals, amendments and compliance requirements
• Develop contract management processes
• Coordinate contract reviews with legal counsel
• Maintain subcontractor and vendor agreements
• Ensure contractual obligations are monitored and fulfilled

Compliance & Risk Management

• Coordinate corporate insurance programs
• Manage insurance renewals and broker relationships
• Monitor accident and claims reporting processes
• Support regulatory compliance initiatives
• Manage public records requests and FOIA responses
• Maintain corporate registrations and documentation
• Coordinate activities with outside legal counsel as needed

Business Intelligence & Analytics

• Develop executive dashboards and KPI reporting
• Lead implementation and management of Power BI initiatives
• Identify trends impacting performance
• Create reporting tools supporting data-driven decision making
• Conduct operational and financial analyses for leadership teams

Technology & Process Improvement

• Lead Microsoft 365 governance initiatives
• Administer and optimize Teams, SharePoint and related collaboration tools
• Develop standardized operating procedures
• Manage technology-related projects
• Improve workflow efficiency and organizational processes
• Ensure proper information management across departments

Project Management

• Lead cross-functional projects from initiation through completion
• Coordinate resources among departments
• Develop project timelines and implementation plans
• Track milestone completion and project outcomes
• Serve as project sponsor for strategic initiatives

Equal Opportunity Statement

MyCity Transportation is an equal opportunity employer. We value professionalism, accountability, integrity, and respect, and we encourage qualified candidates with relevant experience to apply.