Proposal Assistant Jobs in Chicago, IL (NOW HIRING)

About the Role: The Proposal Director is responsible for leading and managing the end-to-end proposal development process for strategic business opportunities across Transdev's portfolio. This role ensures the timely delivery of high-quality, compliant, and competitive responses to Requests for Proposals (RFPs), Requests for Qualifications (RFQs), and other procurement solicitations.
As the leader of a fast-paced proposal team, the Proposal Director ensures proposals reflect project strategy, are well written, compliant to the RFP, and reflect the Transdev brand. This position is responsible for overall proposal content development and submission activities for the Business Development team. The successful candidate must excel in a deadline driven environment, managing multiple concurrent pursuits, maintaining rigorous compliance standards, collaborating with internal stakeholders, and fostering a culture of accountability, responsiveness, and continuous improvement. The ideal candidate is a highly organized proposal leader who thrives in a deadline-driven environment, possesses an exceptional attention to detail, and views compliance as non-negotiable. They can simultaneously manage multiple pursuits, lead diverse teams under pressure, and deliver winning proposals that are fully compliant, strategically positioned, and reflective of Transdev's operational excellence.
Annual Salary Range: $117,000 to $146,000

• Vacation: minimum of two (2) weeks

-Sick days: 5 days
- Holidays: 12 days; 8 standard and 4 floating
- Other standard benefits: 401(k) retirement plan, medical, dental and vision, life insurance, short-term disability, voluntary long-term disability.
Key Responsibilities
Proposal Leadership & Management

• Lead the full proposal lifecycle from opportunity qualification through final submission.
• Develop and manage proposal schedules, work plans, and milestones to ensure on-time delivery of all proposal activities.
• Coordinate with cross-functional teams, including subject matter experts, operations leaders, finance, legal, risk, safety, and executive stakeholders.
• Participate in kickoff meetings, strategy sessions, proposal development meetings, forms/bonds completion meetings, and proposal reviews.
• Establish clear roles, responsibilities, and accountability for proposal contributors.
• Manage the proposal team and the multiple concurrent proposals with varying deadlines and complexity levels.

Compliance Management

• Serve as the primary owner of proposal compliance and submission requirements.
• Analyze RFPs, RFQs, and all other procurement documents to identify requirements, evaluation criteria, risks, and compliance obligations.
• Manage process of identifying and accurately completing all required forms, bonds, insurance certificates, and other required documents.
• Oversee the development of compliance matrices and proposal outlines to ensure complete responsiveness.
• Conduct compliance reviews throughout the proposal development process.
• Ensure all proposal responses adhere to solicitation instructions, page limitations, formatting requirements, and submission guidelines.
• Identify and mitigate compliance risks that could result in proposal disqualification.
• Manage DBE outreach process for inclusion into proposals, including coordinating with DBDs, PCs, Pricing and posting notices.

Proposal Development & Quality Assurance

• Drive development of compelling, customer-focused proposal content that aligns with win strategies and evaluation criteria.
• Oversee content development, editing, proofreading, and quality control processes, including initial proposal submittal and any subsequent submittals (interview presentations, clarification and BAFO responses.
• Coordinate the development of proposal graphics that abide by Transdev branding policies and templates.
• Lead proposal review cycles.
• Ensure proposal messaging effectively communicates Transdev's value proposition, operational expertise, safety culture, and innovation capabilities.
• Maintain high standards for proposal quality, consistency, and professionalism.
• Develop presentation materials that align with the proposal strategy and Transdev branding guidelines.

Team Leadership

• Lead, mentor, and develop Proposal Managers and Proposal Coordinators.
• Promote a high-performance, deadline-driven culture focused on accountability and execution.
• Establish best practices, standard operating procedures, templates, and process improvements.
• Allocate resources effectively across multiple proposal efforts.
• Support employee development through coaching, training, and career progression planning.

Strategic Planning & Process Improvement

• Oversee the process of searching for RFPs and the timely distribution of all RFP materials. Assist in reviewing RFPs, performing and distributing initial evaluation and vetting for Go/No Go
• Partner with Business Development and Operations leadership to support capture and pursuit strategies.
• Track proposal metrics, lessons learned, and win/loss trends.
• Continuously improving proposal processes, tools, content libraries, and knowledge management systems.
• Implement best practices to increase proposal efficiency, compliance, and win probability.
• Manage gathering and analysis of competitor information through FOIA requests and other research.

Qualifications
Required

• Bachelor's degree in Business, Communications, English, Marketing, Public Administration, Transportation Management, or related field.
• 8+ years of experience leading complex proposal development efforts.
• 3+ years of leadership experience managing proposal teams.
• Demonstrated success responding to large, complex RFPs in transportation, public sector, infrastructure, government services, or related industries.
• Strong knowledge of competitive procurement processes and compliance requirements.
• Exceptional project management and organizational skills.
• Outstanding written, verbal, editing, and presentation skills.
• Ability to manage multiple priorities and deadlines in a fast-paced environment.

Preferred

• Experience in public transportation, transit operations, mobility services, or government contracting.
• APMP certification or equivalent proposal management certification.
• Experience leading multi-million-dollar pursuits and strategic bids.
• Familiarity with proposal management and collaboration platforms.

Critical Competencies

• Proposal Leadership
• RFP Compliance Management
• Project and Schedule Management
• Strategic Thinking
• Executive Communication
• Cross-Functional Collaboration
• Quality Assurance
• Team Development
• Attention to Detail
• Risk Management
• Decision Making
• Process Improvement

Success Measures
The Proposal Director will be evaluated on:

• On-time proposal submission rate
• Proposal compliance and responsiveness
• Proposal quality scores and review outcomes
• Team productivity and engagement
• Process efficiency improvements
• Stakeholder satisfaction across business development and operations teams

The above statements are intended to describe the general nature and level of work being performed by people assigned to this classification. They are not intended to be construed as an exhaustive list of all responsibilities, duties, and skills required of personnel so classified.
The physical demands described here are representative of those that must be met by an employee to successfully perform the essential functions of this job. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions upon request.
Transdev is an Equal Employment Opportunity (EEO) employer and welcomes all qualified applicants. Applicants will receive fair and impartial consideration without regard to race, sex, color, national origin, age, disability, veteran status, genetic data, gender identity, sexual orientation, religion or other legally protected status, or any other classification protected by federal, state, or local law.
Reasonable accommodation may be made to enable individuals with disabilities to perform the essential functions. Transdev complies with federal and state disability laws and makes reasonable accommodations for applicants and candidates with disabilities. If reasonable accommodation is needed to participate in the job application or interview process, please contact us.HR.TalentAcquisition@transdev.com
Drug-free workplace
If based in the United States, applicants must be eligible to work in U.S. without restrictions for any employer at any time; be able to pass a drug screen and background check.
California applicants: Please Click Here for CA Employee Privacy Policy.
Job Category: Management
Job Type: Full Time
Work Type: Hybrid Remote
Req ID: 8725
Pay Group: NF2
Cost Center: 821
The above statements are intended to describe the general nature and level of work being performed by people assigned to this classification. They are not intended to be construed as an exhaustive list of all responsibilities, duties, and skills required of personnel so classified.
The physical demands described here are representative of those that must be met by an employee to successfully perform the essential functions of this job. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions upon request.
Transdev is an Equal Employment Opportunity (EEO) employer and welcomes all qualified applicants. Applicants will receive fair and impartial consideration without regard to race, sex, color, national origin, age, disability, veteran status, genetic data, gender identity, sexual orientation, religion or other legally protected status, or any other classification protected by federal, state, or local law.
Drug-free workplace
If based in the United States, applicants must be eligible to work in U.S. without restrictions for any employer at any time; be able to pass a drug screen and background check.
California applicants: Please Click Here for CA Employee Privacy Policy.
About Transdev
Cities, counties, airports, companies, and universities across the U.S. contract with Transdev to operate their transportation systems, maintain their vehicle and fleets, and deliver on mobility solutions. Transdev U.S. employs a team of 32,000 across 400 locations while maintaining more than 17,000 vehicles.
Part of a global company, Transdev is a leader in mobility with operations in 19 countries, proudly operated by 110,000 team members from around the world. As an operator and global integrator of mobility, we are driven by our purpose. Transdev - the mobility company - empowers the freedom to move every day thank to safe, reliable, and innovative solutions that serve the common good. Find out more at http://www.TransdevNA.com or watch an overview video .