RFP/ Grant / Proposal Writer

About Us

Shift AI is a cutting-edge AI-driven fleet management platform revolutionizing how businesses handle logistics, driver safety, and operational efficiency. Our platform delivers a comprehensive suite of tools, including AI-Powered Video Telematics, Intelligent Route Planning, Predictive Maintenance, and Driver Behavior Analytics. We partner with major players across logistics, construction, waste management, and short-term rentals to help them streamline operations, reduce costs, and transition to a more sustainable future. We are at the forefront of the Logi-Tech and AI-powered automation space.

Why This Role Matters

We are seeking a highly organized, persuasive, and detail-oriented RFP/Proposal Writer to join our team. This role is a direct revenue driver, responsible for crafting compelling, compliant, and client-focused proposals that secure new large-scale contracts with governments, municipalities, and major fleet/logistics operators. If you thrive in a deadline-driven environment and can translate complex AI algorithms and SaaS platform capabilities into a winning, value-driven narrative, this is the role for you.

What You'll Do

• Lead the Proposal Lifecycle: Own the end-to-end proposal process for Requests for Proposal (RFPs), Requests for Information (RFIs), and other tenders for our fleet management platform.
• Analyze and Strategize: Deconstruct complex RFP requirements, create compliance matrices, and collaborate with leadership to develop a clear win strategy and key messaging focused on ROI, safety, and operational efficiency.
• Develop Winning Content: Research, write, and edit all proposal sections, including Executive Summaries, Technical Approach, Implementation Plans, and Company Qualifications, ensuring our AI technology is presented clearly and persuasively.
• Collaborate and Coordinate: Work cross-functionally with Subject Matter Experts (SMEs) across Product, Engineering, Data Science, and Legal to gather information and ensure technical accuracy, especially regarding platform integration and data security.
• Maintain Content Library: Develop and manage a robust library of standardized, up-to-date proposal content (boilerplate) focused on platform features, security protocols, and case studies to improve efficiency for future submissions.
• Ensure Compliance: Perform meticulous review and quality checks to ensure every proposal meets all submission guidelines, formatting rules, and deadlines.

What You Bring

• 3+ years of experience as an RFP Writer, Proposal Specialist, or Technical Writer, with a strong preference for experience within the SaaS, Logi-Tech, or Government Tech industries.
• Proven track record of winning multi-million dollar contracts, particularly with municipal or provincial/state government agencies related to transportation, public works, or smart city initiatives.
• Exceptional written and verbal communication skills; the ability to translate complex technical concepts (AI, telematics, predictive modeling) into clear, concise, and persuasive business language.
• Strong project management and organizational skills, with the ability to manage multiple complex proposals simultaneously.
• High proficiency in Microsoft Office Suite (Word, Excel, PowerPoint) and familiarity with proposal automation software (e.g., Loopio, Shipley methodology) is a plus.
• A Bachelor’s degree in Communications, English, Journalism, Business, or a related field.

Why Join Shift AI?

• Impact: Your proposals will directly enable fleets to become safer, more efficient, and more sustainable using cutting-edge Artificial Intelligence.
• Innovation: Be part of a dynamic, AI-native team that is defining the future of commercial vehicle and asset management.
• Growth: This is a high-visibility, high-impact role in a rapidly expanding sector of the tech industry.
• Culture: We foster a collaborative, supportive environment with opportunities for professional development.
• Compensation: Competitive salary package commensurate with experience

Job Type: Full-time

Pay: $40,000.00-$60,000.00 per year

Benefits

• On-site parking
• Paid time off

Ability to commute/relocate:

• Toronto, ON M1S 5K7: reliably commute or plan to relocate before starting work (required)

Experience

• Startup environment: 1 year (required)
• Proposal writing: 2 years (required)

Work Location: In person