Job Description

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-$45,000.00 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