AI Bid & Proposal Manager
TLDR
Own end-to-end RFP lifecycle and build AI-augmented proposal workflows to accelerate submissions and improve win rates across Sales, Product, and Engineering.
You will own and continuously improve the end-to-end RFP and proposal lifecycle while also building the systems that make it faster and more scalable. This includes coordinating cross-functional contributors, ensuring compliance, and delivering high-quality submissions under tight deadlines.
- Manage the full RFP process from intake, bid/no-bid evaluation, coordination, and submission
- Maintain a structured pipeline of active bids and ensure timely execution across competing priorities
- Coordinate input from SMEs across Sales, Product, Engineering, and Professional Services
- Develop and refine a reusable proposal content library, including narratives and standard responses
- Operate and improve an AI-assisted proposal workflow using retrieval-augmented generation (RAG) principles
- Maintain and curate a high-quality answer corpus, including continuous updates and feedback integration
- Ensure proposal submissions meet formatting, compliance, and client-specific requirements
- Track performance metrics such as win rates, cycle times, and proposal quality to drive continuous improvement
- Conduct post-submission analysis and embed learnings into future responses
- 3+ years of experience in RFP, bid management, or proposal development in a B2B software or tech environment
- Hands-on experience using AI tools (LLMs, prompt engineering, or RAG-based workflows) to improve knowledge work
- Strong writing and editing skills with the ability to translate technical content into persuasive narratives
- Excellent organizational skills and ability to manage multiple deadlines simultaneously
- Experience collaborating with cross-functional teams and subject matter experts
- Familiarity with proposal tools (e.g., RFPIO, Loopio, Responsive) is an asset
- Exposure to utilities, ERP, or regulated software environments is a strong plus
- Understanding of data retrieval concepts (e.g., vector search, hybrid retrieval) is an advantage
- Ability to work autonomously while maintaining strong alignment with stakeholders
- Competitive base salary plus performance-based commission
- Comprehensive medical, dental, and vision coverage from day one
- Employee stock ownership and retirement savings matching programs (RRSP/401k)
- 3 weeks of vacation plus 5 personal days
- Remote-first work environment across Canada and the US
- Lifestyle rewards and employee recognition programs
- Learning opportunities and exposure to cutting-edge AI-driven workflows
- Inclusive, collaborative work culture focused on innovation and continuous improvement
Requirements:
You bring experience in managing complex RFP processes in a technology or B2B software environment, combined with strong writing ability and hands-on familiarity with AI-enabled workflows. You are highly organized, comfortable working independently, and able to coordinate multiple stakeholders effectively.
Benefits:
Benefits
Equity Compensation
Employee stock ownership and retirement savings matching programs (RRSP/401k)
Health Insurance
Comprehensive medical, dental, and vision coverage from day one
Learning Budget
Learning opportunities and exposure to cutting-edge AI-driven workflows
Inclusive, collaborative work culture
Inclusive, collaborative work culture focused on innovation and continuous improvement
Paid Time Off
3 weeks of vacation plus 5 personal days
Remote-Friendly
Remote-first work environment across Canada and the US
Jobgether runs the largest remote job platform, effectively linking job seekers with over 200,000 flexible and remote opportunities that match their unique skills and preferences. Our focus is on enhancing the hiring process, ensuring efficiency while prioritizing the candidate experience, particularly in the growing health and wellness sector.
- Founded
- Founded 2020
- Employees
- 11-50 employees
- Industry
- Professional Services