(Remote) AI Bid & Proposal Manager

About the role

Cayenta, a division of Harris, is seeking an AI Bid & Proposal Manager to join their growing team. The role is central to the company's bid strategy and involves managing the entire RFP process, including architecting and operating an AI-assisted proposal workflow.

Responsibilities

• Own the full RFP lifecycle: intake, triage, bid/no-bid recommendation, coordination, and on-time submission
• Maintain a proposal calendar and manage competing deadlines across an active pipeline
• Facilitate bid/no-bid reviews with Sales and leadership, applying clear criteria to protect team capacity
• Coordinate contributions from Subject Matter Experts (SMEs) across Product, Services, and Engineering
• Ensure all submissions comply with RFP formatting, page limits, and mandatory requirements
• Operate and continuously improve a retrieval-augmented generation (RAG) pipeline for proposal drafting
• Curate and maintain a high-quality answer corpus: writing net-new content, retiring stale responses, and implementing corpus writeback from reviewed submissions
• Tune hybrid BM25/embedding retrieval to improve answer relevance and reduce SME review burden
• Manage the human review workflow: route AI-generated drafts to the right reviewers, track feedback, and close loops efficiently
• Identify and implement AI agents and automation tools that reduce manual effort at each stage of the proposal process
• Monitor proposal quality metrics and improve the system over time based on win/loss patterns
• Develop and maintain reusable proposal content: company overviews, capability narratives, differentiator statements, and reference stories
• Translate technical product capabilities into clear, buyer-focused language aligned to utility sector priorities
• Incorporate competitive intelligence into proposal strategy, particularly in contested evaluations (e.g., SpryPoint, NISC, NorthStar)
• Partner with Sales to ensure proposals reflect the pre-RFP relationship context and any known evaluation priorities
• Track proposal activity, win rates, and cycle times; report to the Director of Sales and Marketing
• Conduct post-submission reviews to capture lessons learned and improve future responses
• Maintain documentation of the proposal process and AI workflow for onboarding and audit purposes

Requirements

• 3+ years of experience managing RFP or bid responses in a B2B software or technology environment
• Demonstrated experience using AI tools (LLMs, prompt engineering, or RAG systems) to improve knowledge work - not just awareness, but hands-on application
• Strong writing skills: you can take technical inputs and produce clear, persuasive proposal prose
• Exceptional organizational skills with the ability to manage multiple concurrent deadlines without dropping detail
• Comfort working autonomously as an IC while coordinating across functions

Qualifications

• Experience in the utility software sector (CIS, ERP, AMI, MDM) or adjacent regulated industries
• Familiarity with retrieval-augmented generation concepts, vector search, or BM25 hybrid retrieval
• Experience with proposal automation tools (RFPIO, Loopio, Responsive, or similar) or willingness to build on custom tooling
• Exposure to the Harris/Constellation Software portfolio operating model
• Experience with Power Automate, Microsoft 365 ecosystem, or low-code automation

Skills

• Strong communication and collaboration skills
• Ability to work independently and manage multiple tasks simultaneously
• Knowledge of utility sector regulations and standards
• Experience with data analytics and reporting tools

Benefits

• 3 weeks’ vacation and 5 personal days
• Comprehensive Medical, Dental, and Vision benefits starting from your first day of employment
• Employee stock ownership and RRSP/401k matching programs
• Lifestyle rewards

Pay

$80K - $100K

Schedule

Remote (Canada preferred)

Travel is required as needed, approximately 25%.

Candidates must hold a current, valid passport and be legally eligible to travel internationally. This includes either passport based visa exemption or possession of any required travel visas for entry into Canada, the United States, and the Caribbean.

Company Information

Cayenta is a leading provider of enterprise resource management solutions in the local government, utility and financial industries. Cayenta’s products, services and customer relationships provide the foundation for continued innovation and growth.

Harris is a leading provider of mission critical software to the public sector in North America. As a wholly owned subsidiary of Constellation Software Inc. (“CSI”, symbol CSU on the TSX), Harris has become the cornerstone for CSI’s investment in utility, local government, school districts, public safety, and healthcare software verticals. Our success has been realized through investments in our proprietary software and market expertise. This focus, combined with acquiring businesses that build upon or complement our offerings, has helped drive our success.