AI Bid & Proposal Manager

Role Overview

Cayenta, part of Harris, is hiring an AI Bid & Proposal Manager to anchor bid strategy as the company expands its go-to-market efforts. Cayenta develops utility-focused CIS and ERP software for municipal utilities, co-operatives, and investor-owned utilities across North America.

This is an individual contributor position with ownership of the entire RFP journey, starting from intake and bid/no-bid evaluation through final delivery. A key part of the job is designing and running an AI-enabled proposal process, including building the response library, improving retrieval workflows, and overseeing human review so that every submission remains accurate, competitive, and aligned with the brand.

You will collaborate closely with Sales, Product, and Professional Services to turn Cayenta’s capabilities into persuasive, differentiated proposals, while also improving the systems that make the process faster and more effective.

Success Milestones

Within the first 90 days, you will have documented the current RFP workflow, managed at least one live submission, and identified the gaps the AI process must address. By six months, the response library should be populated, the retrieval pipeline should be functioning, and SME review time should be reduced. By one year, proposal win-rate trends should improve, the system should be learning from previous submissions, and proposal quality should become a strategic advantage.

Work Arrangement, Travel, and Eligibility

This is a remote role open to candidates anywhere in Canada and the United States. Travel is required as needed, at about 25%. Applicants must hold a valid passport and be legally able to travel internationally, including having visa-free access or the necessary visas for entry into Canada, the United States, and the Caribbean.

Compensation and Role Details

Base pay is listed at 80K to 100K, with commission potential of up to 65K. The position sits within Sales & Marketing and reports to the Director of Sales and Marketing. It is a full-time, permanent role at the Individual Contributor level.

Key Responsibilities

Manage the end-to-end RFP workflow, from receipt and prioritization through bid/no-bid recommendation, coordination, and submission on deadline. Keep the proposal schedule organized, balance multiple active deadlines, and run bid/no-bid discussions with Sales and leadership using clear criteria that protect team capacity. Coordinate input from Subject Matter Experts across Product, Services, and Engineering, and confirm that every response meets formatting rules, page limits, and all mandatory requirements.

Run and enhance a retrieval-augmented generation workflow for drafting proposals. Build and maintain a high-quality answer library by writing new material, retiring outdated content, and feeding approved changes back into the corpus from reviewed submissions. Improve search relevance by tuning hybrid BM25 and embedding-based retrieval, and oversee the human review process so AI-generated drafts are sent to the right reviewers, feedback is tracked, and the loop is closed efficiently. Identify practical AI agents and automation tools that reduce manual work across the proposal lifecycle, and monitor quality metrics to drive ongoing improvements based on win/loss trends.

Create reusable proposal assets such as company overviews, capability descriptions, differentiator messaging, and customer reference stories. Translate technical product strengths into concise, buyer-friendly language that reflects utility-sector priorities. Bring competitive intelligence into proposal strategy, especially in competitive evaluations against vendors such as SpryPoint, NISC, and NorthStar. Work with Sales to ensure proposals reflect the pre-RFP relationship context and any known evaluation criteria.

Track proposal volume, win rates, and turnaround times, and report findings to the Director of Sales and Marketing. Lead post-submission reviews to capture lessons learned and strengthen future responses. Keep process and workflow documentation current for onboarding and audit needs.

Candidate Profile

We are looking for someone with at least 3 years of experience handling RFPs or bid responses in a B2B software or technology environment. You should have practical experience using AI tools such as LLMs, prompt engineering, or RAG systems to improve knowledge work. Strong writing ability is essential, especially the ability to convert technical information into clear, persuasive proposal language. You should also bring excellent organization, the ability to manage several deadlines at once, and comfort working independently while coordinating across teams.

Preferred Background

Experience in utility software, including CIS, ERP, AMI, or MDM, or in other regulated industries would be an advantage. Familiarity with retrieval-augmented generation, vector search, or hybrid BM25 retrieval is desirable, as is experience with proposal platforms such as RFPIO, Loopio, or Responsive. Exposure to the Harris/Constellation Software operating model, or experience with Power Automate, Microsoft 365, or low-code automation, would also help.

Benefits

The company offers 3 weeks of vacation and 5 personal days. Medical, dental, and vision coverage begins on the first day of employment. Additional benefits include employee stock ownership, RRSP/401k matching, lifestyle rewards, remote work flexibility, and more.

About Cayenta

Cayenta provides enterprise resource management solutions for the local government, utility, and financial sectors. Its products, services, and customer relationships support continued innovation and growth.

About Harris

Harris is a major provider of mission-critical software for the public sector in North America. As a wholly owned subsidiary of Constellation Software Inc. (CSI), Harris serves utility, local government, school district, public safety, and healthcare software markets. Its growth has been driven by investment in proprietary software, market expertise, and acquisitions that strengthen its offering.