Remote AI Bid & Proposal Manager

Role Overview

Cayenta, part of the Harris group, is looking for an AI Bid & Proposal Manager to take ownership of its bid strategy as the company expands its go-to-market efforts. This is an individual contributor position with broad responsibility for managing the entire RFP lifecycle and shaping a proposal process powered by AI-assisted workflows.

Cayenta is a utility software business focused on CIS and ERP solutions for municipal utilities, co-ops, and investor-owned utilities across North America. The role sits at the intersection of proposal management, content strategy, and AI workflow design, with a strong emphasis on quality, speed, and consistency.

You will collaborate closely with Sales, Product, and Professional Services to turn product and service capabilities into persuasive proposal responses. You will also build and refine the systems behind the process, including the answer library, retrieval logic, and human review steps that keep responses accurate and aligned with brand standards.

Core Responsibilities

You will be accountable for managing bids from intake through final submission, while improving the tools and methods used to draft responses.

• Handle the full RFP process, including intake, triage, bid/no-bid evaluation, coordination, and submission on schedule.
• Keep a proposal calendar current and balance overlapping deadlines across multiple active bids.
• Lead bid/no-bid discussions with sales and leadership using clear criteria that preserve team bandwidth.
• Work with subject matter experts across Product, Services, and Engineering to gather accurate input.
• Verify that all submissions meet formatting rules, page constraints, and required response criteria.
• Run and improve a retrieval-augmented generation workflow used for proposal drafting.
• Build and maintain the answer corpus by drafting new content, retiring outdated material, and feeding approved edits back into the library.
• Refine hybrid retrieval methods, including BM25 and embedding-based search, to improve answer relevance and reduce SME effort.
• Coordinate the review process for AI-generated drafts, route content to the right reviewers, and close feedback loops efficiently.
• Identify AI agents and automation opportunities that cut manual work throughout the proposal lifecycle.
• Measure proposal quality and update the workflow based on performance trends and win/loss insights.
• Develop reusable content such as company overviews, capability summaries, differentiators, and reference stories.
• Convert technical product features into clear, buyer-oriented language for utility-sector audiences.
• Bring competitive intelligence into proposal positioning, especially in evaluations involving SpryPoint, NISC, and NorthStar.
• Partner with sales so proposals reflect prior relationship context and known evaluation priorities.
• Track proposal volume, win rates, and turnaround times, and report findings to the Director of Sales and Marketing.
• Run post-submission reviews to capture lessons learned and strengthen future responses.
• Maintain process and workflow documentation for onboarding, consistency, and audit readiness.

Experience and Requirements

The ideal candidate has managed complex RFPs in a B2B software or technology setting and is comfortable working independently while coordinating across teams.

• At least 3 years of experience handling RFPs or bid responses in a B2B software or technology environment.
• Practical experience using AI tools such as LLMs, prompt engineering, or RAG systems to improve knowledge work.
• Strong writing ability with the skill to turn technical information into persuasive proposal language.
• Excellent organization and time management, with the ability to juggle several deadlines without losing detail.
• Ability to work autonomously as an individual contributor while collaborating across functions.

Preferred Background

• Experience with utility software or adjacent regulated sectors, including CIS, ERP, AMI, or MDM.
• Familiarity with RAG concepts, vector search, or hybrid BM25 retrieval.
• Experience with proposal platforms such as RFPIO, Loopio, Responsive, or similar tools, or a willingness to work with custom systems.
• Exposure to the Harris/Constellation Software operating model.
• Experience with Power Automate, Microsoft 365, or other low-code automation tools.

Compensation and Benefits

The role offers a salary range of 80,000 to 100,000, plus commission up to 65,000.

• 3 weeks of vacation and 5 personal days.
• Medical, dental, and vision coverage starting on the first day of employment.
• Employee stock ownership and RRSP/401(k) matching programs.
• Lifestyle rewards.
• Remote work flexibility and additional company benefits.

Work Location and Travel

This is a remote position open to candidates anywhere in Canada and the United States, with Canada preferred. Travel is required as needed and is expected to be about 25%.

Candidates must have a valid current passport and be legally able to travel internationally. This includes passport-based visa exemption or any visas required for entry into Canada, the United States, and the Caribbean.

About Cayenta

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

About Harris

Harris is a provider of mission-critical software for the public sector in North America. As a wholly owned subsidiary of Constellation Software Inc., Harris supports software businesses serving utility, local government, school districts, public safety, and healthcare markets through long-term reinvestment in people, products, and acquisitions.

Additional Information

Role level: Individual contributor. Department: Sales & Marketing. Reporting line: Director of Sales and Marketing. Employment type: Full-time, permanent. Location: Remote, with Canada preferred.

Expected milestones include mapping the current RFP process in the first 90 days, taking over at least one live submission, and identifying workflow gaps. Within six months, the answer library and retrieval pipeline should be operational and SME review time should decline. Within one year, the system should be improving itself through corpus updates, and proposal quality should become a strategic advantage.

Competitive evaluations may include vendors such as SpryPoint, NISC, and NorthStar.