Remote Operations Manager Startup Jobs in Wisconsin

Cayenta, a division of Harris; is seeking an AI Bid & Proposal Manager who will sit at the centre of our bid strategy as we scale our go-to-market function.

Cayenta is a purpose-built utility software company within the Harris/Constellation Software portfolio, delivering CIS and ERP solutions to municipal utilities, co-ops, and IOUs across North America.

This is a high-impact individual contributor role responsible for owning the end-to-end RFP process - from intake and bid/no-bid assessment through to final submission. What makes this role distinct is that you will also architect and operate the AI-assisted proposal workflow: building and maintaining the answer corpus, tuning retrieval pipelines, and managing the human review loop that ensures every response is accurate, competitive, and on-brand.

You will work directly with Sales, Product, and Professional Services to translate Cayenta's capabilities into compelling, differentiated proposal narratives - and you will continuously improve the systems that make that work faster and better.

In your first 90 days, you will have mapped the current RFP process, taken ownership of at least one active submission, and documented the gaps the AI workflow needs to close. Within six months, the answer corpus is populated, the retrieval pipeline is operational, and SME review time per RFP has measurably decreased. Within a year, win rate trends are moving, the system is self-improving through corpus writeback, and proposal quality is a competitive advantage rather than a cost centre.

This remote role welcomes candidates anywhere in Canada and the US. 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.

Salary:

80K - 100K

Commission Up to 65K

Department:

Sales & Marketing

Reports To:

Director of Sales and Marketing

Employment Type:

Full-Time, Permanent

Location:

Remote (Canada preferred)

Level:

Individual Contributor

What your impact will be:

RFP Process Management

• 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

AI-Augmented Proposal Workflow

• 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

Content & Competitive Positioning

• 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

Reporting & Continuous Improvement

• 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

What we are looking for:

• 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

What would make you stand out:

• 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

What we can offer:

• 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
• Remote work and more!

About Cayenta:

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.

About Harris:

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. Harris will continue to growth through reinvestment - both in the people and products that we offer and making investments in acquiring new businesses.

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