Proposal Specialist

Xello; Toronto; On-site; CAD 80,000 - 90,000; Full time

Job summary

Xello, a Toronto-based education software company, seeks a Proposals Specialist to transform complex requirements into clear, persuasive proposals for RFIs, RFPs, and RFQs. You will tailor responses to school districts and education agencies, collaborating with Sales, Strategy, Product, and Security to differentiate us and win opportunities.

Responsibilities include managing content libraries, templates, and QA, while advancing AI-assisted research and writing.

Qualifications

• Exceptional writing and editing skills with the ability to translate complex information into clear, persuasive content.
• Experience improving proposals processes with measurable impact.
• Strong critical thinking and reading comprehension to understand detailed requirements.
• Natural curiosity and willingness to learn about customers, market, product, and competitive landscape.
• Ability to balance multiple deadlines and collaborate across teams.

Responsibilities

• Coordinate, research, write, edit, and review proposals and bids (RFIs, RFPs, RFQs, vendor applications).
• Refine proposal processes, templates, and playbooks to increase quality and efficiency.
• Work with the proposals team and leadership from initial review to final submission.
• Analyze requirements and research prospective clients to tailor responses.
• Gather input from Sales, Strategy, Product, Client Success, Implementation, Marketing, Finance, Security, and Technology.
• Develop understanding of our platform, services, and markets.
• Use AI and emerging tech to improve research, writing, analysis, and QA.
• Maintain and improve proposal content library and documentation.
• Conduct quality assurance for accurate, compliant submissions.
• Support contracts, renewals, amendments, and related documentation.
• Manage privacy, security, and compliance materials.
• Contribute to win strategy and differentiators to boost win rate.
• Research opportunities using Salesforce, GovSpend, and procurement portals.
• Identify ways to improve proposal quality and efficiency.

Skills

Writing & editing

Proposal management

Cross-functional collaboration

Research & analysis

AI tooling

Attention to detail

Project management

Stakeholder communication

Procurement familiarity

Tools

Salesforce

GovSpend

CRM systems

Microsoft Word

Adobe Acrobat

Google Workspace

Procurement portals

Job description

We are looking for a Proposals Specialist

Who are you?

You’re an exceptional writer who is organized, collaborative, curious, and motivated by doing great work.

You have a talent for taking complex information—technical requirements, product functionality, company experience, and customer needs—and turning it into clear, persuasive, easy-to-understand content. You understand that a great proposal doesn’t just answer questions; it tells a compelling story about why we the right partner.

Naturally curious, you enjoy learning about school districts, states, and education agencies and using that understanding to tailor proposals to their unique priorities and needs.

You’re also comfortable using generative AI tools such as ChatGPT, Claude, and Gemini to research, analyze, write, and work more efficiently. You know how to get value from AI while applying strong judgment, verifying information, and ensuring the final work reflects our voice and standards.

You take ownership, have exceptional attention to detail, and can balance multiple priorities and deadlines while working effectively across teams.

Sound exciting to you? Read on!

What you’ll do…

• Coordinate, research, write, edit, and review proposals and bids, including RFIs, RFPs, RFQs, vendor applications, and other procurement opportunities.
• Continuously refine our proposal processes, templates, and playbooks, identifying bottlenecks, testing changes, and measuring their impact, so we produce higher-quality proposals with less effort over time.
• Work closely with our proposals team and our leadership to take proposals from initial review through final submission.
• Analyze requirements and research prospective clients to understand their priorities, identify opportunities to differentiate us, and develop compelling, tailored responses.
• Gather input from stakeholders across the company, including Sales, Strategy, Product, Client Success, Implementation, Marketing, Finance, Security, and Technology.
• Develop a strong understanding of our platform, services, implementation approach, customers, competitive strengths, and key markets.
• Use generative AI and other emerging technologies to improve research, writing, tailoring, analysis, quality assurance, and overall proposal efficiency.
• Maintain and continuously improve our proposal content library, templates, customer examples, technical content, and supporting documentation.
• Conduct thorough quality assurance to ensure submissions are accurate, compliant, persuasive, professionally presented, and consistent with our brand and voice.
• Support customer contracts, renewals, amendments, and related documentation, coordinating with the appropriate internal stakeholders.
• Manage client and prospective client requests such as privacy and security questionnaires, policy updates, vendor forms, accessibility documentation, insurance requests, and other procurement or compliance-related materials.
• Contribute to proposal and win strategy, including win-loss analysis, message and theme development, and identifying differentiators, to help improve our win rate in a highly competitive market.
• Use tools such as Salesforce, GovSpend, and procurement portals to research opportunities, monitor new RFPs and vendor registrations, and maintain visibility into proposal activity.
• Continually identify ways to improve proposal quality, processes, content, and efficiency, including participating in kick-offs, debriefs, and retrospectives.

What we’re looking for…

• Exceptional writing and editing skills, with the ability to translate complex information into clear, concise, persuasive content.
• Expert attention to detail and a commitment to producing accurate, polished work.
• Experience improving proposals writing processes, with a concrete examples of the changes you made and the measurable impact.
• Strong critical thinking and reading comprehension, with the ability to quickly understand detailed requirements and identify what a prospective client is really asking for.
• Natural curiosity, initiative, and a willingness to learn about our customers, market, product, and competitive landscape.
• Continuously assess and refine how our team uses AI in the proposal process, building reusable prompts and workflows, evaluating new tools, and sharing what works, to drive meaningful, measurable gains in speed and quality across the team..
• Strong project management, organization, and prioritization skills, with the ability to manage multiple deadlines and stakeholders.
• Strong collaboration and communication skills, including the confidence to follow up and respectfully push for information or decisions when needed.
• Comfortable working with contracts, procurement, privacy, security, and compliance-related documentation and knowing when to involve the appropriate subject matter experts.
• A continuous-improvement mindset and an interest in finding better, faster, and more effective ways to work.
• A team-first attitude with positive energy, initiative, and flexibility.
• Proficiency with Microsoft Word, Adobe Acrobat/PDF tools, and Google Workspace. Experience with CRM, proposal management, procurement, or AI productivity tools is an asset.
• Approximately 3+ years of experience in proposal writing, bid management, technical or business writing, communications, or a related role. Public-sector, education, SaaS, or technology experience is an asset.

The compensation range for this role is $80,000 - $90,000 CAD. The final offer will be determined based on the candidate's experience and expertise, as assessed during the interview process.