Proposal Specialist – Legal Software Sales

We are seeking a Proposal Specialist who will own the day‑to‑day project management and process execution of our RFP, RFI, and related questionnaire responses, with a particular focus on public sector and complex private‑sector deals. You’ll coordinate cross‑functional contributors, manage timelines and dependencies, and ensure high‑quality, compliant, and on‑brand responses go out the door on time.

Over the past year, this role has evolved from primarily writing individual answers to orchestrating the entire RFx lifecycle: building schedules, running kickoff and check‑in meetings, tracking review cycles, and partnering with sales teams and SMEs to keep long‑cycle opportunities moving without last‑second “fire drills.”

You will also be a key process and technology optimizer for the proposals function. That includes using and improving tools like SiftHub and AI assistants (e.g., Gemini) for first‑pass responses, compliance checks, and content organization; then triaging and refining that content with SMEs to ensure quality, accuracy, and compliance; tuning prompts and templates; and capturing reusable knowledge so each new RFx is faster, more predictable, and more effective than the last.

Getting started

• We want you to feel like part of the team early on! Our onboarding process will integrate you into the company with informative sessions on our product, policies, processes, and team structure and goals.
• We’re excited for you to learn, grow, and contribute right away. We trust that you’ll bring experience and knowledge that will uplift and uplevel the team, but we don’t expect you to know everything on Day 1.

Key Responsibilities

• Own end‑to‑end RFx project management: Manage each assigned RFx (RFPs, RFIs, security & AI questionnaires, vendor assessments, etc.) as a discrete project, from intake through submission. Define and own assignment and tracking of  timelines, milestones, and owners, and keep all contributors aligned.
• Drive a scalable, high‑quality proposal process: Develop and keep updated; templates, proposal outlines, compliance matrices, and schedules to facilitate the proposal development process and meet submission deadlines, with a particular emphasis on consistency across public‑sector solicitations..
• Leverage and optimize AI and proposal tools: Use SiftHub and similar tools to generate first‑pass responses, manage RFx matrices, and perform compliance checks; triage and refine AI‑generated content in collaboration with subject matter experts while ensuring content is able to be reused in the future.
• Coordinate stakeholders: Partner with internal and external stakeholders to draft, route, and refine responses to detailed client deliverables 
• Enable cross‑functional collaboration: Collaborate closely with account executives, solutions architects, and other stakeholders to align proposal strategy, tailor messaging to the client’s use case, and ensure that pricing, SOW language, and technical responses are internally consistent.
• Continuously improve how we work: Stay informed about industry trends in proposal management, public sector procurement, and legal tech / AI, sharing relevant insights with the team to refine our content and approach over time.

About you

• You have 1–3 years of experience in a project‑oriented, multi‑stakeholder environment role such as proposals, project management, sales operations, consulting, legal operations, technical writing, or a similar field. Direct RFx experience is a plus, but not strictly required for the right early‑career candidate.
• You are highly organized and process‑driven, comfortable managing multiple concurrent projects, deadlines, and stakeholders without dropping details, especially in long‑cycle public sector or enterprise deals.
• You have excellent writing, editing, and proofreading skills, with the ability to turn complex technical and legal information into clear, concise, and persuasive responses tailored to the audience.
• You are curious and comfortable with technology and AI, eager to experiment with tools like SiftHub, Gemini, and other AI assistants to improve quality and efficiency while maintaining sound judgment about when human review is required.
• You enjoy working cross‑functionally, building strong relationships with sales, solutions architecture, secu...