Proposal Manager

LearnLux

$90K — $120K *
US-AnywhereRemote in United States
Business Services
Less than 5 years of experience
Job Overview by Ladders

Qualifications

  • 3-5 years of experience in proposal management or a related B2B SaaS client-facing role with a successful track record.
  • Strong understanding of the sales lifecycle including proposal writing and project management.
  • Experience with RFP management software, ideally Loopio.
  • Excellent writing skills with a history of creating clear, persuasive content.
  • Capable of thriving in fast-paced, ambiguous environments and proactively solving problems.
  • Demonstrated ability to collaborate with cross-functional teams, managing input from experts to ensure timely responses.
  • Mastery of time management with the ability to balance multiple deadlines efficiently.

Responsibilities

  • Lead and coordinate RFx requests from start to finish, ensuring all timelines are met.
  • Translate business and workforce needs into proposals that highlight LearnLux's strengths.
  • Produce compelling proposal content including summaries and competitive positioning.
  • Enhance win rates through innovative content tailored to specific prospect profiles.
  • Facilitate collaboration across departments to ensure proposals are accurate and comprehensive.
  • Manage and update the proposals content library for efficient turnaround without sacrificing quality.
  • Track proposal activity and results to improve visibility of pipeline health.

Benefits

  • Remote-first company environment
  • Medical, dental, and vision insurance
  • 401(k) plan
  • Mental wellbeing assistance via Talkspace
  • Financial wellbeing support through LearnLux
  • Paid vacation and sick leave
  • Paid sabbatical after five years of service
  • Inclusive team culture
  • Continuous learning and growth opportunities in a dynamic startup
Full Job Description
The Role

As a Proposal Manager at LearnLux, you'll lead and coordinate RFI and RFP responses that drive a significant portion of company revenue. You'll turn detailed proposal requirements into winning responses that resonate with benefits consultants, procurement teams, and HR and benefits leaders.

This is a revenue-critical role: your writing and positioning directly influence whether LearnLux advances in evaluation processes to secure annual recurring revenue. You'll work closely with sales, marketing, client success, product, and global operations as you shape how LearnLux competes in some of the most sophisticated buying processes in HR technology.

You'll love this job if you're a natural relationship builder who gets energized by high-stakes deadlines, complex stakeholders, and the challenge of building the mechanisms that make a proposal function run better every quarter.

This is a full-time, remote position reporting to the Senior Proposal Manager.
What you'll do
  • Lead and coordinate end-to-end RFx requests, including reviewing incoming bid requests and setting timelines that keep every deliverable on track.
  • Understand the business and workforce requirements of prospective employers to position LearnLux's platform as the strongest fit, translating financial wellbeing concepts into responses that resonate with HR and benefits leaders.
  • Create compelling, persuasive proposal content, including executive summaries, value propositions, and competitive positioning.
  • Contribute to advancement and win rates through content and process innovation, tailoring proposal content to each prospect's specific workforce profile and industry.
  • Orchestrate cross-functional collaboration among sales, marketing, client success, and global operations, as well as subject matter experts across security, legal, and product, ensuring every section of a response is accurate, current, and complete.
  • Keep the proposal engine running by managing and maintaining the content library and workflow in Loopio, so responses go out fast without sacrificing quality.
  • Improve visibility into pipeline health by tracking proposal activity and outcomes in HubSpot
  • Strengthen the RFx function over time by following and managing the process and suggesting improvements and best practices.
  • Sharpen competitive positioning by identifying patterns across RFP requirements and win/loss outcomes, and feeding those insights back into content strategy.
You should bring
  • 3-5 years of experience in proposal management, RFP/RFI response, or a related client-facing role in B2B SaaS with a track record of winning complex, competitive deals.
  • Strong understanding of the sales lifecycle, including strategy development, proposal writing, and project management skills.
  • Experience with RFP management software (Loopio preferred)
  • Excellent writing skills, with a track record of producing clear, persuasive content under tight deadlines.
  • Comfortable operating in ambiguous, fast-growing environments, with a high-agency approach to solving problems without waiting for direction.
  • Demonstrated ability to collaborate cross-functionally, including managing input from subject matter experts to keep responses accurate and on schedule.
  • Total mastery of time management, with the ability to run multiple deadlines and competing priorities simultaneously without cutting corners.
  • Strong proactive communication skills, with the judgment to flag risks, gaps, or bottlenecks before they become deadline problems.
It would be great if you also
  • Experience in HR technology, employee benefits, SaaS, or fintech
  • Experience adapting proposal content for multinational or multi-country audiences
  • CF-APMP certification, or active progress toward it
  • Knowledge of Shipley and APMP proposal methodologies
LearnLux is a fit for you if you
  • Thrive in fast-moving environments and enjoy building in moments of change. We operate with urgency, and roles, priorities, and approaches evolve as we grow.
  • Like wearing multiple hats and helping define the path forward. At LearnLux, roles evolve as we grow, and employees often help create clarity, structure, and direction where it didn't previously exist.
  • Take initiative and don't wait to be asked. You see problems as opportunities and are comfortable stepping in to move work forward.
  • Are energized by ambiguity and willing to make decisions with imperfect information. We learn quickly by doing, and pace is a competitive advantage for us.
  • Enjoy being hands-on and owning work end to end. While strategic thinking matters, execution, follow-through, and accountability are what drive impact here.
  • Are motivated by high standards and continuous improvement. As we hit new milestones, we intentionally raise the bar on quality, ownership, and outcomes.
  • Value clear, frequent communication and collaboration. As a remote team, staying aligned through proactive communication is core to how we operate.
Benefits
  • Remote-first company structure
  • Medical, dental, and vision
  • 401(k)
  • Mental wellbeing (Talkspace)
  • Financial wellbeing (LearnLux)
  • Paid vacation and sick leave
  • Paid sabbatical after 5 years of service
  • A supportive, inclusive team culture
  • Opportunities for continuous learning and growth at a fast-growing startup at the cutting edge intersection of financial wellness and technology
Salary Range

$90,000-$120,000 USD

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