Proposal Manager

About LearnLux

LearnLux is the leading provider of workplace financial wellbeing, blending fiduciary digital planning with access to one-on-one guidance from Certified Financial Planner™ professionals. Our award-winning program helps employees navigate critical financial decisions—from budgeting and benefits elections to equity compensation, home buying, and retirement—so they can feel confident about their money and focused at work. Advanced reporting helps partners understand impact, driving outcomes like reduced financial stress, increased productivity, and improved retention.

We’re a venture-backed company that has raised over $35M to date, supported by experienced investors and long-term partners. We’re growth-focused, building for scale, and excited by the opportunities and challenges that come with that journey.

Responsibilities

• 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.

Requirements

• 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.
• 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.

Nice to Have

• 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.

Why LearnLux?

• 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 coverage.
• 401(k) retirement plan.
• Mental wellbeing support (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 intersection of financial wellness and technology.

Pay

Salary Range: $90,000 - $120,000 USD. Individual compensation will be commensurate with the candidate's experience and local cost of labor.