Senior Remote Proposal Manager Jobs in Oregon (NOW HIRING)

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 our partners understand impact, driving outcomes like reduced financial stress, increased productivity, and improved retention.

We're building LearnLux with intention. We move quickly, operate with a high bar for quality, and value people who take ownership of their work. If you're energized by solving new problems, taking accountability, and pushing yourself to do your best work every day, you'll find this a rewarding environment.

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

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. 

• 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.

• 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.

• 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

• 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.

• 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

LearnLux strives to be an inclusive workplace and values learning from and engaging across different perspectives. Women, people of color, LGBTQIA+ individuals, and members of other minority or marginalized groups are strongly encouraged to apply.

LearnLux is proud to be an equal opportunity employer and does not discriminate against candidates on the basis of race, ethnicity, color, national origin, age, religion, sex, gender, sexual orientation, gender identity, marital status, disability, or veteran status.

We are committed to fostering an environment that embraces diversity and inclusion and are seeking candidates from a variety of backgrounds, experiences, abilities, and perspectives to join our team. If you are interested in this opportunity but not sure if you fit this role, please apply and include a note to let us know of your interest. We're excited to speak with you about joining our team!