Frontline Education
Proposal Strategist
🇺🇸 Remote - US
🕑 Full-Time
💰 $65K - $70K
💻 Sales
🗓️ October 19th, 2025
CRM
K-12
SaaS
Edtech.com's Summary
Frontline Education is hiring a Proposal Strategist focused on Student Program Management. This role involves leading the development of competitive RFP responses, shaping win strategies, and collaborating across various departments to drive new business and growth by leveraging AI tools and strategic storytelling.
Highlights
- Lead end-to-end proposal development for K-12 Student Program Management opportunities.
- Partner with Sales and Client Success to prioritize and strategize RFP submissions.
- Maintain and optimize an AI-enabled content library with Responsive software.
- Collaborate cross-functionally with Product, Marketing, Legal, Security, and Support teams.
- Use automation and AI tools to improve proposal efficiency and scalability.
- Track performance via win-loss reviews and apply insights for continuous improvement.
- Requires familiarity with AI-enabled proposal automation, Responsive, Salesforce CRM, Microsoft Office, PowerPoint, Adobe, and SharePoint.
- Preferred APMP Foundation Certification and 2-4 years of relevant proposal or strategic communications experience, ideally in EdTech or SaaS.
- Bachelor's degree or equivalent work experience required, excellent writing and project management skills necessary.
- Compensation: $65,000 - $70,000 base salary plus bonus, personalized PTO, 401k match, ESPP, tuition reimbursement, and comprehensive benefits.
Proposal Strategist Full Description
Proposal Strategist
Location: United States
Description
Proposal Strategist
Location Requirements: Hybrid to Wayne or Naperville. Remote candidates will be considered.
Your role on the team:
We’re expanding our proposal strategy team to capture more high-value opportunities and strengthen Frontline’s leadership in Student Program Management (SPM), including Special Education, Section 504, MTSS, and Intervention. The Proposal Strategist – SPM Focus will lead the end-to-end development of competitive, high-quality RFP responses that position Frontline as the trusted partner for K–12 districts. You will shape win strategies, craft persuasive content, and collaborate across Sales, Marketing, Product, and Client Success to deliver proposals that drive new business and long-term growth. By combining strategic storytelling with process efficiency—and leveraging automation and AI-enabled tools—you will help us increase submission capacity, raise our win rate, and capture more of the annual RFP pipeline we lead today.
You can expect to:
- RFP Strategy & Prioritization: Partner with Sales and Client Success to evaluate and prioritize SPM proposal opportunities based on strategic fit, revenue potential, and competitive positioning.
- Proposal Development: Lead the full proposal lifecycle—from kickoff to final submission—for SPM-related opportunities, ensuring consistency, compliance, and compelling storytelling.
- Win Theme & Messaging Alignment: Facilitate kickoff sessions to define competitive win themes and value propositions, ensuring all content aligns with our evolving product roadmap.
- Content Library Management: Maintain and continuously optimize a centralized, AI-ready content library in Responsive, ensuring all proposal materials are accurate, persuasive, and up-to-date.
- Process Improvement & AI Enablement: Leverage automation and AI-assisted tools to accelerate turnaround time, reduce manual effort, and improve scalability without compromising strategic quality.
- Cross-Functional Collaboration: Work with Product, Marketing, Legal, Security, and Support teams to gather technical and strategic inputs that strengthen proposal responses.
- Performance Tracking: Participate in win-loss reviews, capture lessons learned, and apply insights to improve future proposal performance and increase win rates.
What you bring to the role:
- Familiarity with AI-enabled tools for proposal automation and content generation.
- Collaborative, confident communicator who can guide proposal direction across cross-functional teams.
- APMP Foundation Certification preferred; additional certifications in strategic communication, solution selling, or positioning a plus.
- Takes ownership and drives outcomes independently.
- Believes in winning or learning—never standing still.
- Challenges conventional thinking and brings creative problem-solving to complex issues.
- Thrives in a collaborative environment and acts with a strong sense of purpose.
Qualifications:
- Bachelor’s degree or equivalent work experience.
- 2–4 years of experience in proposal development, strategic communications, or related fields, preferably in K–12 EdTech or SaaS.
- Proven ability to manage multiple high-priority RFPs simultaneously under tight deadlines.
- Exceptional writing and storytelling skills with a focus on persuasion and clarity.
- Strong organizational and project management skills with a high attention to detail.
- Experience with Responsive, Salesforce CRM, Microsoft Office Suite, PowerPoint, Adobe, and SharePoint.
Who we are
Frontline Education is a pioneer of school administration software purpose-built for K-12 districts. We provide innovative, connected solutions for student and special programs, business operations, and human capital management with powerful data and analytics to empower educators and administrators. We earn the trust of K-12 leaders across the U.S. by serving as a consistently high-performing, forthright partner of school districts through every dimension of the company.
We're a group of unique and talented individuals that love what we do. We've been lucky enough to land jobs with a rapidly growing tech company that supports an appreciative and friendly customer base. We work hard to make our customers happy, but we like to have a good time in the process. We are a company that strives to think in terms of “we” instead of “me.” We believe in the philosophy of servant leadership and that it’s all about putting others first. We also value the balance between family and work.
Frontline embraces diversity, equity, and inclusivity. We are intentionally building a workplace that respects, supports, and values the identities of all our employees. We believe this to be foundational in developing a strong community in our company. Frontline Education is an equal opportunity employer, and we do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.
The perks of being a Frontliner
Frontline offers a competitive compensation package including a base salary, rewarding bonus structure, 401k match, ESPP, and personalized PTO! Our company growth has created a promising environment for career advancement and rewarding challenges. We offer a tuition reimbursement program for eligible college credit coursework available to employees depending on their status and length of employment.
The salary range for this role is $65,000 - $70,000 per year, based on experience, skills, and internal equity. In addition to base salary, this role includes a bonus, personalized PTO, and comprehensive benefits, including health insurance, 401k, and much more!
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