Frontline Education
Senior Proposal Strategist
🇺🇸 Hybrid - Naperville, IL
🕑 Full-Time
💰 $75K - $85K
💻 Other
🗓️ September 4th, 2025
CRM
K-12
SaaS
Edtech.com's Summary
Frontline Education is hiring a Senior Proposal Strategist to lead the strategy, coordination, and delivery of high-quality, competitive proposals for its Business Solutions portfolio. The role involves developing win themes, managing proposal content, collaborating with multiple teams, and leveraging AI tools to streamline proposal processes and increase win rates.
Highlights
- Lead end-to-end proposal process for ERP, Asset Management, Data & Analytics solutions.
- Develop win strategies and competitive positioning for high-value RFPs.
- Manage content using Responsive and AI-assisted proposal tools to maintain accuracy and consistency.
- Collaborate with Sales, Marketing, Product, Client Success, and Legal teams to craft customer-focused responses.
- Utilize automation and AI to optimize proposal workflows and increase submission capacity.
- Conduct win-loss analyses and continuously improve content standards and storytelling frameworks.
- Provide strategic guidance and overflow support across other solution areas as needed.
- Required skills include expertise in Responsive, Salesforce CRM, Microsoft Office Suite, PowerPoint, Adobe, SharePoint, and familiarity with AI-enabled proposal tools.
- Qualifications include a Bachelor's degree or equivalent experience, 5+ years in proposal development or related fields, strong writing, storytelling, and project management skills.
- Compensation ranges from $75,000 to $85,000 annually plus bonus, personalized PTO, 401k match, ESPP, tuition reimbursement, and comprehensive benefits.
Senior Proposal Strategist Full Description
Senior Proposal Strategist
Location: Naperville, IL, United States
Description
Senior Proposal Strategist
Location Requirements: This position is Hybrid to Wayne or Naperville. Remote candidates will be considered. The role will work hours based on the Eastern Time Zone.
Your role on the team:
We’re expanding our proposal leadership capacity to keep pace with the growth of Frontline’s Business Solutions portfolio, including ERP, Asset Management, and Data & Analytics. The Senior Proposal Strategist will lead the strategy, coordination, and delivery of competitive, high-quality proposals for complex, high-value opportunities. You will be the strategic driver behind proposal win themes, narrative development, and content quality—ensuring every submission showcases Frontline’s ability to solve district operational challenges and deliver measurable impact.
In this role, you’ll collaborate closely with Sales, Marketing, Product, Client Success, and Legal to craft persuasive, customer-focused responses that align with our evolving product capabilities. As the primary content manager for our Responsive platform and AI-assisted proposal tools, you’ll optimize and maintain a centralized content library to ensure speed, consistency, and strategic alignment across all submissions. By leveraging automation and AI-enabled workflows, you will help increase our capacity to pursue more high-value RFPs without sacrificing quality, ultimately driving higher win rates and ARR growth.
You can expect to:
- Strategic Proposal Leadership: Own the end-to-end proposal process for Business Solutions (ERP, Asset Management, Data & Analytics) from intake through submission, ensuring proposals are competitive, timely, and on-brand.
- Win Theme Development: Facilitate kickoff sessions to define win strategies, competitive positioning, and value propositions tailored to each opportunity.
- Content Ownership: Serve as primary content manager for Responsive and AI-assisted tools, ensuring proposal materials are accurate, persuasive, and up to date.
- Cross-Functional Collaboration: Partner with Sales, Product, Marketing, and Client Success to gather strategic and technical inputs that elevate proposal responses.
- AI & Process Optimization: Leverage automation, AI tools, and content governance best practices to streamline proposal development and increase throughput.
- Continuous Improvement: Conduct win-loss reviews, integrate lessons learned into future submissions, and evolve content standards and storytelling frameworks.
- Overflow Support: Provide proposal development and strategic guidance across other solution areas as needed.
What you bring to the role:
- Confident communicator able to lead strategy discussions and guide proposal direction.
- 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.
This role requires:
- Bachelor’s degree or equivalent work experience.
- 5+ years in proposal development, strategic communications, or related fields, ideally in SaaS or K–12 EdTech.
- Demonstrated success managing complex RFPs from kickoff to submission under tight deadlines.
- Exceptional writing and storytelling skills with a focus on persuasion and clarity.
- Strong project management and organizational skills with high attention to detail.
- Experience with Responsive, Salesforce CRM, Microsoft Office Suite, PowerPoint, Adobe, and SharePoint.
- Familiarity with AI-enabled tools for proposal automation and content generation.
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 $75,000 - $85,000 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!
