ESS is hiring a Director of Proposal Development to lead our national proposal process. If you're a collaborative leader who thrives in a fast-paced environment, loves developing strong narratives, and enjoys mentoring writers, this is your opportunity to shape how we grow and serve K-12 school districts across the country.

In this key role, you’ll oversee the entire proposal life cycle, manage a team of four writers and a coordinator, and work closely with leaders across Sales, Marketing, Legal, Finance, and Operations. Your leadership will ensure we deliver thoughtful, strategic, and high-quality responses to a wide range of RFPs, RFIs, and related opportunities, helping ESS expand its reach and impact in districts.

We’re looking for someone who can bring structure to complexity, coach a high-performing team, and roll up their sleeves when needed to support writing and editing. If that sounds like you, we’d love to hear from you.

Key Responsibilities of a Director of Proposal Development 

Leadership & Team Management

• Lead, mentor, and develop a growing proposal team
• Assign projects based on team capacity and complexity
• Foster a culture of accountability, creativity, and excellence
• Provide feedback and coaching that supports professional growth

Proposal Strategy & Oversight

• Own the full proposal life cycle from opportunity review through submission
• Drive strategic planning and response development
• Collaborate with subject matter experts to gather content and data
• Edit and review final responses for accuracy, clarity, and alignment
• Step in to write or contribute to proposals when needed

Process Improvement & Performance Tracking

• Maintain proposal templates, content libraries, and style guides
• Ensure effective use of tools such as Responsive and Salesforce
• Track and report metrics, including win/loss rates and team capacity
• Continuously identify ways to improve workflow and content quality

Qualifications

• Bachelor’s degree (Communications, English, Marketing, or related field); Master’s preferred
• 7 to 10 years of proposal experience, with at least 3 years in a leadership role
• Strong writing, editing, and content strategy skills
• Experience managing high-volume, complex proposals
• Proficiency with proposal tools (e.g., Responsive, Loopio, or RFPIO) and CRM systems like Salesforce
• Strong collaboration, project management, and communication skills
• Experience writing proposals for the education sector is a plus

Why Join ESS?

• Meaningful work that directly impacts students and schools
• Supportive and collaborative team culture
• Competitive compensation with comprehensive benefits
• Generous PTO, paid volunteer days, 401(k), and more

Ready to help shape the future of education staffing? Apply today and join our growing team.