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.

PHYSICAL DEMANDS - The physical demands described here are representative of those that must be met by an employee to successfully perform the essential functions of this job. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.

• The employee must occasionally lift and/or move up to 25 pounds.
• While performing the duties of this job, the employee regularly stands, walks, sits, uses hands to finger, handle, or feel, reaches with hands and arms, talk or hear.

VISION REQUIREMENTS - Close vision (clear vision at 20 inches or less) to work on the computer.

WORK ENVIRONMENT - The work environment characteristics described here are representative of those an employee encounters while performing the essential functions of this job.

This position works in an environment with moderate noise level. (Examples: business office with computers and printers, light traffic.)

Note: Nothing in this job specification restricts management’s right to assign or reassign duties and responsibilities to this job at any time. Critical features of this job are described under various headings above. They may be subject to change at any time due to reasonable accommodation or other reasons, with or without notice.  The above statements are strictly intended to describe the general nature and level of the work being performed. They are not intended to be construed as a complete list of all responsibilities, duties, and skills required of employees in this position.