Education Advisor — Former Superintendent

Prosperi; United States; Hybrid; USD 20,000 - 50,000; Part time

Benefits offered by this job

Flexible engagement

Compensation tied to involvement

Influence on educational outcomes

Job summary

Prosperi is seeking current and recently retired superintendents to join their advisory network. This part-time role involves enhancing K–12 counseling capacity through telecounseling services and strong peer networking.

Advisors will work with district leaders, represent Prosperi at key events, and provide insights on funding and policies. The compensation is based on involvement and impact, making it a strategic opportunity to influence educational outcomes.

Qualifications

• Current or recently retired K–12 superintendent.
• Strong relationships with superintendents and district leaders.
• Trusted voice in the region for advice.

Responsibilities

• Help enhance counseling through telecounseling services.
• Host peer roundtables and working sessions.
• Advise on regional dynamics and funding.
• Represent Prosperi at events and conferences.

Skills

Relationship building

Peer networking

Advisory skills

Knowledge of K-12 education

Job description

Company Description

Prosperi gives K–12 districts more counseling capacity without more headcount. We combine licensed telecounselors with AI-powered software to extend what counseling teams can deliver — surfacing early-warning signals on students who are slipping before they fall through the cracks, cutting the administrative load that pulls counselors away from students, and driving measurable movement on the KPIs superintendents are accountable for: graduation rates, attendance, and college and career readiness. Districts get added capacity, earlier intervention, and outcomes they can take to the board.

Role Description

We're looking for current and recently retired superintendents to join our advisory network as we expand into new districts and states. This is a relationship-driven advisory role for leaders with strong peer networks across K–12 — superintendents who are respected in their region, active in state and national associations, and willing to open doors to other district leaders who would benefit from what we're building.

This is a flexible, part-time engagement with compensation tied to involvement and impact.

What You'll Do

• Help the Prosperi team superpower academic, career, and college counseling through novel telecounseling services and state-of-the-art software and AI
• Host or co-host peer roundtables, dinners, or working sessions with district leaders
• Provide warm referrals and context for districts evaluating counseling solutions
• Advise on regional dynamics — funding, policy, association activity, and competitive landscape
• Represent Prosperi at superintendent convenings, state association events, and conferences where appropriate
• Share feedback on positioning, messaging, and procurement experience from a district leader's perspective

Who We Are Looking For

• Current or recently retired K–12 superintendent with an active peer network
• Strong relationships with other superintendents, cabinet members, or state association leaders
• Trusted voice in your region — others call you for advice on vendors and initiatives
• Genuine belief in the problem we're solving: counselor capacity and student outcomes

Nice To Have

• Active involvement in AASA, state superintendent associations, or regional consortia
• Experience leading multi-district initiatives or consortia purchasing
• Background in counseling, student services, or whole-child initiatives at the district level

Why Prosperi

• Mission that matters — help districts improve the outcomes superintendents are measured on: graduation, attendance, and college and career readiness
• Strategic role with real influence on how we grow and the impact we have on student performance and outcomes
• Flexible engagement — your involvement scales with what works for your schedule
• Compensation: Advisory retainer scaled to your level of involvement, plus fixed bonuses for qualified introductions.