Regional Vice President, FL/GA

PowerSchool Group LLC

9d • Remote

About The Position

At PowerSchool, we are a dedicated team of innovators guided by our shared purpose of powering personalized education for students around the world. From the central office to the classroom to the home, PowerSchool supports the entire educational ecosystem as the global leader of cloud-based software for K-12 education. Our employees make it all possible, and a career with us means you’re joining a successful team committed to engaging, empowering, and improving the K-12 education experience everywhere.
Team Overview
The Sales team gets PowerSchool into the hands of the educators and students who need it. Working side by side with Solution Consulting and Customer Success, we build executive relationships, lead account planning, and run deals end to end to renew on time and expand multi-suite adoption, delivering predictable bookings and revenue retention that empower better K-12 outcomes.
Description
The Regional Vice President, Field Sales owns expansion and retention performance for a field region by leading a team of Enterprise sellers and coordinating cross-functional resources to land, adopt, and expand within large K–12 accounts. The role sets the operating cadence, elevates executive engagement, and enforces deal and account standards that drive predictable multi-suite growth. This role is the day-to-day commercial leader for the region and a thought partner to leaders in sales and across the company in territory strategy, state plans, capacity, and GTM improvements.

Requirements

• Consistent track record leading sales team attainment on bookings and revenue retention, including multi-suite expansion across named accounts.
• Experience leading teams with 9+ month complex sales cycles centered on cross-sell, public-sector procurement, and multi-persona executive engagement; able to coach others to turn a champion in one persona into wins with others (e.g., CFO to CHRO or CAO).
• Proven capability to recruit, ramp, and retain high-performing enterprise sellers; recognized coach on complex pursuits and executive communication.
• Demonstrated operating cadence leadership including weekly forecast reviews, monthly business reviews, and quarterly executive reviews with actionable follow-through.
• Demonstrated ability to enforce pipeline and forecast discipline in CRM across the team, inspection-ready for weekly, monthly, and quarterly reviews, with a track record of improving forecast accuracy.
• Proficiency with modern deal methodology and mutual close plans, for example MEDDPICC, with all elements captured and kept current in CRM and used to drive stage exits at a team level.
• 10+ years enterprise SaaS sales experience or equivalent with 5+ years managing field sellers in complex public-sector environments.
• Bachelor’s degree or equivalent experience.

Nice To Haves

• K–12 or public-sector fluency, including funding cycles, board approvals, RFPs, and use of co-ops or state purchasing vehicles.
• Advanced Salesforce proficiency for pipeline inspection, forecast variance management, and portfolio risk reviews across a region.

Responsibilities

• Hire, develop, and lead Account Executives (AEs) to consistent attainment of on-time renewals, multi-suite expansion, and new logo expansion.
• Run a rigorous operating cadence that includes weekly forecast reviews, weekly 1:1s, monthly business reviews, and quarterly business reviews with clear actions and owners and dates.
• Inspect pipeline quality and deal health in Salesforce; coach to stage exit criteria, mutual close plans, MEDDPICC hygiene, risk mitigation, and slip reduction.
• Approve and enforce account plans that map whitespace, executive sponsors, state initiatives, services attach, and next plays by persona; ensure governance with customers is in place and effective.
• Partner with Customer Success and Services leaders to improve adoption, services attach, retention readiness, and renewal execution across the book.
• Coordinate state strategy with Area leadership and the State Strategy function including stakeholder mapping, procurement vehicles, and coordinated pursuits.
• Remove blockers and orchestrate overlay teams including Solution Consulting, Services Sales, and Sales Development to raise win quality on complex pursuits.
• Provide market, competitive, and policy insights to inform offer structure, pricing, options, and regional GTM refinements.
• Travel regularly (50–60%), including multi-state trips, to support high-impact initiatives such as advancing strategic deals, leading onsite demos, and facilitating executive workshops, especially during peak business cycles.

Benefits

• Comprehensive Insurance Coverage (including Medical, Dental, Vision, Pharmacy benefits, Life Insurance and AD&D)
• Flexible Spending Accounts and Health Savings Accounts
• Short-Term Disability and Long-Term Disability
• Comprehensive 401(k) plan
• Generous Parental Leave
• Unrestricted paid time off (known as Discretionary Time Off - DTO)
• Wellness Program, including ClassPass & Employee Assistance Program
• Tuition Reimbursement
• Optional Benefits: Pet Insurance, Identity Theft Protection, Student Debt Repayment Program and Prepaid Legal coverage

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level