Fast Facts

Join PowerSchool as a Regional Vice President, Field Sales, where you will lead a team of Enterprise sellers to drive expansion and retention in large K-12 accounts, ensuring predictable multi-suite growth and improved educational outcomes.

Responsibilities: Oversee a team of Account Executives to achieve sales goals; develop operating cadence for performance reviews; enhance pipeline quality and deal health; partner with Customer Success to promote retention and adoption; and provide market insights to refine strategy.

Skills: Proven track record in leading sales teams, experience with complex public-sector sales cycles, strong coaching abilities, proficiency in CRM and deal methodologies, and advanced understanding of enterprise SaaS sales.

Qualifications: 10+ years in enterprise SaaS sales with 5+ years in managing field sellers; bachelor's degree or equivalent; preferred K-12 or public-sector knowledge; advanced Salesforce skills.

Location: The position is based in the United States and requires regular travel (50–60%) across multiple states.

Compensation: $179600 - $225100 / Annually

Overview

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.

Responsibilities

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.

Your day-to-day job will consist of:

• 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.

Success Indicators

• Region delivers or exceeds expansion and retention targets with visible multi-suite expansion across priority accounts.
• Forecasts are inspection-ready and land within agreed variance at weekly, monthly, and quarterly levels.
• Slip rate and stage aging decline while win rate and renewal performance improve.
• Account plans and governance are in place for all strategic accounts with committed next expansions and executive sponsorship.

Qualifications

Minimum Qualifications

• 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.

Preferred Qualifications

• 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.

Compensation & Benefits

Compensation & Benefits

PowerSchool offers the following 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

A reasonable estimate of the base compensation range for this position is $179,600 - $225,100 USD plus applicable commission. This compensation range is specific to the United States and it incorporates many factors including but not limited to an applicant's skills and prior relevant experience and training; licensures, degrees, and certifications; internal equity; internal pay ranges; and market data/range parameters.

EEO Commitment

EEO Commitment

PowerSchool is committed to an inclusive workplace. PowerSchool is an equal opportunity employer and does not discriminate on the basis of race, national origin, gender, sexual orientation, disability, age, or other legally protected status. Our inclusive culture empowers PowerSchoolers to deliver the best results for our customers. We not only celebrate the diversity of our workforce, we celebrate the diverse ways we work. If you have a disability and need an accommodation regarding our recruiting process, please let us know by emailing accomodations@powerschool.com.

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