Director, Sales Enablement

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.

The Director, Field Enablement is a senior leader responsible for driving field adoption, manager effectiveness, and sustained behavior change across the sales organization. This role ensures that enablement strategies, plays, and GTM changes translate into consistent execution through frontline managers and sellers across regions and segments. 

Reporting to the VP of Revenue Enablement, this role partners closely with Sales Leadership, Solution Enablement, Product Marketing, and Revenue Operations to embed enablement into field rhythms, coaching models, and operational workflows. The Director, Field Enablement is critical to ensuring that enablement efforts deliver measurable improvements in productivity, pipeline quality, and revenue outcomes.

Field Adoption & Reinforcement 

• Own the adoption strategy and reinforcement plans (30/60/90‑day) for priority enablement initiatives, including Tier 1 plays. 
• Ensure enablement initiatives are embedded into existing sales rhythms such as pipeline reviews, forecast calls, deal inspections, and QBRs. 
• Drive consistent execution across NAM Field & Named, NAM Inside, International account segments while maintaining local relevance. 
• Use data and field insights to continuously improve enablement approaches and reinforcement strategies. 

Manager Enablement & Coaching 

• Design and scale an Account Manager enablement system that includes coaching kits, call review rubrics, and deal inspection frameworks. 
• Partner with Sales leadership to drive consistent manager coaching behaviors aligned to selling motions, value articulation, and deal quality. 
• Enable frontline leaders to coach observable behaviors and outcomes, not just activity or results; Monitor adoption and execution of priority plays and coaching motions. 

Change Management & GTM Enablement 

• Lead field enablement for major GTM changes, role transitions, and tool or process transformations. 
• Partner with Enablement Hub and Revenue Operations to sequence rollouts, support readiness, and provide post‑launch reinforcement and hypercare. 
• Act as the voice of the field in readiness and go/no‑go decisions to ensure changes are adoptable and executable. 
• Partner with Enablement Operations and Revenue Operations to define and track adoption, proficiency, and leading performance indicators. 

Collaboration & Communication 

• Partner with Solution Enablement to ensure plays and solution motions are practical, usable, and aligned to field realities. 
• Provide structured feedback to Hub, Solution Enablement, PMM, and RevOps on adoption challenges, content usability, and process friction. 
• Build strong relationships with Sales VPs, RVPs, and frontline managers to drive shared accountability for execution. 

Leadership & Talent Development 

• Lead and develop a team of Field Enablement Leads, aligning priorities to business objectives. 
• Establish clear expectations, success measures, and development plans for team members. 
• Foster a culture of focus, accountability, and continuous improvement within the field enablement function. 
• Support Enablement Business Reviews (EBRs) with clear insights into field execution and impact. 

Minimum Qualifications

• Bachelor’s degree required; or equivalent years of experience.  
• 10+ years of experience in sales, sales enablement, or sales leadership. 
• Demonstrated success driving adoption and change in complex, matrixed GTM environments. 
• Proven experience working closely with frontline sales managers and leaders. 
• Preferred Qualifications
• Recognized as a mentor or team lead that contributes to the development of frameworks or tools that have been scaled across teams (e.g., demo libraries, objection handling tools, solution architectures).
• Experience working closely with Marketing, Product, or Enablement teams to improve GTM effectiveness.

Preferred Qualifications

• Strong organizational, planning, and change‑management skills. 
• Excellent communication, facilitation, and influencing capabilities. 
• Ability to operate independently while collaborating effectively across teams. 
• Comfort balancing strategic leadership with hands‑on execution. 

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 $154,500 - $193,100 USD plus applicable bonus. 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

PowerSchool is committed to a diverse and inclusive workplace. PowerSchool is an equal opportunity employer and does not discriminate on the basis of race, national origin, gender, gender identity, sexual orientation, protected veteran status, 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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