Sr. Director Enablement - Sales Leader & Transformation Initiatives

As the Sr. Director of Sales Leader Enablement & Transformation Programs, you will serve as a strategic leader and transformation catalyst across the sales organization.  This role is responsible for driving cross-functional initiatives that enhance sales leader skills, improve sales productivity, streamline operations, and align enablement efforts with business growth objectives, focusing first and foremost on frontline managers. You will partner closely with executive leadership, sales operations, and enablement teams to design and lead targeted programs with measurable impact delivered in partnership with our Revenue Enablement & Sales Experience / Operations enablement teams.

Key Responsibilities

• Design, deliver and drive transformation programs that align sales processes with corporate objectives, and in doing so, lead strategic initiatives to improve sales efficiency, focusing first on sales leaders.
• Oversee cross-functional program management, including working through our enablement organization, to ensure seamless execution and delivery of sales initiatives & enablement programs at large. 
• Champion change management efforts to support adoption of new sales methodologies and tools to efficiently reinforce and support those change efforts. 
• Monitor and analyze sales performance data and KPIs to identify gaps and provide actionable insights.
• Develop and monitor KPIs to measure the impact of transformation programs on sales performance.
• Iterate enablement design and plan to evolve to meet the needs of the team.
• Act as a trusted advisor to sales leadership, offering insights and recommendations to improve leadership skills and sales team productivity.
• Provide ongoing coaching and support to managers to help them meet and exceed targets.

Qualifications

• Bachelor’s degree in business, Marketing, or related field; MBA preferred.
• 10+ years of experience in Sales, Sales Enablement, Sales Operations, or Program Management roles in Saas, technology or educational organizations.
• Sales leadership experience with background in a quota-carrying sales role.
• Proven experience in leading large-scale sales transformation programs involving strategic planning and cross-functional collaboration.
• Excellent leadership and communication skills with the ability to influence at all levels.
• Ability to analyze complex data and translate insights into actionable strategies.
• Strong understanding of sales methodologies (e.g., MEDDICC, Challenger, SPIN).

Nice to Haves

• Familiarity with instructional design or adult learning principles.
• Experience with sales enablement platforms and CRM systems (e.g., Salesforce, Highspot, Seismic, Gong) a plus

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 $127,900 - $164,900 USD. 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; specific geographic location; 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 accommodations@powerschool.com.