Lead Sales Readiness & Execution

Position Overview

The Lead Sales Readiness & Execution is the enablement owner for the Field/Inside SDR, Inside Sales Account Managers, and Sales Manager readiness and execution transformation.

This role influences and operationalizes Field/Inside SDR, Inside Sales Account Managers, and Sales Managers readiness strategies, sales capability frameworks, and execution standards that support successful commercial transformation. The role influences organizational, role and territory readiness decisions while establishing scalable approaches to leader effectiveness, seller proficiency, manager reinforcement, and measurable business outcomes.

Essential Responsibilities

• Define and govern Field/Inside SDR, Inside Sales Account Managers, and Sales Manager readiness frameworks, capability models, certification methodologies, and proficiency standards across Field/Inside SDR, Inside Sales Account Managers, and Sales Managers.
• Define readiness strategies and capability requirements in response to evolving go-to-market priorities, organizational changes, territory models, and sales processes, ensuring alignment across sales functions.
• Serve as the enablement lead for the sales organization, absorb daily change in leadership, territory and process, and adjust readiness and onboarding support quickly.
• Across the Inside and SDR organization, readiness criteria, certification frameworks, and proficiency standards that govern role preparedness across sales functions.
• Design extended ramp and coaching support for new and transitioning Field/Inside SDR, Inside Sales Account Managers, and Sales Managers; including manager tools, coaching standards, inspection routines and reinforcement plans.
• Operationalize prospecting for both teams 6 sequences, call blocks, messaging, objection handling 6 so onboarding produces pipeline, not just completed training.
• Cross-pollinate the two disciplines: SDR prospecting rigor into Inside Sales, Inside Sales closing and forecasting discipline into SDR.
• Design and coach sales methodology and forecast accuracy and hold managers to the reinforcement and inspection routines that make it stick.
• Direct and govern the network of facilitators, coaches, subject matter experts, and enablement partners responsible for program execution through defined standards, success measures, and quality controls.
• Bring outside expertise on modern selling practices and customer expectations to define what readiness should look like for the sales teams going forward.
• Advise leadership on organizational capability gaps, readiness risks, sales effectiveness priorities, and strategic investments that impact revenue growth and commercial transformation.

Measures of Success

• Improved time to readiness for new and transitioning Inside sellers and leaders.
• Observed seller-skill proficiency and manager validation against defined role expectations.
• Manager coaching and inspection routines operate consistently in the field.
• Improved pipeline quality and conversion, including qualified pipeline, stage progression and opportunity-to-close conversion.
• Across the Inside and SDR organization, adoption of readiness frameworks, methodologies, and operating standards.
• Measurable improvements in organizational productivity, sales effectiveness, and business performance are attributable to readiness initiatives.
• Successful implementation of future-state capability models and transformation priorities.

Required Qualifications

• 8+ years of relevant experience in sales, sales leadership, sales enablement, or a related field.
• Proven experience leading sales readiness or enablement in complex B2B software, education technology, recurring revenue, renewals, expansion, or multi-role GTM environments.
• Strong knowledge of seller development, manager coaching, sales methodology, practice, certification, and behavior change.
• Ability to turn GTM, role, territory, or operating model changes into clear readiness and reinforcement plans.
• Ability to influence senior leaders, shape direction, and drive outcomes through expertise and indirect influence.
• Excellent facilitation, communication, design judgment, and influence skills.
• Success defining future-state capability strategies, operating models, or sales-effectiveness frameworks with broad impact.
• A bachelor7s degree is required.

Preferred Qualifications

• Experience supporting a major sales-location, leadership or organizational transition.

Along with our highly market competitive base compensation, 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