Sales Enablement Director: Onboarding & Playbook Mastery

Watchtower Security; Maryland Heights (MO); On-site; USD 120,000 - 170,000; Full time

Job summary

Watchtower Security in Maryland Heights, MO, is seeking a Corporate Sales Training and Enablement Professional to design and own the company's full enablement program. This is not a training coordination role; it is a program leader mandate aimed at accelerating new hire ramp and sales cycle performance.

The Director will build a 12–18 month enablement roadmap, define engagement rules, develop onboarding paths for regional and national sales teams, implement a structured coaching cadence, and

Qualifications

• 7+ years of progressive experience in sales enablement, revenue enablement, or sales leadership in a B2B environment
• Proven success building onboarding programs that reduce ramp time and improve early-tenure retention
• Experience working in or selling into complex, multi-stakeholder environments; property management, PropTech, or security software is a plus
• Direct experience with CRM platforms (Salesforce preferred), LMS tools, and modern sales enablement technology
• Familiarity with structured sales methodologies (e.g., MEDDPICC, Challenger, Sandler, SPIN)
• Strong facilitation skills and executive stakeholder engagement
• Bachelor's degree in Business, Organizational Development, Communications, or related field

Responsibilities

• Enablement Charter and Roadmap: define mission, scope, and success metrics
• Build 12-18 month enablement roadmap aligned to sales headcount growth
• Establish RACI and cadence with Sales Leadership, RevOps, and HR
• Design onboarding anchored to Watchtower Sales Playbook with milestones
• Create role-specific onboarding paths for Regional and National Sales Managers and Customer Account Managers
• Develop certification gates to validate seller readiness
• Conduct train-the-trainer sessions
• Sales Playbook Activation: refresh content as ICPs and messaging evolve
• Develop workshops, certification programs, and field reinforcement tools
• Ongoing Training and Skills Development: cover core selling skills and blended learning
• Design and manage an LMS to track and certify content
• Manager Enablement and Coaching Cadence: structured coaching playbook and cadence
• Equip managers to deliver real-time coaching and tie to performance data
• Monthly/quarterly enablement touchpoints tied to seller performance
• Measurement: define the enablement KPI dashboard and report ROI

Skills

Sales Enablement

Leadership

CRM (Salesforce)

LMS Tools

Program Management

Coaching

Education

Bachelor's degree in Business or related field

Tools

Salesforce

LMS

Job description

Watchtower Security in Maryland Heights, MO, is seeking a Corporate Sales Training and Enablement Professional to design and own the company's full enablement program. This is not a training coordination role; it is a program leader mandate aimed at accelerating new hire ramp and sales cycle performance.

The Director will build a 12–18 month enablement roadmap, define engagement rules, develop onboarding paths for regional and national sales teams, implement a structured coaching cadence, and