Director of Sales Training and Enablement

Watchtower Security LLC • Maryland Heights, MO

9h

About The Position

Watchtower Security is the nation's leading provider of all-inclusive, fully managed video surveillance solutions, exclusively dedicated to the multifamily housing industry. For over two decades, we have partnered with property management groups across the nation, empowering them to provide peace of mind to their communities. As a rapidly growing and dynamic organization, we pride ourselves on a fast-paced, collaborative environment where innovation, critical thinking, and a commitment to excellence drive our success. We are seeking passionate individuals eager to contribute to a team that values strong communication, attention to detail, and a shared dedication to making a tangible difference in multi-family communities. Watchtower is seeking a Director of Sales Training and Enablement to build and own the company's training and enablement program. This is not a training coordination role; it is a program leader mandate. The Director will design, operationalize, and sustain a full-cycle enablement system that accelerates new hire ramp and sales cycle from the current average to a new lower threshold.

Requirements

• 7+ years of progressive experience in sales enablement, revenue enablement, or sales leadership in a B2B environment with demonstrated ownership of a full enablement function (not just program delivery)
• Proven success building onboarding programs that measurably reduced new hire ramp time and improved early-tenure retention
• Experience working in or selling into complex, multi-stakeholder environments; property management, PropTech, or security software experience is a plus but not required
• Direct experience with CRM platforms (Salesforce preferred), LMS tools, and modern sales enablement technology
• Familiarity with at least one structured sales methodology (e.g., MEDDPICC, Challenger, Sandler, SPIN)
• Strong facilitation skills. Comfortable leading sessions with competitive field sellers and executive stakeholders alike
• Exceptional program management skills; ability to prioritize and deliver in a resource-constrained, fast-moving environment
• Bachelor's degree in Business, Organizational Development, Communications, or a related field

Nice To Haves

• Prior quota-carrying sales experience (AE, AM, or SDR).
• Experience operating in a growth environment with rapid headcount scaling
• Familiarity with instructional design frameworks (ADDIE, Kirkpatrick) and adult learning theory
• Professional certifications: CPTD (Certified Professional in Talent Development), ATD Training Certificate, or equivalent

Responsibilities

• Define the mission, scope, and success metrics for Watchtower's enablement function from the ground up
• Build a 12-18 month enablement roadmap aligned to Watchtower's sales headcount growth plan (through FY29)
• Establish rules of engagement, RACI, and working cadence with Sales Leadership, RevOps, and HR
• Design and operationalize a structured 30/60/90-day onboarding program anchored to the Watchtower Sales Playbook, with clear milestones and a classroom-to-field progression
• Build role-specific onboarding paths for Regional Sales Managers, National Sales Managers, and Customer Account Managers
• Develop milestone-based checkpoints and certification gates to validate seller readiness before full territory assignment
• Conduct train-the-trainer sessions to equip Watchtower's internal team to deliver and sustain the program independently
• Own ongoing activation and reinforcement of the Watchtower Sales Playbook across all GTM roles
• Refresh playbook content as ICP, messaging, and competitive landscape evolve
• Develop workshops, certification programs, and field reinforcement tools (call plans, pre-call briefs, opportunity review templates) to drive behavior change, not just content awareness
• Build and deliver a sequenced, ongoing curriculum covering core selling skills: discovery, qualification, objection handling, competitive positioning, and negotiation
• Leverage blended learning modalities: instructor-led, virtual, self-paced eLearning appropriate to a distributed, national sales team
• Design and manage a Learning Management System (LMS) to house, track, and certify all program content
• Design a structured coaching playbook for frontline Sales Managers, defining cadence, format, and accountability mechanisms
• Equip managers to deliver real-time, in-field coaching that reinforces onboarding and playbook content
• Create monthly and quarterly manager enablement touchpoints tied to seller performance data
• Define and own the enablement KPI dashboard: ramp-to-quota time, voluntary attrition by tenure cohort, win rate, quota attainment by cohort, and content adoption
• Use CRM and call recording data (e.g., Gong) to identify patterns in high-performer behavior and close skill gaps across the team
• Report program outcomes and ROI to Sales Leadership and PE sponsor on a quarterly basis

What This Job Offers

• Job Type: Full-time
• Career Level: Senior