Corporate Sales Training and Enablement

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

Full Time HQ, Maryland Heights, MO, US

Corporate Sales Training and Enablement

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 Corporate Sales Training and Enablement Professional 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.

Primary Responsibilities:

• Enablement Charter and Roadmap
• 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
  
• Sales Playbook Activation and Maintenance
• 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
• Ongoing Training and Skills Development
• 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
• Manager Enablement and Coaching Cadence
• 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
• Measurement and Continuous Improvement
• 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

Qualifications:

• 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

Preferred Qualifications

• 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