Corporate Sales Training and Enablement Professional

Watchtower Security is the nations 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 companys 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 Watchtowers enablement function from the ground up
  • Build a 12-18 month enablement roadmap aligned to Watchtowers sales headcount growth plan (through FY29)
  • Establish rules of engagement RACI and working cadence with Sales Leadership RevOps and HR
• New Hire Onboarding Program
  • 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 Watchtowers 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
• Bachelors 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