Corporate Sales Training and Enablement Professional

Primary 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
• Develop 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
• 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
• Build and deliver 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

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
• 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