Director of Sales Training and Enablement
On-site · Maryland Heights, Missouri, United States
Job Summary
Director of Sales Training and Enablement to build and own Watchtower’s full-cycle sales enablement program. Responsibilities include defining the enablement charter and roadmap, designing and operationalizing onboarding (30/60/90-day programs) for Regional/National Sales Managers and Customer Account Managers, owning the Sales Playbook activation and continuous improvement, delivering a sequenced curriculum covering core selling skills, managing a Learning Management System to house and certify content, designing a structured coaching cadence for frontline managers, and defining KPI dashboards to measure ramp-to-quota time, retention, win rate, and content adoption. The role requires leading enablement initiatives end-to-end with cross-functional alignment to Sales Leadership, RevOps, and HR, leveraging blended learning modalities for a distributed national sales team, and ensuring ongoing engagement with field sellers and executive stakeholders. A Bachelor’s degree is required, and 7+ years of relevant experience in sales enablement or leadership is preferred; CRM (Salesforce) and LMS experience, familiarity with sales methodologies (MEDDPICC, Challenger, SPIN, etc.), and certifications in talent development are advantageous.
Required 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
- Experience building onboarding programs that reduced ramp time and improved early-tenure retention
- Experience in complex, multi-stakeholder environments; property management, PropTech, or security software experience 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 and executive-level engagement
- Exceptional program management skills with ability to operate in fast-moving environments
- Bachelor's degree in Business, Organizational Development, Communications, or related field
- Preferred qualifications: prior quota-carrying sales experience; experience with growth environments; instructional design frameworks; professional certifications CPTD/ATD Training Certificate or equivalent
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