VP of Sales — Enterprise (AI Roleplay + XR Workforce Productivity)

VP of Sales — Enterprise (AI Roleplay + XR Workforce Productivity)

CGS Immersive | TeamworkAR / Cicero
Location: USA/Canada (Remote)
Travel: ~25%

Company Profile:

CGS Immersive builds products that help enterprises improve performance where it matters most: the moments that drive revenue, productivity, quality, safety, and customer outcomes. Our portfolio includes Cicero, a world-leading AI roleplay and workforce productivity application, and TeamworkAR, an immersive solution set using AR/XR/VR to support frontline execution, training, and readiness.

We sell into complex enterprise environments—often Business Units and operational leaders, and in some cases through Learning organizations as stakeholders or co-owners.

Role Overview:

We are seeking an experienced, successful VP of Sales to lead and scale our enterprise sales team. This leader will build a predictable revenue engine by:

• Driving a repeatable enterprise motion (pipeline → close → expansion)
• Standardizing pilot-to-rollout conversion
• Coaching senior IC sellers to win across business-unit and learning-led paths
• Improving forecast accuracy and raising execution standards across the team

This role is ideal for a leader who can balance strategic executive selling with hands-on deal coaching and operating rigor.

Key Responsibilities:

Revenue leadership & team management

• Lead and coach a team of enterprise sales executives.
• Set clear standards for activity, pipeline, qualification, and conversion.
• Maintain regular sales processes: pipeline and deal reviews, forecasts, and QBRs.
• Drive territory and account planning, focusing on priority verticals.
• Recruit, onboard, ramp talent, and manage performance decisively.

Enterprise deal strategy (Fortune 1000)

• Support and coach complex deals, including executive meetings and negotiation strategy
• Implement and maintain qualification discipline (MEDDICC or similar)
• Boost win rates with improved discovery and stakeholder mapping
• Advise AEs on handling enterprise stakeholders across business units, operations, IT/Security, procurement, legal, and HR

Pilot-to-rollout conversion engine

• Create standardized pilot packages that include:
  • Success metrics linked to productivity, readiness, quality, safety, and customer results
  • Timeline and rollout plan
  • Metrics and reporting strategy
  • Decision checkpoints and pilot conversion plan
• Ensure pilots are designed to convert to enterprise rollouts and expansions (sites/roles/use cases)

Value engineering & storytelling

• Build and operationalize ROI tools and executive narratives that connect to measurable outcomes:
  • Faster onboarding & time-to-proficiency
  • Improved execution quality and consistency
  • Reduced rework/escalations/downtime
  • Increased conversion and improved customer interactions
  • Improved compliance/safety outcomes where relevant
• Coach a consistent story that resonates with BU and Learning buyers without positioning as “training-only”

Cross-functional leadership

• Partner with Product, Delivery/CS, and Marketing to:
  • Sharpen ICP and messaging
  • Improve demos and proof assets
  • Create scalable sales enablement content (plays, decks, talk tracks, case studies)
  • Close the loop on win/loss feedback into roadmap and packaging
• Coordinate with Finance/Legal/InfoSec to reduce enterprise friction and speed cycle times

Required qualifications

• Demonstrated sales leadership overseeing independent contributor enterprise sellers
• Proven success leading teams targeting Fortune 1000 accounts with complex buying committees
• Expertise in developing reliable pipelines and enhancing forecasting accuracy
• Experience selling enterprise solutions related to workforce productivity, performance improvement, enablement, artificial intelligence coaching/simulation/roleplay, and immersive technologies (AR/XR/VR)
• Exhibits strong executive presence, advanced communication skills, and effective storytelling abilities
• Special consideration will be given to candidates that have been directly involved in Learning Transformation
• Highly adept at navigating ambiguous, fast-paced environments and implementing structure and repeatable processes

Preferred qualifications

• Proven track record in selling solutions that combine AI with human performance, including coaching, simulations, roleplay, and assessments
• Knowledge of immersive technology deployment, such as handling devices, developing content strategies, driving adoption, and measuring success
• Experience growing a sales team by managing hiring, training, processes, and creating playbooks