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

About Us

For more than 40 years, CGS has empowered global enterprises to drive breakthrough performance through innovative business applications, enterprise learning and outsourcing. CGS Immersive® is an innovation lab and training transformation engine modernizing training programs and delivering immersive experiences tailored to meet the evolving needs of organizations across industries.

Learn more about CGS Inc® and CGS Immersive® in our websites:

https://cgsinc.com/en
https://cgsimmersive.com/