Turning “pre-work” into real competitive prep

The challenge

Reps weren’t showing up to Sales Kickoff (SKO) ready for high-stakes security conversations. Long courses did not stick, and last-minute searching did not help. We needed a fast, hands-on way to build credibility with CISO stakeholders.

What we built

• Prep course: Security Foundations (escape room). A short, puzzle-style eLearning that warms up core ideas before the simulation. I wrote the prep escape-room course, defined the simulation patterns, and used ChatGPT workflows to speed design. Our Learning Experience Designer developed and designed the course experience, scenarios and the escape-room interaction.

• Chatbot simulation. A CISO decision practice where reps answer in their own words and get instant graded feedback. A second Learning Experience Designer on my team designed the chatbot. Scenarios use real customer objections and language from top sellers, so it feels like the job, not homework.

• Real scenarios from the field. Subject-matter experts from extended teams worked with us to define the use cases and scenarios for the course, the escape room, and the chatbot.

• Built for scale. We partnered with our OpenAI CSM to support hundreds of learners on the existing stack, without adding new licenses.

How it works

• Complete Security Foundations to learn the moves and unlock the simulation

• Choose a simulation scenario and respond naturally

• Get a score and an explanation, then try again as difficulty ramps

• Managers see clear signals to coach against across both assets

SKO: live, custom simulation

For the SKO event, we partnered with Thoughtium, Sales Enablement leadership, and Executive Business Partners to build a custom, live, in-person simulation. It ran in breakout sessions over two days across AMER, APJ, and EMEA and included role-based learning paths. The Security Foundations escape room and the chatbot pre-work served as the foundation for the in-person session and raised the floor so we could work advanced scenarios on site.

Impact

• 94% completion among enrolled reps vs a ~30% historical baseline

• 788 completions and 151 in progress at launch

• 18% QoQ lift with security stakeholders
  Leaders championed it because it showed up in the room: reps skipped basics and worked advanced scenarios.

My role

I designed the vision, framework, and overall plan for the pre-work and owned it end to end with the team. I set direction, defined success, and removed friction. Kept quality and security in view, ensured we stayed inside the existing toolset, and made the system easy for teams to own day to day.

I wrote the Security Foundations escape-room script. One Learning Experience Designer built the escape-room experience. Another Learning Experience Designer designed the chatbot. A Curriculum Developer on my team designed all of the videos. I stayed hands on as a player-coach to keep quality and speed high, coordinated SME input, and ensured we stayed within our existing toolset.

Fast facts

• Security Foundations escape room unlocks the chatbot simulation

• Private, on-demand practice with graded feedback

• Built with our OpenAI CSM for scale and reliability

• Pre-work fed a two-day live simulation at SKO

• Now part of onboarding and pre-call prep