KeepWOL

KeepWOL (short for "Keep Wondering Out Loud") is a Phoenix, Arizona-based software company that sells a team effectiveness platform to employers. The product begins with a short heartbeat survey that sets a baseline across six areas — team dynamics, engagement, innovation, cultural intelligence, job satisfaction and psychological safety — and then applies an "Experience, Reflect, Grow" methodology. In the Experience phase, teams take part in live verbal conversation sessions built on psychology-based multiplayer games, drawing on a library of ready-made session themes or custom sessions generated with an AI builder. Post-session reflections feed real-time views of team health, individual progress and group goals, and session data is used to generate curated learning content and action plans.

Platform features include an AI game builder, AI learning pathway and action plan builders, AI-generated resource and training recommendations, user learning dashboards, team collaboration and metrics dashboards, single sign-on, and integrations with existing learning management, performance management and HRIS systems. Reported third-party tooling includes HubSpot Analytics, Microsoft Clarity, Calendly, Amazon Web Services, Google Workspace, Sentry, Webflow and Airtable. The company also maintains an online store selling its original consumer conversation card games and expansion packs, described as available while supplies last.

KeepWOL is a Cisco Select Developer Partner and a member of the African American Cisco Partner Community (AACPC) Program, which it says provides access to Cisco technology, consulting, training and capital programs. It identifies itself as minority-owned, women-owned and a women-owned small business.

Founding story

Founder and CEO Lauren Fitzpatrick Shanks created Keep Wondering Out Loud as a card game for personal relationships and new connections, selling more than 1,000 games across three continents. Her motivation came from her own experience as an outsider: she was the first Black woman to graduate from the University of Kansas's Aerospace Engineering department and one of two women in her graduating class, and during 14 years at Fortune 500 companies she found diversity, equity, inclusion and belonging programs focused on vanity metrics rather than retention, with managers receiving no training on leading and communicating across different backgrounds. During the pandemic and Great Resignation she shifted the business model toward building communication skills for enterprise teams and expanded the methodology into structured pathways. She has said she deliberately proceeded without a co-founder after an early mismatch, having already built a working prototype and launched beta testing before assembling a leadership team.

Business model

KeepWOL licenses its platform to organizations under tiered plans: a per-team plan that bundles onboarding, one customized learning pathway of six games, a certified KeepWOL facilitator and a scheduled facilitation cadence; an Enterprise plan with 17 out-of-the-box games, five out-of-the-box learning pathways, unlimited gameplay, AI builders, dashboards and SSO integration; and a Consultants plan offering the game and pathway libraries plus AI builders and client-facing action plans. A separate direct-to-consumer store sells physical card games and expansion packs priced between $19.99 and $29.99.

Subscription/plan-based software sales to organizations (per-team and enterprise tiers, plus a consultant tier), supplemented by direct sales of physical card games through the KeepWOL online store.

Traction

Company-reported figures include 94% of users recommending KeepWOL, a 93% average experience rating, 90% of users feeling more understood, 89% of teams holding sessions at least monthly, 87% of teams saying sessions surface new insights and 86% of users reporting improved team relationships, with an overall experience score of 9.3 out of 10. The company reports hundreds of teams seeing double-digit growth across its six categories and a 49% improvement in team dynamics within a quarter across multiple organizations. More than 1,000 units of the original card game were sold across three continents. Third-party data lists estimated annual revenue of $1M–$10M and 2–10 employees (9 on another listing).

Latest developments

In late 2023 KeepWOL launched a new iteration of its platform for commercial clients with an AI game builder, action plans and a team engagement metrics dashboard, and in January 2024 it was reported to be planning to close an additional funding round in the first quarter of 2024. The website continues to advertise team, enterprise and consultant plans, and the separate card-game store notes stock is limited.