Checkbox is a no-code service automation platform that empowers business functions such as Legal, HR & people, IT, compliance, procurement and finance to automate tedious, manual processes and streamline services.

The strength of Checkbox is its ability to turn area experts into citizen developers enabling them to automate their knowledge and processes in service requests, contract automation, service automation, review and approvals and self-service knowledge etc.

The Checkbox drag-and-drop studio allows solution authors to create a series of forms routed together via decision and logic trees to generate documents and streamline & manage your workflows.

 

My Role

My role at Checkbox is Head of Design, heavily emphasising product strategy, product design and team building.

Key Responsibilities

  • Drive innovation and identify high-value opportunities

  • The reinvention of the platform to make Checkbox top of category

  • User, prospect, and product research to determine usability, ICP & PMF

  • Product strategy, implementation strategy and PLG motion (Road map to scale)

  • Product design of new features and improvement or removal of old features

  • Business strategy and facilitation

  • Implementing product design with the development team for the best user outcomes

  • Advising on GTM strategy, production, people & culture

Achievements

  • Complete platform redesign with new UX and IA - New feature design which improved UX and product usability, including features that provide significant account uplift

  • Improvement of product education and the implementation of in-app product education served as the user needs it as well as on demand

  • Delivery of features delivering a significant rise in ARR

  • Creation and implementation of a design system

  • The strategy and rollout of a PLG motion

  • Introduction of strategy and tactics to better improve organizational health and business growth

Features designed

  • Database

  • Templates

  • Platform & user Governance

  • E-Sign

  • Runtime assessment

  • Workspaces

  • Form builder

  • Advanced app preview

  • Solution versioning

  • Testing and issue flaging.

  • Activity page

  • Error handling and debug messaging

  • Libraries

  • Variable library

  • Expression builder

  • Integrations

    • Salesforce

    • Docusing

    • Adobe sign

    • Xakia

    • LawVu

  • User Groups

  • Design system

    • Figma

    • Storybook

  • Introduction of R&D and user experience analytics tools (Qualitative and Quantitative)

    • Full story

    • Amplitude

    • Dovetail

  • Introduced onboarding tools and user experience using;

    • App cues

    • Userflow

  • Self-serve signup & trial

  • Dashboard and widget redesign

  • Assessment portals

  • SSO config

  • Checkbox product portal

  • Document review (Redlining)

  • Platform Governance

  • Checkbox 2.0 (Full platform redesign eta start 2025)

  • Work management

  • User education

 

Strategy, GTM and organisational transformation

Checkbox COO and I designed and drove various initiatives across the business.

These included;

  • Cross-department meetings and collaborative workshops to gather insights to drive better GTM acquisition & conversion as well as customer outcomes and experience

  • Implementing and testing various growth models

  • Assessment of PMF and ICP

  • Exploration of alternate market segments

  • Feature planning to increase revenue uplift and growth

  • Introduction of design thinking and tools across the organisation

  • Push for change in GTM personnel, tactics and communications

One of a series of sting videos I created to target specific market segments with meaningful pain points to establish awareness and drive prospects to a self-serve product trial experience filtering prospects for sales (End goal to drive product lead growth).