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).