Commerce Platform: Billing & Checkout

Context

Atlassian was migrating its product suite to cloud. The existing billing infrastructure was monolithic and couldn't support the complexity of 15+ products, 500+ Marketplace apps, multiple pricing models, and enterprise purchasing workflows. A new commerce platform needed to be built from scratch.

Problem

• Legacy billing system couldn't handle diverse pricing models (per-seat, usage-based, tiered)
• 200K+ customers and products needed migration to the new cloud platform
• Enterprise and SMB billing UX was overly complex, leading to high support contacts
• No unified checkout experience across Atlassian products and Marketplace apps
• In-product purchase, upgrade, and reactivation flows had significant friction

My Role

Built and led the end-to-end billing and checkout journey. Defined product strategy through impact analysis, user research, and competitive insights. Aligned engineering, design, finance, and GTM teams on a 4-quarter roadmap and success metrics.

Decisions & Trade-offs

Microservices from day one

Launched core microservices (subscriptions, usage, quotes, payments) from 0→1 rather than extending the monolith. Higher upfront investment but necessary for scaling to diverse billing needs across 15+ products.

Data-driven UX simplification

Simplified enterprise & SMB billing UX through data analysis rather than redesigning from scratch. Focused on reducing time on top tasks and eliminating unnecessary steps.

Growth experiments in billing

Ran growth experiments for in-product purchases, upgrades, and reactivations — treating billing as a growth lever, not just infrastructure.

4-quarter migration roadmap

Defined migration strategy for 200K+ customers using impact analysis and user research rather than a big-bang approach. Phased rollout reduced risk.

Metrics & Results

• $1B ARR processed through the new platform
• +9% SEQ (Satisfaction with Experience Quality) improvement
• -20% time on top billing tasks
• -15% support contacts related to billing
• +3% first full purchase growth
• -4% churn from reactivation experiments
• 15% reduction in launch time through GTM optimization
• 200K+ customers successfully migrated

Links

Learnings

• Billing is a growth surface. Most companies treat billing as back-office infrastructure. We treated it as a product surface — optimizing checkout flows directly impacted revenue growth and churn reduction.
• Migration is a product problem, not just an engineering problem. Migrating 200K+ customers required product thinking: impact analysis, user segmentation, phased rollout, and success metrics — not just data migration scripts.
• KPI-based leadership updates drive alignment. Drove org-wide alignment through KPI-based leadership updates. Making goals and impact visible across teams was as important as the technical execution.
• Simplification beats feature addition. The biggest wins came from removing steps and reducing complexity, not adding features. -20% time on tasks came from subtraction, not addition.