Jason Calleiro
Keeping it simple, making it beautiful, and thinking of you.
01
Works
02
Experience
MAY 2023 - AUG 2025
Lead Product Designer, Atlassian
Led design for enterprise-scale products focused on regulated customers, helping Atlassian expand into larger and more complex markets. Worked at the intersection of product, engineering, legal, and compliance to turn constraints into shippable systems.
Partnered closely with product and engineering leads to align design decisions across multiple teams and initiatives, especially where ownership and requirements were unclear.
Drove the design of AI-powered experiences, defining practical patterns for how AI shows up in enterprise admin workflows.
Helped define a long-term compliance vision, translating regulatory requirements into workflows that reduced friction for product teams.
Led visual and interaction design for core surfaces in Admin Hub, setting standards for clarity, scalability, and trust in high-stakes administrative flows.
MAY 2023 - AUG 2025
Lead Product Designer, Atlassian
Led design for enterprise-scale products focused on regulated customers, helping Atlassian expand into larger and more complex markets. Worked at the intersection of product, engineering, legal, and compliance to turn constraints into shippable systems.
Partnered closely with product and engineering leads to align design decisions across multiple teams and initiatives, especially where ownership and requirements were unclear.
Drove the design of AI-powered experiences, defining practical patterns for how AI shows up in enterprise admin workflows.
Helped define a long-term compliance vision, translating regulatory requirements into workflows that reduced friction for product teams.
Led visual and interaction design for core surfaces in Admin Hub, setting standards for clarity, scalability, and trust in high-stakes administrative flows.
MAY 2023 - AUG 2025
Lead Product Designer, Atlassian
Led design for enterprise-scale products focused on regulated customers, helping Atlassian expand into larger and more complex markets. Worked at the intersection of product, engineering, legal, and compliance to turn constraints into shippable systems.
Partnered closely with product and engineering leads to align design decisions across multiple teams and initiatives, especially where ownership and requirements were unclear.
Drove the design of AI-powered experiences, defining practical patterns for how AI shows up in enterprise admin workflows.
Helped define a long-term compliance vision, translating regulatory requirements into workflows that reduced friction for product teams.
Led visual and interaction design for core surfaces in Admin Hub, setting standards for clarity, scalability, and trust in high-stakes administrative flows.
SEP, 2021 - aPR, 2022
Senior Product Designer, Brex
Worked on core platform experiences at Brex during a period of rapid growth, helping establish consistency across products while supporting international expansion. Worked with key partners to create a dedicated team focused on creating seamless, universal experiences across product surfaces.
Helped form and shape a dedicated design team focused on cross-product experiences, improving consistency across key financial surfaces.
Led design for features supporting global expansion, including international card services and shipping, balancing regulatory requirements with usability.
Redesigned the app’s navigation and global information architecture, reducing fragmentation as the product surface area grew.
JAN, 2022 - SEP, 2023
Senior Product Designer, Brex
Worked on core platform experiences at Brex during a period of rapid growth, helping establish consistency across products while supporting international expansion. Worked with key partners to create a dedicated team focused on creating seamless, universal experiences across product surfaces.
Helped form and shape a dedicated design team focused on cross-product experiences, improving consistency across key financial surfaces.
Led design for features supporting global expansion, including international card services and shipping, balancing regulatory requirements with usability.
Redesigned the app’s navigation and global information architecture, reducing fragmentation as the product surface area grew.
JAN, 2022 - SEP, 2023
Senior Product Designer, Brex
Worked on core platform experiences at Brex during a period of rapid growth, helping establish consistency across products while supporting international expansion. Worked with key partners to create a dedicated team focused on creating seamless, universal experiences across product surfaces.
Helped form and shape a dedicated design team focused on cross-product experiences, improving consistency across key financial surfaces.
Led design for features supporting global expansion, including international card services and shipping, balancing regulatory requirements with usability.
Redesigned the app’s navigation and global information architecture, reducing fragmentation as the product surface area grew.
sep 2020 - SEP 2021
Product Designer, Facebook
First designer on a new team working at the intersection of Ads, ML systems, and business tooling, focused on making automated decision-making more understandable and trustworthy for advertisers. Collaborated with AI teams to enhance transparency in our ML/AI decision-making processes
Partnered with ML and Ads teams to design interfaces that explained how automated systems made decisions, helping users understand outcomes without exposing unnecessary complexity.
Designed experiences that balanced regulatory requirements with usability, translating policy and compliance constraints into clear product behaviors.
Defined an explainability framework for ML-driven products, giving other designers concrete patterns for communicating model behavior and data usage.
Worked closely with product, engineering, and policy partners to clarify how user data was used, reducing confusion and increasing confidence in the platform.
sep 2020 - SEP 2021
Product Design Lead, Facebook
First designer on a new team working at the intersection of Ads, ML systems, and business tooling, focused on making automated decision-making more understandable and trustworthy for advertisers. Collaborated with AI teams to enhance transparency in our ML/AI decision-making processes
Partnered with ML and Ads teams to design interfaces that explained how automated systems made decisions, helping users understand outcomes without exposing unnecessary complexity.
Designed experiences that balanced regulatory requirements with usability, translating policy and compliance constraints into clear product behaviors.
Defined an explainability framework for ML-driven products, giving other designers concrete patterns for communicating model behavior and data usage.
Worked closely with product, engineering, and policy partners to clarify how user data was used, reducing confusion and increasing confidence in the platform.
sep 2020 - SEP 2021
Product Design Lead, Facebook
First designer on a new team working at the intersection of Ads, ML systems, and business tooling, focused on making automated decision-making more understandable and trustworthy for advertisers. Collaborated with AI teams to enhance transparency in our ML/AI decision-making processes
Partnered with ML and Ads teams to design interfaces that explained how automated systems made decisions, helping users understand outcomes without exposing unnecessary complexity.
Designed experiences that balanced regulatory requirements with usability, translating policy and compliance constraints into clear product behaviors.
Defined an explainability framework for ML-driven products, giving other designers concrete patterns for communicating model behavior and data usage.
Worked closely with product, engineering, and policy partners to clarify how user data was used, reducing confusion and increasing confidence in the platform.