Josiah Olivieri

Extended beyond the engineering org, operating as a partner to Finance, Legal, and Enterprise Risk on how the company builds, buys, and governs software.

• Responsible for an engineering organization of 110+, across Developer Experience, Frontend, Backend Services, and Custom Solutions.
• Partnered with Finance on vendor procurement, contract renewals, and rationalizing the software stack against ROI, Legal to align product features and releases with risk tolerance, and Enterprise Risk to quantify blast radius and mitigations of engineering systems.
• Worked closely with go-to-market client teams to produce client-facing documentation and contract terms.
• Partnered with University Recruiting on the internship program for program support and placement.
• Drove cost-effective AI adoption company-wide: added a new budget escalation/approval process for AI spend and expanded open-source/self-hosted model options, curbing 40% MoM AI spend growth to flat and landing on budget.

Turned Developer Productivity from an internally focused org into a service organization solving problems for engineering at large.

• Identified the opportunity, proposed, and took on ownership of the Developer Productivity org.
• Shifted culture from textbook-perfect execution to rapid experimentation, redirected from internal tool-building to solving for other teams' productivity and development needs.
• Redesigned the build and release process to improve release velocity and reliability from 72% to 99%, cutting build times from 90+ to under 50 minutes, driving developer satisfaction from 65% to 85%+.
• Delivered the Unified API vision on GraphQL — first-ever UI/API parity across the client-facing platform.
• Procured org-wide SourceGraph adoption, sustaining 300+ active users against license constraints.
• Established Mac as a first-class dev environment; partnered with IT to validate impact and inform hardware investment.
• Gave engineers space to experiment with AI tooling and produced an AI-assisted code review agent.
• Rolled out Cursor and Claude Code org-wide.
• Grew and promoted engineering leaders, including one direct report to Director.
• Supported feature launches: OpenTTD ahead of Q1 and accelerated Kokai service development with GraphQL tooling improvements.
• Built a team and individual developer productivity scorecard.

Joined as lead of a single scrum team and grew scope through increased responsibility, hiring, and expanding business needs.

• Quickly expanded scope from API Integrations into Small and Medium Business (SMB), Custom Solutions, and Permissions & User Management + Auth.
• Identified "custom solution" business opportunities were routinely mislabeled with inflated value estimates, with no way to verify cost or usage, prototyped and led delivery of an entity-level telemetry system, capturing usage of every accessed entity across API integration.
• Used the data to hold teams accountable for spend estimates and help engineering prioritize endpoints by cost and value.
• Refined the API+UI usage picture to better account for API engagement and value; the dataset continues to be used today to justify investment decisions.
• Served as regional hiring lead for the Pacific Northwest, owning all engineering hiring decisions for the region.
• Partnered with engineering leaders to evolve the hiring program: strengthened intake questions, piloted process improvements, and improved panel evaluation criteria.
• Drove REST-based API reliability from the mid-90s% to over 99.9%.

Owned the end-to-end Lightsail product experience, expanding it into new markets and deeper integration with the broader AWS ecosystem.

• Led multiple engineering teams, with dotted-line oversight of UX, product management, and documentation; owned Lightsail end-to-end: new business initiatives, support, maintenance, and operations.
• Shipped Lightsail in Canada, South Korea, and Paris AWS regions.
• Delivered resource export to AWS, giving customers a graduation path as they outgrew Lightsail.
• Launched managed databases in Lightsail, enabling customers to vertically scale their application stack.
• Enabled third-party integration with GoDaddy to cross-market managed WordPress sites for Lightsail customers.

Led cross-platform delivery for OneDrive while pushing the team to experiment beyond the roadmap.

• Led cross-functional engineers to ship features and improvements for OneDrive consumers and business customers on iOS, Android, and Windows.
• Led alignment of client telemetry — keys, values, and scenarios — across OneDrive and SharePoint apps on iOS, Android, and Windows using strongly typed generated code.
• Delivered a OneDrive VR experience using Unity and VRTK at the OneWeek hackathon with a small team.