Nick Simmonds

Toil — manual, repetitive, and low-value work — drains engineering capacity and slows down innovation. This session explores how SRE and platform teams are automating routine operational tasks to reclaim developer time and improve reliability. From self-healing infrastructure to intelligent alerting and workflow orchestration, we’ll look at the strategies and tools helping teams scale their operations without scaling their headcount.

• Identifying and eliminating sources of operational toil.
• Building automation into incident response, runbooks, and maintenance workflows.
• Using AI and ML to detect anomalies and trigger automated remediation.
• Measuring the impact of automation on team efficiency and system health.
• Best practices for scaling automation across diverse teams and environments.

GroupOn operates as a much leaner business today as a public company than in its days as a unicorn startup. As the company has scaled down, the engineering team faces the challenge of maintaining and reengineering a system built without cost constraints to be more cost conscious and sustainable. This session explores how GroupOn is tackling legacy complexity, consolidating tooling, and finding the right balance between buying and building to right-size for the future.

• How GroupOn’s tech stack became too big to manage efficiently.
• The hidden costs of legacy tooling in smaller orgs.
• Strategies for consolidation, integration, and simplification.
• What we’re buying vs. what we’re building.
• Lessons learned from cleaning up a system built for scale.