New York

October 15–17, 2025

Berlin

November 3–4, 2025

London

June 2–3, 2026

Why software maintenance is stuck in 2015

Your software delivery practices have evolved, but your maintenance is still catching up. Here’s how to close the gap before chaos hits.

Tal Kimhi, Abiodun Olowode, Jon Thornton, Reggie Davis and Sally Lait

Date & time

17:00

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The past decade has seen evolutions in software delivery that have made it almost unrecognizable – with new tools, programming languages and methodologies that have redefined an industry. The tech stack looks nothing like it did ten years ago, but the maintenance of these systems hasn’t kept pace, remaining slow, reactive and stressful.

Whether it’s the delay of critical updates sprint after sprint, or tech debt rapidly accumulating through AI-generated code, systems become harder to change over time. 

In this panel discussion, we’ll help move you to a proactive software maintenance approach. You’ll leave with a deeper understanding of how to build systems that stay healthy, and treat maintenance as a core engineering discipline, with automation and clear ownership guiding your efforts.

Key learnings:

  • How to future-proof your systems with proactive maintenance that prevents chaos before it starts
  • Strategies for making invisible work visible – and incentivizing your team to prioritize it
  • Where automation can reduce the burden of software maintenance, freeing up your team to getting back to doing more of what they love

panelists:

Tal Kimhi

Tal Kimhi

Co-founder & CEO
Draftt
Jon Thornton

Jon Thornton

Director of Engineering
Squarespace

Reggie Davis

Sr. Site Reliability Engineer

Abiodun Olowode

Engineering Manager
Cleo

Moderator:

Sally Lait

Engineering Director – Trust & Safety