Staff Software Engineer, Builders

EvenUp EvenUp · Vertical AI · Toronto, ON · Hybrid · Engineering

Staff Software Engineer role focused on leading technical resolution of complex customer issues, driving architectural improvements, and defining technical strategy for a high-growth vertical SaaS company using AI. The role requires strong systems-thinking, product-mindedness, and influencing skills to reduce escalations and improve reliability.

What you'd actually do

  1. Lead technical resolution of the most complex, multi-system escalations — the ones that require deep cross-functional understanding and careful architectural thinking
  2. Identify systemic weaknesses across the product that generate escalations and partner with other engineering teams to address them at the root
  3. Define and drive the technical strategy for the squad: observability, tooling, runbooks, incident response patterns, and reliability standards
  4. Partner closely with the CPO and EM to shape the squad's roadmap, balancing urgent reactive work with high-leverage proactive investments
  5. Serve as a technical advisor and force multiplier for other engineers on the squad — reviewing approaches, accelerating investigations, and raising the ceiling on what the team can handle

Skills

Required

  • 8+ years of software engineering experience
  • demonstrated track record at the Staff level or equivalent
  • Exceptional diagnostic and systems-thinking skills
  • Deep technical credibility: you can write and review code, design systems, and make sound architectural trade-offs under time pressure
  • Experience driving improvements across team boundaries
  • Strong communication skills with engineers, product leaders, and non-technical stakeholders
  • A bias toward permanent fixes over repeated patches
  • Deeply product-minded
  • Experience at a high-growth SaaS company

Nice to have

  • Experience building or leading reliability engineering, SRE, or platform functions at a growing company
  • Deep familiarity with AI/ML product systems and the failure modes they introduce (data quality, model drift, pipeline failures, etc.)
  • Experience working in regulated industries or with enterprise customers who have high SLA expectations
  • Prior background in incident command or escalation management frameworks

What the JD emphasized

  • highest-priority customer issues
  • most complex investigations
  • hardest problems
  • deep technical credibility
  • permanent fixes over repeated patches