Support Engineering & Escalation Lead

Location: Remote (U.S. preferred)
Reports to: Director of Customer Support
Type: Full-Time

About the Role

Leonardo247 is hiring a technically strong, high-agency individual contributor to serve as the primary customer-to-engineering translation layer.

This role owns complex technical escalations end-to-end - investigating platform issues, assessing customer impact, and converting real-world friction into clear, prioritized engineering work.

You will operate at the intersection of customers, support, and engineering - ensuring that the highest-impact issues are resolved first, and that engineering time is directed with clarity and precision.

This is an execution-heavy role to start. Over time, you will help shape and mature our Support Engineering function as the company evolves.

What You’ll Own

Investigation & Escalation

• Deeply investigate complex customer issues across our SaaS platform.

• Diagnose integration failures, platform edge cases, and sequencing risks.

• Assess severity and customer impact.

• Identify root cause patterns where possible.

• Ensure escalations are reproducible and well-scoped.

Engineering Translation

• Convert customer-facing issues into structured, high-signal GitHub issues.

• Reduce clarification loops between Support and Engineering.

• Improve escalation quality and artifact discipline.

• Partner with Engineering to collaboratively prioritize work based on impact.

Tier 2 Operations

• Own the Tier 2 escalations ticket queue.

• Strengthen troubleshooting standards before tickets reach Engineering.

• Coach Tier 1 team members on investigation quality.

• Identify fragile or high-risk platform areas and introduce guardrails.

Function Building

• Improve escalation workflows over time.

• Increase clarity and predictability in how customer impact becomes engineering work.

• Build trust across Support, Product, and Engineering.

• Help define what “great” looks like for Support Engineering at Leonardo247.

What Success Looks Like

Within 6 months:

• Escalations are consistently high-signal and reproducible.

• Engineering prioritization reflects true customer impact.

• Support and Engineering trust escalation quality.

• Platform edge cases are better understood and documented.

• The Tier 2 function operates predictably and with discipline.

What You Bring

• 3–6+ years in Support Engineering, Technical Support, or similar role in a B2B SaaS environment.

• Strong technical investigation skills (logs, integrations, system behavior).

• Experience writing structured engineering issues (GitHub or similar).

• Clear and concise written communication.

• Ability to operate with limited guardrails.

• Sound judgment around impact and prioritization.

• Calm, methodical decision-making under pressure.

• Ownership mindset - you see problems through to resolution.

• Interest in growing toward broader support or operational leadership over time.

Nice to Have

• Experience with Zendesk or similar ticketing platforms.

• Familiarity with observability tools (e.g., Datadog).

• Experience working in GitHub-based engineering workflows.

• Experience supporting multi-product SaaS platforms.

• Interest in applied AI and workflow automation.

Why This Role Matters

Customer trust is one of Leonardo247’s strongest assets.

This role ensures that customer-impacting issues are understood deeply, translated clearly, and resolved with discipline. You will directly influence how effectively engineering resources are deployed and how reliably our platform serves customers.

This is a foundational role in strengthening our support and product feedback loop.

Growth Potential

This role begins as an individual contributor with significant ownership.

As the company evolves, there is opportunity to expand influence within Support Engineering and broader operations depending on performance and company trajectory.

Compensation

Competitive salary based on experience.