Senior Technical Support & Customer Success Engineer (H&L POS)

H&L POS is an Australian hospitality technology company with over 30 years of experience providing integrated point-of-sale and business management solutions. Designed by hospitality professionals for hospitality professionals, H&L’s solutions support hotels, pubs, restaurants, clubs, bars, cafés, and retail liquor outlets across Australia.

About the Role

This is a senior individual-contributor role that owns H&L's hardest customer problems: the escalations and complex cases the frontline cannot resolve. It's not just about closing them. Each one gets turned into a product fix, an enterprise solution, or the automation and tooling that stops it from recurring.

The work spans the entire go-to-market organization, from Sales through to Support. It involves identifying difficult, recurring, and high-impact cases, owning them until resolution, and collaborating with Customer Success, Product, Engineering, and AI Operations to deliver clear customer outcomes.

The short-term focus is clearing the critical backlog and taking complex work off the frontline. Longer-term, the goal is to identify where the support model keeps breaking and fix it, ensuring those issues are resolved faster, automated where appropriate, or handled confidently by the wider team.

Key Responsibilities

Escalations & Complex Case Resolution

• Proactively identify complex, high-impact, aging, or repeatedly escalated cases.
• Take end-to-end ownership of difficult issues, from diagnosis through resolution and follow-up.
• Clear the critical aged backlog and act as a bridge across Support, Sales, Professional Services, Customer Success, Product, and Engineering.
• Communicate clearly with customers through sensitive, ambiguous, or technically complex situations.

Proactive Product Fixes

• Help evolve the support organization from reactive ticket handling toward proactive problem prevention.
• Analyze recurring and high-impact issues to find root causes.
• Drive underlying fixes with Product and Engineering to remove whole classes of problems.
• Provide structured, evidence-based feedback from real customer cases into the product roadmap.

Enterprise Solutions & Automation

• Develop workflows, internal tools, AI-assisted processes, routing rules, and self-service solutions that reduce manual support work.
• Deliver enterprise-grade solutions for complex, high-value customers where standard support falls short.
• Partner with AI & automation engineering to improve diagnostics, tooling, and resolution paths.
• Validate that new automations improve customer outcomes rather than simply deflecting tickets.

Enablement & Operational Insight

• Turn complex resolutions into reusable playbooks, decision trees, and knowledge-based content.
• Coach the team on new issue types and tools, setting clear criteria for what is handled by the frontline, automated, or routed.
• Track recurring themes and systemic risks, communicating them to leadership.
• Measure the effect of improvements on resolution time, repeat contacts, escalations, CSAT, and ticket volume; maintain a prioritized backlog of automation and improvement opportunities.

What Success Looks Like

Success is not measured only by the number of difficult tickets closed. It is measured by whether those problems become easier or unnecessary the next time they occur. Key outcomes may include:

• Critical aged backlog cleared and held down.
• Fewer repeat escalations for previously solved issue types.
• Increased share of cases resolved by the frontline team without escalation.
• Reduction in manual support work through automation and improved tooling.
• Measurable reduction in recurring ticket drivers.
• Stronger feedback loops among Support, Professional Services, Customer Success, Product, and Engineering.

Ideal Qualifications

• Significant experience in technical support, customer success, support operations, or a related function.
• Demonstrated ability to resolve ambiguous, technically complex, or cross-functional customer issues.
• Strong root-cause analysis and systems-thinking skills.
• Experience creating support automations, workflows, internal tools, or AI-assisted processes.
• Ability to translate individual customer problems into broader operational improvements.
• Strong written and verbal customer communication skills.
• Experience developing documentation, training materials, and team enablement.
• Ability to influence Product, Engineering, and operational stakeholders without relying on formal authority.
• Comfort working as a highly autonomous individual contributor.