Fresh Prints - Technical Support & AI Engineer (Full Time, Remote)
Requirements
• 2-3 years in a technical support, support engineering, or technical escalation role • Knowledge areas: • networking, firewalls, and VPNs; • softphone or CCaaS integrations; • log/observability tooling (Datadog or equivalent); • basic code literacy (Python, JSON, HTML/CSS/JS) to understand integration behavior; • Salesforce Service Console or equivalent case-management tooling • Demonstrated ownership of ambiguous, multi-stakeholder problems through to resolution • Strong project-management ownership: experience holding multiple open threads, knowing when to escalate vs. keep driving • Support case triage: experience owning problems within support’s wheelhouse, but determining when it needs additional resources • Demonstrated experience using different AI tools and a general understanding of prompting • An exceptional written and verbal communicator, with experience communicating complex technical issues to both technical and non-technical audiences • A critical thinker with the capacity to understand a complex technical problem • Self-motivated, detail-attentive, and able to continuously learn • Prior experience in a tier-2/tier-3 support or technical escalation role, ideally in a SaaS or contact-center technology environment • Familiarity with CCaaS platforms • Performance Milestones30 Days • Performance Milestones • 30 Days • Fully ramped on the support queue and escalation triage workflows. • Key technical systems (Datadog, Salesforce Service Console, CCaaS) and internal runbooks mastered. • Active shadowing of enterprise escalations completed, with participation in live customer troubleshooting calls. • 60 Days • Independently diagnose and route new escalations against defined criteria without prompting. • Own multi-part enterprise escalations end-to-end, coordinating smoothly across Engineering and Implementation. • Actively utilize AI tooling to accelerate issue diagnosis and documentation write-ups. • 90 Days • Full fluency on Engineering and Implementation escalation boundaries and cross-functional relationships. • Serve as the primary trusted owner for complex, multi-stakeholder escalations through to final resolution. • Establish and adopt AI-assisted workflows that measurably improve operational speed and efficiency. • Job Details: • Competitive Annual Salary • Shift: Monday–Friday, 8:00 AM – 5:00 PM EST. • Health Benefits, Equipment, and Paid Leaves • Type: Full-time REMOTE role.
Responsibilities
• Serve as the primary escalation point for the Support team's Technical Success Specialists (TSS) on cases that exceed T1/T2 complexity • Investigate and diagnose complex technical issues: integration failures, connector/softphone problems, platform behavior that doesn't match documentation • Own multi-part enterprise escalations end-to-end: track every open thread, assign next steps, keep the customer and internal stakeholders informed, and close the loop. This is a project-management function as much as a technical one. • Troubleshooting complex integration/softphone issues, and act as a technical consultant on networking, firewall, and connectivity questions • Help maintain the technical documentation and runbooks that let the tier 1/tier 2 support team resolve more on its own over time • Partner directly with Engineering (including the existing tier-2 escalation path) and Implementation Managers as a peer, not just a hand-off
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