Technical Support & Platform Operations Specialist

Company: REWORK. Digital

Location: Remote (Global / Toronto HQ Alignment)

Mission: Automate Smarter. Grow Faster.

About REWORK. Digital

REWORK Digital is the world's leading AI and automation platform connecting scaling B2B businesses with verified specialists across 160+ countries. We are disrupting the legacy hiring market—plagued by 30–50% agency markups and unverified resumes—by providing an ecosystem powered by cryptographic Proof of Work, milestone-based escrow protection, and a disruptive platform fee.

From autonomous AI customer support agents to complex data engineering pipelines, our platform matches businesses with top 1% experts in under 18 hours with a 94% re-hire rate.

The Role

We are hiring a high-empathy, operationally rigorous Technical Support Specialist to manage all multi-channel platform communications, user inquiries, ticket routing, and account resolutions.

You won't just be answering tickets or pasting generic canned replies. As the human touchpoint behind REWORK, you will act as a revenue and retention engine, delivering account-aware B2B support to two key groups:

Businesses & Founders: Guiding them through project posting, escrow milestones, and AI audit recommendations.

AI & Automation Experts: Assisting with profile verification, proof-of-work submissions, Trust Tier upgrades (Bronze to Diamond), and payout releases.

Key Responsibilities

Omnichannel Inquiry Resolution: Manage inbound user inquiries across email, live chat, platform messages, and ticket queues with speed, precision, and warmth.

Account-Aware Response System: Apply our 3-layer support framework (Subject, Body, Account Context) to ensure enterprise accounts ($30k+ ARR) and early-stage founders receive tailored, context-rich support.

Empathy-Driven Problem Solving: Utilize the Acknowledge-Explain-Offer framework and proven empathy principles to de-escalate frustrated users, resolve billing or scope questions, and protect customer satisfaction.

Escrow & Milestone Coordination: Help employers and experts navigate milestone escrow deposits, deliverable reviews, and dispute-free payment releases.

Support-to-Product Intelligence Loop: Identify churn risks, feature requests, and platform friction during daily support interactions and route actionable insights to Product and Engineering.

Outage & Incident Communication: Execute clear, empathetic service notices during platform maintenance or technical updates following the ALERT protocol.

Qualifications & Customer Support Playbook

B2B SaaS / Marketplace Experience: 2+ years handling customer support, technical helpdesk, or platform operations for a SaaS marketplace or B2B software platform.

Mastery of De-Escalation & Communication: Fluent in active listening, non-technical translation of complex product features, and setting firm, professional boundaries without losing customer trust.

Account Context Awareness: You understand that every ticket is account-health data. You know when to use an automated workflow vs. when to deliver a 100% personalized human response.

Technical Aptitude: Familiarity with modern AI/automation stacks (Zapier, n8n, Make, OpenAI/Claude APIs, CRM integrations) and ticketing platforms (Zendesk, Help Scout, or Helply).

Speed & SLA Discipline: Commitment to maintaining sub-2-hour first response times and maintaining high First Contact Resolution (FCR) rates.

Why Join REWORK Digital?

Disruptive Mission: Work at the forefront of AI, blockchain verification, and automated operations across 160+ countries.

High-Trust Culture: Be part of a platform engineered for trust, transparency, and clinical excellence.

Growth & Impact: Direct visibility into company leadership with clear career advancement paths into Customer Success Management (CSM) or Operations.

Competitive Compensation: Remote flexibility, performance bonuses tied to CSAT/NRR, and full platform perks.

How to Apply (Proof-of-Work Application)

Do not send a generic resume. Show us your support craft. Reply with:

De-Escalation Sample: Draft a response to an enterprise client ($50k ARR) who is frustrated because an automation expert delivered a milestone 24 hours late. Use the Acknowledge-Explain-Offer framework.

Account Context Test: In 3 sentences, explain why a generic "we apologize for the inconvenience" email fails in B2B SaaS.

Performance Metric: Share your historical CSAT score or average First Response Time (FRT) from your previous role