Customer Support Specialist (AI)

Location: Fully remote, but candidates must be based in Chicago

Salary: £75,000–£85,000 annually, plus equity

Company

hirify.global is building an AI executive assistant that handles emails, scheduling, and follow-up for client-facing professionals.

What you will do

• Own frontline customer support across chat, email, and video, resolving issues end to end.
• Diagnose and troubleshoot complex technical problems, escalating to Product Engineering when needed.
• Identify recurring customer issues and turn them into process improvements, knowledge base content, and actionable insights.
• Coordinate across Support, Sales, Product, and Customer Success to ensure customer issues are addressed.
• Help design support tooling, workflows, and team playbooks as the function scales.

Requirements

• 5+ years of experience in product or technical support within a B2B SaaS environment.
• Strong troubleshooting and customer problem-solving skills.
• Currently using AI in daily workflows and able to assess its capabilities and limitations.
• Human-in-the-loop mindset for customer-facing and escalation-critical work.
• Experience with support tools such as Zendesk, Intercom, Jira, or Linear.
• Must be based in Chicago; the role is fully remote.

Nice to have

• Startup experience and the ability to work in a fast-moving, hands-on environment.
• Strong interest in AI and the future of work.

Culture & Benefits

• High ownership, autonomy, and minimal bureaucracy.
• Remote work with proactive communication and close cross-functional collaboration.
• Private medical coverage, pension, and lunch provided daily.
• Support from Customer Success and Product Engineering teams, with training and career growth opportunities.

Hiring process

• CV review without a cover letter.
• 30-minute introductory call with the hiring team.
• 45-minute customer case study with a panel, followed by a 30-minute meeting with additional team members.