Senior Technical Support Lead — B2B SaaS & AI Tools

Jobtailor; California (MO); On-site; USD 70,000 - 95,000; Full time

Job summary

Jobtailor is seeking an experienced Support Specialist to handle technical customer inquiries across phone, email, and chat in a fast-paced B2B SaaS environment. You will resolve complex issues, document findings, and mentor junior teammates while partnering with Product, Engineering, and CS teams.

The role emphasizes empathy, structured problem solving, and proactive communication, with opportunities to improve workflows and contributed knowledge bases.

Qualifications

• 3+ years of technical customer support experience in B2B SaaS or similar complex product environments.
• Ability to explain technical issues clearly to customers and internal teams.
• Strong documentation habits and clear internal notes.

Responsibilities

• Handle moderately complex product questions, configurations, integrations, and edge cases using account context and product knowledge.
• Own escalated issues through structured investigation with ticket history, logs, and evidence.
• Communicate complex issues clearly to customers, teammates, and internal partners.
• De-escalate frustrated customers with empathy and clear next steps.
• Mentor L1 teammates and improve support workflows and escalation quality.

Skills

Technical support

Troubleshooting

Documentation

Zendesk

Multilingual

Collaboration

Tools

Zendesk

Monitoring tools

PMS workflows

AI tools

Job description

Jobtailor is seeking an experienced Support Specialist to handle technical customer inquiries across phone, email, and chat in a fast-paced B2B SaaS environment. You will resolve complex issues, document findings, and mentor junior teammates while partnering with Product, Engineering, and CS teams.

The role emphasizes empathy, structured problem solving, and proactive communication, with opportunities to improve workflows and contributed knowledge bases.