Head of Technical Support and AI Integration

Clerk Chat • San Francisco, CA

135d • $180,000 - $210,000

About The Position

Clerk Chat's mission is to make every business conversational. We are achieving this by building the leading messaging application, integrating AI where it matters, and crafting our own telecom infrastructure. It's big and bold and needs spirited adventurers to join our growing team. We've built Clerk Chat organically into a profitable business over the last 2 years. We're a team that believes in achieving your highest potential but not at the expense of work-life balance. That's why we have flexible vacation time, healthy quarterly bonuses, and creative freedom at the forefront. We're Silicon Valley-based entrepreneurs who have sold companies, gone through the exclusive HF0 AI residency, having previously built teams at Lucasfilms, Samsung, Netflix, DocuSign, and Series B+ Startups. Clerk Chat is a hybrid team of in-office and remote employees. Our headquarters is based in San Francisco, just three blocks south of the Embarcadero BART station, making it easy to commute and stay connected. Our in-office team appreciates being in the office five days a week because it fosters real-time collaboration, builds stronger relationships, and helps us move faster. The remote team is strategically based around the US to provide the best experience for our customers and drive impact. This is an exciting time to join Clerk Chat. We’re small enough that every individual has a big impact, but we’re growing fast enough that there’s tremendous room for career advancement.

Requirements

• 10+ years in technical support, platform operations, or support engineering, including 2+ years managing teams.
• Experience at an early-stage (Seed/Series A) company, with the ability to both build and execute.
• Familiarity with AI-driven workflows and the curiosity to actively leverage AI tools to improve support efficiency.
• Hands-on experience with support analytics and tooling, including building dashboards and driving ticket automation.
• Experience working with Engineering and Product teams to diagnose technical issues and influence product direction.
• Strong leadership and communication skills, with a track record of building high-performing teams and influencing cross-functional stakeholders.
• Experience building and optimizing support processes that balance speed, quality, and personalization at scale.

Nice To Haves

• Experience with telecom, messaging, or infrastructure-focused platforms.
• Familiarity with early-stage startup environments and a passion for building from scratch.
• Comfort with AI, LLMs, or conversational automation tools and how they can enhance support.

Responsibilities

• Lead and mentor our Support team, focusing on technical excellence, customer empathy, and professional development.
• Act as a player-coach: lead the team 70% of the time while also directly handling complex issues 30% of the time (e.g., porting or SMS debugging).
• Partner with Engineering and Product to resolve platform issues, improve tools, and automate workflows using AI and other technologies.
• Drive continuous improvement by analyzing support data, identifying patterns, and implementing process and product improvements that reduce ticket volume and increase CSAT.
• Create systems and frameworks to ensure support SLAs are met while maintaining a high standard of quality and thoughtful human support.
• Build and maintain dashboards, processes, and documentation to ensure support insights are surfaced to the broader team.
• Be the voice of the customer internally, flagging product friction, bugs, or opportunities for new features, and representing support in cross-functional planning.
• Design a scalable foundation for a support org that can handle complex issues, emerging AI tools, and future global growth.

Benefits

• Competitive compensation and equity packages
• Health, dental, and vision insurance
• Flexible vacation time (Unlimited PTO)
• 401k with 4% match

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Number of Employees: 11-50 employees