Technical Support Team Lead - AI & Automation Focus

About Us

Chekin is a fast-growing SaaS company transforming how hospitality businesses manage guest check-ins, identity verification, and communication. With millions of check-ins processed and strong traction in international markets, we are entering our next phase: becoming an AI-native platform.

We are building the infrastructure for the future of guest identity and automated operations in hospitality.

About the Role

We’re looking for a Technical Support team lead to lead and evolve our support function.

This is not a traditional support role.

You will be responsible not only for managing the team, but for building a more scalable, efficient, and tech-enabled support operation, with HubSpot at the core.

You’ll combine technical expertise, process optimization, and team leadership, managing a team of 5 while actively improving systems, workflows, and the way support is delivered.

Responsibilities

Lead and Develop the Technical Support Team

• Manage, mentor, and grow a team of 5 support agents
• Ensure high-quality, consistent, and customer-centric support delivery
• Create structure while maintaining flexibility in a fast-changing environment

Own Support Operations

• Maintain excellent SLA performance for top clients and partners, leveraging deep technical knowledge of SDKs and APIs to resolve complex integrations and escalations."
• Oversee daily operations, ticket prioritization.
• Adapt quickly to changing priorities and business needs
• Ensure efficient handling of technical issues and escalations

Own and Optimize HubSpot

• Take full ownership of our HubSpot support setup (tickets, workflows, automation, reporting)
• Continuously improve processes to reduce manual work and increase efficiency
• Design and implement scalable support workflows

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Implement AI and Automation in Support

• Identify and implement AI-driven solutions across the support lifecycle
• Improve ticket triage, response quality, and internal workflows using AI tools
• Leverage automation to increase team productivity and scalability

Cross-Functional Collaboration

• Work closely with Product and Engineering to surface issues and improve the product
• Translate customer feedback into actionable insights

Reporting and Continuous Improvement

• Define and track KPIs (response time, resolution time, CSAT, efficiency)
• Use data to drive decisions and improve support performance

Qualifications

Experience

• 4–7 years in technical support, with at least 2+ years in a leadership role
• Experience managing small teams in dynamic environments

HubSpot Expertise

• Strong hands-on experience with HubSpot
• Comfortable owning, optimizing, and building support systems

AI & Automation Mindset

• Experience using AI and automation tools in support or operations

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• Strong interest in applying AI to improve real workflows and processes

Technical Skills

• Comfortable with technical troubleshooting and support tools
• Experience with no-code/low-code tools and integrations is a strong plus

Leadership & Communication

• Proven ability to lead and develop a team
• Strong communication skills, both technical and non-technical

Fast-Paced Environment

• Comfortable working in a startup environment where priorities can shift
• Proactive, adaptable, and solution-oriented

Languages

• English (C1+ required)
• Additional European languages (Spanish, Italian, French, or German) are a plus

What We Offer

• High ownership and impact in a key role
• A fast-paced, growing startup environment

Job specs

• Base salary ranging from €40,000 to €45,000 per year
• 100% remote work in an international working environment.