Customer Support Automation Lead

Role Overview

Puffy, a Top 5 US mattress brand with over $1 billion in sales, is seeking a hands-on builder for the Customer Support Automation Lead role. This position involves owning the entire customer support tech stack, designing, launching, and optimizing AI-powered workflows to automate Tier-1 inquiries, maximize containment, and ensure seamless AI-to-human handoffs. You will also lead and enable a team of agents, driving adoption through coaching and real-world workflow improvements.

What Is In It For You:

This isn't just another customer support role; it's an opportunity to become a true industry architect.

• Build the AI-First Support Playbook: You'll architect systems that eliminate tickets, owning the full tech stack (Zendesk, Alhena AI, voice, sentiment analysis), designing automated workflows, and pushing containment rates higher than industry benchmarks. You will build systems from first principles, unlike most support managers who inherit them.
• Partner with the 1%: Work with a Top 5 Mattress Brand in the USA, certified as a Great Place to Work, and collaborate directly with a Forbes Council Member CEO. Gain firsthand exposure to strategic decisions and high-velocity execution driving a global brand.
• Embrace Radical Flexibility: Work from anywhere in the USA. Enjoy a remote setup with no commute or cubicle, building your ideal work environment while leading a team across time zones and driving impactful results.
• Lead the Human-AI Integration: Develop the training playbook that transforms support agents into "AI-first" operators, directly impacting revenue and customer experience.

What You'll Need:

• 5+ years of experience in customer support or operations management within a high-performance e-commerce environment, with hands-on ownership of support systems and automations.
• A deep, systems-thinking mindset, obsessed with process mapping, AI workflow optimization, and building scalable, automated solutions.
• Proven ability to lead and develop teams, including hands-on enablement and change management for new tools, technologies, and processes.
• Highly analytical and data-fluent, comfortable building dashboards, interpreting complex data sets, and using findings to drive strategic decisions.
• Expert-level, hands-on Zendesk administration experience (personally configured automations, routing logic, custom fields, and integrations).
• Hands-on experience working with AI/LLMs.
• Direct experience building, tuning, and troubleshooting chatbot or AI-driven support flows (like Alhena AI).
• Proficiency with data visualization tools (e.g., Looker).

The Puffy DNA

Puffy is restless, perpetually hungry, and fast-paced, driven by an unwavering belief in outperforming competitors. Our core tenets include:

• Be the Owner: We welcome owners accountable for results, not just activity.
• Execute with Urgency: We thrive in high-stakes environments, making thoughtful decisions quickly and acting decisively.
• Demand Excellence: We solve hard problems, pushing the boundaries of our craft.
• Be AI-First: Daily multi-turn AI conversations challenge assumptions.
• Go All-In: We rally as one team when the mission demands it.

Your Total Compensation & Benefits

• Compensation: Monthly performance bonuses (up to 10%). Total annual package up to USD $125,800.
• Health & Protection: Comprehensive medical, dental, and vision insurance.
• Time Off: Generous Paid Time Off (PTO) + US Public holidays.
• Work Environment: AI-First organization with access to an AI-native tool stack, remote-first setup, learning & development opportunities, and international team collaboration (14+ nationalities).
• Rewards & Recognition: Eligibility for Leaders Club (premium wellness, senior leadership networking, annual retreats) and 'We Are' Champion of the Month (gift vouchers, company-wide celebration).
• Other Benefits: 401(k) with Company Match, Free Puffy mattress post 6 months, $1,000 Puffy/Halo Board store credit post 1 year.

Key skills/competency

• Customer Support Automation
• AI Workflow Optimization
• Zendesk Administration
• Systems Thinking
• E-commerce Operations
• Team Leadership
• Process Mapping
• Data Analysis
• Chatbot Development
• Change Management