Customer Support Automation Lead, AI-First

Position: Customer Support Automation Lead, AI-First

Compensation: USD $110,000 per annum + up to 10% Performance Bonus

Total Annual Package: Up to USD $125,800

Location: Remote

Role Overview

Puffy is a Top 5 US mattress brand with over $1B in sales. This role is for a hands-on builder who will own the entire customer support tech stack—designing, launching, and optimizing AI-powered workflows that automate Tier-1 inquiries, maximize containment, and ensure seamless AI-to-human handoffs.

You'll 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. This is your chance to become a true industry architect.

1. Build the AI-First Support Playbook

You won't just manage tickets—you'll architect the systems that eliminate them. Own the full tech stack (Zendesk, Alhena AI, voice, sentiment analysis), design automated workflows, and push containment rates higher than industry benchmarks. Most support managers inherit systems. You'll build them from first principles.

2. Partner with the 1%

🏆 Top 5 Mattress Brand in the USA with Over $1 Billion USD in Sales

🌍 Great Place to Work Certified

💡 Work with Forbes Council Member CEO

Gain firsthand exposure to strategic decisions and high-velocity execution that drives a global brand.

3. Embrace Radical Flexibility

Work from anywhere in the USA. No commute. No cubicle. Build your ideal work environment while leading a team across time zones and driving results that matter.

4. Lead the Human-AI Integration

You'll build 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; you are 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; you are comfortable building dashboards, interpreting complex data sets, and using your findings to drive strategic decisions
• Expert-level, hands-on Zendesk administration experience (you have 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

We're restless, perpetually hungry, and fast-paced, driven by an unwavering belief that we can outperform any competitor — regardless of their size.

• Be the Owner: We don't hire employees; we welcome owners. You're accountable for results, not activity.
• Execute with Urgency: We thrive in high-stakes environments by making thoughtful decisions quickly and acting decisively.
• Demand Excellence: We solve the hard problems that others can't, pushing the boundaries of our craft.
• Be AI-First: Daily multi-turn AI conversations challenge your assumptions.
• Go All-In: When the mission demands it, we rally as one team to cross the finish line.

✨ Your Total Compensation & Benefits

💰 Compensation:

• Monthly performance bonuses (up to 10%)

🏥 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 AI-native tool stack
• Remote First: Work from the comfort of your home office
• Learning & development opportunities
• International team collaboration (14+ nationalities)

🏆 Rewards & Recognition:

• Eligibility for selection to the Leaders Club — an elite recognition program featuring premium wellness memberships, exclusive networking with senior leadership, and annual leadership retreats
• Eligibility for nomination as 'We Are' Champion of the Month — monthly recognition with gift vouchers and company-wide celebration for exceptional contributions

✅ Other Benefits:

• 401(k) with Company Match
• Free Puffy mattress post 6 months completion
• $1,000 Puffy/Halo Board store credit post 1 year completion

Ready to Shape Your Story?

Click "Apply" and take the first step.