Customer Support Manager, AI-First (Remote)

Position: Customer Support Manager, 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 the Top 5 Mattress Brand in the USA with over $1 Billion in sales. We're seeking an AI First Customer Support Manager to architect a scalable, AI-powered support infrastructure that transforms how luxury e-commerce delivers customer experiences.

You’ll own the entire customer support technology stack—optimizing systems, workflows, and data while automating low-value interactions to build a nearly autonomous support system that frees the sales team to drive growth.

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 Future of AI-Powered Support

You won’t just manage a helpdesk—you’ll engineer an autonomous support ecosystem. From training and tuning chatbots to designing AI-to-human handoff protocols, you’ll create systems that most CS leaders only read about in case studies. This is hands‑on architecture work that positions you at the forefront of AI‑first customer operations.

2. Partner with the 1%

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

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. Own the Full Technology Stack

Zendesk, Alhena AI, data visualization tools, sentiment analysis, predictive support—you’ll have the authority and resources to research, pilot, and integrate cutting‑edge technologies. When you identify a better solution, you deploy it.

What You’ll Need:

• 5+ years of experience in a customer support or operations management role, with a proven track record in a high-performance e-commerce environment
• A deep, systems-thinking mindset; you are obsessed with process mapping, workflow optimization, and building scalable, automated solutions
• Demonstrated ability to lead and develop a team, with specific experience in training agents on new 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 knowledge of Zendesk administration (macros, triggers, workflows)
• Hands‑on experience training and tuning a chatbot (like Alhena AI)
• Proficiency with data visualization tools (e.g., Looker, Tableau)

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.
• Monthly performance bonuses (up to 10%)
• Comprehensive medical, dental, and vision insurance
• Generous Paid Time Off (PTO) + US Public holidays
• AI First organization with access to AI-native tool stack
• Remote First: Work from the comfort of your home office
• International team collaboration (14+ nationalities)
• 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