Remote Global | Reports to the CEO | Up to USD $72,600 total annual cash compensation
Base salary up to USD $66,000 plus a monthly performance bonus of up to 10%, with comprehensive benefits included.
WHERE THIS ROLE CAN LEAD
Executive Personal Assistant
Senior Executive Personal Assistant
Growth in specialized functions
Career progression that takes 4-5 years elsewhere can happen in 1-2 years here for high performers.
Own the personal operations behind a $1Billion+ e-commerce brand's CEO. Turn ambiguous requests into trusted decisions and seamless experiences.
AI-first since December 2023: Company-provided AI tools are part of your resources, and AI agents and automations are available alongside them. Understanding the CEO's needs, checking the evidence and deciding whom to trust remain your responsibility.
APPLY NOW
Hear directly from our team about what it’s like to build your career at Puffy.
Want to see more? Follow the team’s journey on Instagram: @PuffyCareers
The Opportunity
At Puffy.com, a $1Billion+ e-commerce brand, you'll own the CEO's personal operations across lifestyle experiences, research, provider relationships and calendar coordination. Reporting directly to the CEO, you'll take requests from clarification to completion within agreed priorities and approved boundaries. This is a hands-on role combining AI-led research and planning with personal judgment, discretion and reliable execution, freeing the CEO to focus on scaling the business.
The Problems You'll Own
Primary: High expectations with limited attention
The remit spans coveted reservations, unfamiliar purchases and personal appointments, each shaped by the CEO's preferences and standards. Requests can be ambiguous, while availability, provider quality and booking terms require independent verification. The challenge is reaching the right outcome without turning every decision or obstacle into another demand on the CEO's attention.
Secondary: Reliable service beyond one request
Personal operations depend on trusted providers and accurate knowledge of preferences, commitments and follow-ups. The supporting challenge is making that knowledge dependable across requests, so quality does not rely on repeated chasing or recollection.
Resources Provided
You’ll have access to our latest company-provided AI tools, including ChatGPT and Claude, multiple AI agents, bots, plugins, AI projects, and automations through platforms such as n8n. You’ll also receive the department tools, relevant data, assets and specialist support needed to deliver your work. We expect you to use these resources to automate routine work and deliver high-quality results quickly.
Decision-making authority
You can decide independently
Research and recommendations: Break down requests, choose research methods, define selection criteria, compare options and make non-binding provider enquiries within agreed preferences.
Routine spending and bookings: Execute routine purchases and bookings within pre-approved budgets, preferences and booking terms, including applicable cancellation and refund conditions; retain confirmations and payment records.
Working methods and follow-ups: Organize execution within agreed priorities and test low-risk process improvements using approved tools and allocated resources, without changing access, sensitive-data handling or live shared workflows.
Approval required
Exceptions and commitments: Obtain Arthur's or his authorised delegate's approval before exceptions, spending or commitments outside pre-approved limits, accepting different booking or contractual terms, or changing agreed priorities.
Information and systems: Obtain appropriate authorization before sharing confidential personal information beyond an approved purpose or recipient, entering it into AI tools without approved safeguards, or changing tools, access, live workflows or resource allocations.
If a budget, preference or booking term is unclear, confirm it before committing. Urgency does not expand these boundaries.
Who You'll Work With
Meet the team you'd be working with, and what you'd work on together:
What You'll Own
Personal Operations Responsibilities
Deliver tailored experiences: Secure coveted reservations, coordinate exclusive event access and design experiences suited to the CEO's preferences. Use AI to develop options and draft itineraries, then personally verify availability, details and terms and carry the booking through to completion.
Turn ambiguity into a recommendation: Break down unclear requests, research unfamiliar subjects and define relevant selection criteria. Use AI to develop research plans, synthesize findings and produce a concise recommendation; independently verify material claims, explain trade-offs and recommend the best option rather than simply presenting comparisons.
Build trusted provider relationships: Develop and maintain a dependable network across lifestyle, wellness, automotive and home services. Use AI to organize non-sensitive research into provider summaries, then personally vet providers, build relationships and keep usable records of service quality and alternatives.
Anticipate and coordinate needs: Manage the personal calendar, appointments, preferences and follow-ups proactively. Use approved AI workflows to draft schedules and checklists with appropriate data safeguards, then verify timing, dependencies and commitments yourself.
Close the loop: Own each request from inception to completion, resolve obstacles independently within approved boundaries, coordinate providers and maintain clear confirmations and status updates until the outcome is delivered.
Personal Operations Outcomes
Decisions made easier: Deliver concise, verified recommendations that match the CEO's preferences and make the best option clear.
Dependable execution: Keep bookings, appointments and personal requests accurate, confirmed and followed through, with credible alternatives when plans change.
Quality Standards
Evidence and accuracy: Check provider suitability, availability, total costs, dates and material terms against reliable sources or direct confirmation. Correct AI errors before relying on or sharing an output.
Discretion and ownership: Handle confidential personal information responsibly, share only what is necessary and exercise sound judgment with providers and AI tools. Remain accountable for the final recommendation and outcome.
Delivery Pace
Prompt turnaround: Complete requests promptly within agreed deadlines, flag obstacles early and maintain credible alternatives.
Early contribution: Begin contributing during onboarding as access and context are established, and carry assigned requests through completion without repeated chasing.
What You Bring
What you must demonstrate
Relevant experience: 2-3 years of experience in personal assistance, concierge services, lifestyle management, hospitality or executive assistance focused on exceptional execution.
Research judgment: The ability to break down ambiguous requests, investigate unfamiliar subjects, define selection criteria, use AI effectively, independently verify findings and recommend the best option with clear reasoning.
Polished communication: Professional communication that represents a CEO well, builds trusted provider relationships and works comfortably in premium service environments.
Resourcefulness and detail: Practical problem-solving, meticulous attention to detail and reliable follow-through without missed commitments.
Discretion: Responsible handling of confidential personal information and sound judgment when communicating with providers or using AI tools.
AI workflow capability: Demonstrated ability to build and test reusable AI workflows for recurring research and coordination requests. Carry relevant preferences and constraints between requests, verify consequential outputs, handle exceptions and improve the workflow to reduce manual effort while maintaining accuracy and discretion.
Technical confidence: Proficiency in Google Workspace, quick adoption of new systems and personal ownership of AI-produced work and its validation.
Must be willing to work extended hours and weekends as needed.
Additional advantages
Languages: Fluency in Russian or Armenian alongside English, strongly preferred for seamless coordination.
Provider network: An established network of trusted premium service providers.
Coordination tools: Experience with Asana or project management tools.
Relevant environments: A background in luxury hospitality, lifestyle management or family office environments.
WEEK 1
— Land well
Set up approved Google Workspace and calendar access. Complete Asana training and your role-specific AI-Native Starter Pack: request clarification, research criteria, verification and confidential-data boundaries. Meet the CEO and executive support.
WEEK 2
— Get the full picture
Review current requests, preferences, providers and approval limits. Discuss previous service failures or unsuitable recommendations, where records exist, and trace a request from intake to completion.
WEEK 3
— Start contributing
Own an initial bounded request, using AI for substantive research and drafting. Verify the findings independently and present your recommendation and reasoning to the CEO.
WEEK 4
— Your first ship
Complete a request within approved boundaries, document the outcome and share your early view of what would make personal operations more reliable.
Meet GIA, your AI talent partner, who will share how and why this is more than just a job!
Our team includes alumni from some of the world's most competitive institutions and companies. When you join Puffy, you're joining colleagues who push each other to be better.
A few of the many ways we invest in you, applicable based on your work location and eligibility
Pay and Recognition
Monthly performance bonus of up to 10%
Annual salary review every January
Monthly leader awards and Leaders Club
Merit-based progression
Up to 50% product discount, free mattress after one year
Growth
Learning budget for courses and certifications
Career progression as we grow
Quarterly feedback
Health and Time Off
Premium health insurance
Leave entitlement follows your location, plus public holidays
How We Work
AI-native since 2023
State-of-the-art tech and tools, equipment provided
A team spanning many nationalities
Additional benefits vary by location. See Where You'll Work for details.
Remote, Global
This role is fully remote. You are employed through an Employer of Record, so statutory leave, social contributions and any mandated cover follow your own country.
Laptop and equipment provided
Premium health insurance
Work from your own country
Optional Dubai desk
Our Friday lunches and office socials are hub-based, so they are not part of a remote role. Other benefits are subject to your work location and eligibility.
If you would rather be in Dubai
You are welcome to join our Dubai hub instead, a workplace of 65+ team members from 16+ nationalities.
Full relocation support
Flight to Dubai
Two-week hotel stay
Annual flight home
Team life insurance
Catered Friday lunch
Arthur Andreasyan, Puffy CEO, Founder & Forbes Council Member
Hi there,
If you're reading this, you're probably asking whether Puffy is the right place for your next chapter. I founded Puffy in 2017 after a simple question: "What would it feel like to sleep on a cloud?" That question became a business, and I wanted to build a company where ambitious people could grow with us.
That same mindset is why we became AI-first in December 2023, well before it became a standard way of working. We move quickly, stay relentless and hungry, question the usual way of doing things, and give people real ownership. We believe a focused team can outperform much larger companies. What matters here is the quality of your work, the decisions you make, the problems you solve before anyone asks, and the impact you create.
If you join us, I'll expect a lot from you, and I'll make sure you have the trust, context, and support to do meaningful work. If that kind of challenge excites you, I'd be glad to have you build Puffy with us.
Looking forward to working with you,
ArthurA
Arthur Andreasyan
Puffy CEO, Founder & Forbes Council Member
At Puffy, we want to get to know you and the strengths you bring.
Our hiring process gives you a chance to show your skills and explore the work you could do.
2-phase process, as quick as 7 business days.
Note: Our process is 100% free. We never use third-party agencies or ask for payment.
1
YOUR TIME
Up to 60 minutes total
Show how you think and apply your skills in two parts:
Phase 1A: Role-Based Questions
Up to 30 minutes · Without AI
Answer role-specific questions that assess the skills and knowledge you would use in the role.
Phase 1B: Technical Case Study
30 minutes · AI encouraged
Apply your skills to a practical problem relevant to the role. Explain your approach and the reasoning behind your proposed solution.
OUR RESPONSE
Within 2 business days of completing both parts
2
Phase 2A: Hiring Manager Interview
YOUR TIME
45-60 minutes
Discuss your experience, approach to the Technical Case Study and use of AI with the hiring manager.
Learn more about the role, team and expectations.
OUR RESPONSE
Within 2-3 business days after your interview
Phase 2B: Final Interview
YOUR TIME
Around 30 minutes
Discuss how you work, what motivates you and the practical details of joining, including location, compensation expectations and availability.
OUR RESPONSE
Within 2 business days after your interview
From application to a clear yes or no, either way.
Can you tell me more about Puffy's benefits?
Puffy knows that happy, healthy employees do good work. Here’s a list of full benefits in addition to the highlights mentioned above:
Learning and development support (we pay for courses you need to upskill)
Career progression opportunities — you grow as we grow
Up to 10% monthly performance bonus
Annual salary review every January
Quarterly feedback
Commitment to diversity and inclusion
Merit-based progression and achievement recognition
State-of-the-art tech and tools
Premium health insurance
Team life insurance coverage
Annual flight home (Dubai roles)
Generous annual leave entitlement (vacation, sick leave, parental, maternity, study leave), in addition to public holidays
Free catered lunch for the
entire team on Fridays
Kitchen restocked daily with healthy
snacks, fresh fruits, and beverages
Regular social activities and events
Monthly Puffy leader awards to
recognize achievement
Puffy product discount of up to 50%
for employees and eligibility for a
free Puffy mattress after 1 year of service
Why do I have to take an online test if I have the relevant skills and experience?
We’d love to see how you put your skills and experience into practice. Through role-based questions and a technical case study, you can show us how you think and solve problems while getting a feel for the work at Puffy. We use consistent criteria for candidates applying to the same role, giving you a fair opportunity to demonstrate your strengths.
Is there an expiry date for the online test? When do you expect me to complete the online assessment?
The invitation link for the online test only expires once the position is filled. However, our hiring process moves quickly, so we highly recommend you complete it as soon as you can.
Please note these important details:
Session Time: Once started, the test has a 4-hour inactivity timer before it auto-submits your answers.
Returning Candidates: If you applied for this same role within the last 6 months, our system may use your previous assessment score. In this case, you may be taken directly to a confirmation page.
Top Tip: The invitation email may go to your spam or junk folder, so please check there if you haven't received it.
If you still encounter any issues, please reach out to us at careers@puffy.com.
Does Puffy offer flexible or remote working arrangements?
Our goal is to create the optimal environment for you to do your best work. Our approach is tailored to the focus of each role:
Dubai Hub (On-site): Our Dubai office is our hub for deep, in-person collaboration. All roles here are on-site to help our teams move fast and innovate together.
North Hollywood Hub (On-site): Our North Hollywood office brings teams together for close, in-person collaboration. Roles based here are on-site to support fast decisions, strong teamwork, and shared momentum.
Remote US: Some roles are designed to be fully remote across the US, giving us access to exceptional talent while keeping teams closely connected and aligned.
Remote Global: Selected roles are open globally, allowing us to bring exceptional people together regardless of where they are based.
Not every position is available remotely. You’ll always find the location and working arrangement clearly stated in the job posting, whether the role is based in Dubai, North Hollywood, Remote US, or Remote Global.
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