Trolley Co
Job Description:
Job Details Location:
Remote (Must be based in North or South America and work within PST or EST time zones) Hours:
Full-time, with flexibility for occasional evening and weekend support. Executive Assistant (EA) Virtual | Full-Time | PST or EST Time Zones
Who Were Looking For
We're looking for an elite-level Executive Assistant who is
ten steps ahead, thrives in high-stakes environments, and executes flawlessly . This isn't a passive support role. This is about
owning responsibilities, amplifying efficiency, and ensuring the executive's world runs seamlessly, both
professionally and personally. You'll
manage high-profile relationships, optimize workflows, oversee high-stakes travel and negotiations, and eliminate distractions
so the CEO can focus on
big-picture strategy and execution . This role is
not for the hesitant or
reactive; it's for someone who is decisive, proactive, and deeply aligned with the executive's
vision . This is not your first time supporting a CEO and founder; you
thrive alongside executives with big energy, matching their pace and intensity . If you excel under pressure, can
execute at an elite level , and thrive on
making things happen instead of making excuses , this is for you.
Who You'll Work With
About the CEO
The executive you will support is a
Type 8 - The Challenger , known for being ambitious, independent, and driven to lead. They are highly analytical, deeply thoughtful, and approach challenges with confidence and intensity. They value efficiency, strategic thinking, and people who take initiative. The right EA for this role thrives next to a strong-willed, high-energy executive, understands their unique leadership style, and knows how to complement their strengths while bringing their own expertise to the table. This role reports directly to the
CEO and Managing Partner
and works closely with the
Senior Bookkeeper, investment team, legal partners, operations, marketing, and key external vendors and teams
to manage
both professional and personal
responsibilities. We are a
fast-moving, high-performance venture
that values
clarity, execution, and results . Our team is
dynamic, ambitious, and deeply committed to excellence . The
expectation is that you come in ready to contribute at a high level, align quickly, and deliver without hesitation.
How You Do the Job & Why
EXHIBIT A: Operating Framework, Expectations, and Deliverables
At the core of this role is a
fundamental expectation :
PLAY TO WIN, NOT TO AVOID MISTAKES. THE OBJECTIVE IS EXECUTION, NOT EXCUSES.
Phase 1: Core Deliverables & Mindset (0-9 months)
You will be exceptional in this role if:
You
operate with full alignment
to my vision and decision-making framework. When you speak,
you speak for me and with my authority.
If you are wrong, I will correct you. You
extend my influence
by managing
high-value relationships , ensuring seamless execution across
CRM, LP management, investor relations, and strategic initiatives . You
remove from my plate
all responsibilities that
do not require my direct input . You
anticipate
and
think through problems as the executive does , aligning your thought process with strategic expectations. You are an avid reader and researcher, always seeking knowledge to enhance problem-solving and decision-making. You
add expertise, reinforcing and deepening my strategies , not simply mirroring them. You do
not make sloppy errors,
this includes
inaccurate data, incomplete reports, and failure to track critical updates . You
over-communicate execution status;
every single priority is documented, with
recap updates delivered daily at 10 PM PST . You are self-regulated, composed under stress, and skilled at de-escalation, ensuring smooth execution even in high-pressure situations. You
own your role within the organization, deciding
when to be a
gatekeeper vs. a facilitator , balancing
authority and efficiency accordingly . You have strong personal boundaries, are curious, and are not afraid to try new things. Phase 2: Mastery & Expansion (9-12 months)
Develop and manage high-value talent pipelines
you identify, recruit, and maintain an ecosystem of
strategic relationships . Create leverage,
you
delegate, automate, and systematize
to move lower-priority tasks off your plate. Systemize everything
you standardize workflows and export best practices across the organization. Master a core domain
you fully
own and execute within a key business function . Act as a proxy for the executive
you operate
on behalf of leadership in select areas , particularly in
relationship-driven interactions . Take ownership of inefficiencies
you identify and solve operational gaps that
others overlook . Use strategic influence,
recognizing that
small, high-impact gestures
create
long-term business opportunities . Final Operating Principles
Play the long game.
Every move must be
strategic, not reactive . Zoom out.
View the business as
a system, not just a collection of tasks . Leverage information.
You will have
more access to critical data than anyone else
use it intelligently and efficiently. You have a strong sense of self, are highly self-aware, and know how to manage relationships with humor and diplomacy. Stay ahead of the executive.
If leadership has to
follow up on something basic , you are already behind. Do this for yourself.
If you don't see the
personal growth and long-term benefit in executing at this level , this role is
not
for you. Key Responsibilities
1. Elite Travel, Luxury Bookings & Negotiation
Book first-class travel experiences , ensuring VIP-level treatment. Negotiate and secure upgrades, flights , hotels, dining, and exclusive perks. Manage complex international itineraries, handling
last-minute changes with ease. Leverage concierge relationships
to unlock high-end services. 2. Executive Calendar & Prioritization
Own and optimize
the executives schedule,
ensuring every commitment is aligned with priorities . Anticipate scheduling conflicts
before they happen and
solve them proactively . Manage investor, advisor, and high-profile relationships , ensuring seamless coordination. 3. Customer Service & Online Shopping Expertise
Negotiate the best deals & refunds
from
luxury fashion to tech purchases . Handle all customer service issues , escalating only when necessary. Secure rare or high-demand items , using strategic sourcing and vendor relationships. 4. Business & Investor Operations
Act as a gatekeeper and trusted point of contact
for key partners. Own CRM, LP tracking, and follow-ups
for high-stakes relationships. Manage strategic gifting, investor relations, and professional outreach . 5. Personal & Household Management
Oversee all personal scheduling, household logistics, and vendor management . Handle prescriptions, medical records, and wellness coordination . Ensure seamless execution of family vacations, events, and experiences . Submit your application here:
https://forms.clickup.com/9017085020/f/8cqbk2w-42657/T7JQY66VJ95C7NMLJ3
About Us
Who We Are
Trolley is a fast-growing creative operations company delivering high-impact digital and marketing solutions. We collaborate with high-profile clients to strategize, produce, and optimize compelling content that drives engagement, brand visibility, and business growth. Our creative team functions as a fully integrated power-house combining strategy, design, production, and performance analysis to deliver world-class results.
We Operate Under Founder Mode
Trolley is built on a Founder Mode mindset - an operating system rooted in ownership, strategic thinking, and execution at speed. Here, we look for people who take initiative, think like entrepreneurs, and use tools like AI to optimize how work gets done. But Founder Mode isn't about going it alone, it's about working within high-trust, collaborative teams where contribution matters more than control. We value creativity, resourcefulness, and clear communication. If you're driven by impact, thrive in dynamic environments, and believe in scaling through systems, not stress - this is the place for you.
Why Join Us?
Work with the Best: We recruit globally to connect top talent with forward-thinking companies. Tech-Driven Efficiency: Leverage the latest AI and tools to amplify your impact. Human-Centric Approach: Our systems are designed to support and elevate people, not replace them. Training for Success: We provide world-class training to ensure you excel in every aspect of your role.
Be Part of the Future of Work
Trolley is now accepting applications from ambitious professionals who want to work at the intersection of technology and creativity. Join us in shaping the next era of work.
Required Skills: • Wellness • Medical Records • Strategic Initiatives • Operations • Logistics • BASIC • EASE • CRM • Fashion • Clarity • Strategic Thinking • Bookings • Pipelines • Steps • Zoom • Refunds • Export • Deals • Excel • Ownership • Vendor Management • Energy • Sourcing • Decision-Making • Travel • Deliverables • Strategy • Negotiation • Records • Vendors • Pressure • Scheduling • Marketing • Customer Service • Business • Leadership • Management
Job Details Location:
Remote (Must be based in North or South America and work within PST or EST time zones) Hours:
Full-time, with flexibility for occasional evening and weekend support. Executive Assistant (EA) Virtual | Full-Time | PST or EST Time Zones
Who Were Looking For
We're looking for an elite-level Executive Assistant who is
ten steps ahead, thrives in high-stakes environments, and executes flawlessly . This isn't a passive support role. This is about
owning responsibilities, amplifying efficiency, and ensuring the executive's world runs seamlessly, both
professionally and personally. You'll
manage high-profile relationships, optimize workflows, oversee high-stakes travel and negotiations, and eliminate distractions
so the CEO can focus on
big-picture strategy and execution . This role is
not for the hesitant or
reactive; it's for someone who is decisive, proactive, and deeply aligned with the executive's
vision . This is not your first time supporting a CEO and founder; you
thrive alongside executives with big energy, matching their pace and intensity . If you excel under pressure, can
execute at an elite level , and thrive on
making things happen instead of making excuses , this is for you.
Who You'll Work With
About the CEO
The executive you will support is a
Type 8 - The Challenger , known for being ambitious, independent, and driven to lead. They are highly analytical, deeply thoughtful, and approach challenges with confidence and intensity. They value efficiency, strategic thinking, and people who take initiative. The right EA for this role thrives next to a strong-willed, high-energy executive, understands their unique leadership style, and knows how to complement their strengths while bringing their own expertise to the table. This role reports directly to the
CEO and Managing Partner
and works closely with the
Senior Bookkeeper, investment team, legal partners, operations, marketing, and key external vendors and teams
to manage
both professional and personal
responsibilities. We are a
fast-moving, high-performance venture
that values
clarity, execution, and results . Our team is
dynamic, ambitious, and deeply committed to excellence . The
expectation is that you come in ready to contribute at a high level, align quickly, and deliver without hesitation.
How You Do the Job & Why
EXHIBIT A: Operating Framework, Expectations, and Deliverables
At the core of this role is a
fundamental expectation :
PLAY TO WIN, NOT TO AVOID MISTAKES. THE OBJECTIVE IS EXECUTION, NOT EXCUSES.
Phase 1: Core Deliverables & Mindset (0-9 months)
You will be exceptional in this role if:
You
operate with full alignment
to my vision and decision-making framework. When you speak,
you speak for me and with my authority.
If you are wrong, I will correct you. You
extend my influence
by managing
high-value relationships , ensuring seamless execution across
CRM, LP management, investor relations, and strategic initiatives . You
remove from my plate
all responsibilities that
do not require my direct input . You
anticipate
and
think through problems as the executive does , aligning your thought process with strategic expectations. You are an avid reader and researcher, always seeking knowledge to enhance problem-solving and decision-making. You
add expertise, reinforcing and deepening my strategies , not simply mirroring them. You do
not make sloppy errors,
this includes
inaccurate data, incomplete reports, and failure to track critical updates . You
over-communicate execution status;
every single priority is documented, with
recap updates delivered daily at 10 PM PST . You are self-regulated, composed under stress, and skilled at de-escalation, ensuring smooth execution even in high-pressure situations. You
own your role within the organization, deciding
when to be a
gatekeeper vs. a facilitator , balancing
authority and efficiency accordingly . You have strong personal boundaries, are curious, and are not afraid to try new things. Phase 2: Mastery & Expansion (9-12 months)
Develop and manage high-value talent pipelines
you identify, recruit, and maintain an ecosystem of
strategic relationships . Create leverage,
you
delegate, automate, and systematize
to move lower-priority tasks off your plate. Systemize everything
you standardize workflows and export best practices across the organization. Master a core domain
you fully
own and execute within a key business function . Act as a proxy for the executive
you operate
on behalf of leadership in select areas , particularly in
relationship-driven interactions . Take ownership of inefficiencies
you identify and solve operational gaps that
others overlook . Use strategic influence,
recognizing that
small, high-impact gestures
create
long-term business opportunities . Final Operating Principles
Play the long game.
Every move must be
strategic, not reactive . Zoom out.
View the business as
a system, not just a collection of tasks . Leverage information.
You will have
more access to critical data than anyone else
use it intelligently and efficiently. You have a strong sense of self, are highly self-aware, and know how to manage relationships with humor and diplomacy. Stay ahead of the executive.
If leadership has to
follow up on something basic , you are already behind. Do this for yourself.
If you don't see the
personal growth and long-term benefit in executing at this level , this role is
not
for you. Key Responsibilities
1. Elite Travel, Luxury Bookings & Negotiation
Book first-class travel experiences , ensuring VIP-level treatment. Negotiate and secure upgrades, flights , hotels, dining, and exclusive perks. Manage complex international itineraries, handling
last-minute changes with ease. Leverage concierge relationships
to unlock high-end services. 2. Executive Calendar & Prioritization
Own and optimize
the executives schedule,
ensuring every commitment is aligned with priorities . Anticipate scheduling conflicts
before they happen and
solve them proactively . Manage investor, advisor, and high-profile relationships , ensuring seamless coordination. 3. Customer Service & Online Shopping Expertise
Negotiate the best deals & refunds
from
luxury fashion to tech purchases . Handle all customer service issues , escalating only when necessary. Secure rare or high-demand items , using strategic sourcing and vendor relationships. 4. Business & Investor Operations
Act as a gatekeeper and trusted point of contact
for key partners. Own CRM, LP tracking, and follow-ups
for high-stakes relationships. Manage strategic gifting, investor relations, and professional outreach . 5. Personal & Household Management
Oversee all personal scheduling, household logistics, and vendor management . Handle prescriptions, medical records, and wellness coordination . Ensure seamless execution of family vacations, events, and experiences . Submit your application here:
https://forms.clickup.com/9017085020/f/8cqbk2w-42657/T7JQY66VJ95C7NMLJ3
About Us
Who We Are
Trolley is a fast-growing creative operations company delivering high-impact digital and marketing solutions. We collaborate with high-profile clients to strategize, produce, and optimize compelling content that drives engagement, brand visibility, and business growth. Our creative team functions as a fully integrated power-house combining strategy, design, production, and performance analysis to deliver world-class results.
We Operate Under Founder Mode
Trolley is built on a Founder Mode mindset - an operating system rooted in ownership, strategic thinking, and execution at speed. Here, we look for people who take initiative, think like entrepreneurs, and use tools like AI to optimize how work gets done. But Founder Mode isn't about going it alone, it's about working within high-trust, collaborative teams where contribution matters more than control. We value creativity, resourcefulness, and clear communication. If you're driven by impact, thrive in dynamic environments, and believe in scaling through systems, not stress - this is the place for you.
Why Join Us?
Work with the Best: We recruit globally to connect top talent with forward-thinking companies. Tech-Driven Efficiency: Leverage the latest AI and tools to amplify your impact. Human-Centric Approach: Our systems are designed to support and elevate people, not replace them. Training for Success: We provide world-class training to ensure you excel in every aspect of your role.
Be Part of the Future of Work
Trolley is now accepting applications from ambitious professionals who want to work at the intersection of technology and creativity. Join us in shaping the next era of work.
Required Skills: • Wellness • Medical Records • Strategic Initiatives • Operations • Logistics • BASIC • EASE • CRM • Fashion • Clarity • Strategic Thinking • Bookings • Pipelines • Steps • Zoom • Refunds • Export • Deals • Excel • Ownership • Vendor Management • Energy • Sourcing • Decision-Making • Travel • Deliverables • Strategy • Negotiation • Records • Vendors • Pressure • Scheduling • Marketing • Customer Service • Business • Leadership • Management