Executive Assistant

Caddie AI
is helping hire this role on behalf of
Unicorn Labs.

Unicorn Labs
transforms managers into confident leaders who drive results. They help growth-stage companies build strong, scalable teams through world-class leadership training. Their programs have impacted over
70,000 people across 100+ companies
, and they're growing fast.

They're looking for a
highly organized, detail-obsessed, and proactive Executive Assistant / Client Success Manager
to support their leadership team and clients. This is a
full-time, remote position (40 hours/week)
that operates on
Eastern Standard Time (EST)
.

About the Role

This role blends
executive support
,
operations
, and
client success
.

You'll be the right hand to Unicorn Labs' leadership, managing calendars, travel, and logistics, while also supporting client programs, ensuring every workshop, report, and cohort session runs seamlessly.

You'll collaborate closely with the operations and client delivery team to support tasks like scheduling, reporting, workshop coordination, and post-session documentation. The work is fast-paced, dynamic, and highly detail-oriented, ideal for someone who thrives in a "no two days the same" environment.

Key Responsibilities:

Executive & Administrative Support

• Manage complex scheduling and travel arrangements (flights, hotels, cars, calendar coordination)
• Handle personal matters to the CEO and administrative tasks such as ordering materials, booking appointments, or online purchases
• Maintain clear documentation for all admin processes (SOPs, checklists, schedules)
• Anticipate needs and plan ahead; ensure logistics make sense before confirming

Client Success & Cohort Delivery

• Support live training cohorts: attend calls, manage recordings, capture detailed notes, and organize follow-ups
• Assist with weekly client communications, assessments, and program tracking
• Compile workshop notes and Miro board inputs into client-ready reports and summaries
• Format and polish reports, decks, and tracking documents for consistency and quality
• Coordinate scheduling for client coaching sessions and leadership cohorts

Operations & Process Management

• Own recurring workflows like onboarding new cohorts, tracking client deliverables, and report compilation
• Document and improve internal systems; ensure every task is "plug-and-play" reproducible
• Maintain accurate course schedules, reports, and metrics dashboards
• Support leadership with tracking OKRs and project milestones
• Collaborate cross-functionally with team members across operations and delivery

Who Unicorn Labs is Looking For:

Must-Haves:

• Exceptional organization skills
  : you think in systems, lists, and clear next steps
• Strong English communication (written & verbal)
  : 10/10 proficiency required
• Detail-oriented mindset
  : you catch mismatches and inconsistency before anyone else
• Process-builder
  : you love turning chaos into structure with clear documentation
• Reliable tech setup
  : stable high-speed internet and a backup workspace
• Availability
  : 9 AM–5 PM EST, full-time (40 hours/week)
• Experience supporting founders, executives, or agency leaders

Nice-to-Haves:

• Background in client success, virtual assistance, or operations
• Experience managing workshops, reports, or coaching programs
• Strong business acumen; you understand how your work supports company goals

You'd Be Perfect For This Role If You Are

• A
  high-C personality type
  : structured, meticulous, and detail-driven
• A
  proactive problem solver
  : you think two steps ahead
• Calm under pressure and steady in fast-paced environments
• A supportive, reliable teammate who loves making things run smoothly
• Proud of turning complexity into clarity and efficiency

Compensation

• USD $800–$1,200/month
  (based on experience and skill level
• Full-time, remote role
• Long-term stability and growth potential

Application Process

1. Initial Screening:
   Resume review and brief questionnaire
2. Interview #1:
   Chat with Operations Manager
3. Project Assignment:
   A short take-home exercise to showcase organization and attention to detail (e.g., travel agenda or reporting task)
4. Final Interview:
   Conversation with company leadership

Why Join Unicorn Labs

• Work with a passionate, high-performing team transforming leadership development
• Be part of a mission-driven company helping startups scale through better leadership
• Grow your skills in operations, client experience, and executive support
• Enjoy a people-first culture with meaningful work and room to grow