Executive Assistant to a High-Velocity Entrepreneur & CEO Job at Complily, Inc., Rockville, MD

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  • Complily, Inc.
  • Rockville, MD

Job Description

Location: On-Site (Rockville, MD)

Type: Full-time

Compensation: $90K–$110K base + performance bonus + equity pathway

Reports to: CEO (with direct coordination with long-time Chief of Staff)

Future Path: Chief of Staff

This is not a normal job.

You won’t just manage a calendar.

You’ll be supporting a high-output, public-facing entrepreneur building a multi billion-dollar AI holding company, launching a health franchise, raising capital, speaking on stage, creating content, building community, and acquiring companies — all at once.

We need someone sharp, fast, and relentlessly proactive, someone who will earn trust quickly, lead from the front, and grow into a true operator.

You’ll become the CEO’s right hand, representing him internally and externally, driving team culture, and helping automate and scale his content, brand, and time.

About UgenticAI

UgenticAI is an agentic AI holding company on a mission to raise $200 million, acquire and grow 100+ AI-powered businesses across 20+ verticals. We move fast, acquire smart, and build companies that run with intelligent systems and minimal human friction.

We are also launching a new health-focused franchise brand based in Gaithersburg, MD — combining longevity, biohacking, and concierge wellness with modern marketing.

Our founder is also the face of a fast-growing marketing education company with thousands of loyal followers, where he teaches founders how to scale, distribute, and grow through unconventional, high-leverage strategies.

You’ll help him organize, schedule and create the content that powers it.

Your Mission

You will be the operational and executional extension of the CEO — helping him move faster, scale his impact, and stay focused on what only he can do.

You’ll also be a cultural anchor inside the company, working closely with the Chief of Staff (Olga, with us for 11 years) to create internal momentum and external polish.

You’ll manage meetings, chase follow-ups, rep the CEO in communication, assist in content development, drive special projects, and use AI to automate as much of his life and business as possible.

This is the path to becoming Chief of Staff — with the opportunity to grow into a strategic operator over the next 12–24 months.

What You’ll Own

Execution & Ownership:

- Own the CEO’s schedule, priorities, meetings, and travel, ruthlessly protect his time

- Attend or shadow calls to capture next steps, manage follow-ups, and drive action

- Represent the CEO in external comms: with investors, partners, collaborators, and event hosts

- Send polished emails, confirmations, and strategic nudges on his behalf

- Be the gatekeeper and bridge between the CEO and the outside world

Office Setup & HQ Operations:

- Lead the full setup of our new Gaithersburg office (approx. 4,000 sq ft)

- Source and coordinate with interior designers, furniture vendors, contractors, and tech providers

- Oversee the build-out timeline, manage budgets, and find the best deals

- Once launched, manage the day-to-day of the HQ: supplies, maintenance, logistics, local staffing support, and vendor relationships

- Keep the office running like a luxury hotel — organized, welcoming, and optimized for performance

Internal Culture & Team Momentum:

- Help lead and reinforce a high-trust, high-performance, no-politics culture at UgenticAI

- Serve as the pulse of internal ops — ensuring deliverables move, people are aligned, and nothing falls through the cracks

- Drive weekly rhythms (team check-ins, investor updates, internal dashboards) in coordination with the Chief of Staff.

AI-Enabled Workflow & Automation:

- Use tools like ChatGPT, Notion AI, Zapier, ElevenLabs, Descript, and others to automate processes, synthesize information, and increase output

- Help architect systems that scale communication, scheduling, research, and reporting

- Constantly ask: “Can this be done faster with AI?”

Content Creation & Brand Support:

- Support the CEO’s content calendar across his marketing education brand (email, social, video, courses, book)

- Use AI to generate drafts, prep outlines, transcribe audio, and convert recordings into high-leverage content

- Coordinate with ghostwriters, editors, designers, and video teams to get content shipped fast

Logistics, Ops & Personal Optimization:

- Coordinate travel, event planning, logistics, bookings, vendor relations, and contracts

- Oversee personal optimization workflows (labs, supplements, IVs, peptides, etc.)

- Handle errands, special projects, gifts, and other behind-the-scenes responsibilities

Who You Are:

- 5–10 years experience supporting a founder, CEO, investor, or high-performance exec

- Experience inside startups, VC-backed companies, agencies, or investment firms preferred

- Ridiculously organized, lightning fast, tech-native, and calm under pressure

- A phenomenal written communicator who can speak and write like the CEO

- Curious about AI, automation, systems thinking, and building workflows

- Obsessed with efficiency, accountability, and speed

- Someone who thrives in chaos, doesn’t need hand-holding, and loves moving the needle

- Based in or near Gaithersburg, MD — hybrid is required

What We Offer:

- Competitive salary ($90K–$110K) + bonus

- Equity or phantom stock pathway after proven performance

- A clear, accelerated track to Chief of Staff and operational leadership

- A seat at the table as we build a $1B+ portfolio of companies

- Health, wellness, and optimization perks

- A deeply entrepreneurial environment where speed is rewarded and trust is earned

Apply If You…

- Have supported a crazy founder before — and liked it.

- Want to work with someone building fast and thinking bigger than most.

- Are eager to lead behind the scenes while building a future leadership role.

- Can confidently say, “I get sh*t done — better than anyone else you’ll meet.”

To apply: Send a short note and your resume or LinkedIn to anik@complily.com.

Bonus points if you share a wild story about how you saved the day for a past exec.

Job Tags

Full time, For contractors, Local area,

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