Strategic Executive Assistant to the Founder

Mission of the Role

To act as the Founder’s operational partner: transforming his vision into execution, priorities into systems, and complexity into clarity.

This is a high-trust, high-autonomy role for someone who thrives in a detail-driven environment and sees executive support as a long-term, strategic career path. The Executive Assistant will work directly with the Founder to build out the operational backbone of the business — starting with fulfillment, then extending across onboarding, marketing, and sales — while managing the Founder’s time, calendar, and communications for maximum impact.

What This Role Is Really About

This is not a “VA” role. This is an embedded, right-hand strategic operator. Someone who:

• Operationalizes the Founder’s priorities so energy is spent on the right work at the right time

• Owns and organizes the process of documenting how the business runs

• Builds and maintains a centralized operating system as the company scales

• Acts as a communication filter and execution partner so the Founder can lead without being the bottleneck

Core Accountabilities

1. Founder Enablement

   • Manage the Founder’s calendar to reflect strategic priorities

   • Filter and flag key emails; draft replies and updates when appropriate

   • Prep the Founder for meetings, projects, and decision-making

   • Help the Founder focus by organizing tasks and inputs just-in-time

2. Fulfillment Systemization (Phase 1 Focus)

   • Co-develop internal documentation for current deliverables

   • Translate Founder processes into SOPs, checklists, and templates

   • Track fulfillment progress and support client communication

   • Create visibility into where we are and what’s next in delivery

3. Centralized Operating System

   • Maintain the single source of truth for company processes (Google Workspace)

   • Build and refine systems for onboarding, marketing, and sales alongside the Founder

   • Track progress and ensure handoffs are clean and documented

   • Assist in hiring and onboarding support roles as systems are clarified

4. Client Communication & Coordination

   • Coordinate weekly client updates (via email or Loom)

   • Support in scheduling and preparing for calls

   • Ensure no balls are dropped — all tasks, updates, and next steps followed through

Who You Need to Be

You have 5+ years’ experience working as an Executive Assistant to a founder, ideally in a fast-moving, B2B entrepreneurial environment. You understand the pace, adaptability, and trust required to operate effectively at the founder level.

Key Traits:

• High Detail Orientation – You notice what others miss. You spot gaps in process, follow threads to completion, and ensure things are executed with consistency. Documentation, naming, and follow-through matter to you.

• High Autonomy – You don’t need micromanagement, just clarity on priorities and outcomes. You take initiative, ask smart questions, and move projects forward without waiting for direction.

• Process-minded: You see chaos and want to bring order, clarity, and structure

• Founder-aligned: You understand how to work with driven founders — pushing back when needed, but always in service of the vision

• Builder: You’ve built internal systems before. You’ve helped a founder “get out of the weeds” by turning their work into documentation

• Communicator: You write clearly, handle email elegantly, and can own both internal and external communication

Cultural Match:

• You care about clarity and follow-through

• You take pride in building systems that others can use

• You’re energized by taking ideas and turning them into action

• You value calm, focused execution — not hustle for hustle’s sake

• You want to be deeply involved in building something lasting

Role Logistics

• Reports To: Founder (Christopher Harris)

• Works Closely With: Fulfillment lead(s), future hires in fulfillment/marketing/sales

• Tools: Google Workspace (Including AppSheet); Notion (moving away from); Loom; Whimsical; HighLevel

• Authority:

  • Owns and manages the Founder’s calendar and inbox

  • Owns the centralized operating system for the company — responsible for where documentation lives, how it’s structured, and how it’s kept current

  • Leads the organization and process of documenting how the business runs — including fulfillment, onboarding, marketing, and sales systems

  • Drives execution across fulfillment and ops in partnership with the Founder

What Success Looks Like

• The Founder’s time is aligned with the highest-leverage work — no more reactive scheduling

• Client fulfillment runs with documented systems that others can follow

• The company’s operating system lives in one place and is trusted by the team

• The Executive Assistant knows what’s going on across departments and helps drive execution, not just organization

• The Founder is no longer the bottleneck in delivery, communication, or ops — because the right hand is running point

Success Metrics

1. Founder Enablement

   • Calendar reflects strategic priorities 90%+ of the time

   • Founder is prepared for all meetings and tasks without having to track details

   • Key messages (communications) are drafted or sent without requiring Founder input

2. System Ownership

   • All key fulfillment processes are documented and organized in a centralized system

   • The operating system (Google Drive/Notion) is actively maintained, current, and accessible

   • Systems, Checklists, and SOPs are being used and improved across fulfillment, marketing, and sales

3. Execution & Accountability

   • Weekly priorities are clear and actively tracked for the Founder and EA

   • No client deliverables or internal priorities fall through the cracks

   • EA runs or leads internal meetings with clear agendas and follow-ups

Work Environment & Benefits

• Fully remote,  contract position

• Monday–Friday, primarily working Central Time hours

• Salary - $2,500-$4,000/month

• Professional Development Opportunities

• Small supportive team with clear systems and a focus on autonomy

• 10 Paid Holidays 

• 2 Weeks paid time off

Application Process

Here is the outline of the whole application process, so you know what to expect:

1. Fill in and submit the application form.

2. Several video interviews (between 15-60 minutes long) where we try to get to know you better and give you a chance to get to know us, as well as talk about your previous experiences and future goals.

3. Top candidates will be invited for a test project.

4. If that goes well, we will make an offer and continue working together!

About Simple Automations

Simple Automations is an Agency Growth Infrastructure Architect that transforms chaotic agency operations into streamlined systems that actually work. We specialize in implementing HighLevel for established agencies that have outgrown their scattered tech stack using our proven "Just in Time" approach - delivering focused modules that create momentum without overwhelming your team.

We serve ambitious agency owners who find themselves buried in manual tasks, juggling multiple software tools, and struggling to create predictable growth. These are agencies that have successfully grown but now find that scaling further feels like pushing a boulder uphill.

We don't just set up software; we design and build the operational infrastructure that allows agencies to scale without adding complexity. By consolidating scattered tools, automating manual processes, and creating clear visibility, we free agency owners to focus on what truly matters - serving clients and growing their business.

Our mission is transformation. Our strategy is simplification. Our vision is freedom.

Simple Automations asks respectfully to only apply through the application form and not email/apply to them directly. Recruiters and Agencies please do not contact Simple Automations directly.