Strategic Assistant to Visionary Entrepreneur (Integrator Role)
Strategic Assistant to Visionary Entrepreneur (Integrator Role)
Location: Remote-friendly (must work EST hours: 8:30–5:00, Monday–Friday)
Type: Full-time, 1099 contractor position
Reports to: CEO of a growing tech-enabled coaching company
About the Role
Are you equal parts organized project manager, tech-savvy executive assistant, and creative problem solver? Do you thrive on bringing order to chaos and enabling visionary leaders to soar?
If so, read on – you might be the critical right-hand we’re looking for.
Who We Are
We’re on a mission to empower high-performing entrepreneurs by leveraging modern AI tools and proven productivity hacks to simplify their operations and life. (Yes, AI – we’re not just talking about it, we’re using it daily!)
Our CEO, Tom, is a visionary innovator and industry thought leader. He’s the kind of entrepreneur who is always pushing the envelope – big ideas, high energy, and yes, sometimes a sprinkle of ADD.
You’ll also work closely with Christine, our Director of Operations and Program Success. We’re a small team, tight-knit, positive, and growth-oriented. We live by a strict “Only Good Vibes, No Jerks” policy – life’s too short to work with people who don’t lift you up.
We move fast, but we care deeply about doing great work and continuously improving.
Who You Are
A strategic doer. You love the idea of being the “yin” to a visionary’s “yang” – complementing creativity with execution.
• You naturally build checklists, spreadsheets, and processes to streamline work.
• You’re flexible enough to handle urgent curveballs.
• Resourceful might as well be your middle name – you’ll Google it, figure it out, or find someone who can.
• You take pride in being two steps ahead, anticipating needs before they’re spoken.
• Holding others accountable doesn’t scare you; in fact, you excel at diplomatically nudging a busy exec to focus or follow through – and you do it with empathy and humor.
• You’re tech-curious – the latest app, AI tool, or productivity hack excites you, and you’re eager to learn.
• You take ownership of your responsibilities. You don’t wait to be told what to do—you act, bring potential solutions, and ask for input when needed. You’re an independent thinker with a teamwork attitude.
Most importantly, you’re looking for more than a job – you want a long-term team where you can grow, make an impact, and be appreciated for the superstar you are.
What You’ll Do
This role blends executive assistant + project coordination + process optimization responsibilities.
Everything you do should run through these filters:
• How can I protect Tom’s time?
• How can I take things off his plate to provide him with more focus time?
• How can I make things easier, faster, simpler for Tom and the company?
• How can I strengthen relationships and communication with clients, partners, and the team?
• How can I align this work with our company’s goals and values?
Key responsibilities include:
• Be the CEO’s right hand – manage Tom’s calendar, appointments, and travel so that his days align with his top priorities. Triage his email inbox, draft responses in his voice, and keep him focused on what matters most.
• Drive execution of ideas – Tom has no shortage of ideas. You’ll help make them happen by turning brainstorms into project plans, coordinating with team members or vendors, and tracking progress. You’ll use task managers, calendars, and maybe a dash of AI magic to keep everything on track.
• Streamline and optimize – Create processes for recurring tasks where none exist (client onboarding, webinars, reporting templates). Always ask: “How can we make this easier, faster, simpler?” – then implement the improvement.
• Keep Tom accountable and organized – Run brief daily/weekly check-ins to lock in priorities. Be the person who says, “Hey, let’s refocus on your top 3 goals for today” – and he’ll thank you for it.
• Support client and team relationships – Act as a friendly point of contact with clients, partners, and team members. Schedule meetings, prep Tom with background info, and follow up on action items. Handle communications with warmth and professionalism.
• Special projects & “other duties as assigned” – We’re small, so we all wear many hats. You might help Christine with an operations research task one day and coordinate a marketing email the next. No two days look the same, and you’ll get to touch many facets of the business.
Core Values
We live, hire, fire, and promote by our four core values:
• Grow
• Be the Hero
• Work Smart
• Embrace Change
Qualifications
• 3+ years experience as an Executive Assistant, Operations Coordinator/Manager, or similar role directly supporting a senior executive or entrepreneur. (Startup or small business environment preferred.)
• Exceptional organizational skills – you’ve managed complex calendars, juggled multiple projects, and kept teams on schedule. Words like “SOPs,” “checklists,” and “efficiency” make you happy.
• Strong communication skills – you write clearly and can adapt to someone else’s voice/tone. (We’ll want to see that in your cover letter and may ask for a writing sample.) You also speak up tactfully when needed.
• Tech & Tools – Experience with Google/Office suite, project management tools, Slack, and Apple/Mac technology. Enthusiasm for AI tools (ChatGPT, automation, data analysis) is a big plus. If you’ve built an automation or used AI to draft an email, we want to hear about it!
• Proactive mindset – you don’t wait for instructions; you see what needs to be done and do it.
• Problem-solving attitude – your first thought is, “How can we make this work?” not “It can’t be done” or “How do I do it?” (or immediately asking someone else how to do it).
• High integrity & reliability – you can be trusted with sensitive information and critical tasks.
• Positive energy – attitude matters as much as aptitude. You stay level-headed and solutions-focused, even under stress.
Bonus points if you have:
• Experience with productivity/coaching programs (EOS/Traction, Strategic Coach)
• Familiarity with Kolbe/Strengths profiles – if you’ve taken them, we’d love to know your results
Why Join Us
This is a unique opportunity to play a pivotal role in a company doing cutting-edge work with AI and productivity for entrepreneurs.
• You’ll work one-on-one with a CEO who values his assistant – you’ll be a partner, not “just admin.”
• You’ll also have the mentorship of Christine, our Director of Operations and Program Success.
• You’ll have free access to our productivity and AI programs to level up your own skills.
• We offer flexibility (we care about results, not clock-punching).
• We celebrate wins, learn from failures, and invest in our team’s growth.
We also promote from within: the last two people in this role grew into senior leadership—one is now CEO of GlobalMac IT, and the other is Director of Operations and Program Success here at AI Simplifier.
How to Apply
Please send your resume and a short cover letter telling us:
• Why you’re excited about this role
• An example of a time you brought order to chaos or solved a tough problem
• Kolbe A or StrengthsFinder results, if you’ve taken them (we’d love to know!)
We can’t wait to meet our new partner in crime – the good kind, of course!
Job Type: Contract
Pay: $3,500.00 - $4,000.00 per month
Benefits:
• Paid time off
Application Question(s):
• This is a 1099 contractor position, not a W2 role. Are you comfortable with that arrangement?
• What tools or systems do you currently use to manage projects, calendars, or workflows?
• Our core values are Grow, Be the Hero, Work Smart, and Embrace Change. Which one resonates most with you and why?
• Do you have experience working directly with entrepreneurs or executives in a small business or startup environment?
Work Location: Remote
Apply Now
Apply Now
Location: Remote-friendly (must work EST hours: 8:30–5:00, Monday–Friday)
Type: Full-time, 1099 contractor position
Reports to: CEO of a growing tech-enabled coaching company
About the Role
Are you equal parts organized project manager, tech-savvy executive assistant, and creative problem solver? Do you thrive on bringing order to chaos and enabling visionary leaders to soar?
If so, read on – you might be the critical right-hand we’re looking for.
Who We Are
We’re on a mission to empower high-performing entrepreneurs by leveraging modern AI tools and proven productivity hacks to simplify their operations and life. (Yes, AI – we’re not just talking about it, we’re using it daily!)
Our CEO, Tom, is a visionary innovator and industry thought leader. He’s the kind of entrepreneur who is always pushing the envelope – big ideas, high energy, and yes, sometimes a sprinkle of ADD.
You’ll also work closely with Christine, our Director of Operations and Program Success. We’re a small team, tight-knit, positive, and growth-oriented. We live by a strict “Only Good Vibes, No Jerks” policy – life’s too short to work with people who don’t lift you up.
We move fast, but we care deeply about doing great work and continuously improving.
Who You Are
A strategic doer. You love the idea of being the “yin” to a visionary’s “yang” – complementing creativity with execution.
• You naturally build checklists, spreadsheets, and processes to streamline work.
• You’re flexible enough to handle urgent curveballs.
• Resourceful might as well be your middle name – you’ll Google it, figure it out, or find someone who can.
• You take pride in being two steps ahead, anticipating needs before they’re spoken.
• Holding others accountable doesn’t scare you; in fact, you excel at diplomatically nudging a busy exec to focus or follow through – and you do it with empathy and humor.
• You’re tech-curious – the latest app, AI tool, or productivity hack excites you, and you’re eager to learn.
• You take ownership of your responsibilities. You don’t wait to be told what to do—you act, bring potential solutions, and ask for input when needed. You’re an independent thinker with a teamwork attitude.
Most importantly, you’re looking for more than a job – you want a long-term team where you can grow, make an impact, and be appreciated for the superstar you are.
What You’ll Do
This role blends executive assistant + project coordination + process optimization responsibilities.
Everything you do should run through these filters:
• How can I protect Tom’s time?
• How can I take things off his plate to provide him with more focus time?
• How can I make things easier, faster, simpler for Tom and the company?
• How can I strengthen relationships and communication with clients, partners, and the team?
• How can I align this work with our company’s goals and values?
Key responsibilities include:
• Be the CEO’s right hand – manage Tom’s calendar, appointments, and travel so that his days align with his top priorities. Triage his email inbox, draft responses in his voice, and keep him focused on what matters most.
• Drive execution of ideas – Tom has no shortage of ideas. You’ll help make them happen by turning brainstorms into project plans, coordinating with team members or vendors, and tracking progress. You’ll use task managers, calendars, and maybe a dash of AI magic to keep everything on track.
• Streamline and optimize – Create processes for recurring tasks where none exist (client onboarding, webinars, reporting templates). Always ask: “How can we make this easier, faster, simpler?” – then implement the improvement.
• Keep Tom accountable and organized – Run brief daily/weekly check-ins to lock in priorities. Be the person who says, “Hey, let’s refocus on your top 3 goals for today” – and he’ll thank you for it.
• Support client and team relationships – Act as a friendly point of contact with clients, partners, and team members. Schedule meetings, prep Tom with background info, and follow up on action items. Handle communications with warmth and professionalism.
• Special projects & “other duties as assigned” – We’re small, so we all wear many hats. You might help Christine with an operations research task one day and coordinate a marketing email the next. No two days look the same, and you’ll get to touch many facets of the business.
Core Values
We live, hire, fire, and promote by our four core values:
• Grow
• Be the Hero
• Work Smart
• Embrace Change
Qualifications
• 3+ years experience as an Executive Assistant, Operations Coordinator/Manager, or similar role directly supporting a senior executive or entrepreneur. (Startup or small business environment preferred.)
• Exceptional organizational skills – you’ve managed complex calendars, juggled multiple projects, and kept teams on schedule. Words like “SOPs,” “checklists,” and “efficiency” make you happy.
• Strong communication skills – you write clearly and can adapt to someone else’s voice/tone. (We’ll want to see that in your cover letter and may ask for a writing sample.) You also speak up tactfully when needed.
• Tech & Tools – Experience with Google/Office suite, project management tools, Slack, and Apple/Mac technology. Enthusiasm for AI tools (ChatGPT, automation, data analysis) is a big plus. If you’ve built an automation or used AI to draft an email, we want to hear about it!
• Proactive mindset – you don’t wait for instructions; you see what needs to be done and do it.
• Problem-solving attitude – your first thought is, “How can we make this work?” not “It can’t be done” or “How do I do it?” (or immediately asking someone else how to do it).
• High integrity & reliability – you can be trusted with sensitive information and critical tasks.
• Positive energy – attitude matters as much as aptitude. You stay level-headed and solutions-focused, even under stress.
Bonus points if you have:
• Experience with productivity/coaching programs (EOS/Traction, Strategic Coach)
• Familiarity with Kolbe/Strengths profiles – if you’ve taken them, we’d love to know your results
Why Join Us
This is a unique opportunity to play a pivotal role in a company doing cutting-edge work with AI and productivity for entrepreneurs.
• You’ll work one-on-one with a CEO who values his assistant – you’ll be a partner, not “just admin.”
• You’ll also have the mentorship of Christine, our Director of Operations and Program Success.
• You’ll have free access to our productivity and AI programs to level up your own skills.
• We offer flexibility (we care about results, not clock-punching).
• We celebrate wins, learn from failures, and invest in our team’s growth.
We also promote from within: the last two people in this role grew into senior leadership—one is now CEO of GlobalMac IT, and the other is Director of Operations and Program Success here at AI Simplifier.
How to Apply
Please send your resume and a short cover letter telling us:
• Why you’re excited about this role
• An example of a time you brought order to chaos or solved a tough problem
• Kolbe A or StrengthsFinder results, if you’ve taken them (we’d love to know!)
We can’t wait to meet our new partner in crime – the good kind, of course!
Job Type: Contract
Pay: $3,500.00 - $4,000.00 per month
Benefits:
• Paid time off
Application Question(s):
• This is a 1099 contractor position, not a W2 role. Are you comfortable with that arrangement?
• What tools or systems do you currently use to manage projects, calendars, or workflows?
• Our core values are Grow, Be the Hero, Work Smart, and Embrace Change. Which one resonates most with you and why?
• Do you have experience working directly with entrepreneurs or executives in a small business or startup environment?
Work Location: Remote
Apply Now
Apply Now