Find & Apply For Executive Assistant Jobs in Westport, Connecticut

Executive Assistant to CEO |

AI, Content & Operations Location:

Connecticut |

Hybrid:

Remote +

In Person Employment:

Full-Time Invest Diva is an established, fast-growing financial education company that has been in business for 15 years , on a mission to help one million households take control of their financial future and create the freedom to live the life they truly desire. Founded and led by Kiana Danial , an 8-figure investor, Wall Street Journal bestselling author, former engineer, and financial educator, Invest Diva teaches busy professionals and entrepreneurs how to turn their income into long-term wealth through Triple Compounding™ . After 15 years of growth, we're entering our next chapter. We're building for the future. We're rapidly growing our content, community, educational programs, and technology while aggressively exploring how AI, automation, and AI agents can help a small, high-performance team operate at 10X and eventually 100X productivity. That means this isn't a job where you'll sit quietly behind the scenes managing a calendar. You'll work directly alongside the CEO , get exposure to nearly every part of a rapidly growing entrepreneurial company, and help us move faster, create better content, serve more people, automate what shouldn't be done manually, and turn ambitious ideas into reality. We move fast. We experiment. We learn. We execute. And we're looking for someone who gets genuinely excited by that. Want to get a feel for Kiana, the brand, and what we're building? Check out @investdiva on Instagram before you apply.

THIS IS NOT A TRADITIONAL EXECUTIVE ASSISTANT ROLE.

We are looking for an unusually driven, tech-savvy, AI-hungry Executive Assistant to work directly with the CEO of a rapidly growing company. Yes, you'll handle executive support. But we're looking for much more than someone who manages calendars and books flights. We want a CEO force multiplier. Someone who can move fast, learn ridiculously fast, solve problems independently, obsess over details, leverage AI to 10X their productivity, and gradually take an enormous amount off the CEO's plate. You'll have exposure to almost every part of the company, including executive operations, AI and automation, content production, social media, communications, meetings, projects, and day-to-day business operations. If you're the kind of person who sees something that needs to get done and your natural reaction is: "I'll figure it out." Keep reading.

WHO WE'RE LOOKING FOR

You are:

EXTREMELY PROACTIVE.

You don't wait to be told every next step. You anticipate what's coming and act. URGENT. You naturally move faster than most people around you. When something can be done today, you don't put it on next week's list.

A DOER, NOT A TALKER.

You prefer execution over endless discussion. You don't need three meetings to decide how to schedule another meeting.

AI-OBSESSED AND HUNGRY TO 10X YOUR PRODUCTIVITY.

You don't just use AI when someone tells you to. You're genuinely excited about what AI makes possible. You experiment with new tools. You want to learn how to build AI agents, automations, and workflows.

You constantly ask:

"How could AI make this 10X faster, easier, or better?" You want to figure out how to accomplish in 10 minutes what used to take two hours.

A VERY FAST LEARNER.

You can be shown something once, understand the goal, and figure out the rest.

OBSESSIVE ABOUT DETAILS.

You catch the typo, broken link, forgotten follow-up, wrong date, missing attachment, or inconsistency before anyone else does.

HUNGRY FOR GROWTH.

You actively want more responsibility, greater skills, bigger challenges, and a front-row seat to building a rapidly growing company.

HIGHLY RESOURCEFUL.

When you don't know how to do something, your instinct isn't to say, "I don't know." It's to say: "Let me figure it out."

AN EXCELLENT COMMUNICATOR.

You can communicate clearly, quickly, and professionally through email, Slack, social media, meetings, and executive correspondence.

CALM UNDER PRESSURE.

Rapidly growing companies don't always operate in perfect order. You can prioritize, adapt, and execute without becoming overwhelmed.

HIGH OWNERSHIP.

If something falls under your responsibility, you make sure it gets across the finish line.

DISCREET AND TRUSTWORTHY.

You'll have access to sensitive business and personal information and must exercise exceptional judgment.

LOW EGO, HIGH STANDARDS.

No task is beneath you, but you're constantly looking for ways to make yourself, the CEO, and the entire company more effective. We value speed, ownership, resourcefulness, accuracy, curiosity, growth, and results. We do not value bureaucracy, unnecessary meetings, excessive hand-holding, or talking about work instead of doing it.

WHAT YOU'LL DO

Your responsibilities will evolve as the company grows. That's part of the opportunity.

CEO SUPPORT

Manage and protect the CEO's calendar, time, and priorities Manage scheduling, appointments, travel, logistics, and follow-ups Help manage the CEO's email and Slack communication Draft responses and communications in the CEO's voice Determine what actually requires the CEO's attention versus what you can handle independently Make sure commitments, conversations, and action items never fall through the cracks Prepare the CEO for meetings with relevant information, research, context, and talking points Attend selected meetings on behalf of the CEO Take ownership of meeting follow-ups, decisions, deadlines, and action items Coordinate with team members, vendors, partners, clients, and other stakeholders Anticipate problems and solve them before they become the CEO's problems The ultimate goal: Free the CEO to spend more time on the highest-value work only she can do.

AI, AUTOMATION & 10X PRODUCTIVITY AI

is a major part of where our company is going. Our goal isn't simply to "use AI." We want to build an increasingly AI-powered company where humans are supported by AI agents, automations, and systems that allow us to move 10X, and eventually 100X, faster. You will help us get there.

You will:

Constantly identify tasks, workflows, and bottlenecks that can be eliminated, automated, delegated to AI, or dramatically accelerated Learn how to build, use, and manage AI agents and AI-powered workflows Experiment with emerging AI tools and determine which ones are actually useful Use AI to accelerate research, communication, content production, meeting preparation, project management, and operations Turn repetitive CEO and team tasks into systems, automations, and agents wherever possible Build AI-assisted systems that increase your own productivity Help identify opportunities to deploy AI throughout the company Document successful AI workflows so they can be replicated by the team Stay curious about emerging AI capabilities and proactively bring new ideas to the company Continually ask: "Why are we still doing this manually?" Continually ask: "How could we make this 10X faster?" You do not need to already be an AI engineer. But you need to be extremely hungry to learn. We would rather hire someone who says: "I've never built that before, but give me tonight and I'll figure it out." than someone who waits for a step-by-step

SOP. CONTENT & SOCIAL MEDIA

You will also work closely with the CEO's personal brand and content operation.

Responsibilities may include:

Assist with the CEO's content-production workflow Help organize and manage short-form and long-form content Coordinate videos, social posts, captions, creative assets, deadlines, and publishing Work with editors, designers, copywriters, and other members of the content team Help manage the CEO's social media calendar Identify content opportunities from meetings, conversations, events, business activity, and current trends Make sure content moves quickly from idea → production → approval → publishing Help research content topics and opportunities Understand the CEO's voice and brand well enough to protect consistency across platforms Use AI wherever appropriate to dramatically accelerate the content-production process

PROJECTS & OPERATIONS

You will: Drive projects forward without requiring constant supervision Follow up relentlessly until deliverables are completed Create checklists, workflows, SOPs, and systems when needed Identify bottlenecks and recommend ways to eliminate them Research tools, vendors, opportunities, people, and solutions Coordinate across departments and make sure priorities are moving Track deadlines, deliverables, decisions, and outstanding items Take messy ideas and turn them into executable next steps Help create order as the company grows Solve problems before they become bigger problems When the CEO says, "Can we figure out how to do this?" Your instinct should be: "Yes. Let me research it."

Not:

"Who should we ask?"

YOU'LL PROBABLY LOVE THIS ROLE

IF... You find yourself saying things like: "Already handled." "I figured it out." "I noticed this was falling behind, so I fixed it." "I automated that because we shouldn't be doing it manually anymore." "Here are the three options. I recommend option two, and here's why." You enjoy being close to the action. You want exposure to entrepreneurship, marketing, content, investing, leadership, AI, technology, and business operations. You love learning. You like speed. You get genuine satisfaction from checking things off, solving problems, and getting a ridiculous amount accomplished in a day. And you don't need a perfectly defined job description before taking action.

THIS ROLE IS PROBABLY NOT FOR YOU

IF... You need detailed instructions for every assignment You frequently say, "That's not my job" You need multiple reminders to complete something You prefer talking about problems over solving them You are uncomfortable with changing priorities You prefer slow-moving, highly structured corporate environments You dislike technology You see AI as something you "have to use" rather than something you're excited to master You resist learning new software You tend to identify problems without proposing solutions You enjoy long meetings more than execution You need constant praise or supervision to stay motivated You want an assistant role where your responsibilities remain exactly the same year after year This company is growing quickly. The role will grow quickly too.

QUALIFICATIONS

Ideally:

5+ years of experience as an Executive Assistant, Chief of Staff, Executive Operations Manager, Project Manager, Content Manager, or similar high-responsibility role Experience directly supporting a CEO, founder, entrepreneur, or senior executive Exceptional organization and attention to detail Excellent written and verbal communication Strong project-management skills Advanced comfort with modern technology and productivity tools Highly proficient with AI tools or demonstrably obsessed with becoming highly proficient Strong interest in learning AI agents, automation, prompt engineering, and AI-powered workflows Naturally experiments with technology to increase personal productivity Comfortable independently researching and learning new technology at high speed Experience with Slack, Google Workspace, project-management software, social media platforms, and AI tools Experience supporting content creation or social media is strongly preferred Ability to work independently and make good judgment calls without constant approval Ability to occasionally attend meetings, events, shoots, and other activities in person Must be able to work in Connecticut as part of a hybrid remote/in-person schedule

WHAT SUCCESS LOOKS LIKE

The CEO becomes dramatically more productive because you are there. Things stop falling through the cracks. Communication gets faster. Projects move faster. Content gets produced faster. Repetitive tasks get automated. AI handles work humans shouldn't still be doing manually. Problems increasingly reach the CEO with solutions attached. And the CEO spends less time managing details and more time doing the highest-value work only she can do. Over time, you become someone the CEO can trust with increasingly important decisions, projects, meetings, and responsibilities.

GROWTH OPPORTUNITY

This is not intended to be a stagnant assistant position. For the right person, this can become an extremely high-impact role with significant exposure to how a rapidly growing entrepreneurial company operates. You'll have an opportunity to become exceptionally good at AI, automation, executive operations, content, leadership, and business. As your capabilities grow, your responsibilities can grow. As trust grows, your autonomy can grow. We are looking for someone who wants that. Someone who isn't simply looking for their next job. Someone who wants to build, learn, move fast, become extraordinarily capable, and see how far they can grow.

TO APPLY

Please submit your resume along with short answers to the following: 1. Why does this particular role appeal to you? 2. Tell us about a time you noticed a problem nobody asked you to solve and took ownership of fixing it. 3. What AI tools do you currently use, and how have you used AI to make yourself more productive? 4. If we gave you 30 days to use AI to 10X your effectiveness in this role, what would you learn, build, automate, or delegate to AI first? 5. Tell us about something you didn't know how to do but taught yourself quickly because the result depended on it. 6. Your CEO sends you 10 urgent requests at the same time. How do you decide what gets handled first? BONUS Send us a 60-90 second video introducing yourself and answering one question: Why do you believe you would be exceptional in this role? We're looking for someone with an unusual combination of hunger, intelligence, urgency, resourcefulness, attention to detail, and an obsession with getting things done. If reading this job description makes you think: "This sounds intense." This probably isn't your role.

If it makes you think:

"Finally. This sounds like me." We want to hear from you.

Pay:

$89,740.40 - $120,128.23 per year

Benefits:

401(k) Dental insurance Flexible schedule Health insurance Paid time off Parental leave Professional development assistance Referral program Retirement plan Vision insurance Ability to

Commute:

Westport, CT 06880 (Preferred)

Work Location:

Hybrid remote in Westport, CT 06880