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About This Role
Executive Assistant to CEO | AI, Content & Operations
Location: Connecticut | Hybrid: Remote + In Person Employment: Full-Time Experience: Ideally 2+ years
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
Salary Context
This $89K-$120K range is in the lower quartile for AI/ML Engineer roles in our dataset (median: $175K across 1356 roles with salary data).
View full AI/ML Engineer salary data →Role Details
About This Role
AI/ML Engineers build and deploy machine learning models in production. They work across the full ML lifecycle: data pipelines, model training, evaluation, and serving infrastructure. The role has evolved significantly over the past two years. Where ML Engineers once spent most of their time on model architecture, the job now tilts heavily toward inference optimization, cost management, and integrating LLM capabilities into existing systems. Companies want engineers who can ship production systems, and the experimenter-only role is fading fast.
Day-to-day, you're writing training pipelines, debugging data quality issues, setting up evaluation frameworks, and figuring out why your model performs differently in staging than it did on your dev set. The best ML engineers are obsessive about reproducibility and measurement. They instrument everything. They know that a model is only as good as the data feeding it and the infrastructure serving it.
Across the 8,943 AI roles we're tracking, AI/ML Engineer positions make up 75% of the market. At Invest Diva, this role fits into their broader AI and engineering organization.
Demand for AI/ML Engineers has been strong and consistent. Unlike some AI roles that spike with hype cycles, ML engineering is a foundational need. Every company deploying AI models needs people who can keep them running, and the gap between research prototypes and production systems keeps growing.
What the Work Looks Like
A typical week might include: debugging a data pipeline that's silently dropping 3% of training examples, running A/B tests on a new model version, writing documentation for a feature flag system that lets you roll back model deployments, and reviewing a junior engineer's PR for a new evaluation metric. Meetings tend to be cross-functional since ML touches product, engineering, and data teams.
Demand for AI/ML Engineers has been strong and consistent. Unlike some AI roles that spike with hype cycles, ML engineering is a foundational need. Every company deploying AI models needs people who can keep them running, and the gap between research prototypes and production systems keeps growing.
Skills Required
Python and PyTorch dominate the requirements. Most roles expect experience with cloud platforms (AWS, GCP, or Azure) and familiarity with ML frameworks like TensorFlow or JAX. RAG (Retrieval-Augmented Generation) has become a top-3 skill requirement as companies integrate LLMs into their products. Docker and Kubernetes show up in about a third of postings, reflecting the production focus of the role.
Beyond the core stack, employers increasingly want experience with experiment tracking tools (MLflow, Weights & Biases), feature stores, and vector databases. Fine-tuning experience is valuable but less common than you'd think from reading Twitter. Most production LLM work is RAG and prompt engineering, not fine-tuning. If you have both, you're in a strong position.
Companies that are serious about AI/ML hiring tend to post specific infrastructure details in the job description: the frameworks they use, their model serving stack, their data pipeline tools. Vague postings that just say 'ML experience required' without specifics are often companies that haven't figured out what they need yet.
Compensation Benchmarks
AI/ML Engineer roles pay a median of $212,000 based on 11,866 positions with disclosed compensation. Senior-level AI roles across all categories have a median of $228,700. This role's midpoint ($104K) sits 51% below the category median. Disclosed range: $89K to $120K.
Across all AI roles, the market median is $213,380. Top-quartile compensation starts at $264,148. The 90th percentile reaches $319,310. For comparison, the highest-paying categories include AI Safety ($253,100) and Research Engineer ($252,000). By seniority level: Entry: $110,408; Mid: $193,200; Senior: $228,700; Director: $272,250; VP: $235,000.
Invest Diva AI Hiring
Invest Diva has 1 open AI role right now. They're hiring across AI/ML Engineer. Based in Westport, CT, US. Compensation range: $120K - $120K.
Location Context
Across all AI roles, 6% (521 positions) offer remote work, while 8,351 require on-site attendance. Top AI hiring metros: New York (2,878 roles, $221,000 median); San Francisco (2,416 roles, $263,811 median); Los Angeles (1,340 roles, $210,000 median).
Career Path
Common paths into AI/ML Engineer roles include Data Scientist, Software Engineer, Research Engineer.
From here, career progression typically leads toward ML Architect, AI Engineering Manager, Principal ML Engineer.
The fastest path into ML engineering is through software engineering with a self-directed ML education. A CS degree helps, but production engineering skills matter more than academic credentials. Build something that works, deploy it, and measure it. That portfolio project is worth more than a Coursera certificate. For career growth, the fork comes around the senior level: go deep on technical complexity (staff/principal track) or move into managing ML teams.
What to Expect in Interviews
Expect system design questions around ML pipelines: how you'd build a training pipeline for a specific use case, handle data drift, or design A/B testing infrastructure for model deployments. Coding rounds typically involve Python, with emphasis on data manipulation (pandas, numpy) and algorithm implementation. Take-home assignments often ask you to build an end-to-end ML pipeline from raw data to deployed model.
When evaluating opportunities: Companies that are serious about AI/ML hiring tend to post specific infrastructure details in the job description: the frameworks they use, their model serving stack, their data pipeline tools. Vague postings that just say 'ML experience required' without specifics are often companies that haven't figured out what they need yet.
AI Hiring Overview
The AI job market has 8,943 open positions tracked in our dataset. By seniority: 175 entry-level, 4,132 mid-level, 3,268 senior, and 1,368 leadership roles (Director, VP, C-Level). Remote roles make up 6% of the market (521 positions). The remaining 8,351 roles require on-site or hybrid attendance.
The market median for AI roles is $213,380. Top-quartile compensation starts at $264,148. The 90th percentile reaches $319,310. Highest-paying categories: AI Safety ($253,100 median, 57 roles); Research Engineer ($252,000 median, 419 roles); AI Engineering Manager ($251,622 median, 51 roles).
Demand for AI/ML Engineers has been strong and consistent. Unlike some AI roles that spike with hype cycles, ML engineering is a foundational need. Every company deploying AI models needs people who can keep them running, and the gap between research prototypes and production systems keeps growing.
The AI Job Market Today
The AI job market spans 8,943 open positions across 16 role categories. The largest categories by volume: AI/ML Engineer (6,739), AI Product Manager (403), AI Software Engineer (402). These three account for the majority of open positions, though smaller categories often have higher per-role compensation because of specialized skill requirements.
The seniority mix tells a story about where AI teams are in their maturity. Entry-level roles (175) are outnumbered by mid-level (4,132) and senior (3,268) positions, reflecting that most companies are past the 'build a team from scratch' phase and need experienced engineers who can ship production systems. Leadership roles (Director, VP, C-Level) total 1,368 positions, representing the bottleneck between technical execution and organizational strategy.
Remote work availability sits at 6% of all AI roles (521 positions), with 8,351 requiring on-site or hybrid attendance. The remote share has stabilized after the post-pandemic correction. Senior and specialized roles (Research Scientist, ML Architect) are more likely to be remote-eligible than entry-level positions, partly because experienced hires have more negotiating power and partly because these roles require less hands-on mentorship.
AI compensation is structured in clear tiers. The market median sits at $213,380. Top-quartile roles start at $264,148, and the 90th percentile reaches $319,310. These figures include base salary with disclosed compensation. Total compensation (including equity, bonuses, and sign-on) runs 20-40% higher at companies that offer those components.
Category matters for compensation. AI Safety roles lead at $253,100 median, while Prompt Engineer roles sit at $141,440. The spread between highest and lowest-paying categories reflects the premium on specialized technical skills versus broader analytical roles.
The most in-demand skills across all AI postings: Python (1,422 postings), Aws (808 postings), Azure (638 postings), Rag (555 postings), Gcp (457 postings), Pytorch (433 postings), Claude (341 postings), Kubernetes (337 postings). Python dominates, appearing in the vast majority of role descriptions regardless of category. Cloud platform experience (AWS, GCP, Azure) is the second most common requirement. The newer entrants to the top skills list (RAG, vector databases, LLM APIs) reflect the shift from traditional ML toward generative AI applications.
Frequently Asked Questions
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