Senior Executive Assistant to the CEO

Senior Executive Assistant to the CEO

Remote | Full-Time

Compensation: $80,000 – $120,000, depending on experience

About Honest Digital

Honest Digital is an 80-person, fully remote digital marketing agency in the automotive vertical.

We’ve won Best Large SEO Agency two years in a row, made the Inc 5000 three years running, earned multiple campaign awards, and were named an Inc Best Workplace in 2026.

We’re also building a new software platform with significant potential, along with a few other important growth initiatives. We’ve been around long enough to have real momentum, but we still believe we’re early in what we’re building.

About the Role

We’re looking for a sharp, senior Executive Assistant to work closely with the CEO and help him operate with more clarity, focus, and follow-through.

This is not a calendar-only EA role.

Yes, you’ll help with inbox, calendar, scheduling, reminders, meeting prep, communication, and follow-up. But the bigger need is someone who can help create structure around the CEO’s business life: the ideas, projects, open loops, loose ends, decisions, and priorities constantly moving through the company.

The CEO is a fast-moving founder with a lot of initiatives in motion. He needs someone who can take scattered inputs and make them feel clear, clean, and manageable.

This role has some Chief of Staff elements, but it is still grounded in executive support and execution. You’ll be a trusted right hand who helps the CEO protect his focus, organize his thinking, move key priorities forward, and keep important things from slipping through the cracks.

This is not for someone who needs the CEO to hand them a perfect system. You should be able to help build the structure: the trackers, rhythms, categories, follow-ups, decision lists, and operating habits that make the CEO easier to support and the work easier to move.

What You’ll Do

• Manage and organize the CEO’s inbox, calendar, reminders, meetings, notes, and follow-ups.
• Capture open loops, ideas, commitments, and action items.
• Create structure around the CEO through simple systems, trackers, decision lists, weekly briefs, and follow-up rhythms.
• Turn vague or half-formed ideas into clear next steps.
• Categorize projects by priority, owner, deadline, status, and decision needed.
• Follow up with internal team members, vendors, partners, candidates, attorneys, and other stakeholders.
• Help move projects forward when the CEO is unavailable or focused elsewhere.
• Lead or own certain projects and key initiatives from start to finish.
• Prepare concise summaries, briefs, recaps, and recommendations.
• Help the CEO decide what should be active, delegated, deferred, escalated, or removed.
• Protect the CEO’s focus and tactfully push him when he is the bottleneck.

You may help coordinate work across marketing, sales, hiring, legal/vendor follow-up, internal operations, product/platform initiatives, and other strategic projects.

You do not need to be the CEO, COO, attorney, product owner, or department head. But you do need to be able to gather context, organize the work, identify what matters, coordinate the right people, and keep things moving.

Who You Are

You have a good head on your shoulders.

You are smart, organized, conscientious, resourceful, and trustworthy. You have strong judgment, good taste, and clear communication. You can sense when something is unclear, overcomplicated, poorly written, under-thought, or not quite good enough.

You bring a calm, steady presence to fast-moving work. You can move quickly without becoming frantic, create structure without becoming rigid, and push for clarity without creating friction.

You are comfortable with ambiguity and do not need every step handed to you. You can listen to a messy thought, spot what matters, ask the right questions, and help shape it into something useful.

You are not just someone who follows structure. You create it in a way that feels simple, useful, and easy for others to adopt.

You like being close to important work, but you are also willing to do the unglamorous follow-through that makes important work actually happen.

You’ll Be a Strong Fit If

• You’ve supported a founder, CEO, owner, or senior executive before.
• You are excellent at organizing and closing open loops.
• You can create structure where none exists yet.
• You can turn vague ideas into clear action plans.
• You are comfortable managing up and respectfully challenging a senior leader.
• You can lead or coordinate special projects with good judgment.
• You write clearly and can adapt to someone else’s voice.
• You work well with executives, operators, vendors, attorneys, internal team members, and external partners.
• You like making messy things feel clear, calm, and manageable.

This Is Not a Fit If

• You want a role that is mostly calendar, inbox, and travel support.
• You need the CEO to give you a fully built system before you can be effective.
• You need predictable tasks every day.
• You need step-by-step instructions before you can begin.
• You avoid hard follow-up, unclear ownership, or uncomfortable bottlenecks.
• You are uncomfortable with ambiguity.
• You struggle to push back when it is needed.
• You want a pure strategy role without admin, coordination, or follow-through.

Requirements

• 6+ years in a senior Executive Assistant, Executive Operations, Strategic Projects, Project Manager, Chief of Staff associate, or similar role.
• Direct experience supporting a founder, CEO, owner, or C-suite executive.
• Strong project coordination experience across multiple stakeholders.
• Excellent writing, synthesis, and communication skills.
• Experience in a fast-moving remote or distributed environment.
• Strong judgment, discretion, and ability to handle confidential information.
• Comfort with tools like Google Workspace, Slack, ClickUp, HubSpot, Notion, Airtable, or similar platforms.
• Comfort & proficiency using AI tools to support research, drafting, synthesis, and workflow creation is a plus.

Compensation & Benefits

This is a full-time, remote role.

Compensation: $80,000 – $120,000, depending on experience.

Benefits include:

• 100% covered Medical
• 100% covered Dental
• 100% covered Vision
• 401k matching (up to 4%)
• Continuing education stipend
• Birthday PTO Day (because no one should have to work on their birthday)
• Holiday, Vacation, Sick PTO

Exceptional candidates may be considered above range.

How to Apply

Please apply with your resume and a short note answering the questions below. Email your application to [email protected] with the subject line “Senior Executive Support Role”.

No generic cover letters, please. We care much more about how you think and how you can create clarity rather than whether you can write a formal cover letter.

In your note, please answer:

1. Why does this role sound like a good fit for how you naturally work?
2. Tell us about a time you helped a founder, CEO, or senior leader turn several ideas, open loops, or different priorities into something organized and actionable. What did you do?
3. Imagine the CEO has 25 open loops across legal, marketing, sales, hiring, vendors, and internal projects. Many have no owner, no deadline, and no clear next step. What would you do in your first week to create structure?
4. Tell us about a time you had to respectfully push back on an executive or senior leader. What happened?

Optional: If you’d like, you may include a 2 - 3 minute Loom or video introducing yourself and explaining why this role caught your attention (or you can answer the above questions via Loom instead as well). This is not required, and written answers are perfectly fine.

We are looking for clear thinking, good judgment, strong writing (or speaking), and evidence that you can create structure without needing every step handed to you.

If you do apply in the above manner, your application will be directly reviewed by a human being (we’re not running these applications through an AI screener with an auto-responder).