Remote: Standard working hours are 6:00 AM - 3:00 PM EST. Additional hours may be required based on business needs, with workloads occasionally exceeding 50 hours per week.
Executive Operations Assistant
Remote | Eastern Time Hours | Full-Time | Reports to CEO & Head of Operations
About The Company
Our Client is an Operational Awareness platform that helps multi-location operators see what's really happening inside their retail stores. We have a team of AI-assisted human analysts who review existing in-store camera footage and record what we call Observed Data. By combining POS data with this Observed Data, we reveal the hidden friction, coaching opportunities, and revenue leaks that traditional reporting misses.We allow owners to monitor every store as if they were standing on the shop floor themselves.
About The Role
We are looking for a high-energy, highly organized Executive Operations Assistant to help the founders run the company with more speed, focus, and accountability.
This person will work directly with the CEO and Head of Operations across the entire business. The main goal is simple: free up founder time while making sure important work keeps moving.
This is not a traditional assistant role focused only on calendars and inboxes. This is an execution-heavy operations role inside a fast-growing startup.
You will help manage customer and pilot cadence, support operations, coordinate analyst workflows, track follow-ups, push accountability across the sales pipeline, and build the processes we need as it scales.
The right person is proactive, assertive, organized, resourceful, and energized by startup ambiguity. We want someone who sees what needs to happen, communicates clearly, and drives work forward without waiting to be told every step.
What You'll Do
Manage the company's operating rhythm across founders, customers, pilots, analysts, and internal projects.
Help ensure we maintain a regular cadence of meetings and touchpoints with pilots and customers.
Schedule customer check-ins, prepare agendas, capture notes, and track follow-up items through completion.
Support the creation of customer success materials, pilot updates, WINS reports, and operational summaries.
Coordinate with our overseas analyst team to make sure daily reviews are completed accurately and on time.
Help review customer-facing reports for accuracy, quality, and clarity.
Help troubleshoot operational issues involving camera reviews, VMS access, reporting delays, and internal handoffs.
Push accountability on sales pipeline follow-ups, next steps, meeting notes, and internal ownership.
Maintain internal trackers, dashboards, SOPs, checklists, and project plans.
Use AI tools to improve documentation, communication, workflows, meeting prep, and internal execution.
Help turn messy founder-led processes into repeatable systems.
What Success Looks Like
The CEO and Head of Operations have more time to focus on growth, product, and higher-level customer work.
Customer and pilot meetings happen consistently.
Follow-ups do not fall through the cracks.
Sales pipeline next steps are clearly tracked and pushed forward.
Analyst issues are documented, escalated, and resolved faster.
Customer-facing reports and updates are more organized and reliable.
Internal processes become cleaner, more repeatable, and easier to manage.
feel more buttoned-up without becoming slow or corporate.
Who You Are
You have at least 5 years of experience in executive support, operations, customer success, project management, business operations, startup operations, or a similar high-ownership role.
You are energetic and proactive.
You are not passive. You do not wait quietly for direction.
You are comfortable pushing busy founders, teammates, vendors, and customers for clarity and next steps.
You communicate frequently and clearly.
You are highly organized and can manage many moving pieces at once.
You are comfortable working inside ambiguity and creating structure where none exists.
You are detail-oriented without being slow.
You are resourceful and willing to figure things out.
You are comfortable using AI tools to work faster and smarter.
You can operate across customers, operations, sales support, reporting, documentation, and internal coordination.
Required Skills
5+ years of relevant professional experience.
Excellent written and verbal English communication.
Strong organization, follow-through, and attention to detail.
Experience managing calendars, meetings, agendas, notes, follow-ups, and project trackers.
Comfort working directly with executives or founders.
Comfort communicating with customers and internal teams.
Ability to work during Eastern Time business hours.
Experience with tools like Slack, Google Workspace, spreadsheets, CRMs, project management tools, or similar systems.
Ability to create and maintain SOPs, checklists, and internal documentation
Nice to Have
Startup experience.
Customer success experience.
Operations or revenue operations experience.
Experience working with offshore or distributed teams.
Experience supporting sales pipeline tracking or CRM hygiene.
Comfort reviewing reports, data, and operational workflows.
Experience using AI tools like ChatGPT, Claude, Gemini, or similar platforms.
This Role Is Not For Someone Who
Needs constant direction or reminders.
Waits for others to notice problems.
Is too passive or too quiet to push work forward.
Gets overwhelmed when priorities change.
Only wants calendar management or repetitive admin work.
Avoids customer communication.
Avoids operational details.
Prefers a polished corporate environment with fixed responsibilities.
Summary
This role is for someone who wants to be close to the center of a growing startup and help the founders move faster.
You will not be asked to “do sales,” but you will help make sure sales, customer success, operations, and internal follow-ups stay organized and accountable.
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