Job Description

About the Job

Title: Chief of Staff – Executive Operations

Location: Remote (US, Eastern or Central time zone)

Type: Full-time (W-2) or Part-time contractor (1099)

Compensation: $75,000–$95,000 annually (full-time) or $42–$55/hour (part-time, ~20 hours/week)

Start: March / April 2026

About Serve Freight

Serve Freight is a high-reliability logistics operator specializing in complex freight execution for mid-market shippers and project-driven industries. We manage transportation, warehousing, and value-added logistics programs for companies that cannot afford missed delivery windows, broken communication, or unreliable carriers. We are scaling fast in 2026 and building the operational infrastructure to support it. This role is part of that buildout.

The Role

We are hiring a Chief of Staff – Executive Operations to serve as the CEO’s operational right-hand, owning the day-to-day rhythm of the business so the CEO can focus on the things only he can do.

This is not a traditional Executive Assistant or operations management position. It is a hybrid role that combines structured operational ownership with cross-functional coordination, process ownership, and real decision-making authority.

You are the person who keeps the CEO out of the weeds. You own the recurring operational cadence, drive accountability on tactical priorities, and make the calls that would otherwise sit in a queue waiting for approval.

50% of your time will be structured operational ownership. 50% will be dedicated to cross-functional problem-solving, process improvement, and team coordination.

What You Will Do

Executive & Calendar Management

• Manage the CEO’s calendar: scheduling, rescheduling, conflict resolution

• Triage and prioritize the CEO’s inbox

• Coordinate travel logistics

• Prepare meeting agendas, pre-reads, and follow-up action items

Data, Dashboards & Financial Support

• Pull and format weekly operational dashboards from Turvo, QuickBooks, and HubSpot

• Run down accounts receivable discrepancies and flag issues

• Prepare financial summaries and talking points for leadership meetings

• Support the company’s strategic advisor with slide deck preparation and data pulls

Process & SOP Ownership

• Draft and maintain internal SOPs for recurring operational processes

• Document workflows across departments as they are formalized

• Research and recommend operational tools within defined budget parameters

• Integrate approved tools into existing workflows

Operational Problem-Solving

• Investigate and resolve operational issues across departments before they reach the CEO

• Triage which priorities you can own directly vs. what needs to be escalated

• Reschedule initiative timelines when circumstances change

• Coordinate with internal team members across operations, accounting, and brokerage

Decision-Making Authority

This role carries real decision-making responsibility within defined boundaries. You will not be waiting for approval on every task.

You will decide: which tools to investigate, which software to select within budget, how to reschedule internal timelines, how to triage and route requests, and how to resolve calendar conflicts.

You will escalate any commitments to external parties, expenditures above the threshold, changes to sales or pricing, and strategic or partnership decisions.

Who You Are

• 5–8 years in operations, chief of staff, or executive support roles at a growing company (under 50 employees preferred)

• Comfortable wearing multiple hats and operating across departments without waiting for a playbook

• Can make decisions without perfect information; does not freeze with ambiguous direction

• Strong written communicator: SOPs, slide decks, and emails without heavy editing

• Data-literate: can pull and present operational and financial data without being an analyst

• You think like an owner, not a task-taker

Tools You Will Use

Turvo (TMS), QuickBooks Online, HubSpot (CRM), Google Workspace, Slack, Notion, Excel/Sheets. You do not need to be an expert in all of these on day one, but you should be comfortable learning quickly.

What Success Looks Like

At 30 days: The CEO has measurably more free time. Recurring tasks are transferred and running on schedule.

At 60 days: You are proactively resolving issues before they reach the CEO. You have recommended or implemented at least one process improvement.

At 90 days: The CEO feels like you are an extension of himself. Internal stakeholders engage with you directly. Minimal oversight needed.

What This Role Is Not

• Not a calendar-only EA role

• Not a system administrator or IT role

• Not a sales or business development role

• Not a strategic advisory role -- but your judgment and recommendations will directly shape how we operate

How to Apply

Submit an application on LinkedIn and send a short note (not a cover letter) to hello@servefreight.com with the subject line: Chief of Staff - Executive Operations - [Your Name]

Answer these three questions:

• Tell us about a time you made a decision on behalf of an executive. What was the situation, what did you decide, and what happened?

• Describe a process you built or improved at a previous company. What was broken, what did you change, and what was the result?

• Give an example of a time you had to figure something out with almost no direction. How did you approach it?

No form letters. No AI-generated cover letters. We read every response.

Job Tags

Similar Jobs