Executive Assistant, Chief of Staff, or Operations Manager: Which to Hire First

Most founders should hire an executive assistant first. An executive assistant takes the calendar, inbox, travel and meeting follow-ups off the founder within weeks, and that frees the hours a founder needs to decide what a chief of staff or operations manager would even own. Hire those two once priorities or processes, not logistics, are the bottleneck.

What does each role actually own?

An executive assistant owns the founder's time, a chief of staff owns the founder's priorities, and an operations manager owns a recurring business process. The three titles get mixed up because all three "take things off the founder's plate," but the plate is different in each case, and so is the person you need to hire.

Read the last row first. Many bad hires in this area start with a founder who named the role before naming the problem.

How do you know which role your company needs first?

A founder can tell which role to hire first by tracking one normal week in half-hour blocks and labeling each block. Hours lost to scheduling, email and prep point to an executive assistant. Hours lost to chasing team decisions point to a chief of staff. Hours spent fixing the same process again point to an operations manager.

Use these labels on the week:

1. Logistics: scheduling, rescheduling, travel, expenses, finding documents, writing routine replies.
2. Coordination: asking leads for status, re-explaining decisions, preparing the weekly leadership meeting, writing investor updates.
3. Firefighting: stepping into fulfillment, vendor problems, staffing gaps or billing errors that recur.
4. Founder work: selling, hiring senior people, product calls, fundraising, strategy.

Here is a hypothetical. A founder of a 25-person services company logs a week and finds 14 hours of logistics, 6 of coordination and 5 of firefighting. The executive assistant is the obvious first hire, because those 14 hours come back within a month. If the numbers were reversed, with most of the week spent firefighting the same scheduling process, an operations manager would come first and an assistant would only make the founder better organized while the process kept breaking.

Most founder-led companies under a few dozen people land in the first pattern. Logistics grows quietly with every new customer, hire and meeting, and founders tend to underestimate it until they write it down.

What does a chief of staff do that an executive assistant doesn't?

A chief of staff runs the founder's agenda across the company. The chief of staff decides what goes to the leadership meeting, writes the decision log, follows up with department leads until the work ships, and prepares board material. An executive assistant schedules that leadership meeting and takes the notes; the chief of staff owns what happens after it.

The difference shows up in three places:

• Authority. Leads answer to a chief of staff on deadlines the founder set. Nobody answers to an executive assistant except vendors and calendars.
• Inputs. A chief of staff needs context on strategy, finances and people problems. An executive assistant needs access to the inbox, calendar and documents.
• Output. A chief of staff produces finished projects and decisions. An executive assistant produces a founder who shows up prepared, on time, with nothing dropped.

A chief of staff hired too early has nothing to run. With five people, there is no leadership team to coordinate, so a chief of staff drifts into the inbox and calendar work and becomes an expensive executive assistant. The useful signal is a leadership team of four or more people who each wait on the founder for decisions.

When does an operations manager come before either?

An operations manager comes first when the founder's week is spent repairing the same business process: late deliveries, crews double-booked, invoices sent wrong, vendors chased by hand. In that company the bottleneck sits in the process, and an executive assistant would organize the founder around a problem that keeps recurring.

Home service companies, ecommerce brands and agencies often hit this point before they need help with the founder's calendar. The founder may not even have a busy calendar; the phone is the problem. An operations manager writes down how the process should run, assigns the steps, picks the tools and reports on the numbers.

A simple test: if you took a two-week vacation, would the business stall because nobody can answer for you (assistant or chief of staff), or because a process breaks without you watching it (operations manager)?

Can one hire cover two of these roles?

One hire can cover an executive assistant role plus light operations work, and that combination is common in small companies. An experienced executive assistant can run vendor relationships, manage a shared inbox for the team, own a simple hiring pipeline and keep the project tracker current. Covering chief of staff work as well usually fails.

The combination that fails is chief of staff plus calendar. The urgent work, a meeting to move or a flight to rebook, always wins over the important work of following up on decisions. If you want an assistant to grow toward chief of staff over a year or two, plan the handoff: add a second assistant or move the calendar to a part-time role when the first one starts running leadership meetings.

For the executive assistant hire itself, start with a clear first month. Our guide to what a CEO's executive assistant should own in the first 30 days lays out the responsibilities and KPIs. Then set up access, SOPs and inbox rules before day one so the person is useful in the first week.

What does each role cost?

An executive assistant is the least expensive of the three in the US. The BLS reports a May 2025 median annual wage of $76,590 for executive secretaries and executive administrative assistants, against $50,980 for all occupations. Chief of staff and operations manager pay varies by company size and industry and usually sits higher.

Cost changes the order less than founders think. An executive assistant who returns 10 or more hours a week pays for the role through the founder's time; a chief of staff hired before there is a team to coordinate costs more and returns less. Many founders also look at remote hiring for the assistant role, since an assistant who works your hours from Latin America can do nearly all of the job. The remote executive assistant role covers calendar and inbox work in your time zone. If that is where you are leaning, you can interview pre-vetted executive assistants now and keep the chief of staff decision for later.

How Remote Latinos can help

If you are still deciding between these roles, the first conversation with Remote Latinos is a 30-minute call to map the role, the tools and the hours, which is a good place to test whether you need an assistant or an operator. Once you choose, the executive assistant keeps your hours from Latin America and sits in on your standups. When the week log points to an assistant, start a search for an executive assistant.

Frequently asked questions

What is the main difference between an executive assistant and a chief of staff?

An executive assistant manages the founder's time: calendar, inbox, travel, meeting prep and follow-ups. A chief of staff manages the founder's priorities across the company, which means running the leadership meeting, chasing decisions and owning projects that no department owns. The executive assistant protects hours; the chief of staff turns decisions into results.

Can an executive assistant become a chief of staff?

Yes, and it is a common path. An executive assistant who already sits in every leadership meeting and tracks every open decision knows the company well. The move works when the assistant shows judgment on business tradeoffs and when someone else takes over the calendar and inbox work.

Do I need an operations manager if I already have an executive assistant?

You need an operations manager when the problems are in recurring processes, such as fulfillment, vendor management, scheduling crews or billing, and nobody owns them. An executive assistant supports one person. An operations manager owns a process and the people or vendors who run it.

How much does a US executive assistant earn?

The BLS reports a May 2025 median annual wage of $76,590 for executive secretaries and executive administrative assistants. For comparison, the median for all occupations was $50,980.

Sources

• BLS Occupational Outlook Handbook: Secretaries and administrative assistants