Ready To Hire Your First Executive Assistant, Office Manager, or Chief of Staff?

A friendly guide for new businesses expanding their office footprint.

This year, San Francisco has seen one of the largest comebacks in commercial office space rentals. The “A.I. boom” and the return to the office for many others signal that downtown, the lively, chaotic, caffeine-fueled version we know and love is coming back to life. With that return comes a very real and very pressing question for growing companies: Who is going to keep this place running smoothly once you move into that shiny new office space?

For many, that means hiring a senior administrative professional, an Executive Assistant, Office Manager, or even a Chief of Staff, to oversee the day-to-day while supporting leadership. But here’s the catch: this can be a very slippery slope if not thought through carefully. Missteps here can lead to burnout, turnover, or a mismatch so glaring that you’ll wonder how it all went sideways.

As a recruiting firm that’s been around since 1976, we’ve seen it all: the dot-com boom and bust, the financial crash, the rise (and fall) of open office plans, and now the A.I. wave reshaping how companies think about productivity. Through every cycle, one truth remains: hiring the right senior admin. support at the right time is often the quiet make-or-break decision for a growing company.

So, before you start crafting that job description or tapping your network, here are the big questions to tackle:

1. Immediate needs compared to the future.

It sounds obvious, but this is the step most companies rush through. Are you drowning in scheduling, vendor management, and office logistics? Or is it more about supporting your leadership team with strategy, research, and investor relations? An Office Manager who thrives at handling facilities and culture-building might not be the same person who can ghostwrite board decks and coordinate international travel.

Make a list of the five biggest pain points you want solved today. If you’re not clear, your hire won’t be either.

2. Experience, and in what industry?

An Executive Assistant from a Fortune 500 might have impeccable polish but could struggle in a scrappy start-up where systems don’t exist yet. Conversely, someone who’s brilliant at scaling chaos into order may feel restless in a large, process-heavy company. Think about the environment you’re in and the type of industry background that will help your new hire hit the ground running. For some start-ups, it’s more about the eagerness and "can-do, make it work" personality type than traditional experience.

3. How will this role evolve over time?

Here’s where many early-stage companies get tripped up. You may hire someone to manage your office logistics today, but six months from now, that same person could be overseeing a team of admins or even grow into a Chief of Staff role. Ask yourself: Will you want this person to grow alongside you, or will the job always be more tactical than strategic? Your answer will shape the profile of who you should hire, and help you avoid turnover when the role shifts.

4. Balance between responsibilities and reporting.

Administrative leaders often juggle multiple hats, supporting executives directly, managing facilities, leading junior staff, and sometimes even dabbling in HR or finance. Be realistic about how much one person can (and should) carry. The clearer you are about which responsibilities matter most, the better your chances of hiring someone who can sustain the role long term.

And don’t forget reporting structure: will they answer to the CEO, COO, or the entire executive team? If so, how do you divide their priorities? Lack of clarity here can create frustration for both the hire and your leadership team.

5. Competitive salary and benefits.

Here’s a secret we’ll let you in on after nearly five decades in this business: talented administrative professionals know their worth. If you want someone who can keep your executives organized and run the office like a well-oiled machine, you’ll need to pay competitively, both in salary and benefits. Benchmark against others in your industry, and remember that underpaying here usually leads to faster burnout and higher turnover (which will cost you more in the end).

6. Culture fit and representing your brand.

Your Executive Assistant or Office Manager isn’t just running schedules or ordering supplies. They’re the face of your company to visitors, new hires, and often your clients. Hiring someone who aligns with your company’s culture and values will pay off tenfold. A great culture carrier can strengthen morale and create a welcoming environment that reflects your brand.

A Word from Experience

During the dot-com boom of the late ‘90s and early 2000s, companies rushed to hire without truly defining what they needed. We watched as talented Executive Assistants and Office Managers burned out under the weight of unclear expectations or left for companies that valued their work properly. The smartest firms learned quickly: clarity, structure, and fair compensation were the keys to both retention and growth.

Fast-forward to today, and the lessons still apply. San Francisco may be buzzing again with new energy, but the fundamentals of building a sustainable team haven’t changed.

Final Takeaway

Call us. At Alan J. Blair Personnel, we know hiring your first Executive Assistant, Office Manager, or Chief of Staff isn’t just about filling a role; it’s about setting the foundation for how your company operates and grows. Take the time to define the scope, think about the future, invest in the right person, and integrate them into your culture.

Done well, this hire can become one of the most valuable players on your team, quietly ensuring your company’s success through every boom, bust, and beyond.