Executive Assistant / Business Operations

Bankey & Co; Washington (District of Columbia); On-site; USD 62,000 - 76,000; Full time

Job summary

Bankey & Co. is seeking a high-autonomy Executive Assistant / Business Operations partner to support a portfolio of growing technology companies.

You’ll own the coordination, follow‑up, research, and administrative work that frees senior leaders to focus on strategy and fundraising. Based in the DC area and about 20 hours per week, you’ll triage requests, keep multiple client engagements moving, manage calendars and invoicing workflows, and stand up better tools where needed.

Qualifications

• Judgment and problem‑solving ability to decide what needs to happen.
• Proactive, organized, and able to work with ambiguity.
• Experience supporting a founder, executive, or small business; tech startup familiarity preferred.
• Comfort with accounting systems and business tools.

Responsibilities

• Keep things organized and moving across multiple client engagements.
• Triage what needs attention vs. what doesn't and track commitments across companies.
• Coordinate directly with clients and their teams to resolve outstanding issues.
• Monitor invoicing and collections workflows and flag exceptions.
• Help stand up better tooling for inboxes and tasks across engagements.

Skills

Judgment

Proactive

Organized

Ambiguity tolerance

Startup experience

Tools

Accounting systems

Email management

Slack

Calendar management

Job description

Bankey & Co. is a fractional CFO and advisory firm working with a portfolio of early-stage and growing technology companies — providing financial leadership, strategic advice, modeling, fundraising support, and the day-to-day problem solving that comes with being CFO to several growing businesses simultaneously.

As the firm has grown, so has the coordination, follow-up, research, and administrative work surrounding that. This role exists to take ownership of that layer, so the firm's time and attention go where they create the most value.

This is also a way to be close to genuinely interesting, high-stakes startup work — fundraising, growth, the real decisions that determine whether a company survives — without betting a career on any single company's outcome. The variety and the exposure are part of what makes this role different from supporting one founder at one startup.

The Role

About Bankey & Co.

Bankey & Co. is a fractional CFO and advisory firm working with a portfolio of early-stage and growing technology companies — providing financial leadership, strategic advice, modeling, fundraising support, and the day-to-day problem solving that comes with being CFO to several growing businesses simultaneously.

As the firm has grown, so has the coordination, follow-up, research, and administrative work surrounding that. This role exists to take ownership of that layer, so the firm's time and attention go where they create the most value.

This is also a way to be close to genuinely interesting, high-stakes startup work — fundraising, growth, the real decisions that determine whether a company survives — without betting a career on any single company's outcome. The variety and the exposure are part of what makes this role different from supporting one founder at one startup.

The Role

This is a high-autonomy Executive Assistant / Business Operations role — not one built around completing a list of assigned tasks. It calls for someone who can take an objective, figure out what needs to happen, and run with it.

The role carries real visibility across the firm and its clients. The expectation is using that context to prioritize, anticipate needs, follow up on loose ends, and keep things moving without constant direction. Done well, this is the kind of role where something can be handed off and not thought about again.

What You'll Own

The work is primarily about keeping things organized and moving across several client engagements at once: triaging what actually needs attention versus what doesn't, tracking commitments across multiple companies so nothing slips between them, coordinating directly with clients and their teams when something's outstanding, and catching problems before they become problems.

A smaller piece involves the financial systems — mainly making sure integrations and connections are working correctly and flagging exceptions that need a closer look, and ensuring invoicing and collections stay on track. Financial literacy matters here because it allows independent judgment and context, not because the job is accounting.

What We’re Looking For

The most important qualification is judgment — someone who naturally asks "what needs to happen here?" rather than "what exactly was I told to do?"

That means proactive, organized, resourceful, comfortable with ambiguity, and comfortable making reasonable calls independently. Prior experience supporting a founder, executive, or small business is preferred — ideally at a tech startup, where the pace and the stakes will already feel familiar. Comfort with accounting systems and general business-tool fluency is a plus.

The bar here is genuinely high, on both sides. There's a clear structure to this role — it exists specifically to take things off Rob's plate, not to require his oversight to function — but it works best as a working relationship built on real trust and mutual respect, not one that needs constant managing in either direction.

This is also meant to be a long-term seat, for someone who wants to be genuinely good at this for years rather than treat it as a short-term stop.

How the Work Happens

Work generally happens in the tools where it already lives — email, Slack, calendar, phone calls, accounting systems, client systems — not a separate task-management layer built to prove activity. Part of this role will likely involve helping stand up better tooling for managing inboxes and tasks across multiple client engagements at once, so multi-client coordination doesn't mean logging into a dozen separate inboxes. Occasionally, something needs to happen in person, which is part of why this role is based in the DC area rather than fully remote.

At roughly 20 hours a week, the expectation isn't constant busyness — it's using that time where it creates the most leverage.

What This Role Isn't

Probably not a fit for someone who prefers waiting for detailed instructions, working strictly from a task list, approval at every step, or passing problems back to whoever assigned them.

What Success Looks Like

Over time, the operational details should require less and less oversight, because they're being handled reliably. A good rhythm looks like: what needs attention, what's already been taken care of, what's in progress, what's blocked and why, and what — if anything — is needed from Rob. Ideally, status updates aren't needed on things already owned.

Applying

Skip the generic cover letter — how you actually work matters more than a list of adjectives describing yourself.

Washington, DC area · Approximately 20 hours/week · $45–55/hour