Executive Assistant / Operations Generalist

We’re looking for a highly capable, proactive Executive Assistant / Operations Generalist to join Sidebench and help our leadership and operations team execute faster.
This is not a traditional VA role where you wait for a list of tasks.
We’re looking for someone who can understand what needs to get done, take ownership, figure things out independently, and consistently remove work from the plates of the people around them.
If you’re the type of person who notices a problem, researches the solution, and comes back with “I handled it” rather than waiting for step-by-step instructions, we’d love to hear from you.

**About Sidebench**
- Los Angeles-based digital and technology consulting firm founded in 2012
- We primarily serve healthcare and other complex U.S. organizations
- Recognized by organizations and publications including Forbes, Inc., Fast Company, and the Webby Awards
- 15+ years of experience working with talented teammates in the Philippines
- 5-star employer rating on Upwork
- Small, entrepreneurial team where strong performers are trusted with meaningful responsibility


**What You’ll Do**
Your job is ultimately to make the people around you more effective.

Depending on the week, that may include:
- Taking ownership of administrative and operational tasks from our leadership and operations team
- Managing follow-ups and making sure action items actually get completed
- Coordinating meetings, schedules, documents, and internal communications
- Researching questions and presenting clear recommendations instead of simply forwarding information
- Supporting recruiting and staffing activities, including candidate research, interview coordination, and tracking
- Organizing information across Slack, email, documents, spreadsheets, and other systems
- Helping prepare meeting materials, summaries, trackers, and internal documentation
- Following up with teammates, vendors, candidates, and other stakeholders
- Identifying small but important tasks that can be taken off someone else’s plate
- Jumping into miscellaneous operational projects when something needs an owner
- Improving processes when you notice something inefficient, unclear, or falling through the cracks


**What We’re Looking For
Must-Haves:
- 3+ years of experience in executive assistance, operations, project coordination, project management, or a similar role
- Excellent written and spoken English
- Very strong organization and follow-through
- Comfortable managing several unrelated priorities at the same time
- Able to work independently without requiring detailed instructions for every task
- Strong research and problem-solving skills
- High attention to detail
- Good judgment — you know when to solve something yourself and when to escalate
- Comfortable communicating directly with senior team members
- Proactive mindset: you notice problems and opportunities before someone has to assign them to you
- Strong comfort with modern productivity and AI tools
- Must not have other clients as this is a full-time role
- Comfortable working significant overlap with U.S. business hours, which will generally mean evening hours in the Philippines


**Bonus Points**
Not required, but helpful:
- Graduate of a strong university with a solid academic record
- Formal executive assistant, operations, or project management training
- Experience working with U.S.-based executives or clients
- Experience at a digital agency, consulting firm, startup, or technology company
- Recruiting, candidate sourcing, or interview-coordination experience
- Experience creating SOPs, trackers, or operational systems
- Experience working remotely with distributed teams

**Compensation & Benefits**
- Starting: at least $1000/month or $5/hr (based on experience)
- Performance-based compensation reviews and opportunities for increases as your responsibilities grow
- Direct USD payments through Paypal — no agency markup
- Healthcare insurance stipend, Equipment stipend
- Additional benefits based on tenure and role

**Growth**
We’re deliberately looking for someone who can grow beyond the initial responsibilities of the role.
As you prove that you can independently own work, solve problems, and make the team more effective, you’ll have opportunities to take on increasingly important operational responsibilities.
Growth here won’t come simply from tenure. It will come from demonstrating that we can give you increasingly ambiguous and important problems and trust you to drive them to completion.

**Why This Role Is Different**
- You’ll work closely with Sidebench leadership and the operations team
- You’ll have visibility into many parts of how the company operates
- You’ll be trusted with real ownership rather than being limited to repetitive administrative work
- Strong performance will lead to broader responsibility
- You’ll work directly with a small team where excellent work is highly visible
- We’re looking for a long-term teammate, not short-term outsourced task support

**Timeline:**
We're looking to hire within 2-3 weeks
- First round: Application + Video interview responses
- Second round: Interview & may have working session with our EA (test compatibility)
- Final: Leadership Interview
Offer and background check