Executive Administrative Partner

Pioneer Square Labs (PSL) is a startup studio and early-stage venture capital fund building the next generation of software companies in the Pacific Northwest. We partner with exceptional entrepreneurs to rigorously develop, validate, and—if needed—kill startup ideas with speed and clarity. The best ideas receive meaningful investment, development support, and the momentum to become category-defining companies.

Over the past 9 years, we've tested over 450 ideas and launched 40+ companies. Our success is powered by a team of engineers, designers, operators, and marketers who are entrepreneur-obsessed, radically collaborative, and relentless in their pursuit of great outcomes. At PSL, we value curiosity, good judgment, and operational excellence—and we have a strict No Jerks policy.

About the Role

We are seeking an exceptional Executive Administrative Partner to support the Managing Directors of our Startup and Venture Studios. This is not just an administrative role—it’s an opportunity to become an indispensable partner in our fast-moving, high-stakes environment.

You will serve as a connector across the organization, anticipate needs before they arise, and bring a proactive-to-a-fault mindset to everything you do. You’ll be surrounded by passionate builders and will play a key role in keeping our operations seamless and our leaders focused.

This full-time, in-office role is based in Seattle, WA.

Key Responsibilities

Executive Support

• Manage complex calendars, prioritizing with good judgment and flexibility
• Coordinate seamless domestic and international travel
• Prepare briefings and follow-ups for meetings with founders, investors, and senior leaders
• Own expense reporting, purchase requisitions, and tracking deliverables
• Keep communication crisp and timely across leadership and stakeholders
• Stay a step ahead—identifying gaps and solving problems before they surface

Organizational Operations

• Plan and execute internal events, team offsites, and all-hands with a collaborative spirit
• Ensure the PSL office reflects our entrepreneur-obsessed, high-standard culture
• Support in-office operations, from space planning to guest experience
• Streamline administrative workflows and propose thoughtful process improvements
• Embrace curiosity—ask questions, seek context, and share learnings

Cross-functional Collaboration

• Build strong, no-ego relationships across teams and with external partners
• Work closely with the Managing Directors on strategic projects and high-priority initiatives
• Drive cross-functional efforts to completion—staying accountable and communicative
• Use good judgment to prioritize what matters and challenge assumptions with confidence
  
  

Minimum Qualifications

• 4+ years of executive administrative support experience, including:
• Calendar and travel management
• Expense reporting and confidentiality handling
• Strong organizational skills and high attention to detail
• Proactive mindset and ability to work with autonomy
• Excellent written and verbal communication
• High EQ, impeccable discretion, and no-jerks DNA
• Ability to thrive in a fast-paced, ever-changing environment
• Tech-savvy—proficient in G Suite, Slack, and productivity tools
• Seattle-based and energized by in-person work
  
  

Preferred Qualifications

• BA/BS degree or equivalent experience
• Prior experience supporting senior executives in startups, VC, or professional services
• Track record of managing strategic projects end-to-end
• Comfort with international time zone coordination
• Experience with event planning
• Naturally inquisitive and curious about everything, always
  
  

Why You’ll Love It Here

At PSL, you’ll work with brilliant, kind people who value collaboration over competition. You’ll play a key role in supporting the next generation of startup founders and help build things that matter. We’re here to solve big problems—together, and with heart.

PSL provides the following benefits for regular, full-time employees: 

• Medical, dental, vision, EAP and life insurance.  Employee premiums are covered at 100% and dependent premiums are covered at 75%
• Long and Short-term disability coverage fully paid for by PSL
• Self-managed paid time off
• Commuter benefit of either a fully subsidized ORCA pass or a parking spot (value up to $300/month)
• Once weekly lunch deliv