Executive Assistant & Office Manager

Wide Open Ventures is looking for a full-time, high-trust Executive Assistant to the CEO and Office Manager to help our CEO stay focused on the highest-impact work — and to keep our internal operations running smoothly.

This role is ideal for someone who thrives in a fast-moving environment, has excellent judgment, and can confidently make decisions without needing constant direction.

This is a hybrid position. It is approximately 20-25 hours/week, with a compensation window of $50-60/hour. These hours can increase as our business grows.

Candidates must be within driving distance of Chicago, with an in-office expectation of 1–2 days per month for direct consultations with the CEO. They must also be available during daylight hours in Chicago.

Our team is committed to justice, equity, inclusion, and anti-racist behavior and practices. We encourage Black, Indigenous, Latinx, Asian, and those who hold other marginalized identities to apply.

• You’re comfortable in a start-up environment and can help shape your role from scratch.
• You can make decisions independently and prioritize confidently.
• You have strong instincts for what’s urgent, what can wait, and what the CEO needs to be successful.
• You’re comfortable and enthusiastic about integrating AI into workflows to improve speed, quality, and consistency.

We are looking for an Executive Assistant to the CEO and Office Manager to serve as the operational backbone for the CEO and the team. This role blends executive support (calendar, communications, preparation, travel) with office operations (coordination, onboarding, organization, and operational upkeep). The right person will bring calm, clarity, and follow-through — ensuring the CEO is supported, priorities stay on track, and the team has what they need to execute.

• Manage the CEO’s calendar and scheduling to protect time and priorities
• Triage inbound communication and help ensure timely follow-up on important items
• Coordinate travel and meeting logistics so the CEO is prepared and organized
• Prepare weekly schedules and meeting briefings to support decision-making
• Track key deadlines and follow-ups to keep work moving
• Support external coordination for speaking engagements and related logistics

• Coordinate onsite meetings and internal logistics
• Support retreat planning and occasional team travel coordination
  
  Assist with contractor coordination and operational documentation
• Support onboarding/offboarding and ensure smooth access/setup for team members
• Maintain clean internal organization, templates, and processes
• Support ordering and logistics for team needs and materials

• 3+ years of Executive Assistant and/or operations experience
• Strong background in executive support, including high-volume calendar and inbox triage
• Excellent judgment and prioritization skills
• Strong organizational skills and reliable follow-through on deadlines
• Comfortable using technology to improve workflows and solve operational problems
• Experience coordinating travel and logistics with accuracy and attention to detail
• Experience using the following tools:
• Travel management tools like Trip It (essential)
• Asana (nice to have)
• Social media management tools like Meta Business Suite (nice to have)
• Design tools like Canva or Photoshop (nice to have)

Wide Open Ventures is a small, fast-moving team that works at the intersection of strategy and emerging technology, with an orientation towards the credit union market. We care deeply about doing excellent work — and doing it in a way that supports our clients, our team, and our long-term mission.

Wide Open Ventures is a place for people who love great work: thoughtful, high-quality, and executed with urgency. We’re tech-forward, ambitious, and always learning — and we’re equally committed to being kind, collaborative, and reliable teammates. If you’re energized by that combination, please apply.