Executive Assistant, Pioneer Fund

Pioneer Fund is a venture capital firm built by Y-Combinator alumni to invest in the world’s most promising early-stage startups. With over 450 YC founders in their network, they offer capital and founder-first support to hundreds of emerging companies every year. They’re a team that runs on strong systems, clear communication, and things running smoothly behind the scenes. That’s where you come in.

How You’ll Make an Impact

As Jason’s Executive Assistant, you’ll be the behind-the-scenes force that keeps the team focused, organized, and ready for anything. From managing a packed inbox and untangling calendar chaos to coordinating investor follow-ups and special projects, you’ll bring calm, clarity, and momentum to every day. You’ll also get exposure to broader operational workflows and investor communications in a dynamic venture environment.

What You’ll Own

• Daily scheduling, inbox management, travel planning, and task flow for Jason
• Superhuman inbox triage: flagging, responding, and following up to keep things moving
• CRM updates: logging investor notes, updating contacts, ensuring clean data
• Special projects and internal initiatives in Notion
• Coordination with a hybrid + remote team across time zones
• Drafting polished investor follow-ups, internal notes, and summaries
• Admin support for fundraising workflows and investor relations

You Might Be a Fit If…

• You’re Toronto-based and thrive with a mix of in-person and independent work
• You’re a natural systems-builder who loves organization and operational excellence
• You’re a clear, proactive communicator who gets context quickly and asks smart questions
• You’ve thrived in fast-paced environments where you juggle priorities with ease
• You care deeply about getting the details right – follow-through is your superpower
• You’re curious about venture capital and eager to learn how the industry works

Logistics & Details

• Location: Toronto, hybrid (Yonge & Eglinton)
  
• Hours: Full-time, ~8am–5pm ET preferred
  
• Tools used: Notion, Superhuman, Airtable, GSuite
  

Reporting to: Jason Gray, Founding & Managing Partner

We understand, accept, and value the differences between people of different backgrounds, genders, sexual orientations, ages, beliefs, and abilities. We are happy to make any accommodations you may need throughout the interview process. We aim to create an inclusive environment and encourage diverse individuals to apply.

We’d love to hear from you – even if you don’t meet 100% of the requirements! Send a note to ashley@artemiscanada.com if you or someone you know is interested!