Location: Remote, based in Canada. Core hours must overlap with Pacific Time.

Reports to: Head of Taskforce Delivery, with a dotted line to the Founder & CEO

Compensation: $75,000 - 90,000K CAD Annual

Type: Full time

About Day1

Day1 is an embedded execution partner for founder-led companies where growth has outpaced the operating model. We do not hand over a strategy deck and leave. We embed alongside our clients and execute the plan. We are a small, fast, AI-enabled, senior team, and we hold ourselves to the same operating discipline we bring to clients.

The Role

This role runs two things at once: the leadership team's time, and the cadence and reporting rhythms that keep the Day1 client portfolio current. You keep calendars, meetings, client-facing documents, and correspondence moving for our leaders. You also own the reporting cycle, keeping every engagement's picture accurate and on schedule. You carry several client contexts at once, anticipate what is coming, and close gaps before anyone has to ask.

What You Will Own

- Calendar command. Own complex, multi-leader calendars across time zones. Anticipate conflicts, make the judgment calls, and coordinate directly with stakeholders to keep things moving.
- Meeting coordination. Run logistics for internal and client meetings end to end: scheduling, agenda prep, briefing materials, and the details in between.
- Portfolio reporting. Own the weekly project status and financial reporting cycle. Pull from multiple source files, check every figure and date for accuracy, and get client-ready reports out on schedule.
- Action follow-up. Track deliverables and deadlines across engagements. Chase owners with context, confirm each task has met its definition of done, and raise a slipping date early, while there is still room to fix it.
- Project mobilization. Stand up new engagements end-to-end: the tracker, the folders, and the project record, so the team starts ready.
- Client-facing documents.



Prepare polished documents and presentations that reflect well on the leaders and the firm.
- Inbox and correspondence. Manage priorities and incoming requests across channels. Draft, route, and follow up on behalf of firm leaders with professionalism and speed.
- Event and offsite logistics. Coordinate team events and client offsites as they come up.
- Confidentiality, always. Handle sensitive information with utmost discretion.

A Week in the Role

You work lean, and because you run the systems well, the output looks like more than one person's. In a recent week you might have:

- Reconciled the time data, built the status and budget-versus-actuals drafts, checked every figure, and had client-ready reports out before the Friday cutoff.
- Rebuilt a leader's week after a client meeting ran long, resequencing three other calls without anyone having to ask.
- Caught a task marked complete before the handoff had landed, flagged it with context, and got it reopened before it reached the client.
- Mobilized a new engagement in a day, with the tracker, folders, and project record stood up before the internal kickoff.
- Drafted and sent a batch of client correspondence on a leader's behalf, in a tone no one could tell wasn't theirs.

What We Are Looking For

- Experience supporting a C-suite or a founder in a fast-paced environment.
- Confident in owning a reporting cadence where accuracy is non-negotiable.
- AI-native. We expect you to use AI to do more in a day than the role used to allow. We also expect you to know when it's wrong,



and to be the one who fixes it.
- Exceptional organization and time management, with the ability to juggle competing priorities across multiple leaders.
- Strong written and verbal communication: polished, professional, and concise.
- Proven ability to handle sensitive and confidential information with discretion.
- Proactive, resourceful, and comfortable operating with ambiguity and minimal direction.
- Solid attention to detail and follow-through. This role runs on accuracy.
- A real sense of urgency. You move without being chased.
- Grit. You stay with a messy problem until it is sorted.
- Composed and effective under pressure.
- Tools & Software:
- Claude, ChatGPT
- Zoom, Wispr, Granola
- Project management tools - Smartsheet, Asana, Linear, or Notion
- Proficiency in Google workspace
- Able to navigate M365/Sharepoint when needed

Preferred Experience and Education

- 3-5 years of experience in a consulting, professional services, or scale-up setting.
- Post-secondary education in business administration or a related field.
- A project management certification (PMP or equivalent) is an asset, not required.

Why Day1

Day1 is a boutique execution partner built for builders. We help companies scale with clarity by bringing structure to chaos and momentum to good ideas. You will join a small, senior team with experience across industries and a shared drive to solve real problems for our clients.

Working at Day1 means

- Partnering with fast-growing companies and founders who value sharp thinking and strong execution.
- Working across industries and business problems. No two projects look the same.
- Learning from a team of experienced operators, analysts, and consultants.
- Having flexibility in how and where you work.

How to Apply

Please apply to the Executive Assistant role on our website by visiting day1.co/careers

📌 Executive Assistant (Canada)
🏢 Day1
📍 Canada