About This Role Stone Owl Family Office is a leading provider of strategic financial solutions for businesses and high-net-worth individuals. We specialize in corporate tax planning, insurance strategies, and financial structuring to help our clients grow and protect their wealth. We are building a firm that values clarity, execution, and trust, and we are at a stage where founder leverage matters.

This role exists to multiply the effectiveness of our Co-Founder, reduce friction, and ensure priorities move from idea to execution without things slipping through the cracks. This is not a traditional administrative role. It is a high-trust, high-context, high-judgment position at the center of daily execution.

If you are looking for a highly structured role with narrow scope and clearly defined tasks, this may not be the right fit. This role requires comfort with pace, ambiguity, and independent judgment. If you thrive in fast-paced environments, enjoy responsibility, and take pride in being the person who keeps everything moving, you may love this role.

We are hiring a full-time, in-office Executive Assistant to directly the Chief Revenue Officer (CRO), who is also a Co-Founder of Stone Owl Family Office. The EA serves as the operational amplifier for the Chief Revenue Officer (CRO), acting as an execution partner responsible for managing priorities, protecting time, capturing follow-ups, and ensuring that important work actually gets done. You will have full visibility into CRO’s day-to-day activities and will be expected to anticipate needs, manage details proactively, and flag conflicts, trade-offs, or misaligned priorities and propose adjustments when needed.

This role is intentionally designed as founder-centric, with clear boundaries to prevent scope creep and protect sustainability. This position requires judgment, discretion, confidence, and speed. You will be trusted with sensitive information, exposed to real decision-making, and expected to operate with maturity and ownership.

What Success Looks

Like CRO, as Co-Founder, is focused on the highest-value work only they can do

Meetings result in clear follow-ups and action, nothing drops The role is working when the EA acts as operational gravity, slowing chaos without killing momentum

Priorities are protected, not overbooked

Work blocks are intentionally planned, monitored, and adjusted to support focus and follow-through

Materials are prepared, polished, and client-ready The pace stays high without chaos taking over

CRO is consistently prepared for firm events, with clear preparation, coordination, and follow-through Key Responsibilities Founder Support & Execution Own CRO’s calendar,



priorities, and daily flow, including coordination of professional and personal scheduling

Act as a gatekeeper of time, proactively managing scheduling, buffers, and trade-offs

Prepare for meetings and capture follow-ups, decisions, and next steps

Track commitments and ensure execution stays on course

Prompt, remind, and re-prioritize as needed to keep work moving

Coordinate CRO-related travel logistics when traveling for meetings, client visits, or events Relationship & Deal Support Coordination is performed in service of CRO’s execution, without assuming ownership of functional domains.

Attend meetings with deal owners to capture decisions, context, and next steps

Ensure tasks from meetings are clearly assigned and completed

Coordinate with internal team members and partners to gather inputs and move work forward

Proactively flag when inputs are missing and adjust plans accordingly

Serve as a reliable through-line across CRO’s work and priorities Inbox & Communications Support inbox management as context and trust are established

Draft and respond to communications where appropriate

Ensure timely follow-up and professional correspondence Materials & Presentation Support Turn rough inputs into polished, on-brand presentations and documents

Prepare client-ready materials using firm branding, fonts, and formatting

Support preparation of financial plans, decks, and meeting materials Event Support (Founder Focused) Support CRO’s preparation for firm events, including presentation readiness, materials, timing, and briefing

Ensure CRO is prepared, aligned, and positioned effectively for seminars and client-facing events

Coordinate inputs related to CRO’s role as required

Event logistics and operations are supported by other team members Office Presence Maintain a professional, client-ready office environment that supports focused execution and client experience This Role Is a Great Fit If You… Are confident managing up and comfortable raising concerns, surfacing trade-offs, and recommending adjustments when priorities compete

Are able to work productively with strong personalities while maintaining professionalism, calm, and clear boundaries

Thrive in fast-moving, high-context environments





Anticipate needs rather than waiting for instructions

Communicate clearly, directly, and calmly under pressure

Take pride in follow-through and execution

Are organized, detail-oriented, and adaptable

Enjoy being trusted with responsibility and ownership

Are comfortable exercising judgment without requiring constant reassurance or validation This Role Is Not a Fit If You… Prefer a slow, highly predictable pace

Need constant direction or reassurance

Avoid difficult conversations or setting boundaries

Are uncomfortable with ambiguity or changing priorities

Want a purely task-based or low-stakes admin role

Want a purely task-based or low-stakes admin role

Are seeking a role that includes personal errands, personal life management, or undefined ongoing responsibilities Required Experience & Skills 4+ years of experience as an Executive Assistant or in a senior administrative or operations role

Solid judgment, discretion, and professionalism

Excellent organizational and follow-through skills

High comfort with calendars, email, and task management

Strong written and verbal communication Preferred / Assets Familiarity with CRM systems (e.g., HubSpot or similar platforms) for documentation and follow-through support (not sales operations ownership)

Experience working in a professional services, advisory, insurance, or family office environment

Exposure to client-confidential, regulated, or trust-based settings

Comfort working with sensitive financial, client, or deal-related information, and supporting documentation, follow-up, and context tracking

Comfort working with sensitive financial or personal information

Experience supporting founders, executives, or principals in high-context roles

Comfort creating or polishing presentations and client-facing documents Compensation & Structure Salary: $85,000–$105,000 CAD, depending on experience and scope

Employment: Full-time employee

Location: In-office (Vancouver) What make us a great place to work At Stone Owl, we offer a dynamic and growth-oriented environment where strategic thinking and client-focused solutions drive everything we do. As part of our team, you’ll collaborate with experienced professionals in tax planning, financial structuring, and corporate benefits, gaining valuable insights into high-level financial strategies. We provide opportunities for professional development, leadership, and the ability to make a meaningful impact on businesses across Canada.

If you’re looking for a role where you can grow, innovate, and help clients navigate complex financial landscapes, Stone Owl is the place for you.

📌 Executive Assistant to Co-Founder (Full-Time) (Vancouver)
🏢 Stone Owl Family Office
📍 Vancouver