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.Â
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.Â
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
Experience & Skills
Required
- 4+ years of experience as an Executive Assistant or in a senior administrative or operations role
- Strong 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.
