Senior Executive Assistant to the Founder & CEO - Fraser & Co. | RE/MAX Hallmark Fraser Group Realty Ltd. | 896 Brock Rd, Pickering (401 & Brock Rd, Closest Intersection: Bayly St & Brock Rd) (in-office) | Full-time, permanent
The Role
Fraser & Co. is a fast-growing boutique luxury real estate brokerage serving Durham Region, built and led by a founder with 25 years in the business. We are hiring a Senior Executive Assistant to support our Founder & CEO, Michelle Fraser, by running the administrative operating layer around her calendar, communications, deals, advisors, commitments, bookkeeping, and personal portfolio.
This is a true executive-support role. Your success is measured by how smoothly Michelle's day runs, how clearly priorities stay aligned, and how much capacity you create for her to focus on high-value work: protecting her focus and amplifying her impact.
What Makes This Seat Different
You will support a founder and top producer in a fast-moving, opportunity-driven business. This is founder-led tempo, not a committee-driven corporate rhythm: decisions are made quickly, opportunities are acted on the moment they appear, and priorities can shift fast, and the right person finds that energizing.
You'll work across many channels (email, WhatsApp, text, phone, and in person), sometimes with full context, sometimes with just the desired outcome. You consolidate the information, identify what matters, ask the one question that is genuinely necessary, and move. You can form a useful preliminary recommendation while being clear about what is known, what is assumed, and what still needs confirmation.
You notice implications, not just activity. When the CEO's availability, priorities, or circumstances change, you see what else is affected (clients, meetings, files, deadlines, travel, team coverage, and personal commitments) and act before each becomes a separate problem.
For the right person, this is the best seat in the company: real trust, owner-level responsibility, fast decisions, candid feedback, and work that matters every day. Candour works both ways, and respect for you, your time, and the boundaries agreed in writing is a commitment we honour.
What You'll Own
- Inbox, communications & gatekeeping: own the CEO's inbox and communication flow end-to-end. Triage, protect her focus, and escalate only genuine decisions. Every communication states what is needed, by when, and what happens next.
- Calendar, priorities & meeting readiness: protect selling and focus time, adapt smoothly to shifting priorities, catch conflicts early, and pre-stage every scheduled meeting with the relevant background, documents, and decision required.
- Anticipation & follow-through: track commitments, follow up proactively, surface risks early, and close every loop.
- Deal & transaction coordination: coordinate contracts, signatures, conditions, deadlines, and closing documentation with the appropriate registrants, lawyers, and advisors. Maintain complete, confidential files and prevent administrative delays.
- Bookkeeping & expense tracking: manage day-to-day bookkeeping across the businesses, including expenses, invoices, reconciliations, and clean records.
- Advisors, portfolio & personal logistics: track open legal, accounting, insurance, partnership, property, and corporate matters across multiple entities. Support appointments, renewals, travel, household scheduling, and other agreed personal logistics within clear privacy boundaries.
- Executive readiness: coordinate vendors, events, travel, and last-minute execution. When a new initiative arises, you make it executable quickly, with the right people informed, the calendar protected, and administrative steps handled smoothly.
How We Work
Initiative on execution; alignment on direction. Within agreed authority boundaries, you decide how to execute. You confirm alignment before acting on strategy, significant spending, legal risk, or key relationships. You bring a clear recommendation, not an open-ended question.
Learn before you improve. Our systems reflect 25 years of experience. You learn them first, execute them reliably, and then help refine them once the foundation is stable.
The first 90 days. You begin beside Michelle doing real EA work. Broader operational responsibilities (sales performance, recruitment, marketing operations, SOP ownership) may be added only after the core executive-support system is stable and any expanded scope is explicitly agreed.
You're the Right Person If
- You thrive in a dynamic, founder-led environment and enjoy supporting someone who moves quickly.
- You see implications, not just tasks, and anticipate needs before they're voiced.
- You bring recommendations, clarity, and solutions, not open loops.
- You are steady, composed, and professional in fast-moving situations.
- You are organized enough to absorb complexity and flexible enough to adapt without friction.
- You are curious, improvement-oriented, and bring a genuine “let's make this work” mindset.
- You have executive presence: clear, discreet, confident, and service-oriented.
- You communicate in outcomes and protect confidentiality absolutely.
- You're energized by being part of building something bigger and committed to the company's future, not just its day-today.
- You measure your success by the increased capacity of the executive you support.
Qualifications
- 5+ years supporting a senior executive or principal, or 3+ years directly beside a founder, business owner, or top producer in a similarly intense environment.
- Exceptional written and verbal communication. You will be tested on this during the hiring process.
- Strong systems skills across calendars, inboxes, spreadsheets, digital filing, and fast, accurate document preparation.
- Advanced technical proficiency: you diagnose and resolve technology issues (devices, applications, accounts, connectivity) quickly and independently, serving as the CEO's first line of technology support.
- Strong proficiency with our tool stack, including but not limited to: Google Workspace and Google Calendar, Zoom, Mac and iPhone, DocuSign, AI tools, Lone Wolf (bookkeeping), our CRMs (Follow Up Boss, SISU, Top Producer), and Ninety.io (EOS), or the proven ability to self-teach new platforms quickly with minimal assistance. This seat is plug-and-play: you arrive ready. Comfortable managing accounts and logins across business and personal matters with care and discretion.
- Hands-on bookkeeping ability (QuickBooks, Lone Wolf, or similar): comfortable with expense tracking, invoices, and reconciliations.
- Experience in real estate, another deal-driven sales environment is a strong asset.
- Post-secondary education is an asset, as are professional designations such as the CAP (Certified Administrative Professional) or PACE (Professional Administrative Certification of Excellence).
- A valid driver's licence and reliable vehicle is required.
- Absolute discretion with confidential financial, legal, business, and personal information.
Compensation, Hours & What We Offer
- $60,000 per year
- Extended health care, dental care, company events, and on-site parking
- Core hours are 9:00 a.m.–5:00 p.m., Monday–Friday, in office in Pickering. Supporting an active real estate business also means regular availability outside core hours for time-sensitive matters; this is a real part of the role, and one we're upfront about. Response expectations, coverage, and how additional hours are recognized will be set out in writing before employment begins.
Hiring Process & How to Apply
- 1. Apply by email to [email protected]: send your resume, a written response of no more than 200 words (questions below), and your completed Crystal Knows personality profile (https://www.crystalknows.com/disc-personality-test) (full PDF).
- 2. Conversation / Interviews: meet Michelle and members of the leadership team. You'll get a genuine feel for the pace and energy of the role.
- 3. Paid working audition: complete a compensated half-day simulation using realistic, anonymized materials, including an inbox to triage, a shifting calendar to rebuild, executive messages to draft, and a simulated deal file to organize. The exercise includes incomplete context, a priority change, and candid feedback so we can see how you reprioritize, communicate assumptions, and close loops.
- 4. References: where reasonably available, provide an executive, principal, or producer who directly observed your work.
Your written response (no more than 200 words) should answer three questions: (1) the fastest-moving executive, founder, or top producer you've supported, and the part you played in keeping their world running; (2) a time you noticed something an executive needed before they asked (what you saw, what you handled yourself, and the result); and (3) why a founder-led seat like this one is what you want next.
Pay: $60,000.00 per year
Benefits:
- Company events
- Dental care
- Extended health care
- On-site parking
Work Location: In person
