Assistant Operations Manager
Top Benefits
About the role
HOMESEEKER VACATION HOMES
Role: Assistant Operations Manager
Waterfront cottage short-term rental management · Muskoka / Georgian Bay / Parry Sound / Lake Simcoe, Ontario
Homeseeker Vacation Homes manages a growing portfolio of premium waterfront cottage rentals across Ontario's lake country. We handle everything for cottage owners — guest experience, pricing, housekeeping, maintenance, and revenue — so their properties earn well and run smoothly. We are scaling, and we are looking for the person who will own how our operation runs day to day.
This is a senior, standard-setting role. You will be the person who makes sure our guests get fast, correct, caring service every time, that our properties are maintained, and that our team hits its standards whether or not the founder is in the room. If you are an experienced operator who takes pride in things running properly — and who wants real ownership rather than a task list — read on.
What you'll own
Service standard & SLAs. You will be accountable for guest and owner response times across the portfolio, holding the team to defined service-level standards (guest responses in minutes, owner responses within the hour) and stepping in when they slip. Operations & triage. Guest issues, property problems, and same-day recovery. You will build and run the triage process so nothing falls through the cracks — and so it works when you are off, not just when you are on. Revenue execution. You will run our daily pricing using our documented playbook and tools (PriceLabs), executing clear rules and flagging the exceptions that need a strategic call. Revenue strategy stays with leadership; disciplined daily execution is yours. Turnovers & maintenance. Housekeeping turnovers, maintenance coordination, and vendor follow-through — making sure every property is guest-ready, every time. Team & accountability. You will lead a small team, hold them to standards with fairness and consistency, document what works, and raise the bar over time.
Who you are
Experienced operator. You have run short-term rental, property management, hospitality, or comparable service operations — and you have held other people to a standard, not just done tasks yourself. High standards. You are the person who notices the small thing that's off and fixes it. Slow or sloppy guest responses genuinely bother you. Systems-disciplined. You are comfortable running defined processes and tools precisely — following an if-this-then-that playbook exactly, and knowing when something is an exception that needs escalation. Reliable & self-driving. The operation runs on your watch whether or not the founder is checking. You take ownership rather than waiting for direction. Calm under pressure. You can have the direct-but-kind conversation when someone misses a standard, and keep the relationship intact.
Nice to have
Direct experience with PriceLabs, Hospitable, Turno, or similar STR tooling. Familiarity with the Ontario cottage / Muskoka market. Experience covering multiple time zones or working with a distributed team.
The details
Reports to: Founder, working alongside our Operations Lead.
Type: Part Time with options for Full Time after probation
Location: Remote / On Site Muskoka
Compensation: Salary + Performance Bonus (Real ownership and growth as the portfolio scales.)
How to apply
Because response speed, care, and communication are the heart of this role, we ask every applicant to send a short (2–3 minute) video or voice recording answering:
(1) Tell us about an operation you were responsible for — what standard did you hold, and how did you enforce it? (2) How would you measure your performance for this role? (3) Why this role?
Applications without a voice or video answer will not be considered — this is our first test of the exact skills the role requires.
Homeseeker Vacation Homes · cottage memories. together. · www.homeseekervacation.com
Not the right fit? Search for Assistant Operations Manager jobs in Toronto, Ontario, Canada
Similar Jobs
Assistant Operations Manager
Top Benefits
About the role
HOMESEEKER VACATION HOMES
Role: Assistant Operations Manager
Waterfront cottage short-term rental management · Muskoka / Georgian Bay / Parry Sound / Lake Simcoe, Ontario
Homeseeker Vacation Homes manages a growing portfolio of premium waterfront cottage rentals across Ontario's lake country. We handle everything for cottage owners — guest experience, pricing, housekeeping, maintenance, and revenue — so their properties earn well and run smoothly. We are scaling, and we are looking for the person who will own how our operation runs day to day.
This is a senior, standard-setting role. You will be the person who makes sure our guests get fast, correct, caring service every time, that our properties are maintained, and that our team hits its standards whether or not the founder is in the room. If you are an experienced operator who takes pride in things running properly — and who wants real ownership rather than a task list — read on.
What you'll own
Service standard & SLAs. You will be accountable for guest and owner response times across the portfolio, holding the team to defined service-level standards (guest responses in minutes, owner responses within the hour) and stepping in when they slip. Operations & triage. Guest issues, property problems, and same-day recovery. You will build and run the triage process so nothing falls through the cracks — and so it works when you are off, not just when you are on. Revenue execution. You will run our daily pricing using our documented playbook and tools (PriceLabs), executing clear rules and flagging the exceptions that need a strategic call. Revenue strategy stays with leadership; disciplined daily execution is yours. Turnovers & maintenance. Housekeeping turnovers, maintenance coordination, and vendor follow-through — making sure every property is guest-ready, every time. Team & accountability. You will lead a small team, hold them to standards with fairness and consistency, document what works, and raise the bar over time.
Who you are
Experienced operator. You have run short-term rental, property management, hospitality, or comparable service operations — and you have held other people to a standard, not just done tasks yourself. High standards. You are the person who notices the small thing that's off and fixes it. Slow or sloppy guest responses genuinely bother you. Systems-disciplined. You are comfortable running defined processes and tools precisely — following an if-this-then-that playbook exactly, and knowing when something is an exception that needs escalation. Reliable & self-driving. The operation runs on your watch whether or not the founder is checking. You take ownership rather than waiting for direction. Calm under pressure. You can have the direct-but-kind conversation when someone misses a standard, and keep the relationship intact.
Nice to have
Direct experience with PriceLabs, Hospitable, Turno, or similar STR tooling. Familiarity with the Ontario cottage / Muskoka market. Experience covering multiple time zones or working with a distributed team.
The details
Reports to: Founder, working alongside our Operations Lead.
Type: Part Time with options for Full Time after probation
Location: Remote / On Site Muskoka
Compensation: Salary + Performance Bonus (Real ownership and growth as the portfolio scales.)
How to apply
Because response speed, care, and communication are the heart of this role, we ask every applicant to send a short (2–3 minute) video or voice recording answering:
(1) Tell us about an operation you were responsible for — what standard did you hold, and how did you enforce it? (2) How would you measure your performance for this role? (3) Why this role?
Applications without a voice or video answer will not be considered — this is our first test of the exact skills the role requires.
Homeseeker Vacation Homes · cottage memories. together. · www.homeseekervacation.com
Not the right fit? Search for Assistant Operations Manager jobs in Toronto, Ontario, Canada