Founder’s Office Lead & Operations Integrator
Owner’s Representative / Senior Management / Operations & Growth
Monster Property Services / Monster Plowing Company is hiring a serious operator to work directly with ownership and help drive the company forward across operations, sales, office, field teams, customer service, winter snow, summer landscaping, staffing, marketing, and internal projects.
This is not a normal office job. This is not a simple admin role. This is not a clean corporate 9-to-5.
This is a senior management role inside a fast-moving service company where things change quickly, problems come from every direction, and the right person needs to create structure where structure does not yet exist.
We are looking for someone who can become a true extension of ownership over time.
The right person will be able to understand priorities, remember details, organize chaos, push accountability, communicate clearly, earn respect across the company, and make sure important work actually gets done.
About Monster
Monster is an established property services company operating in snow and ice management, landscaping, maintenance, commercial property services, field operations, sales, customer support, and internal technology systems.
In the winter, we are an emergency service business. When snow and ice events happen, the company may operate around the clock. In the summer, we run a busy landscaping and property maintenance operation with crews, trucks, equipment, customers, schedules, and constant moving parts.
This is real operations. It is fast, practical, seasonal, demanding, and sometimes messy.
We need someone who can handle that reality and help lead through it.
What This Role Really Is
This is a founder’s office, operations, leadership, and accountability role.
You will work directly with ownership and management to help connect the dots across the company. You will not simply take notes or pass messages. You will be expected to understand what matters, organize priorities, follow up with people, identify blockers, escalate problems, and push work forward until it is complete.
You may be in a leadership meeting one hour, checking on a customer issue the next, reviewing sales follow-up, calling a manager, visiting a yard, helping organize staffing, reviewing internal priorities, or stepping into an operational problem that needs immediate attention.
If the company needs you in the office, you are in the office. If the company needs you on-site, you go on-site. If the company needs you to check a yard, meet a customer, ride with a crew, inspect a property, or help solve a field issue, you do it.
This role is for someone who wants responsibility, not comfort.
Key Responsibilities
- Work directly with ownership to understand company priorities, decisions, concerns, and direction
- Translate ownership priorities into action items, owners, deadlines, and follow-ups
- Drive accountability across office, sales, operations, field teams, customer service, marketing, HR, and internal projects
- Attend meetings, capture key decisions, assign next steps, and follow up until work is complete
- Track open issues, blockers, customer concerns, staffing gaps, operational risks, and unfinished work
- Support managers by clarifying priorities, removing confusion, and pushing execution
- Represent ownership professionally and firmly when following up with staff, managers, customers, and vendors
- Help ensure important tasks do not get lost, forgotten, delayed, or buried
- Support sales, account management, customer follow-up, and business development when required
- Assist with customer escalations, site visits, proposals, internal communication, and operational planning
- Help organize systems, processes, reporting, task tracking, and company communication
- Identify weak points in the business and help turn them into clear action plans
- Operate comfortably between office, field, customer, management, and ownership environments
- Step into practical work when required to help the company get through the day
Who You Are
- You are a serious, high-capacity person with strong personal discipline
- You naturally create order from chaos
- You remember details and follow up relentlessly
- You can earn respect from managers, office staff, field workers, customers, and ownership
- You can communicate firmly without being reckless
- You have strong people skills, but you are not afraid of hard conversations
- You can lead people who are busy, stressed, distracted, or resistant
- You can handle pressure, urgency, conflict, and changing priorities
- You can take direct feedback and keep moving
- You can challenge ownership respectfully when something does not make sense
- You can work independently without needing constant structure
- You are willing to work within the ranks and earn credibility through action
- You are not above basic work when the operation needs help
- You are mentally and physically capable of working inside a real service business
- You want to become a key person in the company, not just hold a title
This Role Is Not For You If
- You need every day to be predictable
- You need a perfectly structured corporate environment
- You are uncomfortable with pressure or urgency
- You avoid conflict, accountability, or difficult follow-up
- You only want strategy and do not want execution
- You are unwilling to get involved in field or operational issues
- You need a narrow job description
- You are looking for a fully remote role
- You do not want to be held accountable for results
- You are uncomfortable dealing with strong personalities
- You are not willing to earn authority through performance
Experience That May Fit
- Operations management
- Chief of staff / founder’s office support
- Executive assistant to an owner/operator
- Project management
- Construction coordination or management
- Snow, landscaping, property services, or facilities operations
- Dispatch or logistics management
- Hospitality or restaurant management
- Property management operations
- Sales management or account management
- Field supervision
- Small business management
- Emergency services, military, logistics, or other high-pressure operational environments
- We are less concerned with a perfect resume and more concerned with capacity, judgment, toughness, communication, memory, follow-through, and ability to drive results.
Requirements
- Strong written and verbal communication skills
- Valid G-class driver’s licence
- Ability to travel locally for office, yard, site, client, and operational needs
- Strong computer and software skills
- Comfortable with spreadsheets, CRM systems, task management, communication platforms, and internal software
- Ability to work in a fast-moving environment with incomplete information
- Ability to follow up firmly and professionally
- Ability to handle confidential ownership and company information
- Strong judgment, discretion, and emotional control
- Willingness to support both office and field operations when required
- Alignment with a seasonal business that includes winter emergency service demands
Schedule and Availability
This is a full-time senior management role with a base expectation of approximately 44 hours per week.
This is not a standard corporate 9-to-5 role.
Winter storms, ice events, customer emergencies, peak operating periods, staffing issues, and business priorities may require flexibility outside standard business hours. The right person must understand that Monster operates as an emergency winter service business and a busy summer landscaping and property services company.
Availability, responsiveness, and operational flexibility are important parts of this role.
Compensation and Benefits
- Expected salary range: $80,000 to $100,000 per year, depending on experience, capability, and demonstrated fit.
- Vacation pay: 4% vacation pay paid on each regular paycheque.
- Paid vacation: Two weeks of paid vacation per year, subject to scheduling approval and operational requirements.
- Benefits: Eligible for the company’s standard group benefits package following the applicable probationary / eligibility period.
- Company vehicle available for approved company use, site visits, client meetings, yard visits, and operational requirements.
- For an exceptional candidate, compensation structure may be discussed.
First 90 Days
In the first 90 days, success will look like:
- Learning how the company operates across winter, summer, sales, office, field, and customer service
- Building trust with ownership, managers, office staff, and field leaders
- Creating clear task tracking and follow-up rhythms
- Improving visibility on what is stuck, late, unclear, or falling through the cracks
- Helping ownership stay connected to the real operating picture
- Taking messy priorities and turning them into organized action
- Proving that you can follow through without needing constant supervision
- Showing that you can handle pressure, people, and operational reality
Why This Role Matters
- The company is growing, and ownership needs a serious person who can help drive execution.
- There are sales opportunities to chase, managers to support, customers to serve, staff issues to resolve, systems to improve, field problems to understand, and priorities that need to become completed work.
- This role exists to make sure the important things move.
- The right person will become a trusted operator inside the company — someone who can help lead, organize, challenge, follow up, and keep Monster moving forward.To ApplyPlease send your resume and a short note answering the following questions:
- Tell us about a time you took a messy situation, organized it, and drove it forward. What did you do, and what was the result?
- Tell us about a time you had to lead or influence people who did not report directly to you. How did you get them moving?
- Tell us about a time you had to stand up to a strong personality, owner, manager, or client. What happened?
Applications without thoughtful answers may not be prioritized. We may use technology, including AI-supported tools, to help review applications and support our hiring process. Final hiring decisions are made by our team. Thank you!
Job Types: Full-time, Part-time
Pay: $80,000.00-$100,000.00 per year
Benefits:
- Company car
- Company events
- Dental care
- Disability insurance
- Extended health care
- Flexible schedule
- On-site parking
- Paid time off
- Vision care
Application question(s):
- Do you have a valid Ontario G-Class Driver’s License?
- Are you legally authorized to work in Canada?
- How would you rate your comfort level using new software tools such as CRM systems or proposal platforms?
- Are you comfortable working in a hybrid environment (mix of in-office, remote, and field-based work)?
- What interests you most about this position and our company?
Education:
- Bachelor's Degree (preferred)
Language:
Work Location: In person
