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HighView Partners
Senior ControllerHighView Partners • Winnipeg, Canada
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Senior Controller

Senior Controller

HighView Partners • Winnipeg, Canada
10 days ago
Job type
  • Full-time
Job description
Our client is a growing real estate investment and operating platform with a highly hands-on leadership team and a strong focus on operational execution, accountability, and long-term portfolio growth. This search is a chance to step into a meaningful Senior Controller role with broad operational exposure, executive visibility, and the opportunity to become a key finance member in a rapidly evolving organization.

Your New Employer Our client is a privately held, owner-led real estate organization with a growing residential and commercial portfolio spanning multiple entities and operating businesses here in Atlantic Canada. The business operates in a highly entrepreneurial environment where finance plays a central role in supporting operations, acquisitions, financing initiatives, and long-term strategic decision-making. The leadership team is collaborative, accessible, and deeply involved in the business, creating an environment where strong performers are trusted with responsibility and given meaningful exposure to the operational side of the organization.

This is not a heavily layered corporate environment where finance operates in silos. The organization values people who are hands-on, solutions-oriented, and willing to step into operational challenges as they arise. You'll work closely with experienced leaders and gain broad exposure across operational finance, treasury, lender coordination, forecasting, compliance, and business operations.

As the business grows, it's strengthening its financial infrastructure, creating a strong opportunity for someone who enjoys building processes, improving reporting clarity, and working closely with the business's decision-making side.

Your New Role As the Senior Controller, you will join the senior finance team and work closely with the CFO and executive leadership team to support financial management, operational finance activities, reporting, treasury support, and compliance for a growing real estate and multi-entity operating platform. This is a highly operational role designed for someone who enjoys solving business problems, navigating complexity, and working closely with leadership in a fast-moving entrepreneurial environment.

This role is not heavily focused on day-to-day transaction processing or basic month-end accounting. The organization already has a team supporting full-cycle accounting, month-end close activities, rent rolls, lender reporting, and property-level processing functions. Instead, the successful candidate will operate at a higher level across operational finance, cash management, forecasting, compliance oversight, and strategic accounting initiatives, working closely with the existing team.

A major focus of the role involves supporting cash management, liquidity planning, and forecasting activities in partnership with the CFO. The successful candidate will help lead cash forecasting processes, determine discretionary payment planning, support financing initiatives, and assist with lender reporting, refinancing deliverables, borrowing base reporting, and financing applications. This role offers more operational and treasury exposure than a traditional controllership role and would be a strong fit for someone who enjoys working closely with the business rather than focusing solely on financial reporting.

The role also includes direct interaction with banks, CRA, external accountants, consultants, and vendors, requiring someone who is comfortable managing external stakeholder relationships and leading compliance-related initiatives. Responsibilities will include overseeing HST reporting, payroll and WCB filings, year‑end coordination with external accountants, lender and CMHC compliance support, audit preparation, and broader operational accounting initiatives across the organization.

From an operational accounting perspective, you will oversee multi‑entity reporting and support the broader finance team in maintaining accurate and reliable financial information across the portfolio. The role includes exposure to CAM reconciliations, construction draw administration, construction‑in‑progress accounting, shared cost allocations, consolidations, and other higher‑complexity accounting matters requiring strong judgment and collaboration across the organization.

The successful candidate will also support budgeting and forecasting initiatives for both internal operational purposes and financing‑related activities, including acquisition integration and divestiture support as required. This role requires someone who can adapt quickly, prioritize effectively, and operate comfortably in an environment where priorities evolve and operational issues arise in real time.

The role is designed for someone who can grow into the CFO’s right hand over time and help strengthen the organization’s operational finance infrastructure.

What Sets You Apart You are a designated CPA with strong operational accounting fundamentals and experience operating within multi‑entity, real estate, construction, development, or entrepreneurial business environments. You are comfortable owning work end-to-end while moving between operational finance, compliance, treasury support, reporting, forecasting, and business problem-solving as priorities shift.

You likely bring approximately 7–10+ years of progressive accounting or finance experience, along with strong exposure to operational finance, forecasting, cash management, and multi‑entity accounting environments. Experience working closely with lenders, external accountants, the CRA, or on financing-related initiatives would be highly valuable, particularly in owner‑operated or fast-moving organizations.

You are collaborative, practical, resilient, and solutions-oriented. You enjoy rolling up your sleeves, navigating change, and helping businesses solve operational and financial challenges in real time. You are comfortable working with imperfect information, building structure where needed, and supporting leadership with timely and decision-ready financial insight.

Strong communication skills, sound judgment, and the ability to remain calm under pressure are essential in this environment, as the role requires ongoing collaboration with both finance and operational stakeholders across the organization.

Why Join? This role offers broader exposure than a traditional controller position and is a good fit for someone seeking operational finance leadership, meaningful ownership, and direct access to executive decision-making. The role provides exposure across treasury, cash forecasting, financing activities, lender coordination, operational accounting, budgeting and forecasting, construction administration, compliance oversight, and strategic business support.

For someone who enjoys working closely with the business and wants to move beyond narrow reporting responsibilities, this is an opportunity to become deeply involved in the operational and financial leadership of a growing, entrepreneurial organization. The right candidate will influence financial processes, support key business initiatives, and grow into a highly strategic finance leadership role over time.

The organization values people who are collaborative, accountable, and operationally minded, and leadership is looking for someone who wants to become an important long-term contributor within the business rather than simply filling a transactional accounting position.

Compensation The organization offers a competitive overall compensation package including base salary, performance-based bonus potential, comprehensive benefits, RRSP matching, professional support, and vacation. Compensation will be commensurate with experience, operational capability, and overall fit for the role and environment.

Additional Information This role is based in Halifax and requires strong in‑office collaboration, with most of the finance team working on‑site four to five days per week. Flexibility is available when needed for appointments, weather, or personal matters, but this is not intended to be a heavily hybrid or remote role.

This posting represents a confidential search. All inquiries and discussions will be handled with discretion. Artificial intelligence–based tools are not used in the screening or selection process for this role.

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Senior Controller • Winnipeg, Canada

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