Job Description

About Picnic Capital

Picnic Capital is a Calgary-based private investment firm focused on long-term value creation through real estate development, construction, and strategic expansion into new industries. Through our operating companies, Highpoint Developments and Highpoint Construction, we are building multi-family residential and mixed-use communities that deliver lasting value to residents, investors, and partners.

As a family office and private equity platform, Picnic Capital owns, operates, and actively evaluates businesses across a range of industries. Our growth strategy is built on disciplined financial management and entrepreneurial vision--identifying new investment opportunities, structuring transactions, and supporting portfolio companies to achieve sustainable success.

As we enter an exciting phase of expansion, Picnic Capital is seeking a Chief Financial Officer (CFO) to lead financial strategy, operations, and capital management across all entities. This role will play a pivotal part in guiding our diversified real estate development and construction group while strengthening our expanding private equity portfolio. The CFO will ensure financial clarity, scalability, and strategic direction as we continue to grow and invest in purposeful ventures that create enduring impact.

Job Summary

As Chief Financial Officer of Picnic Capital, you will set the financial direction of the family office while playing a hands-on role in overseeing the financial performance of Highpoint Developments and Highpoint Construction, a rapidly growing developer and builder with a robust pipeline of multi-family residential projects across Western Canada.

You will operate at the intersection of capital strategy and operations, providing leadership across capital structuring, acquisitions, development financing, and long-term portfolio optimization. This dual focus offers the unique opportunity to combine high-level strategic influence with tangible impact on landmark real estate projects.

As a key member of the executive leadership team and a strategic partner to the CEO, the CFO will oversee financial management across multiple divisions including construction, real estate development, and private equity, ensuring financial clarity, scalability, and alignment with organizational growth. You will lead capital planning, manage banking and investor relationships, oversee accounting operations, and develop systems to support sustainable expansion and value creation.

Responsibilities

Strategic Financial Leadership

Partner with the CEO to define and execute Picnic Capital's long-term financial strategy and growth plan. Lead capital structure planning, including equity raises, joint ventures, debt financing, and investment partnerships. Provide financial insight to support real estate project selection, investment decisions, and portfolio performance. Oversee consolidated financial planning and reporting across all entities within the family office. Establish and monitor key financial metrics and dashboards to ensure visibility into project and portfolio health. Support M&A, divestitures, and portfolio management within the private equity group. Serve as a trusted advisor to the CEO and executive team, providing data-driven recommendations on opportunities, risks, and strategic direction.

Financial Operations & Controls

Lead and mentor the finance team, including the Controller and accounting staff. Establish and maintain strong internal controls, accounting policies, and audit readiness. Oversee preparation of monthly, quarterly, and annual financial statements across entities. Manage cash flow forecasting, budgeting, and variance analysis. Ensure accurate project-level reporting, job costing, and WIP management. Implement and optimize financial systems (ERP, job costing, and reporting dashboards). Create scalable processes to support rapid growth and multi-entity reporting.

Development & Construction Finance

Oversee project financing, draw management, and funding requisitions for all active projects. Manage relationships with banks, lenders, investors, and JV partners to secure and maintain favorable financing terms. Lead financial due diligence, feasibility analysis, and pro forma modeling for new developments and acquisitions. Structure and negotiate financing and capital stack arrangements for real estate projects. Monitor project budgets, variances, and cash flows to ensure alignment between operations and finance. Oversee financial aspects of construction operations, including subcontractor payments, lien management, and insurance coverage.

Private Equity & Portfolio Oversight

Develop consolidated financial reporting and performance tracking for portfolio companies. Evaluate new investment opportunities, capital deployment strategies, IRR/ROI performance, and exit scenarios. Lead financial due diligence, transaction structuring, and integration for acquisitions or divestitures. Partner with portfolio company leadership to optimize operations, performance, and cash flow. Monitor portfolio results and provide recommendations on resource allocation and value creation.

Relationship Management & Leadership

Build and maintain strong relationships with lenders, capital markets, and equity partners. Represent Picnic Capital and Highpoint with professionalism in negotiations with investors, auditors, and government agencies.Present financial results, insights, and forecasts to the CEO, ownership group, and investors. Lead investor and board presentations, translating complex financial data into clear strategic insights. Foster a culture of collaboration, accountability, and continuous improvement within the finance function. Act as a bridge between operations and capital partners to ensure alignment on performance and long-term objectives.

Qualifications

Education & Credentials

CPA designation is an asset but not required. MBA, CFA, or other advanced financial designations are considered assets.

Experience

10-20 years of progressive finance leadership experience, with at least 5-7 years in an executive role (CFO, VP Finance, or equivalent). Extensive experience in real estate development, construction, or private equity environments. Proven ability to manage multi-entity structures, consolidations, and complex capital structures. Strong background in project finance, real estate pro formas, and capital markets. Track record of structuring and negotiating debt facilities, equity partnerships, and joint ventures. Experience building financial systems and processes in growth-stage organization.

Technical Skills

Proficiency in ERP/accounting systems (Sage, Viewpoint, Yardi, Procore, or similar). Advanced Excel modeling, forecasting, and financial analysis skills. Knowledge of tax planning, compliance, and corporate structuring across entities.

Leadership Attributes

Strategic thinker with strong commercial and entrepreneurial instincts. Exceptional communication, negotiation, and relationship-building skills. Hands-on, collaborative leadership style with a high sense of accountability. Confident operating in a fast-paced, entrepreneurial, and evolving environment.
Job Type: Full-time

Work Location: In person