CFO (Strategic Finance) - Toronto/Salt Lake City/NYC, Direct Hiring

About the Company

This organization is an investment and operating group focused on acquiring and scaling established software businesses with strong growth potential. It operates across multiple verticals, including HR technology, fleet telematics, asset management, e-health, document management, and other specialized software niches.

The company is backed by experienced investors and advisors with a track record of building and scaling software businesses in the $10M–$100M ARR range. It operates with a long-term mindset, focused on sustainable value creation over decades.

About the Role

We are seeking a Chief Financial Officer (CFO) to act as a strategic partner to the CEO, with a primary focus on capital markets, financing strategy, and transaction execution.

This is not a traditional operational CFO role. The company already has a well-established finance function responsible for accounting, FP&A, reporting, and day-to-day financial operations.

Instead, this role sits at the center of the company’s growth strategy, with responsibility for:

• Structuring and executing equity and debt financing
  
• Leading complex financial negotiations
  
• Driving capital allocation decisions across the portfolio
  
• Managing relationships with investors and lenders
  
Supporting restructuring initiatives when required

This is a high-impact, high-visibility position suited for a professional who thrives at the intersection of strategy, capital, and execution.

Candidate Profile

The company is at an early stage of a long-term growth journey. This role is ideal for someone who is not seeking a steady-state finance leadership position, but rather an opportunity to actively shape how a growing software holding platform scales and deploys capital.

The ideal candidate brings:

• A proven track record in raising capital (equity, debt, or both)
  
• Deep expertise in financing structures (LBOs, structured credit, earn-outs, etc.)
  
• Strong experience negotiating with investors, lenders, and counterparties
  
• A clear perspective on capital allocation across multiple business units
  
• Comfort operating in lean, fast-paced environments
  
• The ability to translate complex financial strategies into clear narratives
  
• Strong understanding of SaaS business models and key metrics (ARR, NRR, LTV/CAC, Rule of 40)
  

Key Responsibilities

Capital Raising & Financing

• Lead end-to-end equity and debt fundraising processes
  
• Structure financing solutions to support acquisitions and organic growth
  
• Evaluate funding alternatives to optimize cost of capital and flexibility
  
• Build and maintain relationships with lenders, investors, and capital providers
  
• Oversee debt covenants and lender reporting obligations
  

Investor Relations

• Serve as the primary point of contact for investors
  
• Lead investor communications and periodic reporting
  
• Manage equity-related processes (shares, options, warrants, etc.)
  
• Prepare materials for board meetings and investor updates
  

Capital Allocation & Strategic Finance

• Partner with the CEO to define capital allocation strategy
  
• Evaluate investment opportunities, returns, and deal structures
  
• Develop financial models and scenario analyses
  
• Monitor portfolio performance and proactively identify risks and opportunities
  

Restructuring & Corporate Development

• Lead or support restructuring initiatives when necessary
  
• Evaluate strategic alternatives (refinancing, divestitures, recapitalizations)
  
• Identify early warning signals within portfolio companies and define action plans
  

M&A Support

• Support acquisition evaluation and deal structuring
  
• Contribute to post-acquisition financial integration
  

Governance & Oversight

• Ensure strong governance, internal controls, and compliance frameworks
  
• Act as liaison with auditors, tax advisors, and legal partners
  
• Collaborate with the existing finance leadership without duplicating responsibilities
  

Requirements

• 10+ years of experience in investment banking, private equity, corporate development, or capital markets-focused CFO roles
  
• Demonstrated success in executing financing transactions (debt and/or equity)
  
• Strong M&A experience (structuring, negotiation, due diligence)
  
• Deep understanding of SaaS and recurring revenue models
  
• Experience managing financial oversight across multiple business units
  
• Excellent communication skills with investors and stakeholders
  
• Hands-on, execution-driven mindset
  
• High integrity, strong judgment, and long-term orientation