Chief Operating Officer Remote Jobs in Toronto, ON

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Position Overview:

The Director of Corporate Development reports to the CFO and owns the company's inorganic growth agenda: the acquisition pipeline from origination through evaluation and post-close integration coordination, and the routes that reach the same ends without a purchase, including strategic alliances, joint ventures, and major commercial partnerships. The role also partners with the CFO on long-term strategy and on debt and equity financing. The role's center of gravity remains sourcing and screening: building a disciplined flow of qualified targets and ensuring that every opportunity reaching the leadership team arrives with its financial consequences fully understood.

Diligence in this role extends beyond the financial statements: evaluating the leadership, culture, and post-close alignment of a target's principals is a core responsibility, not an afterthought. The role is also the organization's guardrail against deal momentum: every opportunity is scored against a consistent methodology, and recommendations follow the scores, not the level of internal enthusiasm. The role also owns transaction-related financial planning, including acquisition and integration budgets, working alongside the corporate FP&A process rather than running it. This is a hands-on position: you will build the pipeline, frameworks, and models yourself.

Targets are typically tuck-in software and hosting-adjacent businesses in the USD $1 million to $5 million enterprise value range, funded from operating cash flow. We expect 1 to 2 closed transactions per year at steady state, with a pipeline of roughly 2 qualified opportunities under active review at any time. Partnership, alliance, and joint venture opportunities run through the same screening and scoring discipline as acquisitions, so that build, buy, and partner are compared on one basis.

Work is fully remote, with flexible hours, so you can plan your day and work from anywhere in the world.

Join us to make a difference!

Responsibilities:

Origination

• Build and maintain a pipeline of acquisition targets aligned to the company's strategic priorities, through market mapping, competitive landscape monitoring, and thesis-driven target identification.
• Cultivate and manage relationships with investment bankers, brokers, and industry advisors so that the company sees relevant opportunities early.
• Conduct direct outreach and early-stage relationship development with founders and owners of prospective targets.
• Maintain disciplined pipeline records, including passed opportunities and the rationale for each, so the pipeline improves with every decision.

Screening and Evaluation

• Design, maintain, and apply a standardized screening and scoring methodology, approved by the leadership team, that rates every opportunity on consistent criteria: strategic fit, financial thresholds and return, technology and product considerations, integration complexity, and counterparty risk. No opportunity advances to leadership consideration without a score, and the score travels with the deal.
• Ensure accept and reject recommendations follow the scoring methodology and are supported by stated evidence. Where the organization elects to proceed against the score, document the rationale and the specific assumptions that must hold, so the decision is made with open eyes and the record reflects it.
• Prepare concise initial evaluations of screened targets: what it costs, what it returns, what has to be true for the thesis to work, and what happens if those assumptions are wrong.
• Build valuation and deal models for targets under active consideration, including scenario and sensitivity analysis, synergy assessment, and financing considerations.
• Coordinate financial due diligence and partner with Legal, Technology, and functional leaders on cross-functional diligence workstreams.
• Lead counterparty diligence on a target's principals and leadership team: reference checks, background verification within applicable legal limits, litigation and reputation review, and a candid assessment of how the sellers are likely to behave as partners, employees, or earnout counterparties after close.
• Translate counterparty findings into deal structure: retention terms, earnout design, indemnification, and escrow recommendations, developed with legal counsel.
• Support deal structuring and negotiation with responsive analysis, and prepare leadership and board materials for investment decisions, anticipating the questions leadership will ask and answering them before they are asked.
• Track completed transactions against the original deal thesis and report variances honestly, so the organization learns what its acquisition judgment is worth.

Acquisition Budgeting and Financial Planning

• Build the full transaction budget for each deal: purchase consideration, advisory and diligence fees, financing costs, and working capital requirements.
• Build the integration budget for each transaction, with synergy realization and integration cost phasing over the post-close period.
• Incorporate acquisition impacts into the company's forecast and annual operating plan in partnership with the finance team.
• Support capital allocation analysis across competing uses of cash, including scenario and sensitivity analysis for investment decisions.

Integration Coordination

• Own the post-close integration plan for acquired companies, including the 100-day plan, workstream coordination across functional leaders, and escalation of blockers to the executive team.
• Lead the financial integration of acquired entities: reporting onboarding, budget incorporation, and systems transition in partnership with the accounting team.
• Track realized synergies and integration costs against the deal model, and report variances to leadership.

Strategic Alliances, Joint Ventures, and Commercial Partnerships

• Identify and structure strategic alliances (commercial, marketing, or technology-sharing agreements) that deliver a strategic objective without an acquisition, and present them to leadership on the same scoring basis as a purchase.
• Evaluate and structure joint ventures where a shared market or product justifies a separate entity with a partner: economics, governance, contribution and exit terms, and the financial model of the venture itself.
• Lead the financial and commercial evaluation of major distribution, supply, and OEM agreements that expand market reach, in partnership with Sales and Product, including pricing, exclusivity, and minimum-commitment terms.
• Maintain the partnership pipeline alongside the acquisition pipeline, with the same records of passed opportunities and the rationale for each.

Long-Term Strategy

• Partner with the CEO, CFO, and CPO to maintain the company's 3-to-5-year growth blueprint, refreshed annually ahead of the operating plan, with the market landscapes and competitive analyses that determine where acquisition, partnership, and organic investment each apply.
• Translate the blueprint into the strategic priorities that govern the acquisition and partnership pipelines, so that origination effort follows strategy rather than deal flow.

Capital Formation

• Support the CFO in raising debt or equity when the growth plan requires it, including private placements, secondary transactions, and credit facilities: financial model and use-of-proceeds analysis, lender and investor materials, data room preparation, and coordination of counsel and advisers.
• Maintain relationships with lenders and prospective investors alongside the banker and broker network, so that financing options are understood before they are needed.

Corporate Development Function Building

• Establish the playbooks, screening criteria, deal templates, and pipeline infrastructure of a durable corporate development capability.
• As the function grows, hire, coach, and develop team members, and act as a collaborative business partner to leaders across the organization.

Requirements

Professional Requirements

• 8+ years of combined experience across corporate development, investment banking, private equity, and/or transaction advisory, including direct origination experience: sourcing, outreach, and early-stage negotiation with target companies.
• Experience conducting or coordinating due diligence across the financial, legal, and human dimensions of a transaction.
• Demonstrated ability to build institutional-quality financial models from a blank workbook, including three-statement, valuation, and scenario models.
• Experience preparing and presenting analysis to executive or investment-committee audiences, and defending a recommendation under challenge.
• Working knowledge of software or recurring-revenue business models and the metrics that govern them.
• Exposure to post-merger integration, whether leading workstreams or supporting a broader integration program.
• Experience structuring strategic alliances, joint ventures, or major commercial agreements, and exposure to a debt or equity financing process (private placement, secondary transaction, or credit facility).
• Experience contributing to multi-year strategy work with senior leadership: market landscapes, competitive analysis, and growth planning.

Soft Skill Requirements

• Even temperament under pressure and friction. Negotiations stall, diligence surfaces unwelcome facts, and counterparties do not always behave well. The role requires composure when they do not, and the judgment to respond with process rather than emotion.
• Low ego. The role prepares decisions for others to make, and much of the work is unglamorous: pipeline records, diligence checklists, budget reconciliations. We are looking for someone who takes satisfaction in the work being done properly rather than in being seen doing it.
• Persistence through the repetitive and detail-heavy phases of deal work, without cutting corners and without needing the work to be interesting to do it well.
• Sound commercial judgment: the ability to decline an attractive-looking opportunity when the numbers or the counterparty do not support it, and to say so clearly.
• Attention to detail and a commitment to quality and data integrity.
• Effective communicator, able to convey and present information in a concise and well-organized manner, leading with the conclusion.
• Strong interpersonal skills, able to collaborate with different individuals across the organization, and able to partner with all levels of management while relating to their needs and perspectives.
• Discretion in handling confidential and market-sensitive information.
• Displays integrity and is accountable for actions and statements.

Other Valued Attributes

• An MBA would be an asset.
• Big Four transaction advisory experience and/or software industry experience would be an asset.
• Prior experience as the founding or first hire of a finance or corporate development function would be a significant asset.
• An established network among software-sector bankers, brokers, or founders would be a significant asset.
• Experience partnering with or operating within an FP&A function would be an asset.

Benefits

What's in it for you?

• A strong focus on professional development with opportunities for learning and growth:
• Interesting and challenging projects,
• Mentor and other knowledge-exchange programs;
• Fully remote work with flexible working hours, that allows you to schedule your day and work from any location worldwide;
• Paid 24 days of vacation per year, 10 days of national holidays, and unlimited sick leaves to ensure you maintain a healthy work-life balance;
• Compensation for private medical insurance;
• Co-working and gym/sports reimbursement;
• The opportunity to receive a reward for the most innovative idea that the company can patent, fostering a culture of creativity and innovation.

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