Associate Director - Investments

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for an Associate Director - Investments based in Canada.

As Associate Director - Investments, you will take a leading role in identifying, evaluating, negotiating, and closing acquisitions of niche, bootstrapped B2B SaaS businesses across North America and Western Europe. You will operate as a principal investor, taking ownership of investment decisions and allocating significant capital to promising software companies. From initial founder conversations and commercial due diligence to valuation, negotiations, and final agreements, you will lead transactions end to end. Working closely with the Head of M&A, senior executives, and portfolio operators, you will help identify businesses with strong growth potential and sustainable economics. You will also contribute to investment strategy while developing junior team members through hands‑on coaching. This is a fully remote opportunity offering substantial autonomy, direct executive exposure, and the chance to shape the growth of an international SaaS portfolio.

Accountabilities

You will lead investment opportunities from initial assessment through closing, combining commercial judgment, financial analysis, negotiation skills, and stakeholder management. Your main responsibilities will include:

• Investment Analysis and Capital Allocation: Underwrite acquisition opportunities, assess potential value, risks, and returns, prepare investment memoranda, and present recommendations to the Investment Committee.

• Deal Qualification and Offer Development: Evaluate incoming opportunities efficiently, identify transactions that do not meet investment criteria, and issue non‑binding offers for promising businesses. Establish the pricing and deal structure that will guide negotiations.

• End-to-End Deal Leadership: Act as deal captain throughout the acquisition process, from initial founder discussions and non‑binding offers to letters of intent, due diligence, share purchase agreements, and closing. Manage timelines, coordinate workstreams, and remain accountable for transaction outcomes.

• Commercial Due Diligence: Lead internal commercial due diligence, including market sizing, competitive analysis, customer and expert interviews, and assessment of a company's market position and growth potential. Evaluate revenue quality, customer retention, concentration, pricing power, and the sustainability of growth.

• Financial Modelling and Valuation: Build financial models from scratch, covering ARR bridges, customer cohorts, retention, unit economics, scenario analysis, valuation, and investment returns. Challenge assumptions and develop robust financial cases.

• Negotiation and Transaction Structuring: Lead discussions with founders and their advisors on valuation, deal structure, and key contractual terms, balancing seller expectations with investment objectives.

• Due Diligence Management: Coordinate the full diligence process with internal finance, technology, product, marketing, legal, and people teams, as well as external legal, financial, and tax advisors. Translate findings into clear decisions and actionable recommendations.

• Stakeholder Management: Represent the investment team in discussions with founders, brokers, and external advisors. Collaborate with senior executives and the operational leaders responsible for integrating and growing acquired businesses.

• Team Development: Coach and support junior investment professionals while remaining actively involved in transaction execution and analysis.

• Early Impact: During your first 6–12 months, take ownership of opportunity qualification, develop investment‑ready cases, build relationships with key stakeholders, and lead live transactions from letter of intent through to signed agreements.

Requirements

The ideal candidate brings substantial transaction or strategy experience, strong investment judgment, and the confidence to lead complex deals independently. You should be comfortable working directly with founders and senior executives, combining rigorous financial analysis with practical commercial decision‑making. The following qualifications and capabilities are expected:

• At least 6 years of professional experience after university, with a strong track record in transactions, strategy, or a combination of both.

• Experience gained at a leading firm or team in one or more of the following areas:

  • Private Equity: Lower mid‑market transactions, typically involving businesses with less than $10M in EBITDA; experience in software or technology‑enabled services is particularly valuable.

  • Strategy Consulting: Experience at MBB firms (McKinsey, BCG, Bain) or leading strategy consultancies such as Roland Berger, Oliver Wyman, Kearney, L.E.K. Consulting, OC&C, Simon‑Kucher, or Arthur D. Little.

  • Big Four Strategy and Deals: Experience at Strategy& (PwC), EY-Parthenon, Deloitte (Monitor Deloitte or M&A), or KPMG Deal Advisory, particularly in commercial due diligence.

  • Corporate Development or In‑house M&A: Experience within a high‑velocity acquisition platform, aggregator, or buy‑and‑build organization.

  • Investment Banking: M&A advisory experience at a mid‑market or technology‑focused boutique, ideally involving lower mid‑market transactions with enterprise values below $50M.

• Strong investor mindset, with the ability to think like an owner, form independent investment views quickly, and support decisions with robust analysis.

• Hands‑on experience with live transactions, ideally having led deal workstreams or acted as the day‑to‑day deal lead.

• Excellent financial modelling and valuation skills, including the ability to build models from a blank sheet and confidently defend underlying assumptions.

• Demonstrated commercial due diligence experience, covering market sizing, competitive positioning, customer and expert interviews, and quality‑of‑revenue analysis.

• Strong negotiation and stakeholder management skills, with the presence and confidence to engage with founders, C‑suite executives, and external advisors.

• Proven project management capabilities, including the ability to coordinate multiple stakeholders, manage complex timelines, and maintain momentum across transaction workstreams.

• Experience coaching or developing junior professionals, combined with a hands‑on, player‑coach approach.

• Genuine interest in software and SaaS business models; direct software industry experience is an advantage but not essential.

• Fluent written and spoken English. Additional European languages are considered a plus.

• Practical fluency with AI tools, particularly Claude, and a proactive approach to applying AI to research, analysis, financial modelling, and due diligence workflows.

Benefits

• Principal-level responsibility: Lead acquisitions and make investment decisions directly, rather than supporting transactions in an advisory capacity.

• Significant deal exposure: Work on a platform deploying more than $50 million in capital annually across North America and Western Europe.

• Direct executive access: Collaborate with senior leadership and the Investment Committee from the beginning.

• Fully remote work: Work from anywhere, with flexibility over your working location and schedule.

• High autonomy: Operate in a high‑trust environment with the freedom to approach challenges and make decisions independently.

• Lean and efficient structure: Benefit from minimal bureaucracy, limited unnecessary meetings, and a focus on maintaining sustainable momentum.

• Collaborative team culture: Join a friendly, supportive international team that values knowledge‑sharing, mutual assistance, and informal collaboration.

• Professional network: Connect with an entrepreneurial community of SaaS professionals who regularly exchange ideas, expertise, and learning opportunities.

• Flexible time off: Take time away when needed to rest and recharge.

• Growth and impact: Help shape the development of an international portfolio of independent SaaS businesses while gaining exposure to a wide range of investment opportunities.

• Transparent compensation: Salary ranges are adjusted according to location and target local market medians. The compensation range will be provided in writing before the first interview.