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 robust 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 consul

📌 Associate Director (Winnipeg)
🏢 Jobgether
📍 Winnipeg