Find the software businesses we will own for decades, and build the team and systems that find them faster. Lead a subset of LEO’s deal origination function: your own pipeline, a team of Originations Managers, and the AI-enabled workflows that multiply their reach. LEO Software Group buys and operates vertical market software businesses for the long term.

We are part of Vela and Constellation Software, which has acquired more than 1,300 businesses since 1995. Why this roleYou will work closely with our M&A; execution and Operations teams to find, qualify and win the businesses that fit our criteria. You will build relationships with founders, C-suite executives, investment bankers and private equity and venture capital funds around the world, and you will see your work turn directly into acquisitions.

The ambition is an origination function that covers more of the market, with better information, without adding headcount in step. That means combining the judgment and relationships that win deals with research, outreach and reporting systems that do far more of the groundwork. You will shape how this works, and you will have the chance to take part in investment and strategic decisions.

Build a pipeline that produces deals. Own a personal universe of businesses that meet our criteria. Bring the best opportunities to the M&A; execution team and stay involved from initial evaluation through close.

Set targets, review pipelines, and give direct feedback on messaging, outreach and prioritization. Use CRM data to find overlooked prospects and close gaps. Design and ship AI-enabled workflows across lead identification, research, outreach, CRM hygiene and reporting.

Make the pipeline visible.



Own the dashboards and the monthly and quarterly pipeline reporting for divisional and group leadership. Act as the central resource on territory management and company policy.

Own CRM engagement and data quality across the team, and work with divisional and head office operations and compliance leadership on policy matters. What success looks likeWithin your first 12 months, your team’s pipeline has grown in size and quality against an agreed baseline, and you have personally sourced opportunities that reached LOI / investment committee. You have built pipeline from nothing.

Through acquisition sourcing, outbound SaaS sales, corporate development or growth roles, you have won the attention of senior decision-makers who were not looking for you, and you can show the results. You have led, coached or trained a sales or business development team and lifted performance across the team, not just your own numbers. You have built automated prospecting, origination or pipeline workflows yourself.

Recent tools have changed how you work, and you have formed your own views on where they help and where they fall short. You are rigorous with data. You are an advanced CRM user (Salesforce preferred) with a strong grasp of pipeline management and data quality, and you are strong in Excel.

Python or SQL is a plus. You keep the data clean enough to trust. You can hold a credible conversation with an owner about a business they spent twenty years building. You communicate clearly in person and remotely, and you are curious about business strategy and what makes a good investment.

Experience in M&A;, private equity, venture capital or investment banking is a plus, but not required. Using a target vertical, sanitized data and the AI tools you normally use, you will build and prioritize a target list and draft an outreach approach.

📌 M&A Originations Director (Winnipeg)
🏢 LEO Software Group
📍 Winnipeg