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Added 8 mins ago
EI
User Experience Designer
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- Contract
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- $90,000 to $100,000 CAD / year
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Staff AI Developer - Toronto
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Director Consulting Services – Insurance
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Senior Manager, Business Banking Advisory - Tangerine
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Senior Data Engineer (Databricks Focused)
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Senior Data Engineer (Databricks Focused)
BDO Canada
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- Full-time
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LEO Software Group

M&A Originations Director

Canada

Full-time

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Job details

Job type: Full-time
Experience: You will typically have 5+ years of progressive experience in the areas above.
Posting language: English
Posted: Nov 3, 2026

Original job description

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 role

You 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 opportunity to take part in investment and strategic decisions.

What you will do

Build a pipeline that produces deals. Own a personal universe of businesses that meet our criteria. Reach owners through LinkedIn, email, calls, trade shows and in-person meetings, and build relationships that can take years to mature. Bring the best opportunities to the M&A execution team and stay involved from initial evaluation through close.
Build a team that outperforms. Lead your Originations Managers as a player/coach. Set targets, review pipelines, and give direct feedback on messaging, outreach and prioritization. Recruit, onboard and develop people who can perform without you in the room.
Know the market better than anyone. Lead research to map and qualify companies across verticals and geographies, and coordinate coverage across the team. Use CRM data to find overlooked prospects and close gaps. Choose conferences on evidence and come back with meetings.
Rebuild origination around what AI can do now. Design and ship AI-enabled workflows across lead identification, research, outreach, CRM hygiene and reporting. Remove unnecessary steps before automating them. Measure the effect: a tool the team does not use, or that does not increase qualified conversations, is unfinished.
Make the pipeline visible. Own the dashboards and the monthly and quarterly pipeline reporting for divisional and group leadership. Report what is not working as clearly as what is, and use it to change how the team operates.
Keep the system trustworthy. 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 like

Within 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. At least one AI-enabled workflow is in daily use and measurably increasing qualified conversations per originator, so coverage grows faster than headcount.

What you bring

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 make other people better. You have led, coached or trained a sales or business development team and lifted performance across the team, not just your own numbers.
You use AI to change how the work gets done. 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.
Founders trust you. 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.

You will typically have 5+ years of progressive experience in the areas above. Experience in M&A, private equity, venture capital or investment banking is a plus, but not required. What matters is what you personally built, the decisions you owned, and the results you delivered.

How we hire

After reviewing your application, we invite selected candidates to a working session lasting a few hours. 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. We want to see how you find and qualify opportunities, with a scope that reflects the job you would be doing.

You will also meet members of the team you would work with. We confirm the time commitment and payment before you start.

Apply

Send a short note to Andrew Innes (ainnes@fogsoftwaregroup.com) and Suthen Siva (ssiva@leosoftwaregroup.com) covering a pipeline or team you built and the result; an AI workflow you built for prospecting or pipeline management and what it changed; and why acquiring and holding software businesses for the long term interests you.

Apply About employer

More about this job

Responsibilities

Lead a team of Originations Managers, build and manage a personal acquisition pipeline, and develop relationships with business owners and other deal sources. Improve origination through AI-enabled workflows, market research, CRM and territory management, and pipeline reporting while supporting opportunities through evaluation and close.

Requirements

Typically, candidates have 5+ years of progressive experience in acquisition sourcing, outbound SaaS sales, corporate development, growth, or related work, with demonstrated success building pipelines and improving team performance. They should be advanced CRM users, strong in Excel and data management, experienced in building AI-enabled prospecting or pipeline workflows, and able to build trust with business owners; M&A, private equity, venture capital, or investment banking experience is a plus.

Skills

M&A Origination
Pipeline Development
Team Leadership
Coaching
Business Development
Prospecting
Relationship Building
Market Research
AI Workflow Design
CRM Management
Salesforce
Pipeline Reporting
Data Quality
Excel
Investment Evaluation
Territory Management

Visa sponsorship

Not detected in the job text

Hiring contact

Andrew Innes

Hiring contact email

ainnes@fogsoftwaregroup.com

Keywords

M&A
Acquisition Sourcing
Vertical Market Software
Deal Origination
Pipeline Management
Originations Managers
AI-Enabled Workflows
Lead Identification
Prospecting
Outreach
CRM
Salesforce
Excel
Python
SQL
Market Research
Territory Management
Data Quality
Pipeline Reporting
Investment Committee
Letter Of Intent
Corporate Development
Outbound SaaS Sales
Private Equity
Venture Capital
Investment Banking
Founders
Due Diligence
Conference Strategy

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