Director of Corporate Development

CSC Generation•Toronto, ON

5d•Hybrid

About The Position

CSC Generation is the AI-native holding company re-engineering omnichannel retail. We acquire iconic brands and transform them with Genesis, our operating platform combining a Data Fabric, Automation Engine, proprietary tools, and shared services to modernize operations, elevate customer experience, and expand margins. With $1B+ in revenue across 13 brands, our portfolio includes Sur La Table, Backcountry, One Kings Lane, and others that serve as real-world innovation labs. CSC Generation continues to grow through M&A, acquiring iconic consumer and retail brands and revitalizing them through operational transformation. The Investments team needs a Director-level deal professional who can bridge transaction execution and portfolio value creation with greater independence than the current team structure allows. As Director of Corporate Development, you will lead transactions end-to-end from LOI through close, develop sector theses and proprietary deal flow, and partner with portfolio company operators to design and execute value-creation roadmaps. Within your first 6–12 months, success means independently leading at least one acquisition to close, establishing repeatable diligence and integration playbooks, and building trusted relationships with lenders, advisors, and portfolio leadership. This is a lean team. You will own a lot, move fast, and make decisions with full end-to-end responsibility.

Requirements

6–10 years of total professional experience, including 2+ years in investment banking, restructuring advisory, or top-tier strategy consulting and 3+ years in private equity, special situations, or principal investing.
Proven track record as a deal contributor or lead on multiple closed transactions (buyouts, corporate carve-outs, distressed or special-situations deals).
Advanced financial modeling skills: full LBOs, operating models, returns analysis, debt sizing, and capital structure optimization.
Strong command of accounting, cash flows, and credit documentation; comfortable evaluating lender viewpoints.
Solid understanding of operational drivers in consumer and retail: traffic, conversion, AOV, merchandising economics, inventory turns, store productivity, CAC, and retention.
Demonstrated ability to lead deal workstreams independently with VP-level oversight on key decisions.
Strong communication skills; comfortable engaging directly with C-level executives, lenders, and advisors.
Experience drafting investment committee materials and presenting recommendations to senior stakeholders.
Ability to manage junior team members and external advisors simultaneously across multiple live workstreams.
Ability to translate incomplete or messy data into clear insights and actionable recommendations.
High proficiency in Excel and PowerPoint.
Willingness to travel regularly to portfolio companies, partners, and key markets.

Nice To Haves

Experience in consumer, retail, ecommerce, or multi-unit businesses.
Exposure to middle-market companies and complex situations (multi-brand platforms, operational turnarounds, cross-border operations).
MBA or equivalent graduate degree.
Familiarity with BI tools, SQL, or Python.

Responsibilities

Build and maintain relationships with investment bankers, brokers, and advisors to generate proprietary deal flow across consumer, retail, ecommerce, and adjacent sectors.
Lead early-stage screening and high-level modeling for inbound and proprietary opportunities.
Develop and refine sector theses (e.g., omnichannel retail, outdoor and sporting goods, home, specialty consumer) and maintain active target lists.
Prepare go/no-go recommendations with clear return framing and strategic rationale for VP and senior leadership review.
Serve as deal lead on transactions from LOI through close, owning day-to-day workstreams including modeling, diligence, financing coordination, and documentation.
Lead negotiation of key commercial terms with sellers and management teams, with VP oversight on final structure decisions.
Draft and present investment committee materials including investment thesis, value-creation plan, downside scenarios, and risk/mitigant analysis.
Coordinate internal and external diligence teams (legal, accounting, tax, IT, operations) and hold them accountable to timelines and deliverable quality.
Manage lender and co-investor relationships and support financing process management.
Partner with portfolio company operators and CSC functional leads to design and execute 100-day plans and multi-year value-creation roadmaps for newly acquired brands.
Track portfolio performance through dashboards and monthly reviews; flag variances and work with operators to course-correct.
Support initiatives across pricing and promotion, channel mix, merchandising strategy, store fleet rationalization, digital/customer acquisition, and SG&A efficiency.
Partner with CSC's AI and analytics teams to embed automation and data-driven decision-making into portfolio operations.
Evaluate and support execution of add-on acquisitions and strategic partnerships for portfolio brands.
Manage and develop Senior Associates and Analysts on deal teams; set expectations on modeling, research, and communication quality.
Contribute to internal playbooks, templates, and investment processes that help the platform scale efficiently.
Support capital-raising efforts, including data room prep and case study development, as needed.