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Private Equity Senior Associate

1 hour ago

Toronto, Ontario, Canada CSC Generation Full time

CSC Generation is the AI-native holding company re-engineering omni-channel retail. We acquire iconic brands and transform them with Genesis—our operating platform unifying 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 more—premier home and outdoor banners that double as real-world innovation hubs. CSC Generation continues to grow through M&A, revitalizing companies with strong brand recognition and loyal customers. 

We're looking for a Private Equity Senior Associate to join our Investments team. You'll be a core member of small deal teams responsible for sourcing, evaluating, and executing acquisitions, as well as supporting value-creation initiatives across CSC's portfolio of consumer and retail brands.

This role is ideal for a high-performing investor with strong transaction experience who enjoys deep analytics, complex operational challenges (carve-outs, distressed, special situations), and hands-on portfolio engagement.

What you get to do:
  • Investment analysis & evaluation
  • Screen inbound and proprietary opportunities across consumer, retail, ecommerce, and related sectors.
  • Build and refine LBO and returns models, including sensitivity analysis by channel, store fleet, and digital KPIs.
  • Lead market and competitive research to size opportunities and benchmark category performance.
  • Help develop sector theses (e.g., omnichannel retail, outdoor & sporting goods, home, specialty consumer) and maintain target lists.

Diligence & transaction execution
  • Own day-to-day workstreams on live deals: data requests, model builds, Q&A, and coordination with internal teams and external advisors.
  • Analyze historical and projected financial performance, working capital, unit economics, and store / SKU productivity.
  • Partner with CSC's functional leaders (merchandising, supply chain, digital, finance, data/AI) to run operational and technology due diligence.
  • Draft investment committee materials: investment thesis, value-creation plan, risks/mitigants, and exit scenarios.
  • Support negotiation of key business terms, including structure, earn-outs, and go-forward management incentives.

Portfolio value creation & monitoring
  • Help launch 100-day plans and multi-year value-creation roadmaps for newly acquired brands.
  • Track portfolio performance through dashboards and monthly reviews; flag variances and assist operators in course correction.
  • Support initiatives such as pricing and promotion optimization, channel mix improvements, merchandising strategy, store fleet rationalization, and SG&A efficiency.
  • Work with CSC's AI and analytics teams to embed automation and data-driven decision-making into portfolio operations.

Firm building & leadership
  • Mentor and develop deal team members on modeling, research, and communication.
  • Contribute to internal tools, playbooks, and templates that enhance our investment and operating approach
What you bring:
  • 4–7 years of total professional experience, including:
  • 2+ years in investment banking, management consulting, or restructuring/special situations advisory; and
  • 2+ years in private equity, special situations, or principal investing 
  • Experience with consumer, retail, ecommerce, or multi-unit businesses strongly preferred.
  • Exposure to distressed / special situations, corporate carve-outs, or complex integrations is a plus.
  • MBA preferred, but not required.

Technical & analytical skills
  • Advanced financial modeling skills (full LBOs, operating models, returns analysis, debt sizing).
  • Strong command of accounting, cash flows, and capital structures; comfortable evaluating lender viewpoints.
  • Ability to turn incomplete or messy data into clear insights and recommendations.
  • High proficiency in Excel and PowerPoint; familiarity with BI tools or SQL/Python is a plus.
Deal & portfolio skills
  • Meaningful experience running workstreams on live deals (diligence, QofE, legal docs, financing, or integration planning).
  • Strong communication skills and ability to work directly with senior executives and advisors.
  • Comfort operating in lean teams with high ownership.
Mindset & culture fit
  • Low-ego, resourceful, and energized by turnaround and "special situations" environments.
  • Excited to work at the intersection of operations, technology, and investing.
  • Comfortable with ambiguity and high-paced decision-making.
  • Willing to travel to portfolio companies and partners as needed.
What's in it for you? Joining CSC Generation isn't just about having a seat at the table—it's about helping redesign the table entirely. You'll be challenged, stretched, and supported as you grow faster than you thought possible. In addition to competitive compensation, we offer:
  • Executive Access: Work directly with brand CEOs and senior leadership, solving real business problems and earning mentorship from top operators. 
  • AI-First Skill Building: Get hands-on with the most advanced AI tools in the market. From automation to prompt engineering, you'll build a modern tech stack that sets you apart in any industry. 
  • Accelerated Career Path: High performers are quickly entrusted with greater responsibility, new challenges, and leadership opportunities across our portfolio of brands. 
  • Competitive benefits: Paid time off policies, 401(k)/RRSP match, medical/dental/vision and a variety of supplemental policies, and employee discounts at our portfolio companies.
Our interview process:
  •  Step 1: If you align with our vision and meet the qualifications, we'll reach out to schedule a conversation and introduce CSC. 
  •  Step 2: You'll complete a short AI or product-building challenge so we can understand how you approach problems and execution. 
  •  Step 3: Participate in deep-dive interviews with CSC leadership focused on your experience, product mindset, and operational thinking. 
  •  Step 4: Offer. We'll move fast for the right candidate. 

The CSC family of brands provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, provincial, state or local laws.  

Washington state applicants only: If you believe that this job posting does not comply with applicable Washington state law, please notify us by sending an email to  

It is unlawful in Massachusetts to require or administer a lie-detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability. 

The CSC family of brands is committed to providing reasonable accommodations for qualified individuals with disabilities in our job application procedures. If you need assistance or an accommodation due to a disability, please contact