Chief Digital Officer

CSC Generation; Montreal; On-site; CAD 150,000 - 250,000; Full time

Job summary

CSC Generation is seeking a Chief Digital Officer to spearhead their digital business strategy. The CDO will lead initiatives focused on growth and innovation, implement data-driven measures to enhance customer experiences, and oversee marketing efforts while ensuring alignment with financial goals. This is a pivotal role for a leader who thrives in a dynamic environment, fostering a strong team to elevate performance across multiple brands.

Benefits

Generous PTO

401(k)/RRSP match

Medical/Dental/Vision benefits

Employee discounts at portfolio companies

Qualifications

• Proven experience as a CDO or in a similar senior digital leadership role.
• Deep understanding of financial strategies and finance-related performance metrics.
• In-depth knowledge of the digital marketing landscape, including SEO, SEM, social media, and e-commerce platforms.

Responsibilities

• Develop and implement strategic plans that meet the Company’s aspirations and financial goals.
• Drive the company to achieve and surpass sales, profitability, and business objectives.
• Define enterprise roadmap for developing products and features that enhance customer experience.

Skills

Leadership

Digital Marketing

Data Analytics

Customer-Centric Strategy

Education

Bachelor's degree in a relevant field

Advanced degree preferred

Job description

CSC Generation Enterprise (CSC) is an AI-enabled multi-brand platform that acquires and transforms legacy businesses into profitable, digital-first, consumer-centric businesses. CSC's platform is purpose built around its core M&A strategy and drives alpha by encoding revenue growth, unit margin management, and other expert-level retail practices into automation and AI. CSC owns and operates more than 10 companies, including Sur La Table, Backcountry, and One Kings Lane. Together, our companies generate $1B+ in revenue and we employ over 2000 people across North America. We are backed by world-class investors and continue to pursue platform and add-on acquisitions at pace.

The Chief Digital Officer (CDO) will be a strategic leader responsible for spearheading and overseeing the company's digital business. The ideal candidate will have a proven track record of leveraging technology to enhance business operations, improve customer experiences, and drive revenue growth. This role requires a visionary, out of the box thinker with the ability to balance innovation, data-driven decision-making, and operational excellence.

This position will report into the CEO.

What you get to do every day:

1. Digital Strategy & Growth:

• Develop and implement strategic plans that meet the Company’s aspirations and financial goals.
• Identify and evaluate digital opportunities that drive competitive advantage and enhance customer value.
• Collaborate with executive leadership to ensure digital initiatives align with organizational goals.
• Oversee the company’s paid acquisition marketing efforts and expand the program efficiently and with a focus on data driven growth.
• Create and execute on strategies that further enhance the omnichannel business and foster the blur the lines between digital and brick & mortar.

2. Leadership:

• Drive the company to achieve and surpass sales, profitability, cash flow, and business goals and objectives.
• Provide inspirational leadership and direction and ensure the continued development and management of a high performing team.
• Bring an entrepreneurial mindset to the role, exploring innovative digital strategies, taking calculated risks, and driving transformative change within the company.

3. Product & Technology:

• Define enterprise roadmap for developing products and features that enhance the customer experience and drive conversion and profitability.
• Evaluate and implement digital tools and platforms to streamline operations and enhance efficiency.

4. Customer Experience Enhancement:

• Champion customer-centric digital experiences across all touchpoints.
• Implement strategies to enhance the overall customer journey through digital channels.

5. Data-Driven Decision Making:

• Leverage data analytics and insights to inform decision-making processes.
• Implement data-driven strategies for marketing, sales, and operational effectiveness.

What you bring to the role:

• Proven experience as a CDO or in a similar senior digital leadership role.
• Prior start-up experience
• Demonstrated ability to develop and implement successful strategic plans.
• Deep understanding of financial strategies and finance-related performance metrics.
• Proven track record of successfully managing P&L for digital businesses, with a strong focus on revenue and profit growth.
• In-depth knowledge of the digital marketing landscape, including SEO, SEM, social media, and e-commerce platforms.
• Excellent communication and collaboration skills.
• Strong leadership and people management capabilities.
• Bachelor's degree in a relevant field; advanced degree preferred.

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: Generous PTO, 401(k)/RRSP match, medical/dental/vision and a variety of supplemental policies available and employee discounts at our portfolio companies

What our interview process looks like:

• 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.

CSC Generation Holdings 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.

CSC Generation Holdings 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 [e-mail].