Head of Enterprise Accounts - Calico AI

Location: Toronto (Hybrid)

Reports to: Vice President of Brand Management

Experience Level: 8–15+ years

At Calico AI, we help apparel and accessories brands create better products, faster. Our platform combines decades of product building experience, deep sourcing intelligence, and practical AI tools that fit naturally into the product creation process — helping brands move from concept to sample to production seamlessly.

We’re not just building technology; we’re rethinking how brands and factories work together. We believe in close collaboration, transparency, and delivering tangible results for our partners. When our customers win, we win.

We’re looking for a Head of Enterprise Accounts to serve as the primary partner for some of the world’s most creative and ambitious apparel brands. This role is part relationship management, part product creation expertise, part operational leadership, and all hands-on.

As a Head of Enterprise Accounts at Calico AI, you’ll embed within your customers’ design, development, and sourcing teams — helping them integrate our tools into their daily workflow. You’ll guide them through the product creation process using Calico’s AI-powered sourcing technology, be available to coach and answer questions that arise, and ensure that every concept moves efficiently through sampling and into production.

This role is ideal for someone who loves the product process, thrives in dynamic environments, and takes pride in helping others succeed. Calico Brand Managers are expected to be available to work with customers as needed, whether in-office or remote.

Enterprise Account Leadership & Growth

• Own and manage a portfolio of large enterprise fashion accounts, with full responsibility for relationship health, retention, and expansion.

• Build and maintain trusted relationships with senior and executive stakeholders (VP, SVP, and C-level).

• Identify and drive opportunities to expand Calico’s footprint across categories, regions, and business units.

• Lead strategic account planning, including success metrics, growth strategies, and executive-level quarterly business reviews.

• Actively contribute to revenue growth through account expansion and increased adoption.

Strategic Customer Partnership

• Serve as the primary strategic advisor for enterprise fashion customers.

• Align Calico’s capabilities with customer business objectives such as speed to market, margin improvement, and supply chain optimization.

• Lead enterprise onboarding and scaling initiatives across multiple teams and geographies.

• Navigate complex organizations and influence cross-functional stakeholders.

Product Creation & Operational Excellence

• Bring deep expertise in apparel product creation to guide customers from concept through commercialization at scale.

• Partner with design, development, merchandising, and sourcing teams to optimize workflows and improve execution.

• Ensure consistency and scalability of processes across large, multi-brand or multi-category organizations.

Factory & Global Supply Chain Collaboration

• Work closely with global factory partners to ensure alignment, quality, and on-time delivery.

• Leverage strong knowledge of international sourcing and production to inform strategic decisions.

• Bridge communication between enterprise brands and manufacturing partners across regions.

Internal Leadership & Advocacy

• Represent enterprise customer needs internally to influence product roadmap and prioritization.

• Partner cross-functionally with operations, data, and engineering teams to deliver high-impact solutions.

• Help define and scale best practices for enterprise account management at Calico.

What You Bring

• 8–15+ years of experience in apparel or footwear, with a strong background in enterprise account management, merchandising, sourcing, or product development.

• Proven track record of managing large, complex, global fashion brand accounts.

• Deep relationships and credibility within the fashion industry.

• Strong executive presence with the ability to influence senior stakeholders and drive alignment.

• Extensive understanding of the end-to-end product creation and global supply chain process.

• Hands-on experience working with overseas factories and multi-region production.

• Strong commercial acumen with the ability to identify and drive account growth opportunities.

• Exceptional communication, organizational, and stakeholder management skills.

• High level of ownership, independence, and strategic thinking.

• Comfort with digital tools and enthusiasm for AI-driven workflows.

What Success Looks Like

• You establish deep, multi-level relationships across enterprise fashion organizations.

• Your accounts grow significantly over time, with expanded adoption across categories and regions.

• Customers view Calico as a strategic, long-term partner embedded in their operating model.

• You proactively identify risks and opportunities, driving both retention and measurable business impact.

• You help define how Calico scales its enterprise customer relationships globally.