Job Description

Sales Executive – Headless CMS & Digital Experience

Remote (Canada) | Base: $100K–$115K CAD OTE: $200K–$230K CAD

A fast-growing digital consultancy is hiring its first North American Sales Executive to drive pipeline, build relationships, and sell modern digital experience solutions. The business specialises in helping mid-market companies move away from slow, legacy CMS platforms and adopt high-performance headless and composable architectures that empower marketing teams and remove engineering bottlenecks.

This is a hands-on, outbound-heavy role for someone who understands web technology, enjoys consultative selling, and wants a clear path into future leadership.

What You’ll Do

• Build and own the early-stage pipeline through outbound outreach across SaaS, retail, and B2B verticals.
• Identify where modern, headless CMS and composable stacks can replace legacy WordPress/Drupal setups.
• Run discovery, qualify technical and marketing requirements, and shape opportunities.
• Champion marketing stakeholders — helping them gain agility, ownership, and faster time-to-market.
• Maintain momentum in deals, building confidence and trust with multiple personas.
• Partner with a founder and solutions architect team on solutioning, proposals, and late-stage closing.
• Attend events, partner meetups, client visits, and industry conferences to build visibility.
• Bring fresh outbound ideas, prospecting strategies, and new ways to identify opportunities.
• Help define sales processes as the company scales and builds its North American team.

What Success Looks Like (6–12 Months)

• A strong outbound pipeline consistently generated and managed.
• Deep relationships established across marketing and IT personas.
• Clear ability to position modern architecture vs legacy CMS.
• Achieving quota (approx. $1mill annual target).
• Demonstrating potential to grow into a closer or future team lead.

Who You Are

• 2–4 years in a digital agency, CMS/DXP vendor, or web technology sales environment.
• Strong understanding of headless CMS , modern web architecture , and marketers' need for agility.
• Able to navigate both marketing (CMO, VP Marketing) and technical (CTO, VP Engineering) stakeholders.
• Confident running outbound and creating your own opportunities.
• Curious, collaborative, and comfortable in an agile, startup-style environment.
• Strong relationship-builder who inspires confidence early.
• Motivated by progression — you want to develop into a senior or leadership role.

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