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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