Location: Remote or Toronto

Type: Full-time or Contract-to-Hire

Compensation: Base + High Commission + Early Equity

About AlwaysWorks AI

AlwaysWorks AI is building the future of engineering delivery transformation. Currently in stealth mode.

We’re looking for ambitious, driven individuals ready to join us at the ground floor and help shape the future of AI workforce.

Your Role

As the Founding GTM / Sales Rep, you’ll be responsible for identifying potential customers, driving demo signups, and building our early user pipeline. You’ll be on the front lines, hustling for access, pitching our vision, and converting early adopters. You’ll also help build and optimize the GTM playbook.

Key Responsibilities

Identify and reach out to engineering leaders, tech startups & engineering delivery teams likely to benefit from AlwaysWorks AI
Pitch our product vision and schedule early access demos
Convert demo leads into product signups and feedback loops
Work closely with the founder on refining messaging, positioning, and GTM strategy
Track all outreach and outcomes with clear performance metrics
Represent the company with professionalism, energy, and confidence

Who You Are

0–3 years of experience in sales, BD, or GTM (fresh grads welcome with proven hustle)
Tech-savvy and curious about AI, dev tools, and cloud infrastructure
Excellent communicator with strong written and verbal persuasion skills
Comfortable working in ambiguity and building from scratch
Self-starter with a founder mindset: action-oriented, resilient, and fast-moving
Based in or connected to Toronto or startup/tech communities globally

What You Get

High commission structure on converted leads and paid customers
Early equity in a high-potential startup
Access to mentorship and leadership exposure from day one
Be a core part of a mission-driven, no-fluff founding team
Potential to grow into Head of Sales or GTM Lead as we scale

If You’re…

Hungry to make an impact
Wired for ownership and not afraid to fail forward
Excited by AI, devtools, and startup growth stories
Willing to cold DM, cold call, pitch, iterate, and hustle daily

→ Let’s talk. This role is made for you.

AlwaysWorks AI

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