What we do:

We help companies reduce training time, boost productivity, and make software easier for everyone to use. We’re building ShowMe — a voice-enabled, real-time digital adoption platform that acts like a live expert inside any software. Instead of reading help docs or filing support tickets, users and employees just ask, and ShowMe guides them step by step.

The role:

We’re looking for a senior, hands-on sales leader to join as our Head of Sales & GTM. You’ll define and drive our go-to-market approach from the ground up — everything from sales playbooks to pricing strategy to building early traction with B2B customers. This is a founding team role with significant equity. You’ll work directly with the founding team and shape how we grow.

Location: Montreal (Canada)

What you’ll do:

Build and execute our go-to-market plan
Identify ideal customer profiles and land first deals
Own outreach, demos, pipeline, and closing in the early stages
Shape our pricing, messaging, and sales process
Work with product to align roadmap with customer pain
Eventually build and lead a sales org

You might be a fit if:

You’ve sold B2B SaaS or AI products for 8+ years
You have experience in the Digital Adoption Platform (DAP) space or similar (e.g., onboarding, enablement, product tours, support tech)
You’ve owned a quota and closed 5- or 6-figure deals
You love early-stage chaos and figuring things out
You think commercially, act fast, and want a seat at the table

Please, check our demo on https://www.solving.ai, if you think it's the future, share your interest with us!

Note: This is the Montreal based targeted job post

Solving.AI

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Head of Sales & Go-To-Market Strategy