Head of Sales & Go-To-Market Strategy

Solving.AI; Montreal; Remote; CAD 120,000 - 180,000; Full time

Job summary

A leading company in digital adoption is seeking a Head of Sales to define and drive their go-to-market strategy. This role involves building early traction with B2B customers and shaping the sales organization. Ideal candidates have extensive experience in B2B SaaS sales and a strong understanding of Digital Adoption Platforms. Join a founding team with significant equity and influence on growth.

Qualifications

• 8+ years of experience in B2B SaaS or AI sales.
• Experience in Digital Adoption Platform space.

Responsibilities

• Build and execute the go-to-market plan.
• Identify ideal customer profiles and land first deals.
• Shape pricing, messaging, and sales process.

Skills

B2B SaaS Sales

Digital Adoption Platforms

Sales Strategy

Job description

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 : Remote (USA or 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 points
• Eventually build and lead a sales organization

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 [insert platform], and if you think it's the future, share your interest with us!

Note : This is a Canadian-targeted job post.