Head of Sales & Go-To-Market Strategy

Solving.AI; Montreal; Remote; CAD 80,000 - 150,000; Full time

Job summary

An innovative company is seeking a senior sales leader to join their founding team as Head of Sales & GTM. This pivotal role involves defining and driving the go-to-market strategy for a cutting-edge digital adoption platform. You'll be responsible for building sales playbooks, identifying customer profiles, and leading outreach efforts. With a focus on B2B SaaS and AI products, this position offers an exciting opportunity to shape the future of technology adoption in businesses. If you're passionate about sales and thrive in early-stage environments, this is the perfect role for you.

Qualifications

• 8+ years of experience in B2B SaaS or AI sales.
• Experience in Digital Adoption Platforms or similar fields.

Responsibilities

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

Skills

B2B SaaS Sales

Digital Adoption Platforms

Sales Strategy Development

Customer Outreach

Pipeline Management

Job description

Direct message the job poster from Solving.AI

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
• 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 Canadian targeted job post

Seniority level

• Seniority level

  Executive

Employment type

• Employment type

  Full-time

Job function

• Job function

  Sales and Business Development

• Industries

  Technology, Information and Internet

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