About Keak

Keak builds AI products that help businesses operate and grow more efficiently.

We’re hiring a Founding Head of Sales to build and lead the go-to-market motion for Cheaper Inference , our OpenAI-compatible API that helps developers and AI companies reduce their model costs.

Cheaper Inference gives customers access to leading AI models from multiple providers through one API key, with discounted, usage-based pricing. Teams can reduce inference costs without significantly changing how their applications interact with model APIs.

The role

We’re looking for a hands-on sales leader to turn early market demand into a repeatable revenue engine.

You’ll personally source, develop, negotiate, and close strategic customers while building the sales process around you. You’ll work directly with the founders, manage our BDRs, shape our ideal customer profile, and help define how Cheaper Inference is sold to AI companies and technical teams.

This is not initially a management-only position. You should be energized by joining customer calls, running technical discovery, building business cases, negotiating agreements, and closing deals yourself. As the sales motion becomes repeatable, you’ll hire and lead the team required to scale it.

What you’ll ownRevenue and strategic accounts

- Own new revenue for Cheaper Inference across production pilots and larger customer relationships.
- Build relationships with founders, CTOs, engineering leaders, AI teams, infrastructure leaders, and procurement stakeholders.
- Lead discovery to understand model usage, current providers, inference spend, technical requirements, and switching constraints.
- Create clear business cases based on potential savings, operational simplicity, and customer requirements.
- Run the complete sales cycle from initial conversation through evaluation, negotiation, closing, and handoff.
- Convert successful production pilots into sustained, expanding customer relationships.
- Develop account plans for high-potential customers and identify expansion opportunities.

Sales strategy and process
- Define and refine the ideal customer profile, qualification criteria, segmentation, and account priorities.
- Determine which customers belong in self-service, sales-assisted, or production-pilot motions.
- Build the sales playbook, including discovery, qualification, technical evaluation, pricing, objections, negotiation, and closing.
- Create reliable pipeline stages, forecasting practices, reporting, and operating rhythms.




- Establish performance metrics tied to qualified pipeline, customer activation, realized usage, revenue, retention, and expansion.
- Work with the founders on packaging, pricing, commitments, and commercial strategy.

Team leadership
- Manage, coach, and develop Keak’s BDR.
- Set clear expectations for account research, outreach quality, qualification, meetings, and pipeline creation.
- Create a strong feedback loop between business development and closing activities.
- Recruit additional sales team members when the motion is ready to scale.
- Build a high-accountability, customer-focused sales culture.
- Develop compensation plans, territories, quotas, and capacity models as the team grows.

Cross-functional collaboration
- Partner with marketing on target accounts, positioning, campaigns, case studies, and creator-led demand generation.
- Work closely with product and engineering during technical evaluations and customer onboarding.
- Translate customer feedback into actionable product and go-to-market insights.
- Surface recurring objections, feature requests, security requirements, and purchasing barriers.
- Help prioritize integrations and product improvements that materially affect revenue.

What success looks like Within your first year, you will have:
- Established a clear and validated ideal customer profile.
- Built a healthy pipeline of qualified AI companies and technical buyers.
- Closed meaningful production customers and expanded their usage.
- Created a repeatable sales process from initial outreach through realized inference revenue.
- Built reliable forecasting and sales reporting.
- Developed a productive BDR motion with clear qualification standards.
- Documented the sales playbook and identified where additional hires can accelerate growth.
- Produced customer insights that influence product, pricing, and go-to-market decisions.

What we’re looking for
- Seven or more years of B2B sales experience, including experience closing technical or infrastructure products.
- Experience building or substantially improving an early-stage sales motion.
- A record of personally closing complex, high-value customers.




- Experience selling to technical decision-makers such as CTOs, engineering leaders, AI teams, or infrastructure teams.
- Strong discovery, business-case development, negotiation, and closing skills.
- Experience managing and coaching BDRs, account executives, or other sales professionals.
- Solid command of pipeline management, forecasting, sales metrics, and CRM discipline.
- The ability to operate strategically while remaining highly involved in execution.
- Excellent written and verbal communication.
- Comfort working directly with founders in a fast-moving environment.

Especially valuable
- Experience selling AI infrastructure, model APIs, developer tools, cloud computing, data infrastructure, or usage-based SaaS.
- Understanding of AI inference, model providers, token pricing, and production AI workloads.
- Experience selling products where consumption and expansion matter more than traditional seat-based contracts.
- Relationships within the AI startup, developer-tool, or infrastructure ecosystem.
- Experience converting technical evaluations or pilots into production deployments.
- Familiarity with security reviews, procurement, data-retention requirements, and enterprise agreements.
- Experience building a sales team from its first few hires.

Who will thrive here You’ll thrive in this role if you are both a builder and a closer.

You can develop a sales strategy, but you’re equally comfortable finding an account, running discovery, coordinating a technical pilot, working through procurement, and asking for the business.

You don’t need to be an engineer, but you must be able to understand APIs, inference economics, and technical customer requirements well enough to earn credibility with experienced AI and engineering leaders.

Why join Keak

- Build the sales organization for an emerging AI infrastructure product.
- Work directly with the founders and influence company strategy.
- Own the path from early traction to a scalable revenue engine.
- Sell a product with a clear and measurable economic value proposition.
- Recruit and lead the team as the commercial motion grows.
- Receive meaningful performance-based compensation and equity.

Compensation The expected total target cash compensation for this role is $150,000–$250,000 , consisting of base salary and performance-based variable compensation. The final package and base-variable mix will depend on experience, location, and demonstrated ability to build and close an early-stage technical sales motion.

📌 Founding Head of Sales - Cheaper Inference (Canada)
🏢 Keak
📍 Canada