Enterprise Account Executive

Sama; Remote; CAD 60,000 - 80,000; Full time

Job summary

A leading AI training data company in Canada seeks an Enterprise Account Executive to drive sales across various verticals, including Consumer Tech and Autonomous Vehicles. This role involves managing the full sales cycle, developing client relationships, and achieving an annual quota of $1-$2M. The ideal candidate should possess extensive B2B sales experience, particularly in AI solutions, and be adept at navigating complex sales processes with technical buyers. The position offers competitive compensation and a comprehensive benefits package.

Benefits

Medical, dental, and vision insurance

Employer-matching Group RRSP

Monthly fitness stipend

Professional development opportunities

Qualifications

• 3-7 years of quota-carrying B2B sales experience, ideally in AI/ML.
• Proven track record of exceeding quotas in high-velocity environments.
• Excellent communication skills to engage technical and business stakeholders.

Responsibilities

• Manage the full sales cycle from prospecting to close.
• Understand the ML lifecycle and be a strong solutions seller.
• Build and manage a $1-$2M annual quota focused on net-new revenue.

Skills

Quota-carrying B2B sales experience

Sales pipeline management

Technical sales

Communication skills

Understanding of AI/ML environments

Tools

Salesforce

LinkedIn Sales Navigator

Job description

The training data lifecycle is complex - the journey from data collection to delivery is resource-heavy and time-consuming. In the ever-changing world of AI, Sama’s vision is to be a partner in managing the complete ML lifecycle. Today we focus on data annotation, and validation, fine‑tuning and model evaluation for companies like Google, Microsoft, and Nasa building state‑of‑the‑art AI. As a Forbes Top 50 AI company to watch, we are the only AI company certified as a B‑Corp to continue to build on our social mission to “give work.”

In this role as a driven Enterprise Account Executive, you will be responsible for helping to grow one of our key verticals (Consumer Tech, Autonomous Vehicles, Retail & eCommerce). You have a history of selling complex solutions. Being tech‑savvy, strategic, and action‑oriented within your book of business is second nature to you. You will be a part of our growing sales team that is expanding a disruptive technology in Computer Vision and Generative AI. Our ideal candidate will have deep experience selling a SaaS solution to a technical buyer and an ability to develop and navigate senior client relationships resulting in $1M+ annually in new account wins.

Key Responsibilities

• Be responsible for the full sales cycle, from prospecting to close; analyzing, building and managing a sales pipeline with a highly complex and technical, multi‑stakeholder sales process.
• Become a strong solutions seller with depth in Generative AI and Computer Vision, and understand the ML lifecycle from start to finish.
• Deep dive into clients’ and prospects’ ecosystems and communities: Attend conferences, join forums, host webinars and marketing events, and leverage social media to show thought leadership
• Own a $1-$2M annual quota focused on net‑new revenue across AI platform subscriptions, services, and pilots
• Consistently deliver 100–120%+ attainment on quarterly bookings targets
• Build and maintain 3x pipeline coverage through strategic outbound prospecting, AI use‑case targeting, and cross‑functional support
• Manage 30–40 active deals per quarter, progressing through technical evaluation, procurement, and legal stages
• Lead 6–10 qualified discovery calls per week, tailoring outreach to business and technical buyers (VPs of Data, AI, Engineering)
• Conduct compelling discovery and scoping calls often in collaboration with solutions engineers, showcasing measurable value (e.g., data quality)
• Accelerate sales velocity: average sales cycle <120 days for enterprise engagements
• Maintain a win rate of >25% on sales‑qualified opportunities by positioning differentiated capabilities (e.g., human‑in‑the‑loop annotation, foundation model fine‑tuning, GenAI pipelines)
• Work closely with Solutions to craft proposals
• Use Salesforce and Gong to track funnel health, improve conversion at each stage, and forecast revenue within ±10% accuracy

Nice to Have

• Exposure to enterprise AI environments (e.g., computer vision, natural language processing, foundation models)
• Experience using or selling into AI infrastructure providers (e.g., AWS, Azure ML, Databricks, Scale AI, Labelbox)
• Familiarity with sales methodologies like MEDDIC or Challenger

Minimum Qualifications

• 3–7 years of quota‑carrying B2B sales experience, with at least 1–2 years selling AI/ML, data platforms, or analytics solutions in Enterprise environments
• Proven track record of meeting or exceeding quota in a high‑velocity or enterprise sales environment
• Familiarity with AI/ML buyer personas and use cases such as model training, data labeling, synthetic data, LLM evaluation, or AI governance
• Excellent communication and storytelling skills with ability to engage technical and business stakeholders alike
• Proficiency with Salesforce, LinkedIn Sales Navigator, and sales enablement platforms (e.g., Gong)
• Understanding of AI procurement dynamics including pilots, data privacy, IP rights, and technical validation cycles
• Previous experience selling a complex solution to technical buyers in one of our key sectors is preferred.

Preferred Qualifications

• Growth‑oriented while able to have fun at the same time
• Genuine interest in learning about new technologies - especially AI and generative AI
• Deep commitment to building an ethical, world‑class company with technology at its core
• Ability to navigate a fast‑paced environment with a high level of ambiguity
• Startup experience preferred
• Familiarity with sales methodologies like MEDDIC or Challenger
• You embody our Sama values, exemplifying Grit, Integrity, Get things done (GTD), and Humanity

About Sama

Sama provides high-quality training data that powers AI technology for Fortune 2000 companies such as Google, Walmart, Ford, Microsoft, and Marriott. We’re experts in data annotation, supporting text, 2D, 3D image, video, and sensor data for machine learning algorithms and generative AI models. Sama offers the highest quality SLAs in the industry, along with cutting‑edge ML‑assisted annotation tools, QA processes, and security and compliance standards.
Founded in 2008 on the belief that “talent is equally distributed, but opportunity is not”, Sama is driven by the mission to expand opportunities for those who are underprivileged. As a certified B‑Corp, Sama has provided worker training programs to increase economic opportunity for more than 15,000 people from underserved communities. By connecting our customers with amazing talent in East Africa, we've impacted more than 69,000 workers and their dependents.
Today, our vision is to provide data scientists, ML engineers, and data operations teams with an indispensable, integrated platform for AI data preparation, labeling, and collection.

Sama is quite unique. We are a technology company with a social mission. People that thrive in a high‑growth environment, love working on the bleeding edge of technology, and really care about having a positive impact on the world are a great fit for the Sama culture. Our core values are One Team, One Goal - Deliver. Period. - Trust & Transparency - Customer First - Humanity.

Sama offers competitive compensation commensurate with experience and a full benefits package, including: medical, dental, and vision insurance, long‑term disability insurance, life, and AD&D insurance, employer‑matching Group RRSP, generous holiday and vacation policies, a monthly fitness stipend, monthly cell phone reimbursement and professional development opportunities. Our Talent Acquisition team would be happy to discuss our benefits packages with you in more detail during the interview process.

At Sama, we pride ourselves in being a diverse and equal opportunity employer.