Enterprise Data & AI Sales Executive

Insightsoftware; Vancouver; Hybrid; CAD 167,000 - 208,000; Full time

Job summary

insightsoftware is seeking an Enterprise Account Executive to drive new logo growth across North America. This full-cycle role targets enterprise software buyers, data-driven organizations, and technical stakeholders to modernize analytics and AI-powered capabilities within products and workflows.

You will source your own pipeline, engage senior stakeholders, and guide prospects through complex multi-stakeholder sales cycles, delivering solutions that connect business value to technical use

Qualifications

• Bachelor’s degree is required.
• 5+ years of enterprise software sales experience.
• Proven track record of over-achieving quota year-over-year.
• Proven ability to manage and close complex enterprise sales cycles with multiple stakeholders.
• Strong outbound prospecting, pipeline generation, and account development skills.
• Experience selling data, analytics, AI, embedded software, OEM, ISV, or technical platform solutions preferred.
• Ability to understand and communicate technical concepts in a business-value oriented way.
• Comfortable engaging with executive, product, engineering, data, analytics, and technical stakeholders.
• Experience navigating procurement, legal, technical evaluation, and executive alignment during enterprise sales cycles.
• Familiarity with MEDDIC, MEDDPICC, Challenger, SPIN, or equivalent preferred.
• High accountability mindset with disciplined activity planning, pipeline management, forecasting, and execution.
• Thrives in a fast-paced environment with motivation, urgency, and the ability to learn quickly.
• Excellent written and verbal communication skills.
• Must have energy, drive, commitment, and passion.

Responsibilities

• Develop and execute sales plans to exceed goals through prospecting, qualifying, managing, and closing enterprise opportunities.
• Build, manage, and forecast pipeline to meet revenue quotas.
• Source new opportunities through outbound prospecting into enterprise accounts and data-driven organizations.
• Use a consultative sales approach to diagnose customer needs, business drivers, and technical requirements.
• Position AI, embedded analytics, data connectivity, and collaborative BI solutions to stakeholders.
• Navigate complex, multi-threaded deals involving economic buyers, technical evaluators, legal, procurement, and leadership.
• Lead discovery, solution alignment, business case development, proposal creation, negotiation, and close activities.
• Qualify rigorously using MEDDIC, MEDDPICC, Challenger, SPIN, or equivalent.
• Partner with teams to deliver presentations, demonstrations, and proposals.
• Maintain knowledge of products, target industries, competitive positioning, and AI trends.
• Contribute to Go-To-Market strategy by surfacing competitive intelligence and buyer insights.
• WIN — close deals, acquire new customers, and expand the Data & Analytics business.

Skills

Enterprise software sales

Quota attainment

Stakeholder management

Full-cycle sales

Outbound prospecting

Pipeline generation

Account development

Data/Analytics/AI sales

OEM/ISV embedding

Technical concept communication

Procurement navigation

MEDDIC/MEDDPICC

Challenger/SPIN

Accountability

Fast-paced adaptation

Communication skills

Energy and motivation

Education

Bachelor’s degree

Job description

insightsoftware is seeking an Enterprise Account Executive to drive new logo growth across North America. This full-cycle role targets enterprise software buyers, data-driven organizations, and technical stakeholders to modernize analytics and AI-powered capabilities within products and workflows.

You will source your own pipeline, engage senior stakeholders, and guide prospects through complex multi-stakeholder sales cycles, delivering solutions that connect business value to technical use