Enterprise Account Executive

Company Overview

insightsoftware is a worldwide leader offering solutions in reporting, analytics, and performance management that unlock business data potential, transforming how finance and data teams function. Serving over 32,000 organizations, we empower leaders with timely, intelligent decision-making tools. Our extensive portfolio includes Financial Planning and Analysis (FP&A), Controllership, and advanced Data and Analytics solutions that enhance finance teams' productivity, visibility, precision, compliance, and decision-making capability.

Role Summary

As part of the Office of the CTO focusing on Data & Analytics—including Data Connectivity, Artificial Intelligence, Embedded Analytics, and Collaborative Business Intelligence—you will spearhead new enterprise client acquisitions across North America as an Enterprise Account Executive. This role demands full-cycle responsibility for selling cutting-edge technology solutions to enterprise software firms and data-centric organizations aiming to modernize analytics and AI capabilities within their products and processes. You will engage with senior business and technical leaders spanning product, engineering, data, analytics, and executive levels to understand goals and tailor solutions that provide distinct customer value.

Key Responsibilities

• Generate and manage a sales pipeline through outbound prospecting targeting enterprise organizations and strategic software companies.
• Lead prospects through complex, multi-stakeholder sales processes, including qualification, discovery, tailored presentations, product demonstrations, and closing.
• Utilize consultative sales methods to assess customer needs, technical requirements, and outcomes aligning with business drivers.
• Promote data connectivity, AI capabilities, embedded analytics, and collaborative BI products to both technical and business audiences.
• Manage intricate negotiations involving economic decision-makers, technical evaluators, legal, procurement, and executive stakeholders.
• Employ structured sales methodologies such as MEDDIC, MEDDPICC, Challenger, or SPIN for rigorous qualification and sales process management.
• Collaborate cross-functionally with Business Development, Product Specialists, Solutions Engineers, and other teams to design and execute high-impact selling strategies and proposals.
• Maintain a comprehensive understanding of industry trends, competitive landscape, and emerging technologies in AI, analytics, and enterprise data infrastructure.
• Contribute insights and market intelligence to enhance Go-To-Market strategies and referral processes.
• Achieve revenue targets by closing deals and acquiring new customers to expand the Data & Analytics business.

Qualifications

• Bachelor’s degree is mandatory.
• Over five years of experience in enterprise software sales with a consistent record of surpassing sales quotas.
• Demonstrated expertise managing and closing sophisticated sales cycles with multiple stakeholders.
• Proven success in outbound prospecting, pipeline development, and account growth.
• Preferred experience selling data technologies, analytics, AI, embedded software, OEM, ISV, or other technical platform solutions.
• Ability to translate technical concepts into clear business value communications.
• Well-versed in engaging executive, technical, data, and product stakeholders throughout the sales cycle.
• Familiarity with procurement, legal processes, and technical evaluations within enterprise sales environments.
• Experience with structured sales frameworks such as MEDDIC, MEDDPICC, Challenger, or SPIN is advantageous.
• High personal accountability and disciplined approach to planning, pipeline management, and goal achievement.
• Thrives under fast-paced conditions with motivation, urgency, and rapid learning capabilities.
• Strong written and oral communication skills.
• Energetic, driven, committed, and passionate about sales excellence.

Who Will Excel

Successful individuals are proactive hunters who relentlessly build their pipeline without waiting for inbound opportunities. They approach sales with thorough preparation, focus on business outcomes over product features, and confidently engage with both executives and technical prospects. Their conduct is characterized by urgency, clarity, accountability, integrity, and a genuine enthusiasm for winning.

Compensation

The total compensation for this role in Canada ranges from 167,000 to 208,000 CAD annually, inclusive of commission targets for sales positions. Final offers depend on skills, experience, and qualifications. We prioritize transparent and equitable pay practices.

Additional Information

All candidate information is handled confidentially in line with Equal Employment Opportunity (EEO) guidelines. Employment is contingent upon successful background checks as permitted by local laws. insightsoftware is an equal opportunity employer committed to diversity and inclusion, prohibiting discrimination on any protected grounds.