Enterprise Account Executive

Insightsoftware; Canada; On-site; CAD 167,000 - 208,000; Full time

Job summary

insightsoftware in Canada is seeking a high-performing Enterprise Account Executive to drive new logo growth across North America. This full-cycle role targets enterprise software companies, data-driven organizations, and technical buyers seeking to modernize analytics and AI-powered capabilities.

You will source your own pipeline, engage senior stakeholders across product, engineering, data, analytics and executive leadership, and own the full sales cycle.

Qualifications

• Bachelor’s degree required.
• 5+ years of enterprise software sales experience required.
• Proven track record of closing complex enterprise deals.
• Experience with MEDDIC/MEDDPICC or Challenger preferred.

Responsibilities

• Develop and execute plans to exceed goals through prospecting and closing enterprise opportunities.
• Build, manage, and forecast pipeline to meet revenue quotas.
• Source new opportunities via targeted outbound prospecting into enterprise accounts.
• Diagnose customer needs and align solutions to business objectives.
• Position AI, embedded analytics, data connectivity, and collaborative BI to stakeholders.
• Navigate multi-threaded deals with economic buyers, legal, and procurement.
• Lead discovery, business case, proposals, and negotiations.
• Maintain knowledge of products, industries, and trends.
• Contribute to Go-To-Market strategy with competitive intelligence.
• WIN — close deals and expand Data & Analytics business.

Skills

Enterprise software sales

Outbound prospecting

Pipeline management

Stakeholder engagement

Negotiation

Education

Bachelor’s degree

Job description

About Us:

insightsoftware is a global provider of reporting, analytics, and performance management solutions that unlock the potential of business data and transform the way finance and data teams operate. We empower leaders from over 32,000 organizations to make timely and intelligent decisions. Our comprehensive solutions span Financial Planning and Analysis (FP&A), Controllership, and Data and Analytics. We deliver finance teams the insights required to navigate any economic climate and drive greater financial intelligence, while increasing productivity, visibility, accuracy, and compliance. Learn more at insightsoftware.com.

Job Description:

Our Office of the CTO, Data & Analytics portfolio spans Data Connectivity, Artificial Intelligence, Embedded Analytics, and Collaborative BI — and we are looking for a high-performing Enterprise Account Executive to drive new logo growth across North America. This is a full-cycle enterprise sales role focused on selling strategic technology solutions to enterprise software companies, data-driven organizations, and technical buyers looking to modernize how analytics, insights, and AI-powered capabilities are delivered within their products and workflows. You will engage senior business and technical stakeholders across product, engineering, data, analytics, and executive leadership to understand business objectives and position solutions that deliver differentiated customer experiences. You will source your own pipeline, call on enterprise organizations, and guide prospects through complex, multi-stakeholder sales cycles. Through primarily outbound prospecting, you will qualify leads, identify decision-makers, assess customer needs, present and demonstrate our solutions, overcome objections, navigate procurement and legal, and close sales as the owner of the full sales cycle. The solutions you will represent help customers deliver insights directly inside their applications, products, and business processes. Success in this role requires the ability to connect commercial value to technical use cases, including OEM/embedded software models, AI-driven user experiences, enterprise data architecture, and product-led analytics strategies. You will collaborate with Business Development, Product Specialists, Solution Engineers, and other colleagues to execute a high-quality sales motion and help evolve our Go-To-Market strategy. As a new Enterprise Account Executive, you will receive training and development with significant advancement opportunities for top performers. You will report to the DVP, Enterprise Sales.

What You’ll Sell

You will carry quota across insightsoftware’s Data & Analytics product lines, including:

• Data Connectivity & AI — including Simba Intelligence, ODBC/JDBC connectivity, and AI-powered capabilities that help organizations access, translate, and leverage data across leading cloud, database, and analytics platforms


• Embedded Analytics — analytics, dashboards, reporting, and insight experiences embedded directly into enterprise and SaaS applications


• Collaborative BI & Writeback — solutions such as PowerOn, Vizlib, and Fiplana that extend BI platforms with planning, input, writeback, and collaborative capabilities

What You’ll Do

• Develop and execute sales plans to exceed goals through prospecting, qualifying, managing, and closing enterprise opportunities


• Build, manage, and accurately forecast pipeline to meet or exceed monthly, quarterly, and annual revenue quotas


• Source new opportunities through targeted outbound prospecting into enterprise accounts, strategic software companies, and data-driven organizations


• Use a consultative sales approach to diagnose customer needs, business drivers, technical requirements, and desired outcomes


• Position AI, embedded analytics, data connectivity, and collaborative BI solutions to both business and technical stakeholders


• Navigate complex, multi-threaded deals involving economic buyers, technical evaluators, legal, procurement, and executive leadership


• Lead discovery, solution alignment, business case development, proposal creation, negotiation, and close activities


• Qualify rigorously using a structured sales methodology such as MEDDIC, MEDDPICC, Challenger, SPIN, or equivalent


• Partner with Business Development, Product Specialists, Solution Engineers, and internal teams to deliver compelling presentations, demonstrations, and proposals


• Maintain strong knowledge of company products, target industries, competitive positioning, and trends in AI, analytics, enterprise software, and data architecture


• Contribute to Go-To-Market strategy by surfacing competitive intelligence, buyer insights, and win/loss patterns from the field


• WIN — close deals, acquire new customers, and help expand the Data & Analytics business

Qualifications

• Bachelor’s degree required


• 5+ years of enterprise software sales experience required


• Proven track record of over-achieving quota year-over-year


• Proven ability to manage and close complex enterprise sales cycles involving 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 structured sales methodologies such as MEDDIC, MEDDPICC, Challenger, SPIN, or equivalent preferred


• High accountability mindset with a disciplined approach to activity planning, pipeline management, forecasting, goal setting, and execution


• Thrives in a fast-paced environment with a high level of motivation, urgency, and ability to learn quickly


• Excellent written and verbal communication skills


• Must have energy, drive, commitment, and passion

Who Thrives Here

The best performers in this role are relentless prospectors who do not wait for pipeline to come to them. They prepare thoroughly, understand that buying decisions are made around business outcomes rather than product features, and can confidently engage both executive and technical audiences. They operate with urgency, clarity, accountability, and integrity — and they genuinely love winning.

Additional Information

The salary range in Canada for this position is 167,000.00 to 208,000.00 CAD Annual. For sales roles, this range includes the commission target. For non-sales roles, this is a base salary only range; additional bonus eligibility may apply. Your specific offer within this range will be determined by your skills, experience, and qualifications. We are committed to pay transparency and fair compensation practices. If you have questions about our compensation approach, please don't hesitate to ask during the interview process.

All your information will be kept confidential according to EEO guidelines.

Learn more about our high-energy, high-performance global team: Work With Us insightsoftware

About Us:

Hear From Our Team Background checks are required for employment with insightsoftware, where permitted by country, state/province.

insightsoftware is a global provider of reporting, analytics, and performance management solutions that unlock the potential of business data and transform the way finance and data teams operate. We empower leaders from over 32,000 organizations to make timely and intelligent decisions. Our comprehensive solutions span Financial Planning and Analysis (FP&A), Controllership, and Data and Analytics. We deliver finance teams the insights required to navigate any economic climate and drive greater financial intelligence, while increasing productivity, visibility, accuracy, and compliance. Learn more at insightsoftware.com.

All your information will be kept confidential according to EEO guidelines.

At insightsoftware, we are committed to equal employment opportunity regardless of race, color, ethnicity, ancestry, religion, national origin, gender, sex, gender identity or expression, sexual orientation, age, citizenship, marital or parental status, disability, veteran status, or other class protected by applicable law.

We are proud to be an equal opportunity workplace.