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Bentley Systems Logo Bentley Systems · Sales

Director - Sales Systems & Revenue Strategies

Canada, Remote or Ontario · Job Posted March 04, 2026
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Job Description

As the Director of Sales Systems & Revenue Strategies, you will be a pivotal leader in architecting the future of Bentley's commercial engine. This is a highly visible role designed to drive significant growth by creating a world-class revenue technology ecosystem. You will provide the strategic vision and operational leadership to not only optimize our entire sales technology stack—with a focus on Salesforce—but also to transform our rich data assets into actionable revenue strategies. By championing system adoption, process excellence, and cross-functional alignment, you will empower our sales organization to exceed its targets and solidify Bentley's position as a market leader.

Job Responsibility

  • Architect & Lead Revenue Technology Strategy: Develop and own the comprehensive vision and roadmap for the entire revenue technology stack (including Salesforce, Salesloft, etc.), ensuring seamless integration and alignment with overarching business goals
  • Drive Salesforce Ecosystem Excellence: Serve as the senior business owner for the Salesforce platform, leading efforts in advanced administration, strategic enhancement, and workflow automation to unlock new levels of sales productivity and effectiveness
  • Champion Data Integrity & Insights: Establish and enforce best practices for data management to create a "single source of truth" for all commercial data. Leverage this data to deliver critical insights, reporting, and predictive analytics to senior leadership
  • Optimize Go-to-Market (GTM) & Sales Processes: Analyze the entire customer lifecycle, from lead to renewal, to identify and eliminate bottlenecks. Partner with Sales and Marketing leadership to refine GTM strategies, pricing models, and sales methodologies for maximum profitability
  • Steer Strategic Planning & Forecasting: Lead the sales forecasting process, collaborating with Finance and Sales leadership to ensure accuracy. Provide data-driven recommendations for annual planning, budgeting, and territory design
  • Innovate Through Technology: Continuously evaluate emerging sales and revenue technologies, building the business case for adoption and managing the successful implementation of new tools that provide a competitive advantage
  • Empower the Sales Organization: Oversee the development and delivery of high-impact training and enablement programs to ensure exceptional user adoption and proficiency across all sales systems and processes
  • Foster Executive & Cross-Functional Partnership: Act as a key strategic partner to leadership in Sales, Marketing, Finance, and IT, driving alignment and ensuring that all revenue-generating activities are cohesive and effective
  • This role requires communication with Managers, peers and other colleagues of the company in person, and/or by utilizing Microsoft Teams chat, calling and meeting functions
  • Minimum of 20% travel time

Requirements

  • Bachelor’s degree in Business Administration, Marketing, Finance, Information Technology, or a related field, or relevant training and/or experience
  • An MBA or other advanced degree is highly preferred
  • 10+ years of progressive experience in Sales Operations, Revenue Operations, or a similar role within the technology/SaaS industry
  • A minimum of 2 years in a leadership capacity, with proven experience managing and developing a team
  • Demonstrated track record of successfully managing and optimizing a complex revenue technology stack
  • Proven success in driving revenue growth and developing data-driven GTM (Go-to-Market) strategies
  • Expert-level knowledge of CRM platforms, particularly Salesforce, including administration, customization, and workflow automation
  • Experience with sales enablement tools like Salesloft is also critical
  • Strong analytical skills with the ability to interpret large datasets, identify trends, and provide actionable insights
  • Proficiency with BI and data visualization tools such as Tableau or Power BI is required
  • Expertise in sales forecasting, financial modeling, pricing strategies, and revenue planning
  • A deep understanding of sales processes and methodologies with a proven ability to identify and eliminate bottlenecks to improve sales productivity
  • Ability to manage multiple complex projects, from technology implementation to strategic initiatives, ensuring on-time delivery
  • Salesforce certifications such as Salesforce Certified Administrator, Salesforce Certified Sales Cloud Consultant, or Salesforce Certified Platform App Builder are highly desirable
  • Strategic Vision: The ability to think long-term, anticipate future trends, and create a clear vision for the revenue technology stack and strategy
  • Leadership & Influence: A natural leader who can motivate, coach, and guide a team while effectively collaborating with and influencing cross-functional partners in sales, marketing, finance, and IT
  • Data-Driven: A strong inclination to use data and analytics to inform decisions and drive strategy
  • Adaptability & Resilience: Thrives in a fast-paced, competitive market and demonstrates the resilience to navigate challenges and drive change
  • Customer-Focused: A deep understanding of customer needs and a commitment to optimizing processes to enhance the customer experience.

What we offer

  • A great Team and culture
  • An exciting career as an integral part of a world-leading software company providing solutions for architecture, engineering, and construction
  • An attractive salary and benefits package
  • A commitment to inclusion, belonging and colleague wellbeing through global initiatives and resource groups
  • A company committed to making a real difference by advancing the world’s infrastructure for better quality of life, where your contributions help build a more sustainable, connected, and resilient world
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