Sr. Director, Project Management Office and Proposals

Bentley Systems is a world-leading software company providing solutions for architecture, engineering, and construction. The Senior Director, Project Management Office and Proposals will optimize the operational lifecycle of commercial engagements and lead the central bid management and PMO functions to improve operational throughput and client satisfaction.

Responsibilities:

• Provide senior leadership to the PMO, with direct oversight for projects including services work, account-based project management tasks, product gap analysis, data optimization tasks, and the full lifecycle management of all Bentley Services project activities
• Implement a hybrid resource model, aligning Project Managers primarily to projects while also creating account-based alignments by geography and global priority to improve accountability, stakeholder coordination, and client outcomes
• Foster deep cross-functional collaboration, creating tight alignment between Solution Engineering, Services, and Product teams to proactively close delivery gaps and improve account outcomes
• Strengthen core capabilities by collaborating with the Enablement team to build and enhance project management skills and operational acumen across the global PMO
• Work closely with Bentley services operations, ensuring consistent delivery performance and alignment with business objectives from a process and execution standpoint
• Drive transformative change by identifying operational bottlenecks in the bid and delivery process and institutionalizing best practices across all contributing functions
• Champion continuous improvement, leading change management initiatives to create a more agile, efficient, and scalable operational framework for proposals and projects
• Drive significant improvements in service performance, with a clear mandate to reduce "time to initiate" and "time to deliver" by up to 50% through superior process management
• Optimize key performance indicators (KPIs) including resource utilization, Net Promoter Score (NPS), project profitability, and overall operational throughput of the PMO
• Partner with Finance to improve provisioning and activation workflows from a process perspective; drive change management with stakeholder teams to accelerate service start-up times
• Establish and lead a strategic "Bid/No-Bid" qualification process, partnering with Sales and other key stakeholders to ensure resources are focused on the most winnable and strategically aligned opportunities
• Lead the global RFX/RFI process, acting as the central coordinator to balance proposal quality and submission volume, ultimately improving the win rate on qualified deals
• Champion and drive the adoption of technology (e.g., proposal automation software, AI content generation) to streamline the proposal process, improve response quality, and provide analytics to increase win rates
• Work with Services Operations to simplify and standardize SOW templates and service Blueprints, improving the scalability and reducing customization of proposals

Requirements:

• A bachelor's degree in project management, engineering, business administration, or a related field; an MBA or equivalent is preferred
• 12-15+ years of experience in PMO, Engineering, Product, Technical Sales, or Services leadership roles within a software company, including 3-5+ years in a senior management capacity overseeing cross-functional global operations
• Senior leadership experience supporting a mature, enterprise-scale services function, with responsibility for strategy, execution, and long-term operational health
• Proven track record of driving operational efficiency and measurable improvement in service delivery outcomes
• Strong understanding of software or technology service delivery models, including experience with cloud migrations and data optimization projects
• Excellent stakeholder management skills with the ability to collaborate across Finance, Engineering, and GTM functions to achieve shared objectives
• Exceptional analytical, organizational, and communication skills, with the ability to translate strategic goals into executable plans
• Expertise in leveraging modern project management tools and technology to drive superior project outcomes and operational efficiency
• Strong executive leadership and team management skills
• Excellent strategic planning and execution capabilities
• Proficiency in project management methodologies and tools
• Strong analytical and problem-solving skills
• Excellent communication, presentation, and interpersonal skills
• Ability to manage multiple priorities and work under pressure