Sr. Director, Project Management Office and Proposals

Location: Home-based, United States

Position Summary:

As the Senior Director, Project Management Office and Proposals, you will own and optimize the operational lifecycle of our commercial engagements, from bid orchestration to final project delivery. You will lead the central bid management and PMO functions, serving as the key process owner and partnering with Sales, Solution Engineering, Legal, and Finance. Your mission is to dramatically improve operational throughput, increase win rates by implementing a strategic bid qualification process and leveraging technology to ensure flawless project execution, fostering a culture of continuous improvement.

The Senior Director oversees the full lifecycle of delivery execution, including RFX/RFI management, SOW and Blueprint standardization, cloud migration programs, and product gap initiatives. You will be responsible for ensuring consistent project and operational practices that reduce delivery time, improve predictability, and drive client satisfaction worldwide.

Responsibilities:

• PMO & Delivery Excellence
  • 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.
• Strategic & Operational Leadership
  • 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.
• Performance & Efficiency
  • 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.
• Bid & Proposal Orchestration
  • 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.
• This is a full-time role expected to work 40 hours per week, home-based in the United States.
• 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.
• Requires sitting or standing at will while performing work on a computer (or any other physical requirements).

Qualifications:

• A bachelor's degree in project management, engineering, business administration, or a related field; an MBA or equivalent is preferred.
• 15+ years of experience in PMO, Engineering, Product, Technical Sales, or Services leadership roles, including 10+ 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.
• Desired Skills:
  • 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.

What We Offer:

• A great Team and culture – please see our colleague video. 
• An exciting career as an integral part of a world-leading software company providing solutions for architecture, engineering, and construction - watch this short documentary about how we got our start. 
• 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. Discover our latest user success stories for an insight into our global impact. 

#LI-CS1

#LI-REMOTE

About Bentley Systems

Around the world, infrastructure professionals rely on software from Bentley Systems to help them design, build, and operate better and more resilient infrastructure for transportation, water, energy, cities, and more. Founded in 1984 by engineers for engineers, Bentley is the partner of choice for engineering firms and owner-operators worldwide, with software that spans engineering disciplines, industry sectors, and all phases of the infrastructure lifecycle. Through our digital twin solutions, we help infrastructure professionals unlock the value of their data to transform project delivery and asset performance. www.bentley.com

Equal Opportunity Employer:

Bentley is an equal opportunity employer and considers all qualified applicants for employment without regard to race, color, sex, sexual orientation, gender identity, disability, pregnancy, protected veteran status, religion, national origin, age, genetic information or any other protected characteristic.  This commitment extends to all aspects of employment, including, but not limited to, hiring, placement, promotion, compensation, and training. Know Your Rights as an applicant under the law.

Bentley Policy on EEO, Affirmative Action and Pay Transparency Non-Discrimination

Bentley participates in e-Verify / Bentley participate in e-Verify / Right to Work Notice

Request an Accommodation:

As an Equal Opportunity Employer, Bentley is committed to providing reasonable accommodations to applicants with disabilities. We encourage you to request a reasonable accommodation if you are not able to fully use or access our online application system.   You can make an accommodation request by calling 610-458-5000 or sending us an email at disabilityrequest@bentley.com