Head Digital Applications

Locations: US (East Coast Timezone) 

Position Summary 

Bentley Systems seeks a visionary leader with a blend of technical expertise, strategic acumen, and team-building skills to drive digital transformation and business value to guide our digital application strategy across our portfolio of enterprise platforms. The Head of Digital Applications will steer the evolution of our application landscape, transitioning our teams to a product-led model that fosters innovation and partnership.  

This role is not just about managing platforms; it’s about inspiring a cultural shift towards an iterative, product-centric mindset. The Head of Digital Applications will guide Bentley’s enterprise application transformation by integrating Salesforce, Workday, and legacy systems into one cohesive, compliant, and high-performing environment. This role sets the strategic direction for platform interoperability that supports global Sales, Marketing, Quote-to-Cash, Revenue Operations, and Finance and Accounting. 

Responsibilities 

• Lead and define the strategic direction for Bentley’s enterprise platforms, shaping and communicating a clear long-term vision for digital applications from inception through execution. 

• Drive the transition to a modern, agile, and product-led organization. 

• Provide hands-on technical leadership and guidance on our core enterprise platforms.  

• Ensure the reliability, scalability, and security of our application ecosystem. 

• Oversee all financial business processes from Lead to Cash within the platform. 

• Provide leadership and foster a supportive, high-performing team culture for engineers, product managers, and analysts. 

• Champion a product model and iterative delivery mindset, focusing on continuous improvement and value delivery. 

• Serve as a strategic partner by aligning stakeholder relationships and business requirements with scalable technology solutions to drive organisational success. 

Qualifications 

• 15+ years of experience leading enterprise platforms, cloud modernization initiatives, and large-scale digital transformations within global organizations. 

• Prior experience and demonstrated ability to lead multi-platform environments including Salesforce, Workday, and custom enterprise systems is essential, with emphasis on interoperability, governance, and operational excellence. 

• Deep understanding of B2B SaaS business models including consumption and subscription. 

• Experience in transitioning teams to a product-led operating model. 

• A strategic mindset with prior experience of creating and executing long-term roadmaps in collaboration with business stakeholders 

• Strong expertise in platform integration, API strategy, event-driven architectures, and scalable enterprise workflows supporting Quote-to-Cash and financial operations. 

• Proven experience in system performance engineering, including reliability engineering, observability tooling, telemetry-driven monitoring, and optimization of API throughput and transaction latency. 

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.  

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