**Location:** Ireland, Netherlands, UK, Italy, or Spain (Office-Based, Hybrid, or Home-Based) **Position Summary:** The Director, Chief of Staff (CoS) Office of the CTO serves as a key partner and direct report to Bentley’s Chief Technology Officer (CTO), strengthening the Technology organization's success externally and supporting a strong culture internally. This key function facilitates the work of setting and managing Bentley’s Technology strategy, inspiring, and influencing others towards action, and alignment, and ensuring a strong flow of information to and from the CTO. The CoS is responsible for making sure the team is working in sync to achieve targeted goals and meet their responsibilities. The CoS will lead organizational & executive rhythms, run point on cross-company special projects, and be the driver behind the Technology Office’s operations. This role calls for a balance of skills that include leadership, influence, project management, strategic planning, people management, and individual contribution capacity. The successful incumbent can work under pressure, perform to tight deadlines, and must be flexible, thriving in ambiguity and uncertainty. The Chief of Staff will provide the Bentley OCTO leadership team with oversight, identify opportunities and recommendations for organizational challenges, participate in overall strategy discussions, lead assigned key strategic initiatives, and facilitate business execution. This role is an Executive Staff multiplier moving the business forward by enabling sound business decisions. **Your Day-to-Day:** Serves as a critical thought partner and trusted advisor to the CTO and OCTO leadership team. Acts as a strategic partner to help build and implement a comprehensive and successful technology strategy across Bentley. Support the CTO in running a high-functioning Senior Leadership Team by: + Building and facilitating the daily operations of the CTO. + Building and running an operational cadence for leadership meetings, and leadership offsites, including structuring and helping to deliver company-wide communication. + Guiding the process of defining, following up, and reflecting on OKRs for initiatives across OCTO and with the Division CTOs. + Work with the CTO on presentations and reports for the board and the Executive Team + Tracking high-priority initiatives for the CTO to identify any potential obstacles. + Leading cross-functional strategic initiatives, facilitating special projects, and ensuring action items are executed on behalf of the CTO. + Acts as a proxy to the CTO in designated meetings to maximize bandwidth. + Acts as a trusted strategic advisor working alongside multiple business leaders to determine priorities, opportunities & risks, support change management & continuous improvement. + Drives people/talent development initiatives in conjunction with the Business Unit’s Colleague Success Business Partner. Examples can include identifying talent gaps, defining and executing hiring strategies, supporting the development of a learning agenda, assisting with diversity & inclusion initiatives, and instituting policy/guidelines to respond to the group’s feedback/improvement areas. + Develops and cultivates cross-organizational stakeholder relationships to amplify alignment with critical internal partners (connects work streams that would otherwise remain siloed). Builds bridges and champions a spirit of collaboration and open communications. Provides leadership to cross-functional programs, and identifies, leverages, and advises the correct resources to ensure the work is completed. + Fiscal Operations: Partners with Finance to define clear visibility into alignment model (budget) and tracks hiring pipeline against available budget. Maintains ownership of budget, holding leaders accountable for business case-based spending; works with Finance Business Partner and Colleague Success Business Partner to prioritize hiring and spending. + Represents OCTO in Merger and Acquisition activities, including due diligence and integration planning and execution from a colleague and user perspective. + Business Enablement: Provides consultation and advice to the team around operational excellence, headcount, and resource planning; participates in overall group strategy decisions and assists in implementing policies and procedures while focusing on maximizing the effectiveness of the team. + Some travel is required (20-30%). **What You Bring to The Team:** The ideal candidate has previous experience as Chief of Staff, with exposure to the inner workings of leadership teams, including: + Product Development process definition and refinement. + Business planning and approval process. + Budget Management. + Executive leadership workshop facilitation. + Development and expansion of performance management framework (preferably OKRs) for the business. + Technology acumen, ability to understand challenges beyond face value. + The ability to challenge leadership with new ways of managing the operations of the business unit which will improve efficiency, and clarify and communicate organizational priorities. + Adapt quickly to a variety of situations, business needs, initiatives, and technologies. + Solid project management experience, including leading matrixed and inter-departmental initiatives. + Strong business judgment. + Ability to handle and properly compartmentalize all kinds of confidential information. + Courageous in solving problems and overcoming obstacles. + Resilient to pressure and a fast-changing business environment. + Strong alignment with Bentley's core values and behaviors and being a role model as this is a highly visible position. + Knowledge of Bentley's business or the industries it serves is desired, but not a requirement. **What We Offer:** + A great Team and culture – please see our Recruitment Video. (https://www.youtube.com/watch?v=epJImnDsbYE&feature=youtu.be) + An exciting career as an integral part of a world-leading software company providing solutions for architecture, engineering, and construction. + Competitive Salary and benefits. + The opportunity to work within a global and diverse international team. + A supportive and collaborative environment. + Colleague Recognition Awards. **About Bentley Systems:** Bentley Systems (Nasdaq: BSY) is the infrastructure engineering software company. We provide innovative software to advance the world’s infrastructure – sustaining both the global economy and environment. Our industry-leading software solutions are used by professionals, and organizations of every size, for the design, construction, and operations of roads and bridges, rail and transit, water and wastewater, public works and utilities, buildings and campuses, mining, and industrial facilities. Our offerings, powered by the iTwin Platform for infrastructure digital twins, include MicroStation and Bentley Open applications for modeling and simulation, Seequent’s software for geoprofessionals, and Bentley Infrastructure Cloud encompassing ProjectWise for project delivery, SYNCHRO for construction management, and AssetWise for asset operations. Bentley Systems’ 5,200 colleagues generate annual revenues of more than $1 billion in 194 countries. www.bentley.com **Equal Opportunity Employer:** Bentley is proud to be an equal opportunity employer and considers for employment all qualified applicants without regard to race, color, gender/gender identity, sexual orientation, disability, marital status, religion/belief, national origin, caste, age, or any other characteristic protected by local law or unrelated to job qualifications. \#LI-AK1 \#LI-REMOTE Equal Opportunity Employer/Minorities/Females/Veterans/Disabled