Chief of Staff, Product Advancement

Date: May 16, 2024

Location: Remote, PA, US Pittsburgh, PA, US Exton, PA, US Remote, MA, US Philadelphia, PA, US

Company: Bentley Systems

Location: Office-Based / Home-Based / Hybrid – US, East Coast


Position Summary:


The Director, Chief of Staff (CoS) Product Advancement serves as a key partner and direct report to Bentley’s Chief Product Officer (CPO), strengthening the Product organization's success externally and supporting a strong culture internally. This key function facilitates the work of setting and managing Bentley’s Product Advancement strategy, inspiring, and influencing others towards action, and ensuring a strong flow of information to and from the CPO. The CoS is responsible for making sure the team is working in sync to achieve targeted goals and meeting their responsibilities. The CoS will lead organizational & executive rhythms, run point on cross-company special projects and be the driver behind the executive Product Advancement Group team’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 Product Advancement 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.


Measure of Success:


Success will be measured by earning the trust and respect of the CPO and allowing them to focus on what is most important to the company by driving a culture of accountability and ensuring the Product Advancement leadership team functions as a single cohesive unit. The primary measure of success is the content and outcomes of the work and the ability to create impact by influencing others.



Your Day-to-Day:


Serves as critical thought-partner and trusted advisor to the CPO and Product Advancement leadership team. Acts as a strategic partner to help build and run a wildly successful business.

Support the CPO in running a high functioning Senior Leadership Team by

  • Building and running an operational rhythm calendar and ensuring adherence and accountability.
  • Guide the process of defining, following up and reflecting on OKRs for initiatives across Product Advancement.

Acts as a proxy to the CPO 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 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 spend.

Represents Product Advancement 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, resource planning; participates in overall group strategy decisions and assists in implementing policies and procedures while focusing on maximizing the effectiveness of the team.


Requires sitting or standing at will while performing work on a computer.



What You Bring to The Team:


The ideal candidate has a minimum of 10 years work experience, 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
  • Ability to challenge leadership with new ways of managing the operations of business unit which will improve efficiency, 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 judgement.
  • Ability to handle and properly compartmentalize all kinds of confidential information.
  • Courageous in solving problems and overcoming obstacles.
  • Resilient to pressure and fast-changing business environment.
  • Strong alignment with Bentley's core values and behaviors. Be a role model as this is a highly visible position.
  • Some travel is required (<10%).
  • 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.
  • 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 diversely 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.


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, protected veteran status, religion, national origin, age, or any other protected characteristic.  This commitment extends to all aspects of employment, including, but not limited to, hiring, placement, promotion, compensation, and training. EEO is the Law and EEO is the Law Supplement documents provide additional information about 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





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