Remote Executive Assistant — Leadership Ops & Planning

BENTLEY SYSTEMS, INC.; Exton (PA); Hybrid; USD 70,000 - 110,000; Full time

Job summary

Bentley Systems is seeking an Executive Assistant to support the Asset Analytics leadership team. You will manage complex calendars, coordinate cross‑functional meetings, plan travel, and ensure timely execution of strategic priorities.

This role requires discretion, superb organization, and comfort working with senior executives. You will be a proactive partner, turning priorities into action while maintaining an operating rhythm across Product, Engineering, Finance, Sales, and Corporate

Qualifications

• 5+ years of experience supporting senior executives or leadership teams, ideally in a technology, software, engineering, or professional services environment.
• Demonstrated success managing complex calendars, travel coordination, executive communications, leadership operations, and meeting and project management across multiple stakeholders.
• Exceptional organizational skills with the ability to manage competing priorities while maintaining accuracy, follow-through, and attention to detail.
• Strong judgment and discretion when handling confidential business information, executive calendars, and sensitive leadership communications.
• Outstanding written and verbal communication skills, with the ability to engage professionally across all levels of the organization.
• Ability to operate proactively with limited direction, anticipating executive needs before they are explicitly communicated.
• Strong proficiency with Microsoft 365, including Outlook, Teams, PowerPoint, Word, and Excel.
• Bachelor's degree preferred; equivalent experience will be considered.

Responsibilities

• Executive Support and Prioritization
• Manage complex executive calendars for Bryan Friehauf and other Asset Analytics leaders, ensuring time is aligned to the highest-value business priorities.
• Coordinate scheduling across multiple executives, teams, customers, partners, and external stakeholders while balancing competing priorities and shifting business needs.
• Anticipate scheduling conflicts, prepare leaders for upcoming engagements, and proactively manage logistics to maximize executive productivity.
• Serve as a trusted gatekeeper and coordination point, helping leaders stay focused, responsive, and prepared across a demanding operating cadence.
• Leadership Team Operations
• Support the operating rhythm of the Asset Analytics leadership team, including staff meetings, business reviews, quarterly planning sessions, leadership off-sites, and cross-functional governance forums.
• Drive agenda development, meeting preparation, documentation, action item tracking, and follow-up so decisions translate into execution.
• Maintain visibility into leadership priorities and coordinate activities across multiple executives to improve alignment and reduce organizational friction.
• Help establish and continuously improve operating processes that enable the leadership team to function efficiently, consistently, and with clear accountability.
• Communications and Stakeholder Coordination
• Draft, review, and coordinate executive communications, briefing materials, leadership updates, and presentation inputs as needed.
• Act as a coordination point between Asset Analytics leadership and key stakeholders across Product, Engineering, Finance, Sales, Marketing, and Corporate Functions.
• Ensure important decisions, deadlines, and commitments are communicated clearly and followed through consistently.
• Support interactions with external customers, partners, and executive-level visitors, ensuring leaders and stakeholders have the context and materials they need.
• Planning, Travel, and Event Management
• Coordinate domestic and international travel arrangements, including itineraries, meeting logistics, accommodations, and expense management.
• Plan and execute leadership meetings, team events, strategy workshops, customer engagements, and other business-critical activities.
• Anticipate logistical challenges and proactively implement solutions that ensure seamless execution for leaders and participants.
• Support annual planning cycles, leadership off-sites, and special business events requiring significant coordination across multiple stakeholders.
• Special Projects and Business Support
• Support leadership initiatives and strategic projects requiring strong organizational ownership, follow-through, and attention to detail.
• Develop and maintain tracking systems for key initiatives, executive commitments, operational deadlines, and leadership priorities.
• Assist with executive presentations, business updates, reporting materials, and board-preparation support as needed.
• Take ownership of special projects assigned by Bryan Friehauf other Asset Analytics leaders, bringing structure, accountability, and execution discipline to priority initiatives.
• Travel is not required, optional in some cases.
• Requires sitting or standing at will while performing work on a computer (or any other physical requirements ).

Skills

Executive support

Calendar management

Travel coordination

Meeting management

Stakeholder coordination

Microsoft 365

Education

Bachelor's degree preferred

Tools

Microsoft 365

Job description

Bentley Systems is seeking an Executive Assistant to support the Asset Analytics leadership team. You will manage complex calendars, coordinate cross‑functional meetings, plan travel, and ensure timely execution of strategic priorities.

This role requires discretion, superb organization, and comfort working with senior executives. You will be a proactive partner, turning priorities into action while maintaining an operating rhythm across Product, Engineering, Finance, Sales, and Corporate