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This is an opportunity to join Ascot Group - one of the world's preeminent specialty risk underwriting organizations.
Designed as a modern-era company operating through an ecosystem of interconnected global operating platforms, we're bound by a joint mission and purpose: One Ascot. Our greatest strength is a talented team flourishing in a collaborative, inclusive, entrepreneurial culture steeped in underwriting excellence, integrity, and a passion for finding a better way, The Ascot Way.
The Ascot Way guides our people and our organization. Our underwriting platforms collaborate to find creative ways to deploy our capital in a true cross-product and cross-platform approach. These platforms work as one, deploying our capital creatively through our unique Fusion Model: client-centric, risk-centric, and technology-centric.
Built to be resilient, Ascot maximizes client financial security while delivering bespoke products and world-class service -pre- and post-claims. Ascot exists to solve for our clients' brightest tomorrow through agility, collaboration, resilience, and discipline.
Ascot is embedding artificial intelligence (AI) and automation across the organization to enhance decision-making, efficiency, and quality of outcomes. In this role, you will be expected to work confidently alongside AI-enabled tools, apply sound judgment when interpreting insights, and adapt as technology continues to evolve. We value curiosity, critical thinking, and a willingness to embrace change as part of how we work.
Position Overview:
Reporting to the SVP, Infrastructure Operations & Services, and operating within the wider Infrastructure Operations team, the Executive IT Support Engineer provides high-touch, proactive technology support to senior executive leaders and their assistants. The role is responsible for owning complex end-user issues end-to-end and swiftly diagnosing, coordinating, and resolving technical requests with a strong focus on service quality, discretion, and business impact. This is an office-based role, requiring close engagement with stakeholders to ensure a seamless digital workplace experience.
Responsibilities:

• Act as a trusted technology partner to the C-suite and Board, delivering discreet, high-touch, and proactive executive IT support aligned to business priorities and leadership expectations.
• Lead application packaging and controlled software releases via the Ascot Company Portal, ensuring executives have immediate access to approved, business-critical tools with zero-surprise outcomes.
• Administer and govern Microsoft 365 services, serving as a senior subject-matter expert for collaboration platforms and advising leadership on best-practice usage, reliability, and optimisation.
• Take full ownership of the End User Computing (EUC) estate, proactively managing security posture, compliance, and risk remediation in alignment with Ascot Cyber Security Policy-particularly where executive exposure or business risk exists.
• Provide end-to-end ownership of complex technical issues across laptops, tablets, mobile devices, and peripheral ecosystems, coordinating across infrastructure, security, and vendors to ensure rapid and durable resolution.
• Deliver white-glove, executive-grade IT support, including proactive device health management, rapid response for critical matters, and on-site support for senior leaders as required.
• Support and maintain audio-visual and collaboration technology in executive offices and Boardrooms, ensuring faultless delivery for Board meetings, leadership sessions, and high-visibility events.
• Actively participate in Major Incident, Problem, and Change Management, ensuring executive impact is clearly understood, communicated, and mitigated, with a focus on service continuity and confidence.
• Partner with IT Asset Management to maintain accurate lifecycle control of executive devices, ensuring visibility, security, and readiness at all times.
• Design, create, and maintain SharePoint Online sites that support executive workflows, governance, and secure collaboration.
• Identify, evaluate, and drive continuous improvement initiatives that enhance executive experience, operational resilience, and service excellence, managing delivery through to measurable outcomes.
• Develop and maintain high-quality knowledge and runbooks, ensuring a consistent, professional support experience and reducing dependency through repeatable best practices.
• Serve as a visible representative of IT at senior leadership level, consistently demonstrating professionalism, accountability, and sound judgement in high-pressure and high-visibility situations.
• Embody The Ascot Way, fostering trust, inclusivity, and collaboration while setting the standard for service quality, ownership, and individual accountability across the Digital Workplace function.

Requirements:

• Bachelor's degree in Information Technology, Computer Science, or a related discipline, or equivalent senior-level experience supporting executives and business-critical users in complex enterprise environments.
• A minimum of 10 years of overall IT desktop experience of which a minimum 7 years of delivering executive-grade IT support, with demonstrable responsibility for C-suite, Board, and senior leadership technology needs in high-pressure, high-visibility environments.
• Strong expertise in Microsoft Modern Workplace technologies, including Microsoft 365, with the ability to advise, enable, and optimise technology usage for senior leaders, not just reactively support it.
• Advanced knowledge of Windows 11, Active Directory, and Azure Active Directory (Entra ID), with a clear understanding of identity, access, and device controls impacting executive productivity and security.
• Hands-on experience with Microsoft Intune and Azure Virtual Desktop (AVD), ensuring a seamless, secure, and high-performance experience for executives regardless of location.
• Deep understanding of Conditional Access policies, MDM, and identity security, with the judgement to balance executive usability against cyber-risk and regulatory requirements.
• Solid, working knowledge of enterprise infrastructure, networking, and security principles, enabling effective coordination with infrastructure, cloud, and cyber security teams during incidents or changes affecting senior leadership.
• Specialist background within Executive IT Support, Digital Workplace, or EUC, operating confidently with VIP users, sensitive data, and confidential discussions.
• Experience supporting Board meetings, executive committees, and leadership events, including AV, collaboration platforms, and time-critical scenarios where failure is not an option.
• Demonstrated ability to operate with a high degree of discretion, professionalism, and trust, handling confidential information and executive interactions appropriately at all times.
• Insurance or financial services experience is advantageous; however, proven executive support excellence in other regulated or complex industries is equally suitable.
• Highly autonomous, with the ability to anticipate executive needs, proactively identify risks, and resolve issues before they escalate or become visible to leadership.
• Proven capability to own complex problems end-to-end, coordinating across teams and vendors while shielding executives from unnecessary complexity.
• Exceptional communication skills, able to engage credibly with C-suite, Board members, and senior stakeholders, translating technical matters into clear, relevant business language.
• Strong organisational and prioritisation skills, with the ability to manage multiple competing executive priorities calmly and effectively.
• Advanced analytical and troubleshooting skills, enabling rapid diagnosis, decisive action, and durable resolution under pressure.
• Working knowledge of group, role, and identity administration, with a strong appreciation for governance, least-privilege access, and auditability.

Compensation
Actual base pay could vary and may be above or below the listed range based on factors including but not limited to experience, subject matter expertise, and skills. The base pay is just one component of Ascot's total compensation package for employees. Other rewards may include annual cash bonus and other forms of discretionary compensation awarded by the Company.
The annualized base pay range for this role is: $130,000 - $140,000.
Company Benefits
The Company provides a competitive benefits package that includes the following (eligibility requirements apply):
Health and Welfare Benefits: Medical (including prescription coverage), Dental, Vision, Health Savings Account, Commuter Account, Health Care and Dependent Care Flexible Spending Accounts, Life Insurance, AD&D, Work/Life Resources (including Employee Assistance Program), and more.
Leave Benefits: Paid holidays, annual Paid Time Off (includes paid state /local paid leave where required), Short-term Disability, Long-term Disability, Other leaves (e.g., Bereavement, FMLA, Adoption, Maternity, Military, Primary & Non-Primary Caregiver)
Retirement Benefits: Contributory Savings Plan (401k)