Director, HR Business Partner

Ascot Group • Chicago, IL

3h • Hybrid

About The Position

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 common mission and purpose. Our greatest strength is a talented team who flourish in a collaborative, inclusive, and entrepreneurial culture, steeped in underwriting excellence, integrity, and a passion to find 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 Client Centric, Risk Centric and Technology Centric strategies. Built to be resilient, Ascot offers clients leading financial security while delivering bespoke products and world class service — both 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. Reporting to the Senior Vice President, U.S. Head of Human Resources, the Director, HR Business Partner serves as a strategic advisor to business leaders, helping to translate business priorities into people strategies that drive performance, engagement, and organizational effectiveness across Ascot U.S. This role partners closely with leaders to address talent, workforce, and organizational needs while delivering practical, people-focused solutions that strengthen both business outcomes and the employee experience. The successful candidate will bring sound judgment, credibility, and a collaborative approach, and will lead with integrity, trust, and accountability. This is a hybrid minimum of 3-days in office role.

Requirements

• A minimum of 10 years of progressive human resources experience, including at least 5 years serving in an HR Business Partner role.
• Prior property and casualty insurance industry experience is required; experience supporting underwriting teams is strongly preferred.
• Strong foundational HR expertise across talent acquisition, talent development, performance management, compensation, employee relations, and workforce planning.
• Demonstrated ability to partner with senior leaders, align HR strategies to business objectives, and influence decision-making across all levels of the organization.
• Excellent interpersonal, communication, presentation, facilitation, and relationship management skills, with the ability to navigate sensitive matters with discretion and professionalism.
• Strong judgment, problem-solving capability, and initiative, with the ability to manage complex, evolving situations and maintain confidentiality.
• Analytical mindset with the ability to interpret HR data and workforce trends to inform decisions, identify opportunities, and improve business performance.
• Demonstrated ability to manage multiple priorities independently, execute with strong attention to detail, and deliver high-quality work in a fast-paced environment.
• Strong results orientation, sound execution skills, and a hands-on approach to supporting the business and delivering HR solutions.
• Proficiency in Microsoft PowerPoint and Excel.
• Bachelor’s degree required.
• Ability to travel as needed.

Nice To Haves

• experience supporting underwriting teams is strongly preferred

Responsibilities

• Partner with managers and business leaders to implement HR strategies that support business goals, organizational priorities, and operational objectives.
• Serve as a strategic partner and trusted advisor by providing expert guidance on HR matters, including policy interpretation, employee relations, performance management, talent planning, and organizational effectiveness.
• Provide day-to-day performance management support to leaders, including coaching, counseling, career development guidance, and disciplinary actions, while promoting a high-performance and accountable culture.
• Partner with talent acquisition to ensure alignment throughout the process, including creating/validating job descriptions, evaluation, and offer process.
• Collaborate with business leaders to identify and address workforce needs, ensuring the right talent, structure, and capabilities are in place to meet current and future business demands.
• Lead and support initiatives as part of the broader HR team and strategic plan to enhance employee engagement, retention, development, and overall employee experience.
• Manage and resolve complex employee relations issues with sound judgment, ensuring compliance with company policies, employment laws, and regulatory requirements.
• Analyze HR metrics, trends, and workforce insights to inform decision-making, identify opportunities for continuous improvement, and strengthen business and talent outcomes in partnership with the broader HR team.
• Lead change management initiatives, emphasizing the integration of AI technologies and continuous process improvement to enhance organizational effectiveness.
• Support the implementation and execution of HR programs, systems, practices, and policies to ensure consistency, effectiveness, and alignment with business objectives.
• Mentor and develop HR team members, fostering a culture of collaboration, continuous learning, and professional growth across the function.
• Commit to The Ascot Way by modeling integrity, collaboration, inclusivity, and accountability in daily interactions and in support of colleague engagement and development.

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)
• Paid holidays
• annual Paid Time Off
• Sick/Safe Time (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)
• Contributory Savings Plan (401k)

What This Job Offers

• Job Type: Full-time
• Career Level: Director