Executive Vice President, Regional Executive - Southeast

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 flourishes 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 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, U.S. Regional Executive Officer, the Executive Vice President, Regional Executive - Southeast is responsible for driving profitable growth, customer engagement, and market execution within the Southeast region. This role serves as a key field-facing representative of Ascot, partnering closely with customers, brokers, Business Unit leaders, Distribution, and cross-functional colleagues to identify opportunities, deepen relationships, advance Ascot U.S. growth objectives and drive Ascot culture. The Regional Executive develops and executes disciplined territory and client engagement plans, leveraging internal reports, analytics, product knowledge, AI and approved resources to support business development and deliver a consistent, high-impact market presence. While the role does not carry individual underwriting authority, it requires strong commercial judgment, consultative relationship management, compliant communication, and the ability to collaborate effectively across a matrixed organization. This individual will embody The Ascot Way by demonstrating integrity, accountability, inclusion, collaboration, and a commitment to finding a better way for Ascot’s customers and business partners.

Responsibilities:

• Drive sales, production activity, strong Ascot culture and profitable growth within the region, in alignment with Ascot U.S. business objectives and regional priorities.

• Engage with customers, brokers, regional employees and market partners both face to face and virtually to strengthen relationships, identify opportunities, and enhance Ascot’s market presence.
• Develop and implement effective business, territory, staffing and client engagement plans that support disciplined execution and measurable regional impact.
• Identify and execute live and virtual engagement strategies that maximize customer reach, relationship quality, and overall effectiveness.
• Build rapport and trusted relationships with regional employees and customers using sound judgment to sustain engagement and responsiveness.
• Effectively utilize existing and evolving digital tools to support customer engagement, territory management, and business development activities.
• Understand and leverage internal reports, data, and analytics to identify, develop, and implement strategic business opportunities across the assigned region.
• Compliantly leverage product, market, and risk knowledge to educate customers on Ascot’s value proposition, capabilities, and solutions for relevant client needs.
• Strategically utilize approved business, product, and customer resources to support meaningful customer discussions and advance appropriate opportunities.
• Collaborate effectively and compliantly with Business Unit leaders, Distribution, underwriting colleagues, and other enterprise partners to address customer inquiries and support regional growth priorities.
• Monitor regional market dynamics, customer feedback, and performance trends, translating insights into recommendations and actions that improve execution.
• Support talent acquisition, coaching, employee retention and development for the regional underwriting population.
• Serve as a visible culture champion, actively reinforcing The Ascot Way, connecting employees to Ascot’s purpose and values, and promoting an inclusive, high-performing environment within the region.
• Model The Ascot Way by demonstrating collaboration, accountability, inclusion, integrity, and a commitment to excellence in every customer and colleague interaction.

Requirements:

• Bachelor’s degree preferred, with relevant experience in insurance, underwriting, distribution, sales, business development, or related commercial roles.

• Proven ability to drive sales, production activity, relationship development, and business results within an assigned geography or territory.
• A minimum of 20 years of progressive insurance experience. 
• P&L management experience required. 
• Strong customer engagement skills, with demonstrated success with building rapport and maintaining relationships in both face-to-face and virtual settings.
• Experience developing and executing territory plans, call plans, account strategies, or market engagement plans that support measurable business outcomes.
• Strong commercial judgment and analytical capability, including the ability to interpret internal reports, performance data, and market insights to identify opportunities.
• Comfort using digital tools, virtual engagement platforms, CRM systems, analytics resources, and AI-enabled tools to improve customer engagement and execution effectiveness.
• Working knowledge of specialty insurance, underwriting concepts, distribution strategy, broker engagement, and customer relationship management preferred.
• Excellent communication, presentation, and influence skills, with the ability to represent Ascot professionally and credibly with customers, brokers, and internal stakeholders.
• Demonstrated ability to operate compliantly, exercise sound judgment, and use approved resources appropriately in all customer and market interactions.
• Strong teamwork and collaboration skills, with the ability to work effectively across a matrixed organization to address customer needs and advance shared growth objectives.
• Self-directed, organized, and accountable, with the ability to manage competing priorities, travel schedules, and territory demands with limited supervision.
• Ability to travel as needed within the assigned region and to other Ascot locations or customer meetings.

***This position may be filled at a different level, depending on experience***

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)

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