Skyward Specialty Executive and Leadership Team

September, 2026

Leadership Overview

Skyward Specialty has 10 executives leading key functions including communications, professional liability, property underwriting, industry solutions, and operational strategy.

Focused on delivering tailored risk transfer solutions, Skyward Specialty maintains a disciplined underwriting philosophy to address complex commercial needs across the United States insurance landscape.

Leadership Roles at Skyward Specialty

  • President & Lines Professional - Jim Mormile
  • Global President, Property - Douglas Davies
  • President, Industry Solutions-Mining, Crane & Rigging, Renewable Energy, Power Generation - Robin Roberts
  • President, Industry Solutions, Specialty Programs & Captives - Kirby Hill
  • President, Property & Casualty (US) - John Burkhart
  • President, Inland Marine & Transactional Property - Christopher Zitzmann
  • President - Michael Remeika
  • President, Captives & Specialty Programs - Corey LaFlamme
  • Vice President, Communications & Chief Marketing Officer - Haley Doughty
  • Chief People Officer, Skyward Specialty, Operations (US) - Angela Chaumont
  • Jim Mormile - President & Lines Professional

    Jim Mormile, the President & Lines Professional at Skyward Specialty, manages the strategic direction of professional liability portfolios. Overseeing the underwriting discipline for complex risk profiles, the President & Lines Professional ensures that policy frameworks meet the specific requirements of brokers and commercial clients. This leadership role involves evaluating market trends to identify coverage gaps where standard carriers remain less responsive. By refining risk selection criteria, Jim Mormile directly impacts the profitability and stability of the professional liability division. The President & Lines Professional also collaborates with other senior leaders to integrate specialty programs into the broader corporate strategy. Through rigorous analysis of industry-specific data, Mormile drives the expansion of the company's footprint across the U.S. market, ensuring that the organization remains a flexible, high-performing alternative to traditional insurance providers.

    Douglas Davies - Global President, Property

    Douglas Davies, the Global President, Property at Skyward Specialty, architects the overarching strategy for commercial property insurance products. Overseeing the underwriting standards for diverse property risks, the Global President, Property ensures that the company maintains a competitive edge in both admitted and non-admitted surplus lines platforms. This leadership role involves managing the technical assessment of complex assets and designing customized policy solutions for high-value commercial clients. By driving disciplined risk selection, Douglas Davies directly impacts the financial performance of the property division. The Global President, Property also coordinates with regional teams to ensure that underwriting practices remain consistent with the firm's mission of providing tailored risk transfer solutions. Through constant monitoring of market volatility, Davies secures the organization's position as a leader in the specialty property insurance landscape, effectively addressing the unique needs of various industries.
    Douglas Davies

    Robin Roberts - President, Industry Solutions-Mining, Crane & Rigging, Renewable Energy, Power Generation

    Robin Roberts, the President, Industry Solutions-Mining, Crane & Rigging, Renewable Energy, Power Generation at Skyward Specialty, directs the underwriting and service delivery for specialized industrial sectors. Overseeing the development of niche insurance products for energy and heavy equipment clients, the President, Industry Solutions-Mining, Crane & Rigging, Renewable Energy, Power Generation ensures that coverage addresses the specific operational hazards inherent in these fields. This leadership role involves crafting bespoke risk transfer solutions that standard market carriers often overlook. By leveraging deep technical expertise, Robin Roberts directly impacts the company's ability to capture market share in high-complexity industries. The President, Industry Solutions-Mining, Crane & Rigging, Renewable Energy, Power Generation also works closely with brokers to refine policy terms that support the unique requirements of mining and power generation firms. Ultimately, Roberts drives sustainable growth by maintaining rigorous underwriting standards across these critical industrial segments.
    Robin Roberts

    Kirby Hill - President, Industry Solutions, Specialty Programs & Captives

    Kirby Hill, the President, Industry Solutions, Specialty Programs & Captives at Skyward Specialty, manages the strategic growth of alternative risk transfer mechanisms and program business. Overseeing the development of captive insurance structures, the President, Industry Solutions, Specialty Programs & Captives ensures that clients receive flexible, customized solutions for their unique risk profiles. This leadership role involves identifying new opportunities within specialty programs to expand the company's reach across diverse commercial sectors. By fostering strong relationships with distribution partners, Kirby Hill directly impacts the diversification of the firm's underwriting portfolio. The President, Industry Solutions, Specialty Programs & Captives also collaborates with internal teams to ensure that program underwriting remains disciplined and profitable. Through the implementation of innovative risk management strategies, Hill secures the organization's reputation as a premier provider of specialty insurance solutions, effectively navigating the complexities of the U.S. insurance market.

    John Burkhart - President, Property & Casualty (US)

    John Burkhart, the President, Property & Casualty (US) at Skyward Specialty, oversees the operational execution of core property and casualty insurance lines across the United States. Managing the underwriting performance for these essential segments, the President, Property & Casualty (US) ensures that the company maintains a balanced and profitable portfolio. This leadership role involves coordinating with various underwriting divisions to streamline the delivery of commercial insurance products. By optimizing internal processes and risk selection, John Burkhart directly impacts the overall efficiency and market responsiveness of the organization. The President, Property & Casualty (US) also works with the executive team to align regional operations with the company's broader strategic goals. Through consistent oversight of underwriting discipline, Burkhart drives the firm's ability to provide reliable coverage solutions, ensuring that the company remains a preferred partner for brokers and commercial clients throughout the U.S. insurance landscape.

    Christopher Zitzmann - President, Inland Marine & Transactional Property

    Christopher Zitzmann, the President, Inland Marine & Transactional Property at Skyward Specialty, directs the underwriting strategy for specialized inland marine and transactional property risks. Overseeing the development of tailored coverage for mobile equipment and high-value property assets, the President, Inland Marine & Transactional Property ensures that the company meets the complex needs of clients in these niche markets. This leadership role involves managing the technical assessment of risks and designing policy frameworks that provide comprehensive protection. By maintaining disciplined underwriting standards, Christopher Zitzmann directly impacts the profitability of these specific insurance lines. The President, Inland Marine & Transactional Property also collaborates with brokers to provide responsive solutions where standard markets may be less effective. Through a focus on innovation and technical expertise, Zitzmann secures the firm's competitive position, ensuring that the organization remains a leader in providing specialized property insurance solutions across the U.S.
    Christopher Zitzmann

    Michael Remeika - President

    Michael Remeika, the President at Skyward Specialty, provides executive oversight for the company's broad strategic initiatives and overall market performance. Managing the integration of various underwriting divisions, the President ensures that the organization maintains its focus on innovation and niche market leadership. This leadership role involves coordinating with the board and senior management to drive long-term growth and financial stability. By championing a culture of disciplined risk selection, Michael Remeika directly impacts the firm's reputation as a flexible alternative to standard market carriers. The President also oversees the alignment of corporate resources to support the complex needs of brokers and commercial clients across the U.S. insurance landscape. Through strategic decision-making and a commitment to technical excellence, Remeika secures the company's position as a leader in the specialty insurance sector, ensuring that the organization continues to deliver tailored risk transfer solutions effectively.

    Corey LaFlamme - President, Captives & Specialty Programs

    Corey LaFlamme, the President, Captives & Specialty Programs at Skyward Specialty, directs the development and management of captive insurance solutions and specialized program business. Overseeing the underwriting and operational framework for these alternative risk structures, the President, Captives & Specialty Programs ensures that the company provides highly customized coverage for complex commercial entities. This leadership role involves identifying emerging market opportunities and building partnerships that expand the firm's specialty footprint. By applying rigorous underwriting discipline to captive programs, Corey LaFlamme directly impacts the financial health and risk profile of the organization. The President, Captives & Specialty Programs also works with internal teams to ensure that these programs remain responsive to the evolving needs of brokers and clients. Through the strategic expansion of specialty offerings, LaFlamme secures the company's role as a key provider of innovative risk transfer solutions within the broader U.S. insurance market.
    Corey LaFlamme

    Haley Doughty - Vice President, Communications & Chief Marketing Officer

    Haley Doughty, the Vice President, Communications & Chief Marketing Officer at Skyward Specialty, directs all corporate branding and market positioning initiatives. Overseeing the development of strategic messaging, the Chief Marketing Officer ensures alignment between the company's niche market focus and its external distribution partners. This leadership role involves managing complex public relations campaigns that highlight the organization's innovative approach to commercial property and casualty insurance. By optimizing digital engagement and broker outreach, Haley Doughty directly impacts the visibility of the firm within the competitive U.S. insurance sector. The Chief Marketing Officer also coordinates with underwriting divisions to translate technical expertise into clear, actionable value propositions for clients. Ultimately, Doughty secures brand equity and supports long-term growth by maintaining a consistent, professional narrative across all regional operations and industry-specific platforms.
    Haley Doughty

    Angela Chaumont - Chief People Officer, Skyward Specialty, Operations (US)

    Angela Chaumont, the Chief People Officer, Skyward Specialty, Operations (US) at Skyward Specialty, directs the human capital strategy and operational support functions for the organization. Overseeing talent acquisition, employee development, and organizational culture, the Chief People Officer, Skyward Specialty, Operations (US) ensures that the company attracts and retains the expertise necessary to maintain its underwriting discipline. This leadership role involves aligning internal operational processes with the firm's strategic mission to provide high-quality insurance services. By fostering a high-performance environment, Angela Chaumont directly impacts the company's ability to execute its business model effectively. The Chief People Officer, Skyward Specialty, Operations (US) also works with the executive team to ensure that operational resources are allocated to support the growth of various underwriting divisions. Through the management of organizational infrastructure, Chaumont secures the firm's operational stability, enabling the company to deliver consistent value to its brokers and commercial clients.
    Angela Chaumont

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    Frequently Asked Questions Regarding Skyward Specialty Top Executives and Leadership Team

    Who leads Skyward Specialty?
    Skyward Specialty is led by Jim Mormile (President & Lines Professional), along with executives such as Douglas Davies (Global President, Property) and Robin Roberts (President, Industry Solutions-Mining, Crane & Rigging, Renewable Energy, Power Generation).
    Who is part of Skyward Specialty’s executive team?
    The executive team of Skyward Specialty includes leaders such as Jim Mormile (President & Lines Professional), Douglas Davies (Global President, Property), Robin Roberts (President, Industry Solutions-Mining, Crane & Rigging, Renewable Energy, Power Generation) and other senior executives.
    How many executives does Skyward Specialty have?
    Skyward Specialty has 10 executives leading key business areas.
    What roles are included in Skyward Specialty’s leadership team?
    The leadership team of Skyward Specialty includes roles such as President & Lines Professional, Global President, Property, President, Industry Solutions-Mining, Crane & Rigging, Renewable Energy, Power Generation, President, Industry Solutions, Specialty Programs & Captives, President, Property & Casualty (US).