Skyward Specialty Executive and Leadership Team

October, 2026

Leadership Overview

Skyward Specialty has 10 executives leading key functions including communications, marketing, captive insurance, property underwriting, human resources, and industry-specific risk solutions.

Focused on delivering tailored risk transfer solutions for complex commercial needs, Skyward Specialty maintains a disciplined underwriting philosophy to provide flexible coverage alternatives across the United States.

Leadership Roles at Skyward Specialty

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

    Corey LaFlamme, the President, Captives & Specialty Programs at Skyward Specialty, manages the strategic growth and underwriting performance of the captive insurance and specialty program portfolios. Overseeing the design of customized risk transfer structures, the President ensures that these programs address unique commercial risk profiles where standard markets often fail to respond. This leadership role involves close coordination with distribution partners to build scalable, niche-focused insurance solutions. By applying rigorous underwriting discipline, Corey LaFlamme directly impacts the profitability and stability of the captive division. The President also evaluates emerging market trends to identify new opportunities for program expansion across the U.S. insurance landscape. Ultimately, LaFlamme drives the operational success of these specialized platforms by balancing technical risk selection with the need for flexible, client-centric coverage, ensuring that the organization maintains a competitive edge in the complex specialty insurance sector.
    Corey LaFlamme

    Christopher Zitzmann - President, Inland Marine & Transactional Property

    Christopher Zitzmann, the President, Inland Marine & Transactional Property at Skyward Specialty, architects the underwriting strategy for property-related risks and inland marine coverage. Overseeing the deployment of capital across these specific lines, the President ensures that all policy frameworks meet the complex requirements of commercial clients. This leadership role involves managing the technical assessment of property exposures to maintain high underwriting standards. By optimizing the transactional property portfolio, Christopher Zitzmann directly impacts the company's ability to provide responsive solutions in the broader U.S. insurance market. The President also coordinates with internal teams to refine coverage terms for niche industries, ensuring that the firm remains a flexible alternative to standard carriers. Ultimately, Zitzmann secures the financial performance of these divisions by enforcing disciplined risk selection and fostering strong relationships with brokers who require specialized property expertise for their diverse commercial accounts.
    Christopher Zitzmann

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

    Kirby Hill, the President, Industry Solutions, Specialty Programs & Captives at Skyward Specialty, oversees the development and execution of specialized insurance products for diverse industry sectors. Managing the intersection of industry-specific solutions and captive platforms, the President ensures that the company delivers highly customized risk transfer mechanisms. This leadership role involves identifying market gaps where standard carriers lack the flexibility to provide adequate coverage. By driving innovation within these programs, Kirby Hill directly impacts the organization's market position as a leader in specialty insurance. The President also collaborates with underwriting teams to refine risk selection criteria, ensuring that the firm maintains its reputation for technical excellence. Ultimately, Hill secures the growth of these divisions by aligning product offerings with the evolving needs of brokers and commercial clients, ensuring that the company remains a responsive and reliable partner in the complex U.S. insurance landscape.

    Douglas Davies - Global President, Property

    Douglas Davies, the Global President, Property at Skyward Specialty, directs the worldwide underwriting strategy for the property insurance division. Overseeing the management of complex property risks, the Global President ensures that the company maintains a disciplined approach to risk selection across all geographic markets. This leadership role involves setting the technical standards for property coverage and ensuring that the firm provides competitive solutions for commercial clients. By optimizing the global property portfolio, Douglas Davies directly impacts the organization's financial stability and market reach. The Global President also works with regional teams to identify emerging property risks and develop innovative policy frameworks that address coverage gaps. Ultimately, Davies secures the long-term success of the property division by balancing technical expertise with a focus on delivering tailored risk transfer solutions that meet the specific needs of brokers and commercial entities operating in diverse industries.
    Douglas Davies

    Rick Childs - President, Construction & Energy

    Rick Childs, the President, Construction & Energy at Skyward Specialty, manages the underwriting and strategic direction for the construction and energy sectors. Overseeing the assessment of high-complexity risks, the President ensures that the company provides robust insurance products tailored to the unique demands of these industries. This leadership role involves coordinating with brokers to design customized policy frameworks that address the specific operational hazards inherent in construction and energy projects. By maintaining strict underwriting discipline, Rick Childs directly impacts the profitability and risk profile of these specialized divisions. The President also monitors industry trends to ensure that the firm remains at the forefront of providing innovative coverage solutions. Ultimately, Childs secures the firm's reputation as a premier provider in the U.S. insurance landscape by delivering reliable, expert-driven risk transfer services that support the complex needs of commercial clients within the construction and energy markets.

    John Burkhart - President, Property & Casualty (US)

    John Burkhart, the President, Property & Casualty (US) at Skyward Specialty, directs the underwriting operations and strategic growth for the domestic property and casualty portfolio. Overseeing the performance of these core lines, the President ensures that the company delivers consistent and high-quality risk transfer solutions to commercial clients across the United States. This leadership role involves managing the balance between technical risk selection and the need for flexible coverage options. By optimizing the P&C division, John Burkhart directly impacts the organization's ability to compete effectively against standard market carriers. The President also collaborates with other C-suite leaders to align P&C strategies with the company's broader mission of innovation and niche market focus. Ultimately, Burkhart secures the financial health of the U.S. operations by enforcing disciplined underwriting standards and fostering strong, long-term relationships with distribution partners who rely on the firm's specialized expertise.

    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, architects the underwriting strategy for highly specialized industrial sectors. Overseeing the risk assessment for mining, crane, rigging, and energy operations, the President ensures that the company provides tailored coverage for these complex commercial environments. This leadership role involves deep technical engagement to design policy frameworks that address the specific operational risks of each industry. By focusing on these niche markets, Robin Roberts directly impacts the firm's ability to provide solutions where standard markets are less responsive. The President also works with brokers to ensure that the company's offerings remain aligned with the evolving needs of these critical sectors. Ultimately, Roberts secures the organization's market position by delivering expert-driven, disciplined risk transfer solutions that support the operational continuity of commercial clients across the U.S. insurance landscape.
    Robin Roberts

    Michael Remeika - President

    Michael Remeika, the President at Skyward Specialty, directs the overall operational strategy and execution of the company's business model. Overseeing the integration of various underwriting divisions, the President ensures that the organization maintains its commitment to disciplined risk selection and innovation. This leadership role involves coordinating with the executive team to drive growth and maintain the firm's position as a flexible alternative to standard market carriers. By fostering a culture of technical excellence, Michael Remeika directly impacts the company's ability to deliver tailored risk transfer solutions to brokers and commercial clients. The President also manages the strategic alignment of the firm's admitted and non-admitted platforms to maximize market reach. Ultimately, Remeika secures the long-term success of the organization by balancing operational efficiency with a focus on niche market opportunities, ensuring that the company remains a responsive and reliable partner in the complex U.S. insurance landscape.

    Haley Doughty - Vice President, Communications & Chief Marketing Officer

    Haley Doughty, the Vice President, Communications & Chief Marketing Officer at Skyward Specialty, directs all corporate messaging and brand positioning initiatives. Overseeing the development of market-facing strategies, the Chief Marketing Officer ensures alignment between the company's niche underwriting capabilities and broker expectations. This leadership role involves managing external communications to amplify the firm's reputation as a flexible alternative to standard market carriers. By refining the brand narrative, Haley Doughty directly impacts the visibility of specialty programs and industry solutions within the competitive U.S. insurance landscape. The Chief Marketing Officer also collaborates with underwriting divisions to translate technical risk expertise into clear value propositions for commercial clients. Ultimately, Doughty secures long-term brand equity by maintaining consistent messaging across all distribution platforms and digital channels, ensuring that the organization remains a preferred partner for brokers seeking customized policy frameworks.
    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 alignment for the organization. Overseeing talent acquisition, organizational development, and employee engagement, the Chief People Officer ensures that the workforce possesses the technical expertise required to support the company's niche underwriting mission. This leadership role involves integrating operational efficiency with corporate culture to drive high performance across all U.S. divisions. By fostering a collaborative environment, Angela Chaumont directly impacts the firm's ability to attract and retain top-tier insurance professionals. The Chief People Officer also works with executive leadership to ensure that internal structures support the company's strategic emphasis on innovation and disciplined risk selection. Ultimately, Chaumont secures the long-term operational health of the organization by aligning human resources initiatives with the broader business goals of providing tailored risk transfer solutions to 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 Corey LaFlamme (President, Captives & Specialty Programs), along with executives such as Christopher Zitzmann (President, Inland Marine & Transactional Property) and Kirby Hill (President, Industry Solutions, Specialty Programs & Captives).
    Who is part of Skyward Specialty’s executive team?
    The executive team of Skyward Specialty includes leaders such as Corey LaFlamme (President, Captives & Specialty Programs), Christopher Zitzmann (President, Inland Marine & Transactional Property), Kirby Hill (President, Industry Solutions, Specialty Programs & Captives) 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, Captives & Specialty Programs, President, Inland Marine & Transactional Property, President, Industry Solutions, Specialty Programs & Captives, Global President, Property, President, Construction & Energy.