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Over the past four years, we have established a Learning Organization that empowers every employee to excel, providing them with the tools and support to achieve their goals. We are dedicated to fostering a performance-driven culture, where the best and brightest talent in the industry want to work and grow their careers with us.
Explore the career journeys of our colleagues and how they are reaching their limitless potential at Skyward Specialty.
Click on Tracy, Andrew and Lisa to learn more.
“Although Skyward is growing quickly and we execute quickly to continue that growth, there are multiple engagement opportunities for knowledge expansion and career growth. Prior to joining the Company, I knew very little about insurance. Through the generosity of those here, I have expanded my knowledge by asking questions, reading articles and doing my own research.”
Andrew Good – Vice President, A&H Captives
Underwriter
Senior Consulting Underwriter
Assistant Vice President, Captives
“Skyward Specialty has a collaborative, team-oriented culture where you’re trusted to take ownership and grow in your role. Everyone’s ideas are head, and there is a genuine effort to support each other’s success. That kind of positive, empowering atmosphere make a big difference – and I think it shows in the results.”
Underwriter
Supervising Underwriter
Director of Underwriting
Regional Vice President Underwriting
We are committed to developing a Learning Organization, offering our employees resources that both support their growth and drive the Company’s success.
Our commitment to attracting, retaining and developing top talent begins on day one. Taking Flight is a three-day, in-person onboarding experience designed to introduce and integrate new hires into our unique culture.
A 14-week course that guides managers through the entire employee life cycle at Skyward Specialty. Each week, managers explore a phase of the employee experience and discuss best practices for fostering growth and development. This interactive course helps build a strong network of managers across the company and equips them with essential leadership tools and resources.
Our online learning system offers employees the opportunity to build their professional technical skills with more than 4,000 eLearning courses, in partnership with 130 L&D vendors.
These plans, crafted with guided interviews and expert input, outline a structured approach for managers to help employees enhance their skills, knowledge and attributes over a period of one to three years.
A three-month program that pairs employees with senior leaders to gain industry insights, boost career development and prepare for leadership opportunities.
We cover 100% of certification costs, such as materials and testing fees, and offer completion bonuses of $500–$2,500 for most certifications.
87% of Skyward Specialty employees support development initiatives, up 22% from last year.
We are dedicated to empowering our employees with growth opportunities that extend beyond everyday responsibilities, fostering a vibrant culture of professional development. With a strong commitment to cultivating internal talent and building robust leadership pipelines, we offer a suite of dynamic programs tailored to nurture the leaders of tomorrow.
Structured around key competencies like change management, decision-making and emotional intelligence, the six-month program combines self-paced learning with collaborative experiences designed for real-world impact.
This comprehensive initiative is designed to develop highly skilled property underwriters through hands-on, immersive training experiences.
Focused on fostering a values-driven leadership culture, this program equips high-potential leaders to excel in remote/hybrid settings, addressing leadership gaps to enhance engagement and performance in alignment with strategic goals.
At Skyward Specialty, we integrate cutting-edge technology to complement and enhance the skills of our top talent, providing innovative tools that drive continuous learning and development. Below are a few examples of how we empower employee growth and success through technology:
Our advanced AI assistant, customized to meet the needs of each specific business using generative AI, allows employees to move faster and work smarter.
A proprietary, customized underwriter workstation that improves underwriters’ skills, boosts efficiency and enhances risk selection and fidelity.
Our customizable business intelligence platform, designed to transform data into actional insights, drive strategic decision-making and enhance organizational performance.