Skyline Talent Group

Our Story

Skyline Talent Group was founded with a singular goal: to revolutionize the way businesses hire. Recognizing the inefficiencies in traditional recruitment models, we set out to create a service that prioritizes quality, efficiency, and alignment. By focusing on passive candidate engagement and personalized recruiting strategies, we ensure that our clients have access to the best talent in the market—not just the most available.

Meet The Team

After nearly a decade as colleagues, the three founders of Skyline Talent Group chose to embark on this journey together, driven by a shared vision and a deep respect for one another’s expertise. With complementary strengths and a unified mission, they set out to build a firm rooted in trust, innovation, and an unwavering commitment to their clients' success.

Partner

Hayden Crook

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With seven years of experience in recruiting and talent acquisition, Hayden has a passion for connecting great people with great opportunities. He’s built a reputation for being a trusted partner—helping companies find the right talent while guiding professionals toward careers that truly fit. His approach is rooted in relationships, transparency, and a commitment to delivering real results. Whether working with a growing startup or an established enterprise, Hayden takes pride in making meaningful connections that drive long-term success.

A former football player at the University of Oregon, competition and teamwork have always been a part of who he is. The discipline, resilience, and leadership he developed on the field continue to shape the way he works today. He thrives in fast-paced environments, tackles challenges head-on, and brings the same drive and intensity to recruiting that he once brought to game day.

Outside of work, Hayden is a proud father of two, and family is at the heart of everything he does. Whether coaching from the sidelines, spending quality time with his kids, or helping a client make a game-changing hire, he brings the same energy and dedication. For Hayden, it’s all about building relationships—both in business and in life—that stand the test of time.

Partner

Sierra Fletcher

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Sierra Fletcher is passionate about helping businesses make smart, strategic hiring decisions that fuel their success. As a trusted partner to her clients, she works closely with leaders to understand their unique needs and build high-performing teams that drive growth. Her ability to align talent strategy with business goals has made her an invaluable resource to the companies she serves.

With over a decade of experience in recruiting and team-building, Sierra has advised businesses of all sizes on how to attract, hire, and retain top talent. She takes a consultative approach, ensuring that every hiring decision supports the company’s long-term vision. Known for her ability to cultivate strong relationships, she considers many of her clients not just partners, but friends.

Entrepreneurship has always been in Sierra’s DNA. After years of guiding businesses through hiring challenges, she knew it was time to build something of her own—combining her expertise in talent strategy with her passion for helping companies thrive.

Beyond her career, Sierra is a wife, a proud mom to two incredible girls, and a former varsity student-athlete at the University of Wisconsin. Now based in Bend, Oregon, she brings the same discipline, resilience, and competitive spirit from her athletic career into everything she does.

Partner

Joe Chirumbolo

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With over a decade of experience in talent acquisition, partner relationship management, and team leadership, Joe specializes in providing customized strategic recruiting solutions and expert client consulting. He has successfully placed top talent across diverse industries, including architecture, construction, technology, and healthcare, helping organizations build strong, effective teams. With deep expertise in the construction sector, Joe has worked with companies of all sizes—from agile small businesses to large multi-location enterprises—spanning commercial, civil, and residential construction markets. His extensive experience enables him to understand the unique needs and challenges of each client, and he is known for his ability to tailor solutions that align with their goals. He believes in transparency and direct communication, always prioritizing client needs while implementing strategic change to help businesses adapt and thrive in an ever-evolving market.

A former collegiate athlete, Joe was a multi-year letter-winner as a football player at the University of Missouri, where he honed his discipline, teamwork, and leadership—qualities that continue to drive his success in the professional world. Outside of work, he enjoys spending quality time with his wife and their three energetic daughters, embracing the chaos and joy of family life.