Shane Hesters

Shane Hesters brings two decades of hands-on leadership to Anchor Roofing Systems, with experience that spans the full length of Texas, from the Rio Grande Valley to the growth corridors of North Dallas. Before stepping into his current role as General Manager, Shane held key leadership positions across the industry, including Superintendent, Business Development Manager, Division Manager, and Vice President of Operations.

As CEO, Shane oversees the day-to-day execution of Anchor’s projects and performance. He is responsible for equipping our field teams with the resources, planning, and operational discipline required to deliver consistent, high-quality results on every job.

A proud graduate of Texas A&M University, Shane holds a Bachelor of Science in Construction Science and an MBA in Finance and Accounting. His leadership foundation was built in the United States Marine Corps infantry, where he served four years before beginning his career in construction.

Diane Weakley

Since joining Anchor Roofing Systems in 1997, Diane Weakley has been the steady heartbeat of our company. With over two decades of dedicated service, she oversees all aspects of accounting and human resources, ensuring that our operations run smoothly, our team members are supported, and our culture remains strong.

Known for her kindness, approachability, and deep commitment to Anchor’s success, Diane truly embodies what it means to be the “pulse of the company.” Her passion for people and relentless dedication to excellence continue to inspire those around her every day.

Outside of the office, Diane enjoys life with her husband of 46 years and their son and daughter in-law, cherishing time spent with family and friends. She’s always up for a good travel adventure and never passes up a bowl of chips and salsa—two of her favorite things.

Jake Miller

As the Service Director at Anchor Roofing Systems, Jake Miller leads with a clear objective: extend roof life, minimize disruption, and deliver fast, dependable service when clients need it most. With deep expertise in reactive repairs, preventative maintenance, and building envelope diagnostics, Jake oversees a team built to respond quickly and professionally across a wide range of commercial roofing systems.
Jake plays a hands-on role in strategy, team development, and service delivery.

From emergency leak calls to long-term preventative maintenance plans, he ensures every customer interaction is timely, efficient, and solution-driven. His background in client services, strategic planning, and project execution makes him an invaluable resource to property managers, facility directors, and building owners looking to maximize the value of their roofing assets.

A strong communicator and team builder, Jake brings consistency and care to every client relationship—and makes sure the work matches the promise. Outside the office, he’s a proud father of four who enjoys hunting, fishing, and a good round of golf when time allows.

Rick Boyt

With more than 42 years in the commercial roofing industry, and over two decades dedicated to Anchor Roofing Systems, Rick Boyt has earned a reputation among clients, colleagues, and peers as nothing short of “best in class.” His experience spans millions of square feet of roofing and wall panel systems installed across the U.S., and his ability to lead complex projects from start to finish is unmatched.

As Senior Project Manager, Rick serves as the primary point of contact on each project he leads. His responsibilities include estimating, cost control, project management, quality assurance, client communication, and coordination with suppliers, manufacturers, and trade partners. Rick brings technical depth, relentless attention to detail, and a solutions-first mindset to every jobsite, and it shows in the results.

Brad Oberg

brings over 35 years of roofing industry experience to Anchor Roofing Systems, with a career that began in 1988 at his family’s business, Cant Strip Corporation of America. Starting out as an estimator for tapered insulation systems, Brad has spent his entire career immersed in the technical and operational sides of commercial roofing.

In 1997, Brad joined Progressive Roofing in Phoenix, Arizona as an AutoCAD draftsman, later transitioning into estimating and project management. By 2004, he relocated to Texas to establish and lead Progressive Roofing’s new Dallas branch—further expanding his leadership and field execution capabilities.

Brad joined Anchor Roofing Systems in 2022 as a Senior Estimator and Project Manager. He brings deep technical expertise, disciplined project control, and a proven ability to manage complex scopes across commercial roofing systems.

Steve Smith

Steve brings over 33 years of experience in the commercial roofing industry, with a
career that began hands-on in the field as an architectural sheet metal laborer. Over the decades, he has progressed into estimating, sales, and project management roles, successfully overseeing projects of all sizes and complexities. His deep field knowledge and estimating expertise make him a valuable asset on budgeting and design-build projects, where accuracy and constructability are critical.

Outside the office, Steve enjoys spending time with his family and hitting the open road on his Harley.

Ruben Gutierrez

joined Anchor Roofing Systems with a strong foundation in engineering and cross-industry project work. A graduate of the University of North Texas, Ruben earned his degree in Mechanical Engineering in 2017 and has since applied his technical training across aerospace and automotive projects—gaining experience with diverse team structures, timelines, and deliverables.

As an Assistant Project Manager, Ruben plays a key role in supporting Anchor’s Senior Project Managers. His responsibilities include managing project documentation, coordinating change orders, procuring materials, enforcing quality standards, and driving successful project closeouts. Ruben’s precision, organization, and engineering mindset make him a reliable asset across every phase of the build process.

Shannon Vinson

Shannon Vinson is a Service Account Manager with extensive experience in
commercial roofing operations, project management, and customer support. He works directly with building owners, property managers, and general contractors to manage service needs, coordinate repairs, and ensure timely, effective solutions. Shannon’s background overseeing complex commercial projects allows him to quickly identify issues, communicate clearly, and follow through from initial request to completion.
Known for his responsiveness and problem-solving approach, Shannon is committed to protecting clients’ assets and building long-term relationships.

Dylan Undseth

Dylan Undseth serves as Business Development Manager, bringing a strong technical background in commercial roofing service, estimating, and field inspections. His hands-on experience allows him to work closely with clients to identify roofing needs, develop practical solutions, and guide projects from initial consultation through execution. Dylan has supported projects ranging from small service repairs to large-scale commercial re-roofing, giving him a deep understanding of pricing, constructability, and long-term performance. Known for his responsiveness and relationship-driven approach, Dylan focuses on building lasting partnerships and delivering value-driven roofing solutions.

Miles Martin

With more than 42 years in the roofing industry, and 22 of those committed to Anchor Roofing Systems, Miles Martin brings unmatched field experience to his role as Safety Manager. From laborer to foreman, superintendent to heavy equipment operator, Miles has worked every corner of the jobsite. That depth of experience is exactly what makes him a respected and effective leader in the safety arena.
Miles is responsible for aligning each client’s site-specific safety requirements with Anchor’s internal safety culture. His practical knowledge, leadership in high-risk environments, and ability to speak the language of the field crews give him the credibility and clarity needed to maintain Anchor’s best-in-class safety standards across every job.

Manny Diosdado

With over 31 years in the roofing industry, 21 of them with Anchor Roofing Systems, Manny Diosdado is the operational backbone of our field execution. He began his career as a general laborer and has spent the past four decades mastering every facet of the trade. From crew management to quality control, Manny’s leadership is rooted in hands-on experience and deep industry knowledge.
As General Superintendent, Manny oversees day-to-day operations across all active job sites. His responsibilities include project resource allocation, client coordination, and ensuring every roof is built to Anchor’s exacting standards. Respected by crews and clients alike, Manny leads with a steady hand and a commitment to doing the job right the first time.