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Alaska Railroad Executive Team


William G. O'Leary, President & CEOBill O'Leary portrait image

William G. O'Leary is the President and Chief Executive Officer, effective November 1, 2013.  He is responsible for the daily management and operations of the corporation.

Previously, O'Leary served as the railroad's Chief Operations Officer, responsible for the oversight of rail transportation, engineering, mechanical, safety, labor relations, marketing, customer service and grant administration functions. From July 2001 to March 2013, O'Leary was the Alaska Railroad's Vice President of Finance and Chief Finance Officer (CFO), and in this capacity he was responsible for the financial activities of the corporation as well as human resources and supply management functions. He also served as Interim President & CEO from April 1 to September 22, 2010.

A Certified Public Accountant and lifelong Alaskan, O'Leary has worked in a variety of financial positions since 1988, including that of Controller of the Alaska International Airport System, the position he held before joining the railroad.

Born and raised in Fairbanks, O'Leary earned a bachelor's degree in accounting from the University of Alaska - Fairbanks.


Barbara Amy, Chief Financial Officer (CFO)

Barbara Amy was promoted Chief Financial Officer (CFO) in March 2013. She joined the Alaska Railroad in March 2006 as a Financial Analyst, and was promoted to Manager, Corporate Finance in April 2009 and to Director, Corporate Finance in February 2012.

Amy began her career in finance as a securities fraud investigator for the National Association of Securities Dealers (NASD) in New York City and later in Washington, D.C.  She has since spent the past 18 years working in various aspects of corporate finance.  She spent several years working as an investment banker, specializing in the transportation sector where her relationship team called on such clients as Burlington Northern Santa Fe Railway, Illinois Central Railroad, UPS, Fed Ex, United Airlines, Continental Airlines, Schneider National Trucking, and US Freightways among others.  She spent several years as a principal in a private equity firm in Chicago before moving to Alaska in 2002.  In Alaska, she has pursued corporate finance, working for a native corporation in Anchorage, as a consultant, and finally for the Alaska Railroad.

Amy earned a bachelor’s degree in business administration from the University of Connecticut, and a master’s degree in business administration (MBA) from the University of Chicago.  


Doug Engebretson, Chief Operating Officer (COO)

Doug Engebretson is the Chief Operating Officer (COO), effective November 8, 2013. In this capacity, he oversees rail transportation, engineering, mechanical, safety, marketing, customer service and grant administration functions. Previously, Engebretson served as Chief Mechanical Officer (CMO). 

Engebretson is a third-generation railroader with more than three decades experience with the mechanical aspect of train operations. His railroad career began with five years at Burlington Northern (BN) Railroad in Montana, where he became a certified carman (railcar mechanic).  A year after arriving in Fairbanks, Alaska, he joined the Alaska Railroad in 1984 as a Journeyman Carman.  Engebretson’s leadership skills were rewarded with a series of promotions, including to Fairbanks Terminal Supervisor in 1986.  In 1990, he transferred to Anchorage to become Car Operations Manager. In 2006, Engebretson joined the senior management team as Director of Mechanical Maintenance, and at the beginning of 2010, he was named CMO. 

Engebretson has followed in the footsteps of two previous generations. His grandfather Carl Engebretson worked for the Northern Pacific (NP) Railway in Montana, and his father Albert Engebretson worked for NP, BN and eventually retired from the Montana Rail Link.   Born and raised in Missoula, Montana, Engebretson is a military veteran who served as a track vehicle mechanic in the U.S. Marine Corps from 1974 to 1977.  He and his wife of 35 years, Teresa, reside in Anchorage. They have two grown sons, Curtis and Ryan.  


Clark Hopp, Vice President Engineering Clark Hopp Portrait image

Clark Hopp was named Vice President Engineering in May 2013. He has been with the Alaska Railroad since 2001 when he was hired as a capital projects manager. In 2003, he became Manager, Civil Projects and in 2011, Hopp was promoted to Director of Special Projects, overseeing the two mega rail extension projects — Port MacKenzie Rail Extension and Northern Rail Extension, Phase One. 

Before joining ARRC, Hopp worked for Transystems Corporation, a nationwide engineering consulting firm based in Nebraska. From 1995 to 2001, Hopp provided project management services to Burlington Northern Santa Fe (BNSF) and Union Pacific (UP) railroads.

Hopp earned a degree in Construction Engineering Technology from Iowa Western College and completed additional engineering coursework at the University of Nebraska.


William Hupprich, Vice President & General CounselBill Hupprich

William "Bill" R. Hupprich was named Vice President & General Counsel of the Alaska Railroad Corporation (ARRC) on January 1, 2011.  In this position, Hupprich manages and directs the legal and risk management affairs of the corporation and oversees a five-person legal department.  Hupprich joined ARRC in January 1988 as the Senior Attorney for Commercial/Financial Affairs and was promoted to Deputy General Counsel in May 1991.  Prior to joining ARRC he was engaged in private law practice in Anchorage (from 1983 to 1988) and in Washington State (from 1981 to 1983).

Hupprich is a second generation Alaskan and earned a bachelor of science degree in business from Arizona State University and a J.D. from Lewis & Clark Law School in Portland, Oregon.


James W. Kubitz, Vice President, Corporate Planning & Real Estate

Jim Kubitz joined the Alaska Railroad Corporation in 1998 as Director of Project Planning and moved to VP of Real Estate six months later. A 45 year resident of Anchorage, he served on the Anchorage Municipal Assembly from 1986-1993. A graduate of Willamette University with a BA in Economics, he owned and operated a general contracting company, Kubitz Construction for 15 years. More recently, he owned Kubitz & Co. a commercial real brokerage firm in Anchorage. He still holds a Broker's License in the State of Alaska.

He has served on the Alaska Tourism Marketing Council, Anchorage Chamber of Commerce, Anchorage Convention & Visitors Bureau, and the Anchorage Economic Development Corporation.

Mr. Kubitz is married to Susan Urig, an attorney and they have four children, Maxwell, Alexander, Elizabeth and Grace.


Wendy Lindskoog, Vice President, Business Management & Corporate Affairs

Wendy Lindskoog has been with the Alaska Railroad since 1999. She is Vice President of Business Management & Corporate Affairs, and as such is responsible for Corporate Affairs, Government and Community Relations,  Finance and Human Resources.  She also serves as Corporate Secretary to the ARRC Board of Directors, and is responsible for all corporate actions of the Board, coordination of the Board's responsibilities and scheduling of their meetings. 

Prior to joining the Alaska Railroad, Lindskoog was the Communications Director for the Alaska State Senate. Previously, she was part owner of a regional publication; the marketing and group sales manager for a California ski resort; and in high school and college, she worked for a small placer mining operation as the tailings pusher.

Lindskoog earned a bachelor’s degree in journalism from the University of Colorado, Boulder. She serves as a board member and former president of the Resource Development Council for Alaska, board member and former chair of the Alaska State Chamber of Commerce, board member for the Alaska SeaLife Center, and is a member of the Anchorage Athena Society.

Lindskoog resides in Anchorage along with her daughter Tindra Cardwell.


James Ratchford, Chief Information Officer (CIO)

James Ratchford is the Alaska Railroad (ARRC) Chief Information Officer (CIO) and head of the Technology Department.  The CIO is responsible for all aspects of ARRC’s information technology (IT) applications and systems, to include data center, network, telecommunications and radio. Ratchford joined the Alaska Railroad in January 2015. 

Before moving to Alaska, Ratchford held a number of executive IT posts in Washington state. He was Senior VP of Technology for MUSIC Group Services, a global music product holding company; CIO for Seattle Public Schools; Technical Services Director for Walt Disney Internet Group; and IT Infrastructure Director for Boeing Employees Credit Union. While in Seattle (2002-2014), Ratchford also contributed many volunteer hours to develop the local technology trade as president and board trustee for the Society for Information Management (SIM), Seattle Chapter, an association of CIOs, senior IT executives and other IT leaders.   In addition, he served five years as an advisory board member for the University of Washington SIM / Informatics Program. 

Having attained the rank of Chief Master Sergeant, Ratchford retired from the United States Air Force (USAF) in 2001 at the culmination of a 28-year military career.  While in the Air Force, he accepted such challenging assignments as Data Operations Center Director, Security System s Program Manager, and IT Operations Director.  He held his final position as General Manager of IT Operations Europe for nearly five years. 

Ratchford earned a master’s degree in Management Information Systems, and was certified as an information systems analyst, both from Bowie State University, in Bowie, Maryland.  He earned a bachelor’s degree in business management from the University of Maryland in College Park.  Ratchford resides in Anchorage with his wife Birgitt and son Erik.


Eileen Reilly, Vice President, Advanced Train Control Systems Eileen Reily image

Eileen Reilly Reilly is Vice President of Advanced Train Control Systems and is responsible for the development and implementation of positive train control (PTC).  She joined the Alaska Railroad in January 1996 as Information Services Manager and was promoted to Vice President in 2001. Reilly worked as a System Engineer for IBM for 10 years implementing data processing systems throughout the state of Alaska.

Reilly joined the Alaska Railroad to provide leadership in the effort to use technology to achieve the corporate goals, which include improved safety, customer service and efficient operations. Reilly was assigned Project Management responsibilities for the railroad's implementation of Positive Train Control (known as Collision Avoidance System) in 1997 and leads this effort today. This effort has included moving the dispatch function from paper track warrants to a computer-aided dispatch system that now support CTC and enhanced-DTC methods of operations. During this time, Reilly managed the Alaska Railroad's first implementation of CTC signalization on the Anton Anderson Tunnel, Whittier, Alaska, which is North America’s longest shared highway/railroad tunnel with operations that began in the summer of 2000.

Reilly earned a bachelor's degree in Computer Science from Rutgers University. She has been a resident of Alaska since 1981. 


Dale Wade, Vice President, Marketing & Customer Service

Dale Wade is Vice President Marketing & Customer Service, effective March 10, 2013.  He joined the Alaska Railroad as VP Business Development in early January 2012. He is a 30-year veteran of the freight transportation industry, involved in all aspects of freight service logistics, sales and marketing.  Most recently Wade was Founder and President of GoldStar Logistics Solutions in Anchorage.  Previous experience includes managing director and transportation consultant for AFMS Transportation Management in Portland, Oregon; national account executive for FedEx Corporation in Anchorage; and sales manager for CF Freight in Anchorage.

Wade served as a vice president with the Council of Supply Chain Management Professionals (CSCMP) Anchorage Chapter. He studied Business Administration at the University of Anchorage Alaska with a focus on sales and strategic negotiations. Born in Racine, Wisconsin, Wade moved to Alaska in 1978.