Property Management Personnel

Company Information

Craig M. Lessard

Director of Acquisitions

Craig Lessard joined Woodspear Properties in May of 2008. Based out of Denver, Colorado, Mr. Lessard is responsible for executing Woodspear’s investment strategy which entails sourcing new investment opportunities, performing the physical and financial due diligence, overseeing the post-acquisition renovations, and post-acquisition financial monitoring.

Prior to joining Woodspear Properties, Mr. Lessard interned with the President of Retail & Mixed-Use Development for McWhinney. Under this position he was responsible for the creating business intelligence reports and conducting competitive market research for existing and future developments. Mr. Lessard was also heavily involved in the preliminary stages of developing a $400M lodging and retail project adjacent to Disneyland in Garden Grove, California.

Mr. Lessard graduated from Colorado State University in 2008, majoring in Commercial Real Estate. His senior year he was President of the CSU Real Estate Club and was involved in several projects, most notably being a part of the CSU National Association of Home Builders student team that placed fifth in a national residential development competition. Upon graduation he was inducted into the National Real Estate Honor Society, Alpha Sigma Gamma, based on academic performance.

Zakary A. Kessler

General Counsel

Zakary A. Kessler joined Woodspear Properties as Associate General Counsel in September 2013 and was promoted to General Counsel in 2018. He is responsible for legal matters related to all aspects of Woodspear’s commercial real estate business. Mr. Kessler graduated summa cum laude from Gonzaga University in 2005 with a B.A. degree in Political Science. He earned his Juris Doctorate from the University of Colorado Law School in 2013, graduating in the top 1/3rd of his class. Mr. Kessler is licensed to practice law in Colorado and is a member of the Colorado Bar Association and serves as a member of the Real Estate Section Council of the Colorado Bar Association through June 30, 2023.

In addition to being a lawyer, Mr. Kessler has extensive experience in various areas of real estate finance. He began his career as a residential mortgage-backed securities credit risk analyst. Upon moving into the commercial real estate field, he developed expertise in analysis, modeling, and underwriting of commercial real estate while working as a financial analyst in mortgage banking and private equity. In that time, he aided in the origination of multiple commercial real estate debt and equity investments totaling in excess of $450M.

Mr. Kessler gained real estate, securities, and business legal experience while in law school by interning with the Real Estate Legal Department of Red Robin International, Inc. and clerking at Frascona, Joiner, Goodman & Greenstein, P.C. Mr. Kessler’s note, Getting One Step Closer to a Commercial eMortgage, was published in Volume 11 of the Journal on Telecommunications and High Technology Law in December 2013. He co-authored The Attack on Colorado’s TABOR and the Threat to Other States, an Issue Paper published by the Independence Institute in January 2013.

Mr. Kessler lives in Parker, CO and spends most of his free time with his wife and four children. He also enjoys running and playing golf.

Gina Gasio Olson

Director of Accounting

Gina Gasio Olson joined Woodspear Properties in July 2002. Ms. Olson is responsible for the financial accounting and reporting for a portfolio of residential, commercial and various corporate entities, including the Woodspear Properties Corporate entity. Ms. Olson manages the Corporate accounting department in addition to indirectly managing and supporting the Property Management operations.

Ms. Olson has over 30 years of accounting and property operations experience, specifically within the real estate and property management industry. Her diverse experience has consisted of working for various real estate investment firms and a large national property management company. Ms. Olson brings to Woodspear her extensive management and accounting experience, in addition to her property management, budgeting, construction, banking/finance, lending, investor relations, and systems administration background. As an experienced accounting professional, Ms. Olson has worked well with owners, investors, bankers, and lenders building strong business relationships; additionally, she has successfully worked with outside CPA firms and Federal/State auditors.

Ms. Olson graduated from California State University, San Marcos, with a degree in Business Administration with an emphasis in both Accounting and Finance. She is also in the process of completing her CMA certification. She has been a member of the Institute of Management Accountants (IMA) and Construction Financial Management Association (CFMA).

Ms. Olson is married and has a son. She and her family enjoy camping, boating, and spending time with their family and friends.

Erica Jackson

Accounting Manager

Erica Jackson joined Woodspear Properties in August 2021. Ms. Jackson manages and oversees the daily and monthly accounting functions for the residential and commercial properties and various corporate entities. Ms. Jackson manages a corporate staff of two and supports the Property Management operations.

Ms. Jackson’s experience began twenty-two years ago in multiple industries including commercial and residential property management, real estate, construction, non-profit, HOAs, and professional services. With a diverse background in accounting, administration and management, Ms. Jackson has held Accounting Manager/Controller positions within various organizations. In addition to her background, Ms. Jackson has worked with several departments within an organization on variance analytics, construction loans and draws, budgets, forecasting, project management, job costing and WIP allocation. Ms. Jackson also possesses software intelligence; utilizing, migrating and implementing various ERP systems.

As a high achiever who works tirelessly and ensures companywide productivity and effectiveness, Ms. Jackson has developed standard operating procedures and business strategies for operational and transactional functions within an organization. With an unquestionable leadership and management style, she mentors and supervises highly skilled professionals and has built solid business relationships with CPA firms, lenders, developers and owners.

Ms. Jackson is married to CPO Marvin Jackson, USN (Ret.) and they have five children. She enjoys coaching volleyball and traveling abroad.

Shana Passaro

Regional Manager, California

Shana Passaro joined Woodspear Properties in February of 2013 as the assistant to the Director of Property Management. This position entailed directly supporting our 18 residential properties in marketing, training, policies and procedures, and auditing and analysis as well as providing administrative support and acting as the direct liaison between the corporate office and the property personnel. In February of 2017 Ms. Passaro accepted the position of Property Supervisor and now oversees the multi-family operations in California. In December of 2018 Ms. Passaro assumed the title of Regional Property Manager.

Ms. Passaro began her career in Property Management in 1994 starting out as a Leasing Consultant and quickly worked her way up from Leasing to Assistant Manager to Property Manager. Her early experience was with several large property management companies and included extensive training in leasing, marketing, customer service and resident retention.

Ms. Passaro attended Richland College in Dallas, Texas before relocating to California in 1994. She has actively served on her homeowner’s association in some capacity for the last 15 years. She is a mom to two adult children and has resided in Oceanside, California for the last 28 years.

Shelly Smith

Regional Manager, Washington

Shelly Smith joined Woodspear Properties in December of 2019 as the Washington Regional Property Manager.

Mrs. Smith has worked in the Property Management industry since 2003, working in all facets of leasing and management. She has over 18 years of real estate and development experience. Prior to joining Woodspear Properties, Mrs. Smith served as Regional Manager for Tarragon Property Services from 2003-2018 overseeing 3000 multifamily units. She is a seasoned leader with a track record of success and quantifiable results. She is passionate about make a positive difference for the associates and the residents. Shelly holds her Real Estate Brokers License in Washington.

In her spare time, Mrs. Smith enjoys rooting on her Seattle Seahawks, spending time with family and traveling. She is a mother of one twenty-year-old son and has always lived in the Pacific Northwest.

Tiffany Dickason

Regional Manager, Colorado

Tiffany Dickason joined Woodspear Properties in 2022 as Area Manager and was promoted in 2023 to Regional Manager. She loves to inspire staff and work with residents while overseeing the multifamily operations in Colorado.

Tiffany began her career in property management in 2002. With over 20 years of experience in the multifamily industry, she obtained her CAM in 2018 and brings a deep level of knowledge and strong management skills to her role as Regional Manager. Prior to joining Woodspear Properties, Mrs. Dickason served as Regional Manager for Botnick Realty from 2017 to 2020, overseeing operations of 2,000 multifamily units. She is passionate about making a positive difference by developing training programs to increase productivity and growth for the employees and the company.

Her experience with diverse markets and her passion for developing successful on-site teams make her a valued member of Woodspear’s management team.

Tiffany was born in Colorado and loves spending time with her husband and two children. In her spare time, she enjoys baking, hiking, and painting.

Alex Wells

Commercial Property Manager

Alex Wells joined Woodspear Properties in November of 2017 and is based out of Denver, Colorado. Mr. Wells is responsible for the financial monitoring, property management, and oversight of tenant improvement work for industrial, flex, and office buildings in Woodspear’s commercial portfolio.

Mr. Wells graduated from Doane University in 2017 with a B.A. degree in Business Administration and Economics. Mr. Wells enjoys hitting the slopes, the putting greens, and the soccer pitch.

Grace Perrin

Corporate Management Assistant

Grace Perrin joined Woodspear Properties in November 2021 and works in the Colorado office. Grace supports the Woodspear corporate management team as well as the on-site property managers.

Grace graduated from Iowa State University in 2018 with degrees in Event Management and World Languages. She moved to Colorado shortly after graduating for the mountains and enjoys hiking, riding her motorcycle, and enjoying all that Denver has to offer.