Ross is primarily focused on driving investment sales results for Pintail's clients, deal structuring and risk analysis, underwriting of development opportunities and loan negotiations.
Prior to Pintail, Ross began his real estate career in 2004 as a sales executive with the Cliffs Communities where he was directly responsible for over $100 million in real estate transactions as a top producer. In 2011 Ross was asked to take over as Broker-In-Charge for the Cliffs at Keowee Region, overseeing sales and marketing for three master-planned lakefront communities on Lake Keowee. The global economy continued to strengthen and in early 2014, Ross saw the opportunity to return to Greenville and focus his energy on commercial real estate. Since co-founding Pintail in 2015, Ross has enjoyed working on healthcare, retail, and light industrial brokerage, development and investment sales.
A native of Greenville, South Carolina, Ross holds a degree in accounting and business management from Washington and Lee University, where he was a four-year letterman on the football team and Vice President of his fraternity. In addition to spending time with his wife and two daughters, Ross is an avid outdoorsman and sports enthusiast. An Eagle Scout at age 14, Ross enjoys his contribution as a youth mentor with The Outdoor Dream Foundation and the SC Department of Natural Resources “Take One Make One” program. He is a board member and the treasurer of the Foothills Chapter of QDMA, and a former defensive line coach for the Greenville High School 7th and 8th grade football team. Ross serves on the board for the Julie Valentine Center.
Tyson Smoak co-leads the firm’s client engagements, leasing and sales brokerage initiatives, fundraising activities and brand awareness. A Certified Commercial Investment Member (CCIM), he is responsible for all business development, as well as new opportunity origination.
Prior to co-founding Pintail, Tyson spent eight years as a broker with a regional commercial real estate firm. During his last three years there, he focused on the office sector, completing over $60 million dollars in commercial real estate transactions and developing a specialty in tenant representation. He was named the Greater Greenville Association of Realtors 2013 Commercial Realtor of the Year. Since creating Pintail in 2015, Tyson has continued to focus on office sales, leasing and build-to-suit-development, and is licensed in South Carolina and North Carolina.
Born and raised in Greenville, South Carolina, Tyson earned a degree in Political Science from Furman University. He is the former Chair of the Board of Directors for Loaves and Fishes, a past board member of the Greater Greenville Association of Realtors, and currently serves on the Resource Development Committee at Christ Church Episcopal. Outside of work, Tyson enjoys spending time with this wife and three children, bird hunting, and being on the water.
Stuart Wyeth co-leads the growth and strategy of the firm. Stuart brings his creative energies to strategic planning, development programming, government approvals, impact evaluation and thought leadership around the firm’s development activities. He also advises the brokerage team on select assignments.
Stuart began his career in commercial real estate in 2005 as an intern during his final academic year at Clemson University. While at Clemson, he completed a Master’s degree in City and Regional Planning and served as president of the Graduate Student Government. Prior to Clemson, Stuart earned his BA degree in Economics from Denison University, where he completed a summer internship program with the San Diego Padres, assisting a development team in planning for a $4-billion-dollar infill urban mixed-use project revolving around a new baseball stadium - what is now PetCo Park.
Stuart is a member of The Urban Land Institute and participates at the national level as a member of ULI's Small Scale Development Council. He serves on the board of TreesUpstate and the YMCA Metro Board. In addition to his industry activities, Stuart enjoys coaching high school lacrosse, volunteer activities, golf, bird hunting and working in the yard. Stuart lives in Greenville, South Carolina, with his wife Mary Katherine, son MacReynolds, and daughter Wallace.
Penn leads the operations, marketing, and strategic business initiatives for the company, and oversees the creation and execution of Pintail's annual and long-range business plans.
Before joining Pintail, Penn was Director of Resource Development at Christ Church Episcopal, where she planned and executed multiple annual giving campaigns as well as an $8 million capital campaign. Prior to this, Penn worked for many years at ScanSource, Inc., a technology distributor, where she was Director of Merchandising. In this role, she led a team of product managers responsible for managing relationships with multiple vendors and worked to create strategic business and marketing plans to exceed quarterly revenue, gross profit and ROI goals.
Penn holds a Bachelor of Arts degree in Business Economics from Wofford College, where she was Phi Beta Kappa, and an International MBA from the Moore School of Business at the University of South Carolina. Focusing her IMBA studies on brand management, she spent time completing coursework in Germany followed by an internship in Switzerland before ultimately returning to Greenville.
Penn enjoys being a part of CREW (Commercial Real Estate Women) Upstate and currently serves on the Vestry of Christ Church Episcopal. She enjoys serving at her children’s schools and is an enthusiastic supporter of the local arts community, serving on the Board of Directors for the Metropolitan Arts Council (MAC) as well as the Steering Committee of their MAConnect group. Penn appreciates living minutes from Greenville's award-winning downtown with her husband and three busy children.
As Managing Partner of Pintail Property Services, Brian leads the firm’s day-to-day management of retail, office, industrial, and mixed-use properties.
Immediately prior to launching Pintail Property Services, Brian served as the Vice President of Property Services at a Greenville-based commercial real estate firm, where he spent nearly 19 years and managed a portfolio of 2 million square feet of space and oversaw numerous capital and tenant improvement projects in Upstate South Carolina.
A native of Roanoke, Virginia, Brian holds a degree in property management from Virginia Tech. In addition, he is a member of the Institute of Real Estate Management (IREM) and has earned the Certified Property Manager (CPM) designation. As a licensed real estate salesman in South Carolina, he delivers a truly unique property management experience for property owners and tenants alike.
Brian lives in Simpsonville with his wife and two energetic children. He and his family are active members of Mauldin United Methodist Church. He enjoys spending time on the tennis court and watching his children compete in tennis and volleyball tournaments on the weekends.
Jeff is primarily focused on site selection, identifying retail and healthcare investment sale opportunities for the firm's clients, as well as generating development project assignments.
Jeff was the first broker Pintail hired during its inception in 2016, and has developed a robust client list of retailers and developers. Before joining the Pintail team, Jeff managed corporate telecom accounts and network solutions for AT&T in Silicon Valley. He placed top of his class after completing a rigorous business leadership development program in Atlanta and was placed by AT&T in the startup hub of California. Jeff also spent several years as a catastrophe claims specialist who generated new business for local construction companies around the United States. He developed over $1.5 million in new business, gained an intimate understanding of project management, and accrued valuable insurance policy expertise.
Jeff relocated to the Upstate in 2001 from west Texas and now calls Greenville his home. A member of the men’s soccer team, Jeff graduated from Baylor University with a Bachelor of Business Administration degree in Marketing. He is on the Meals on Wheels Young Professional Board, coaches U6 City of Greenville soccer, and has been a member of First Baptist Greenville for over a decade. In his free time, Jeff loves road biking, fishing, playing in several community sports leagues, and hiking with friends.
Daniel fills two roles within Pintail - as Development Associate he assists our Director of Development, Stuart Wyeth, with all aspects of real estate investment and development projects, from financial analysis to market surveys. As Construction Manager, he acts as the Owner’s representative for development projects, managing all activities associated with the construction of and/or interior improvements to a building while adhering to the project schedule and budget.
Daniel completed the Clemson University Masters of Real Estate Development program in December 2021, where he was a Fulbright Scholar. Prior to beginning the MRED program in 2020, Daniel spent seven years in the construction and development industry in his home city of San Jose, Costa Rica. In just three years as a project manager at Volio y Trejos Construction, Inc., he led and collaborated with a team of engineers to construct commercial projects totaling $50M. Prior to that, he served as a project engineer with Madrid-based international geotechnical construction firm, Rodio-Swissboring, Inc.
In addition to a Masters of Real Estate Development from Clemson University, Daniel holds a Bachelor of Science degree in Civil Engineering from San Jose University as well as a technical degree in accounting from Colegio Vocacional Monseñor Sanabria.
In his free time, Daniel appreciates any opportunity to get on one of Greenville’s many nearby lakes to wake surf. He also loves hiking and biking the many trails that Upstate South Carolina has to offer.
Miller leads all marketing and communications initiatives for Pintail. She has a wide breadth of strategic marketing and branding experience, having worked as both an in-house marketing director as well as for a number of Upstate agencies.
Prior to joining Pintail Capital Partners, Miller served as marketing director at South Carolina Children’s Theatre and before that, spent six years as an account manager at VantagePoint Marketing, serving clients across the United States.
Miller is a proud graduate of the University of South Carolina where she earned a degree in Advertising. She loves all things DIY and shares her love of creativity with her husband and two spirited children. Miller volunteers at First Baptist Greenville, where she serves as a deacon and a member of the Children’s Ministry Committee.
As Sales Support Specialist, Callie provides administrative support to all of Pintail's service areas. Her work is dedicated to attention to detail, focusing on the care of clients and her team members.
Callie attended the University of South Carolina where she earned her Bachelor’s degree in Public Relations. She joined Pintail with a background in commercial property management, advertising sales and marketing. She is an active member of CREW Upstate, currently serving on the board as communications chair. She volunteers with the Greenville chapter of March of Dimes, serving on the executive leadership team for their annual Real Estate and Economic Development luncheon.
A Greenville native with a passion for her community, Callie enjoys volunteering for local organizations. She's a self-proclaimed exercise and food enthusiast, spending her free time at community fitness classes or indulging in the Upstate’s food scene with friends.
Anna joined Team Pintail as an intern in 2020 and earned her real estate license the following year. As a Broker Associate, Anna works primarily with Josh Tew, CCIM and Monty Todd, focusing on general brokerage and investment sales. In 2021, she supported her team in closing more than $100M in transactions on behalf of their clients.
Anna received her Bachelor’s degree in Marketing from Clemson University. During her time as an undergraduate, she was an active member of the Clemson University Rally Cats, Sales Innovation Program and Alpha Delta Pi sorority. Anna has continued her education and will receive her Masters in Business Administration (MBA) from Clemson University in May 2022. When she isn't in the office or in class, Anna works as a dance instructor at Shock Dance Center.
Lakin brings nearly a decade of experience in commercial real estate to Pintail. He specializes in advising clients on the acquisition and disposition of single tenant net lease (STNL) properties throughout the Southeastern United States. By leveraging his broad experience across STNL retail, medical, flex and industrial asset classes, Lakin leads his clients in maximizing the value of their CRE investments in an increasingly competitive environment.
A Greenville native, he is a graduate of High Point University where he earned a degree in Business Administration. Like fellow Pintail team member Ross Kester, Lakin is an Eagle Scout. He is an active member of ICSC (International Council of Shopping Centers) and regularly volunteers as a member of the Meals on Wheels executive council.
When he's not working, you will likely find Lakin traveling, cycling, running, mountain biking, or riding motocross. He and his wife Paige enjoy living off Augusta Road, just minutes from Downtown Greenville.
Robert works primarily with David Sigmon, CCIM, SIOR and Matt Vanvick, CCIM supporting their team needs in brokerage-related tasks for sales and leasing.
Robert graduated from Clemson University in August 2021, receiving his Bachelor’s degree in Economics with a minor in Finance. Hailing from Columbia, he began his undergrad at the College of Charleston where he played baseball for two years before transferring to Clemson.
Prior to joining Pintail, Robert completed an internship with Aflac and founded a start-up software company in Atlanta. Outside of the office, you can usually find Robert at the lake, hunting, fishing or attending sporting events with family and friends.
A fourth-generation commercial real estate broker, David focuses on the sale and leasing of general, medical and flex office properties, as well as the disposition/acquisition of investment properties. Born and raised in Greenville, David has enjoyed watching his hometown grow over the years and loves putting his local knowledge of the area to work for his clients.
Prior to joining the Pintail team, David was consistently a top producer at a local full service real estate firm where he spent 16 years. During his tenure there, he brokered over $300 million of commercial sales and leases. He is a graduate of the University of South Carolina with a double major in Real Estate and Marketing. David earned his Certified Commercial Investment Member (CCIM) designation in 2012. In 2019, he added the Society of Industrial and Office Realtors (SIOR) designation (the leading global professional office and industrial real estate association).
David is the immediate past Chair of the Board of Directors for the Caine Halter YMCA of Greenville. He is the current Treasurer of the CCIM South Carolina Chapter Board as well as a Committee Chair for the SIOR Carolinas Chapter Board. He also currently serves as a Campaign Cabinet Member with the United Way of Greenville County. David is a graduate of Leadership Greenville Class 39 with the Greenville Chamber of Commerce. Outside of his career, David enjoys spending time with his wife and two children, outdoor cooking, and fishing down at the South Carolina coast.
Josh works with investor clients to build and realize value in commercial real estate investments and portfolios. His expertise includes general brokerage and regional investment sales, with experience in the sale, leasing, and renovation of retail, office/medical, flex, and light industrial assets. He leverages broad experience in real estate services and asset classes to advise in the structure and management of investments optimized for his clients’ objectives. In 2021, Josh led his team to close more than $100M in transactions on behalf of their clients.
Before joining Pintail, Josh spent several years with a local full-service real estate firm where he gained experience in sales, leasing, property management, and value-add renovation. Prior to his real estate career, Josh gained experience in geotechnical and materials engineering as well as construction management.
Josh is a Certified Commercial Investment Member (CCIM) and active member of both the International Council of Shopping Centers (ICSC) and the Urban Land Institute (ULI). He earned a BS degree in Civil Engineering and an MBA with emphasis in Real Estate Development from Clemson University, where he was active in graduate student government and has since served as President of the MBA Alumni Association. Josh is a graduate of Leadership Greenville Class 45, is a Clemson Young Alumni Roaring 10 honoree, and is an active member of the Greenville community. He enjoys the outdoors and traveling with his wife, Liz.
Monty Todd focuses on general brokerage as well as regional investment sales. Monty is a graduate of the Master of Real Estate Development Program (MRED) from Clemson University and is an active member of the International Council of Shopping Centers (ICSC) and the Urban Land Institute (ULI). Monty is also ARGUS Developer-certified. Together with his team, in 2021, Monty closed more than $100M in transactions on behalf of their clients.
Prior to joining Pintail, Monty worked with DK Development in Charleston, SC, where he gained experience in construction management, property management, market research, potential property due diligence, accounting/bookkeeping, and financial underwriting support. Monty also spent more than two years working in the orthopedic device and pharmaceutical sales industry.
A native of Columbia, South Carolina, Monty holds a degree in political science from The University of Alabama, where he was an active member of Kappa Alpha Order fraternity, Phi Sigma Theta Honor Society, and was the Marketing Director of Ducks Unlimited, UA chapter. In addition to having a strong passion for commercial real estate, Monty loves spending time with his family and friends.
Matt focuses primarily on office, healthcare, and flex leasing and sales, and brings to his clients an expertise in investment property underwriting and acquisitions.
A Greenville native, Matt started his career in banking where he gained experience in underwriting and executing personal, residential, and commercial loans. Prior to joining Pintail, Matt worked at a local real estate firm for over six years. During his time there, he quickly became a top producer, closing over $150 million in commercial real estate transactions for his clients.
Matt is a proud graduate of The Citadel with a Bachelor of Science in Business Administration. He is a Certified Commercial Investment Member (CCIM), a member of the First Citizens Bank Advisory Board, and active member at Grace Church. Matt and his wife, Virginia have two daughters, Olivia and Emma, and a son, Grady. When Matt is not at work, he enjoys hunting and spending time at the lake with family.