The Shore To Slope Team


Gary Kennedy RCM, Licensed Property Manager and President of Shore to Slope Management Services Inc.

From 1988 to 1994, he was the Property Manager of Cranberry Village, then a Resort that contained 14 Condominium Corporations which blossomed to 23 Standard Corporations over that 6 year period.  Responsibilities included every aspect of Property Management from tendering the original engineering technical audit upon registering of the Condominium, to collection of common expense fees and dealing with the ongoing 3 P’s of Condominiums, People, Pets and Parking. Gary incorporated Shore to Slope Management Services Inc. in 1991 and had his first client contract later that same year.  In 1994 the Shore to Slope Portfolio was growing and he resigned from Cranberry Resort to go fulltime at STS.


  • Was a speaker at an International Conference in New Orleans on the subject of “Building Strong Relationships between Property Management and Home Owners Associations”.
  • Sat on a panel of industry professionals at a seminar entitled “Taking the Mystery out of Condominiums”.
  • Has been quoted in the international publication “Perspective” on the issue of creating a fun and well attended Annual Meeting. 
  • Incorporated Shore to Slope Management Services Inc. (STS Management) in February 1991, and developed an infrastructure, which today incorporates leading edge technology.
  • Has earned his Property Managers designation RCM from ACMO.
  • Proud member of the Canadian Condominium Institute (CCI) and the Association of Condominium Managers of Ontario (AMCO)


Jeff Struewing is our Vice President of Operations and Licensed Property Manager. He was hired at Shore to Slope in February 2002 and has been instrumental in keeping our communications and computer technology up to date and well maintained. Jeff has received his AFO certification and has developed and manages our growing Maintenance Department, Recreation Department and has established and takes care of our Commercial Property Management clients including the Cranberry Mews Plaza in addition to part of our residential portfolio. Jeff has resided in the Collingwood area since 1990. He has been highly involved in growing and maintaining our client base. Jeff is an active member of ACMO (Association of Condominium Managers of Ontario) and CCI (Canadian Condominium Institute) and is often attending seminars, conferences and continuing education sessions in order to share knowledge and resources with our team. Jeff became a Board Member at CCI- Huronia Chapter in 2016. It was Jeff’s vision to design and construct our new office location at the Cranberry Mews Plaza in 2011 providing our staff with much needed space and a modern work environment while providing better access and service to our clients. Jeff’s great knowledge in building materials and construction help with day to day maintenance at our properties, large scale renovation projects and clear understanding and input with reserve fund studies. This knowledge is very helpful when dealing with contractors and we have a great report and built some great relationships with many in the area. Jeff has successfully taken on the role of Project Manager for several large renovations ranging from thousands of dollars to millions of dollars making sure work is completed as contracted and on budget. In his spare time, Jeff’s interests include home improvement projects and keeping up with technology while balancing family life and has recently taken the plunge into glamping with his first RV.


Jacinta Richens is our Manager of Compliance & Administration and has resided in Collingwood for 49 years.  She has been in the property management/resort business since 1992.  Jacinta has education in Accounting and graduated with honours as a Legal Secretary.  Jacinta was employed part-time with Re/Max as Office Administrator during her College years and met Gary originally at Cranberry Resort where she held many positions over a 10-year period from ‘Accounting Clerk’ to ‘Administrative Assistant to the General Manager’.  Jacinta came on board in September 2004 after 2 years at Georgian Manor Resort in Member Services.


Carol Benson is an Office Administrator and began as our Receptionist in 2015.  She has been the friendly voice that greets callers and visitors to our office.  Carol brings great administrative background, bookkeeping and customer service skills and is a valuable member of our team. Carol will be working closely with Jacinta in a more administrative role coordinating the new information certificates, notices and tracking Director education as required by the new regulations.


Mike Kennedy is currently a Licensed Property Manager and has been with Shore to Slope since 2014. Mike was born and raised in Collingwood and throughout his years has developed a passion for the Collingwood area and what it has to offer.  During his youth he has held various positions within Shore to Slope and as a young adult he left Collingwood to pursue an education in Business Administration at George Brown College.  After graduating he returned to Collingwood to take a Client Services Administrator position with Shore to Slope. During his employment with Shore to Slope Mike pursued an education in Condominium Management through Mohawk College, finishing in December 2017.


Sheila Krivsky is currently a Licensed Assistant Property Manager and was hired in early 2017 to work as a Client Services Administrator. In 2015, Sheila and her fiancé made the decision to move to Collingwood from Alberta to be closer to his family. Sheila has experience in customer service as well as 6 years of experience in day to day maintenance and renovations during her rental management of apartment, condo and single-family homes while in Alberta. She is excited to pursue and expand her knowledge of condominium management here in Ontario and has been completing condominium management education. Recently Sheila was promoted to Assistant Property Manager in 2017 and works closely with our Property Managers and Client Services Administrators.


Susan Roy is our Accounting Manager and has resided in Collingwood for more than 35 years. She graduated from the University of Waterloo in 1990, where she specialized in accounting and economics. Susan continued her education after university and successfully earned the Certified Financial Planners (CFP) designation and completed the Canadian Mutual Fund and Canadian Securities courses. Sue has been awarded the Certified General Accountant (CGA) and Chartered Professional Accountant (CPA) designations. Susan was hired June 2005 and oversees our accounting department.


Jessica Bennett is our Accounts Receivable Clerk and works closely with Sue in our Accounting Department. Jessica has successfully completed many accounting, finance and business courses and has plenty of experience with accounting and finance. In her spare time she enjoys spending time with family, reading, recreation and church involvement. 


Ashley Bloomfield joined our team in December 2017 as a Client Service Administrator. Our Client Services Administrators are usually the first voice on the phone or when clients visit our office and look after many of the day to day administrative tasks, scheduling and coordinating maintenance and contractors for our clients, providing support to our Property Managers, as well as communicating with owners on a regular basis. Ashley started her career journey after graduating in 2004 from the Travel and Tourism program at Sir Sandford Fleming College. Since then, she has worked in the industry bringing many years of customer service with her. Ashley enjoys spending time with her family and being a new mom to a very energetic toddler.


Allie Field is the newest member of our team, as a Client Service Administrator. Allie has over 7 years experience in office administration and 2 years of experience in the property management field.  Allie is eager to grow her knowledge in the condominium industry and is currently working on completing her condominium management education.  Having lived in Collingwood her whole life, she has watched the growth of condo developments over the years and is familiar with many condo projects in and around the Collingwood area. Working alongside the rest of the Shore to Slope team Allie hopes to become more involved in the condominium management side of the business, sharing her friendly and upbeat personality with clients both in the field and in the office.


Kristen Clarke began her career in property management in 2014 as our receptionist and currently works in our accounting department as an Accounts Payable Clerk. Kristen has enjoyed living and working in the Georgian Triangle area her whole life and spending time with her family.


10 Keith Ave, Suite 303
Collingwood , ON L9Y 0W5

Phone /Fax Number(s):

Phone - 705-444-5139
Fax - 705-445-0944