T.J. started his career in the insurance industry with Crossroads Insurance in 1988 after attending the Universities of Winnipeg and Manitoba. He obtained his Canadian Accredited Insurance Broker designation in 1996. In 1997, T.J. purchased the shares of Crossroads Insurance and became President. Over the years T.J. has been very involved with the Insurance Brokers Association of Manitoba serving on various committees including Past Chair of the Young Broker Network as well as serving as a Director on the IBAM Board. T.J. lives in East St. Paul with his wife and children.
More About Us
We take our commitment to our customers in earnest, served by our family of dedicated employees and the trusted insurance companies we represent. Crossroads Insurance committed to ensuring that you and your family are protected. We work with you to understand your insurance requirements, helping you to identify and analyze your exposure to loss, and then selecting the best methods possible for dealing with those exposures. We find providers who offer you the broadest possible coverage for your needs. Should a loss occur, we represent you during the claims process as your advocate, ensuring that you and your family are properly cared for and receive the benefits you're owed. The value of an insurance product is not based solely on its price – it's also reflected in the service you receive, how losses are covered, and if your expectations are met.
We are here to support our clients as they take steps towards protecting what matters to them. We set ourselves apart by committing to personal relationships so our clients will never feel like “just a number”. Our focus is providing the best customer experience. We accomplish this through simplifying insurance by educating, guiding and providing choice.
Meet The Team
In 1967 Tony immigrated to Canada from Waterford Ireland. At the age of 27 he founded Crossroads Insurance, working out of his home with his wife Dianne. Tony has 4 children, 8 grand children and 3 great grandchildren. Now that he is semi-retired he gets to enjoy his favourite hobbies such as golfing, gardening, reading and music.
Kelsey began her journey in the Insurance industry with Crossroads Insurance in 2007. Since then she has graduated with a BA in Psychology & Conflict resolution, and obtained her CAIB designation. Kelsey has explored her way through Autopac, Personal Lines and the Commercial Department during her career and is now enjoying her position as Operations Manager with Crossroads Insurance.
Nella DiGirolamo, CAIB
After completing her diploma in Business Administration at Red River Community College in 1994, a friend approached Nella to see if she wanted to work at a little agency on Corydon and on January 2nd, 1995 she began her career in the Insurance Industry. Nella joined the Crossroads family in 1999, and has been a pivotal member of the team ever since. She is now enjoying her role as Residential Insurance managers. She takes on this role with passion and an excitement to teach and guide team members.
After completing her Bachelor of Arts with a major in Political Science in 2000 in the Philippines, Grace worked as a legal secretary before moving to Canada. She then embarked on her Insurance career and joined Crossroads Insurance in December 2007. She has since become a Canadian citizen & obtained her CAIB designation. She has been an asset to the team ever since with her wide variety of MPI and Personal Lines knowledge.
Tiana has been in the Insurance industry since 2002. Being a part of a family owned business, she followed in her Grandpa’s tracks, and embarked on a career as an Insurance Advisor. Tiana has a passion for people and will always make you feel comfortable. She is here to help you with your MPI and Home Insurance needs. You will always find Tiana making a personal connection whether it be through humour or sharing her love for old westerns. She enjoys spending time outside of work with her family, and traveling on new adventures near any body of water.
Shelley started her Insurance career when joining the Crossroads family in 1991. She enjoys being in the Customer Service Industry and is always a happy familiar face to help with your MPI service needs, with a level of expertise you can count on. Numbers are Shelley’s thing, and you can always count on her to balance every cent. Shelley and her husband, are enjoying empty nesting with two grown children. She loves to spend her summers at the lake and also getting away for the winter to a hot destination when she can.
Samantha embarked on her insurance career by happenstance in 2009. She happily joined the Crossroads team in 2013, where she has enjoyed many facets of the insurance industry, from MPI, personal and commercial lines, and moved into a full time roll within the commercial department back in 2014. In 2018, Samantha completed her CAIB designation with honors and has actively pursued additional educational opportunities. She thoroughly enjoys the day to day challenge of the fast paced and constantly changing commercial insurance industry.
Peter graduated from the University Of Manitoba with a Bachelor of Arts degree in Economics. He has been in the Insurance Industry since 1984, and joined the Crossroads Insurance family as an Account Executive in 2000. He is here to help with your Home Insurance and Commercial Insurance needs. Peter is fluent in English, Cantonese and Mandarin. He is respected in the community for his dedication and care to all his clients. He really enjoys working with the public and being able to help his clients with all of their Insurance needs.
Maria graduated from College in Manila Philippines after completing her Bachelor of Arts with a Major in Communication Arts in 2002. As a woman with many interests, she went from working as an associate producer for a reputable Television Station in the Philippines for 9 years, while becoming a licensed scuba diver to help preserve marine life, to working with children, to a career in Insurance. She came to Canada in 2011 and became a permanent resident. She joined the Crossroads family in 2015, where she launched her Insurance career.
Eleanor has worked in the Insurance Industry for over 30 years, and has been with the Crossroads Team since 1989. She has valuable years of experience as a Personal Lines Advisor, and a recognized face for many loyal customers. You can always trust her to take care of you and never miss a detail. She is a true Country girl at heart, from attending school in Vita Manitoba, she still thoroughly enjoys living the country life and enjoying country music. She loves spending time with family, and taking in her nieces and nephews.
Cody embarked on his career in Insurance in 2014, as a Commercial Insurance Advisor. Prior to this, he has spent nearly a decade working in risk management. Cody loves education and a challenge, so with that he obtained his CAIB designation in only 2 years. He is currently continuing his education and working on obtaining his CIP designation though the Insurance Institute of Canada.
Stacey graduated with Honours from the Business Administration program at Red River College with a major in Financial Services in 2015. Shortly after graduating, she began her career working in Commercial Insurance. Stacey has been a contributing member of the Crossroads Insurance team since 2019. She is an avid cyclist who enjoys photography, petting dogs, and playing soccer in her down time. Stacey is passionate about volunteering and supporting important causes and has been involved with the MS Society of Canada and ALS Society of Canada for several years.
After completing a Bachelors Degree in Commerce in 2013 Kiran immigrated from Australia and dove into life in an opposite climate. She worked in hospitality for over 5 years before starting her career in Insurance with Crossroads In January of 2019. She is using her love for learning to take in all there is to know about Insurance, and is doing so very quickly! You will always find Kiran ready for a new challenge. She is here is help you with your MPI and Personal Lines needs. When she is not at work, she enjoys spending time with friends and exploring new places
Rahat graduated from Manitoba Institute of Trades and Technology in 2016 with a diploma in Hotel & Hospitality Management. After working in customer service for 2 years, she decided to step into the Insurance industry in 2018, and joined the Crossroads family in early 2019. She is here to help you with your New Personal lines and MPI needs. She is enjoying her role as a Home Insurance advisor and is ready to greet you with a smile. In her spare time you will find her spending some quality time with her friends and binging all the Netflix she can.
Vahinika graduated from Engineering College, with a degree in Electronics in 2014.. She went on to complete a Masters of Business Administration in 2016. She has accumulated over 2 years of customer service in the Banking Industry. After moving to Canada in 2019, Vahinika joined Crossroads Insurance and started her career as an Insurance Advisor. She has a passion for gardening and she enjoys watching movies.
Navdeep graduated in 2002 with a Bachelor of Science degree in Majoring in Botany ,Zoology and Chemistry. She also went on to complete a Bachelor of Education in 2003. Navdeep also completed her master’s degree in English Language in 2005. She has gained valuable experience through her 13 year career in Education as an elementary School teacher.
Nina graduated from Red River College in 2014 with a Business Administration diploma. Nina is new to the Insurance Industry and joined Crossroads Insurance in 2019. She has proven to be a very fast learner, and obtained her Insurance licence in record time. In her spare time, Nina enjoys working out regularly, enjoying Marvel Movies and exploring new food at local restaurants.
Sandra graduated from the University of Manitoba in 2016 with a Bachelor’s Degree in Human Ecology; majoring in Family social Sciences, with a minor in Psychology. Throughout this time Sandra volunteered and worked in social services for five years in various capacities. Her interest has since been peaked to also pursue a Human Resource Management certification.
After obtaining her bachelor’s degree from the University of Manitoba in 2018, with a Major in Economics and a minor in Psychology, Mary started in the workforce as a Customer service Representative. In 2019, she joined the Crossroads family. Irrespective of her early professional stage, she is anxious to expand her knowledge in the field, and pursue her next Insurance level. She is happy to be working with a team who will help guide her along. She is excited to see where her career will take her at Crossroads.
Chuck started working in the insurance industry in 1999 in southern Ontario, before moving back to Manitoba in 2012, to continue his career path. He joined the Crossroads team in 2019, and is eager to assist with your Home Insurance and MPI needs. Having access to many different insurance providers means that he can offer both selection and value to his clients. Chuck will explore the various insurance companies Crossroads offers, to find you the best fit to protect you and your family, while providing peace of mind.