Skip to main content

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.

Our Mission

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

Nella DiGirolamo, CAIB

Residential Insurance Manager

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. You will always find Nella cracking a joke and earning the love and respect from all staff.  You can always strike up a great conversation with her, whether it be about her passion for food, candies, pastries or the Winnipeg Jets.

Read Bio + Read Bio -

T.J. McRedmond, CAIB

President

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. He enjoys spending time with his family, golfing, and traveling. T.J. splits his time at Crossroads Insurance between managing the day to day operations of the brokerage, and servicing new and existing commercial clients.

Read Bio + Read Bio -

Kelsey Carriere, BA, CAIB

Operations Manager

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 thoroughly enjoying her position as Operations Manager with Crossroads Insurance. She hopes to be able to continue to contribute to the family-owned fun environment that Crossroads is.  Kelsey loves being able to travel and spend time with friends & family her precious daughters, husband, 2 dogs & cat. You will always find her talking about how much she enjoys exploring all the local restaurants Winnipeg has to offer!

Read Bio + Read Bio -

Grace Cabales, CAIB

Branch Manager

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. She has become a trusted guiding force to customers and staff, and practices this as Branch Manager to our Tyndall Park office.  She is famous around the office for her delicious traditional Filipino spring rolls, and no one can ever get enough. Her early rising to satisfy our tummies is just one example of her dedication.

Read Bio + Read Bio -

Eleanor Lischynski

Senior Insurance Advisor (On Leave)

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. You know that nice weather is coming when Eleanor starts wearing sandals, at the first sign of spring. We look forward to continuing to enjoy her famous layered salad and trifle at work potlucks.

Read Bio + Read Bio -

Maria Bernadette Basco-Pasahol

Insurance Advisor

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. She is happy to help you with your Home Insurance needs. You will always find Maria, as her happy, easy going self, belting out a tune around the office. She will always make you feel welcome and cared for.

Read Bio + Read Bio -

Shelley Berard

Branch Manager

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. In her role as Branch Manager at the St Vital office and is here to support her staff and customer 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. 

Read Bio + Read Bio -

Tiana McRedmond

Insurance Advisor

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 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.

Read Bio + Read Bio -

Tony McRedmond

Founder

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.   

Read Bio + Read Bio -

Cody Malcolm, CAIB

Senior Commercial Account Manager

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. In 2017, Cody happily joined the Crossroads Insurance family where he enjoyed his role as Commercial & Life Account Executive and now as Senior Commercial  Account Manager and working with both his clients, colleagues, and the charitable causes they support throughout the city. When he isn’t in the office you will find that his interests lie with the 3 F’s. Family, Fitness, and Food. 

Read Bio + Read Bio -

Chuck Laing

Insurance Advisor

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.  In his spare time, he loves following the Blue Bombers and Jets, attending old car shows, while taking in everything  Manitoba has to offer.

Read Bio + Read Bio -

Stacey Napoleone

Commercial Account Manager

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.

Read Bio + Read Bio -

Rahat Sharma

Senior Insurance Advisor

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 has since obtained her level 2 insurance licence. She is enjoying her role as a Senior 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.

Read Bio + Read Bio -

Nina Ilas

Insurance Advisor

 Nina graduated from Red River College in 2014 with a Business Administration diploma. Nina was new to the Insurance Industry when she joined Crossroads Insurance in 2019. She has proven to be a very fast learner, and obtained her Insurance licence in record time. She is here to help with your Home, travel and MPI needs.  In her spare time, Nina enjoys working out regularly, enjoying Marvel Movies and exploring new food at local restaurants. 

Read Bio + Read Bio -

Melissa Penner

Senior Insurance Advisor

Melissa started her journey in the Insurance Industry in December 2018. She was very happy to join the Crossroads Family in Fall of 2020, and it has been a natural fit since day one.  She is here to help you as a Home Insurance Advisor and with MPI services. She enjoys guiding customers by helping them understand their Insurance needs and the best option for them. As she continues to educate herself, she has also since obtained her level 2 Insurance licence.  Melissa’s positivity is contagious and you will always find her ready to help; whether it be getting through a hard day of work or helping with a friendly competition between offices. You may find Melissa in her free time weight training or with a paint brush in hand. Her adoration for dogs is apparent as she greets them and is ready to be friends for life. 

Read Bio + Read Bio -

Benjamin Cohen

Insurance Advisor

Benjamin has worked in the field of customer service for over 10 years. He graduated from MITT in electrical application in 2013, which he has pursued as a hobby. He has developed a passion for learning about the mysterious functions of electricity, and an affinity for electronics.  He has been in the wine industry since 2015, and from there he has decided to join the Insurance industry as a means of assisting customers in a whole new capacity, when he joined Crossroads Insurance in 2021. He is here to help with a positive, and calming demeanor. Benjamin is a fun and enthusiastic person filled with lots of enjoyments in life, whether it be taking care of plants, weight training, or honing his chef skills. With BBQ as his passion, you will find him also perfecting his skills while sharing with friends (and hopefully co-workers too!). He is an explorer at heart and he enjoys this through connecting with nature while camping and hiking. 

Read Bio + Read Bio -

Kamalpreet Kaur (On Maternity Leave)

Insurance Advisor

Kamalpreet immigrated to Canada in 2010, and proceeded to study in London Ontario, where she completed her degree in Information security management at Fanshawe College. She has enjoyed her journey in Canada and is proud to have obtained her citizenship in 2018. She has worked in the customer service industry since 2013, where she has gained many skills and been able to self-develop. Insurance has been on her mind for quite some time, and after moving back to Manitoba from another province in 2020, she was guided to finally pursue her career desires after being encouraged by her friend. She completed her Fundamentals of Insurance and joined the Crossroads family in 2021. She has felt at home since. She wishes she pursued this path sooner, but as we know timing is everything and happy she was led to us when she was. In her spare time Kamal enjoys spending time with family (including her 2 sweet nephews), watching movies on Netflix and listening to Indian music.

Read Bio + Read Bio -

Manu Sharma

Insurance Advisor

Manu came to Canada in 2014 with her family. Despite her path not always being smooth, with a background in customer service and education, she decided to make a shift and equip herself with Fundamentals Insurance to join the Insurance industry. She was welcomed into the Crossroads family in 2021, and is eager to continue the journey of learning that is Insurance. You will always see Manu welcoming you with a smile, as she is dedicated, kind-hearted person, looking to always help her customers. In her spare time she loves cooking (and her Crossroads family loves eating- a match made I’d say) and also listening to music. 

Read Bio + Read Bio -

Scott Yingling

Insurance Advisor

Scott has been in the customer service industry since 2006. His variety of job experiences in the field, have lead him to launch his future into a career in Insurance. He joined our Crossroads family in 2021, and it’s been a match from day one. If he is not at home spending time with his partner and 5 cats, then you will find him in his shop making barber's shave brushes made of resin. Fun Fact, Scott also has a musical background as he was in a touring band for over 10 years. You might call him a jack of all trades, and this allows him to help the office and his customers in many facets.  Scott is here to help as a trusted Personal Lines advisor to help his customers with their Home Insurance (and MPI ) needs. We looks forward to watching his career flourish at Crossroads. 

Read Bio + Read Bio -

Luzviminda Hidalgo

Insurance Advisor

Luz immigrated from the Philippines to Canada in 2013 with her diploma in Bachelor of Science in Business Administration with a major in Accounting. She started her new adventure in Winnipeg equipped with a background in banking where she worked in one of the top three banks in the Philippines. Luz is passionate about customer service and dealing with customers and colleagues with kindness. She started working as an Insurance Broker in Winnipeg in 2014. She found herself in familiar territory from her experience in banking. She joined the Crossroads team in 2021 and is excited to continue her career, while perfecting her expertise in the field, and growing her knowledge from there.  She will be here to help you with your Home Insurance and MPI service needs. In her downtime, she enjoys gathering with family and friends for some great conversation or even just chatting over the phone.  She has a green thumb and loves taking care of her various plants.

Read Bio + Read Bio -

Simon Klassen

Commercial Account Manager

Simon entered the insurance industry after graduating from the University of Western Ontario in 2020. His focus has always been Business Insurance, as Simon enjoys working with Manitoba businesses to manage their risk effectively. In 2022, Simon joined the Crossroads Insurance Team as a Commercial Account Manager. In the summer he visits his family cottage on Lake of the Woods for some outdoor time sailing, fishing, and exploring the lake by boat. In the winter months Simon snowmobiles, plays floor & ice hockey, and of course catches up on the latest TV series

Read Bio + Read Bio -

Hayley Hofley

Insurance Advisor

In 2009, Hayley completed a Bachelor of Arts in Political Science and a Certificate of Public Policy and Administration from the University of Winnipeg. She proceeded to work in the Federal Public sector for Indigenous affairs and journeyed through a few positions before starting with her Insurance career at Crossroads Insurance in 2022. Hayley has been a natural fit from the beginning, and loves being a part of the family-like environment of such a positive team at Crossroads.  She is energized from interacting with clients and truly enjoys helping people out. She is ready to grow her knowledge base with crossroads and continue to learn all there is to know about insurance. You will always find Hayley cheering on her favorite local Hockey Team, The Winnipeg Jets .

Read Bio + Read Bio -

Angel Ristic

Insurance Advisor

Angel was born in Winnipeg, and after growing up all over western Canada and the outskirts of the city, she landed back in Winnipeg to follow a career at the Winnipeg Airport Authority. After 13 years she decided it was time to make career move into Insurance and joined the Crossroads team in 2022. She welcomes the change and is enjoying learning all that there is in insurance.  In her spare time she enjoys baking and cooking for others. There are plenty of welcome taste testers here at Crossroads for her. As a big animal lover, one day Angel along with her long time partner, aspire to own a small farm with chickens, mini goats and a donkey.

Read Bio + Read Bio -

Reese Zeemel

Insurance Advisor

After pursuing studies through the University of Manitoba, and working in the customer service industry for 5 years, Reese took a leap into the Insurance Industry when she joined Crossroads Insurance in 2022. She knew it was a fit with the motivational, supportive and positive atmosphere provided. She is excited to see where her journey with Crossroads will take her, with the opportunity for growth and learning.  Her friendly face is ready to greet customers as they enter the office. Ready to help you with MPI & Home Insurance Needs. When she isn’t working she loves to go on scenic walks and hikes with her dog. Crossroads is her place to be with all her foodie coworkers, always ready for the next potluck. 

Read Bio + Read Bio -

The Crossroads Insurance Advantage

We shop for you so you can be confident you are receiving the most competitive rates.

Convenient locations in the north and south of Winnipeg

Family owned, Manitoban company

24-Hour claim service

Multi-cultural team that can do business 10+ languages

We offer choice and guidance above all else

40+ years in the business

Support and advocacy in the event of a claim