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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.

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T.J. McRedmond, CAIB


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.

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Kelsey Carriere, BA, CAIB

Operations Manager (On Maternity Leave)

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. 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 daughter, husband, 2 dogs & 2 cats. You will always find her talking about how much she enjoys exploring all the local restaurants Winnipeg has to offer!

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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.

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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.

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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.

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Peter Leung

Account Executive

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. Peter was born in Hong Kong, China and is married with 3 children and 1 wonderful grandson. In his pastime, you will find Peter enjoying a game of golf, and cheering on the Winnipeg Blue Bombers & Winnipeg Jets.

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Samantha Norton, CAIB

Senior Commercial Account Manager

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. Sam enjoys spending time at her country home and at the lake with family and her dog. You will always find Sam with a coffee in hand, talking all things fashion, dogs and where the best brunch spots are.

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Shelley Berard

Administrative Coordinator

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.

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Tiana McRedmond

Insurance Advisor (On Mat Leave)

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.

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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.   

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Cody Malcolm, CAIB

Account Executive

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 enjoys his role as Commercial & Life Account Executive 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.

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Sandra Cindric

Insurance Advisor

 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. She joined the Crossroads team in 2019, and looks forward to continuing her education in this field as well, and pursuing her next Insurance licence level, through her love of learning.  When not reading a textbook, Sandra enjoys reading for pleasure, yoga, and hopes to travel to Europe again soon.

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Mary Oguezue

Insurance Advisor

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. Mary may seem quiet and soft spoken but you will always find her ready for a laugh.

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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.

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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.

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Rahat Sharma

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 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.

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Nina Ilas

Insurance Advisor

 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.

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Melissa Penner

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.  With her love of learning she plans to work towards achieving her level 2 Insurance Licence in the future.  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.

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Benjamin Cohen

In training

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. 

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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

COVID-19 Updated Notice

Reopening to the Public

Crossroads Insurance has been monitoring and assessing developments with COVID-19. The health and safety of our customers and staff is our priority. Crossroads Insurance’s response continues to evolve as developments change.

Effective Monday January 25th, 2021, our offices will reopen to the public with social distancing protocols in place. For your convenience, Crossroads Insurance can still handle the majority of your MPI Services/Autopac, Home, Business, and Life insurance needs over the phone, by email, or online.

We have taken additional precautions to keep our offices safe, including protective shields, extensive cleaning and sanitizing.

We are confident there will be little impact on our service capabilities and responsiveness as a result of these changes. There may be times when our team members are dealing with increased call volumes. Please be patient during this time. Please leave a voicemail and one of our Insurance Advisors will return your call as soon as they are available. You can also send your inquiries by email, fax, and through our website.

Thank you for your patience as we work through this rapidly changing situation. We will continue to monitor the situation closely and provide you with regular updates.

Please do not hesitate to contact one of our Insurance Advisors who are here to help and ready to assist you.

We are here to support you as we work through this together,
Your Crossroads Insurance Team