On the first Tuesday of every month, we’ll announce a new Fearless Female, including a video interview of them sharing their business story. Want to be featured as a Fearless Female?
Contact Memberships for more details. The Fearless Female Program would not be possible without our Title Sponsor, Scotiabank.
To learn a little more about the Scotiabank Women Initiative, and why they’ve chosen to sponsor this program, see the video below.
The Fearless Female we’re featuring for the month of June is Amy Denstedt, Founder, Tailored Transitions.
Amy Denstedt is the founder of Tailored Transitions, a senior move management company serving Waterloo Region and surrounding communities. With over 20 years of experience in customer service and a background in human resources, Amy brings a thoughtful, people-first approach to helping seniors and their families navigate one of life’s most emotional transitions.
Through Tailored Transitions, Amy provides full-service support—including planning, packing, moving coordination, and settling in—ensuring each client feels respected, supported, and understood throughout the process. Her work goes beyond logistics; she acts as a steady, compassionate presence for families facing complex and often overwhelming decisions.
Amy is deeply committed to her community and has built strong relationships with local businesses, realtors, and senior living providers to better support her clients. Known for her warmth, attention to detail, and ability to bring calm to challenging situations, she is passionate about creating a more supportive and dignified moving experience for seniors.
Outside of her work, Amy enjoys spending time with her family, relaxing outdoors, and unwinding with a good book.
To learn more about Amy’s journey as a Fearless Female, watch the interview below (or read the written format).
Tell us more about your company and your role in it
So, we support seniors that are moving from their long-term homes into retirement residence or long-term care residences. We like to help them with full service, so we do the initial consultation, we do the planning, packing, any downsizing or decluttering. We organize movers and then we help the family set up their new retirement residence at the end so that when the senior moves in everything is set up and ready to go.
What inspired you to start this business?
I was lucky I had six grandparents that most of them lived well into their 90s so we moved them quite a few times, so I did have some experience with that, with helping to facilitate their moves into their new retirement residences so that was part of it.
I’ve been in the Waterloo region for a long time, so I knew that there, we have some well-established neighborhoods in Waterloo Region. People live in their homes for a long time in in Waterloo Region but we’re also really lucky to have over 50 retirement and long-term care residences in the community so I knew that there was a gap from people that had been in their homes for a long time and we’re looking to transition into retirement care so there was an opportunity there and from my experience with my family and trying to help them move I knew that there was an opportunity to help people through that transition and support them with that, so I thought I would take that on and I’ve always had a background in customer service too and customer support so for me that helped lead into it is I like to help people through it and it’s especially when they’re dealing with something that’s a little bit more challenging you have to think outside of the box that sort of fit what I like to do to start with.
Tell us more about your educational background
So, education wise I had a background in human resources. I had a certificate from Conestoga College in human resources and then when I was working I have always been in customer service so I have 20 plus years of customer service experience in different organizations and different roles but I’ve always been forward-facing to the customer it was always really important to me to be sometimes even the middleman to support people through whatever it is that they were looking for whatever challenges they had I always like to do that I always like to help people so it was a sort of natural progression from the customer service side and customer support to just move into continuing to support people and be there when they need help.
What are some of the accomplishments of your career so far?
Highlights are always when I’m able to help somebody right so any of the clients that I’ve moved to date that’s always that always becomes a highlight reel for me is being able to support my clients.
When you have families that come back and you can see how much they appreciate the support that we’re able to provide and how much we can help them that that always is a highlight reel for me in the long run.
Some other highlights I think are just the emotional side of it it’s being able to take that stress away for other people and be able to help them through their journey and through their transition because it’s moving is a lot it’s always a lot to manage I mean it’s a lot for us but when you’re a senior and you’ve got you know you might have mobility challenges you’re not sure what next steps are, you don’t know how to arrange necessarily all the components of the moving whether it’s the movers to begin with the coordinating of the retirement residents at the other side it can be overwhelming.
I find it very rewarding to be able to help people with that and to help families and just see that sort of that stress melt away that they know that they can entrust me to take care of those pieces and that becomes you know a highlight for me to and the business to work through that with them.
What are some of the challenges that you have faced so far?
Some of the challenges are probably sheer logistics like I mentioned moving is always you know different there’s different components there’s different coordination of things that you have to take care of so that can be a challenge. I mean just trying to run a business as a solopreneur is also difficult right you have to manage when you’re out taking care of things for clients but then you’ve also got things that you need to be doing at your desk and at the office and so trying to find that balance is always challenging. Obviously too as being a solopreneur but then having a family as well is can be challenging, so again trying to find the balance and making sure that you’re making time for your family time for yourself is really important and try to make sure that I’m cutting that time out and making sure that I’m making space for that is important just for my own mental health and well-being as well so I try to focus on that as much as I can.
If you could go back in time is there anything you’d do differently?
I think maybe the only thing that I would do differently currently was that I maybe would have started a little bit sooner you know I had the idea in the back of my mind for a while and waited for the opportunity to sort of present itself and I maybe would have started a little bit sooner to get at it, but you know I like to do things methodically so it was important to me to make sure that I had all my ducks lined up before I you know took the business on and got going with it and then it was really important to me that all the pieces were in place before I presented the business to my clients and to the outside world so that was important to me.
I think maybe I would have started a little bit sooner or had more trust in myself to get going which is important obviously I went and had a conversation with friends and family and you know put the idea out there and wanted to get some other you know some feedback on how other people thought that it would go but I think if I had put a little bit more trust in myself from the get-go which I think we’re all guilty of sometimes right but I think if I had done that I maybe would have got started a little bit more.
What methods and resources have you used to improve your career?
I try to work on the networking component of it, that’s huge for myself and for my business a lot of my business comes from referrals and networking and events like that, so I try to focus on that.
I also try to work on professional development always being curious always trying to learn more I mean it’s that age-old adage where it’s always learn something new every day right and when I’m out and working with my clients and things like that there’s always something that maybe triggers and I think I’m going to go back and look into that find out what that means so I think it’s you know it keeps you young and keeps you moving if you’re always curious and always reaching out to learn more so that’s important to me too and making connections with the right people right and learning how to build your team or your networking or just your crew behind you that people that you know you can depend on and count on or just go to if you’ve got questions especially as a new business and a new business owner it’s important for me to have those people in place that I can trust and that I can go to for questions to support my business as it grows.
How do you personally define success?
For me success is making sure that clients are happy and feeling less stress and feeling connected with their new space. Success for me is making sure that families are still connected right because there can be a lot of stress and a lot of overwhelm and family dynamics are tough right – it’s hard when you’re taking on a big project like moving especially for someone who’s been in their home for a long time it could be the family home there’s a lot of dynamics involved in that so success for me is coming out at the other side where the client is in their new suite and they’re feeling comfortable and they’re relaxed and they’re happy and you see that family unit sort of come back together and there’s not as much stress as there was before and they’re feeling relieved that things are taken care of and that they’re feeling good, so for me that’s a big part of the success.
Alternatively as well, success for me is referrals you know getting people reaching out and saying that they heard from somebody else about my business and they’re interested to learn more and bringing opportunities to me to support people so for me that’s a way to determine success as well because if people are reaching out and you are getting referrals then I think you’re doing something right and that’s important.
Tell us more about your clientele
Every client is different and every scenario is different, every story is different, so part of that initial consultation is to get to know the family get to know the client you know learn all the ins and outs of what they’re dealing with what the circumstances are because you don’t want to just go charging in and take a hold of everything and because that can add to the chaos that may be already there so it’s important to get in and get to know my clients and understand what their goals are what their timelines are what they’re working towards right so that we can figure out how best to help them through the situation and help them with their move, so for me that’s really important and for like I said for every family it’s different so you have to sort of reset after each one so that when you’re going in you don’t have these expectations and you don’t have these assumed biases because you’ve done another project before that you can’t assume you know it’s going to be the same.
But, when you’re actually working when I’m actually working with clients I really try to pay attention to how they’re handling things what they’re feeling like checking in with them on a regular basis right and providing constant feedback and going back and forth with them because they want to be involved in the process and especially if they’ve been in their homes for a long time they have a lot of questions they want to make sure that their belongings are being handled appropriately and taken care of so I would like to include them in the process as much as possible, so having those regular check-ins and just you know keeping them updated and letting them know how things are going that’s important to me I mean that’s and that’s just good customer service and customer support is making sure that you’re providing that feedback and giving them you know updates on how things are going that helps.
People only start to get caught up in themselves and caught up in questions and concerns when they don’t know what’s going on right and they don’t and that’s just that’s human nature that’s how we are that’s we get you know worried and upset when we can’t see what’s coming down the tunnel right so but if you can try to reduce that as much as possible then that helps to make them feel more comfortable and make the whole process smoother.
What are some of the core values that you have integrated into your business?
Compassion and respect, number 1, I mean in both of those cases they play huge roles in my business right. I mentioned before people are you know worried about what’s coming in the future they’re worried about their belongings they want to make sure everything’s taken care of there’s lots of family dynamics going on so I think being compassionate about what people are going through, what changes are coming for them and how they’re managing that is key. Making sure that you’re compassionate about understanding those components is important and then respect is huge right and again it comes back to human nature and just who we are as people everybody wants to be respected you know and my clients don’t want to be treated like children they want to be treated with the respect that they deserve and so if you go in and you treat people with respect and show them that you’re you care and you value their time and their belongings and everything else then I think everything just runs more smoothly and it builds that trust right it builds trust and that consideration that they want to have with you that you know develops the relationship for both sides.
What methods do you use to grow your team and recruit talent?
Well we’re a small team right now a team of one on most days, but yeah I think again it comes back to working with people that have the same values and morals right working with bringing on team members to support tailored transitions that you know understand respect and understand compassion, and really like what they do really like being involved in what we’re doing which is supporting people right and if they have that already in their background then that certainly helps right.
But, I think you have to have those core values of respect and compassion and wanting to support people because that’s really what we’re doing all the time is helping other people right and you have to sort of have that in your bones if you don’t if you’re not empathetic or you know can’t get past some things that might come up then that’s going to be a challenge you need to be willing to work with people and understand how they’re processing things and processing the transition that they’re going through.
Do you have a moving team?
So I bring in contracted team packers to help my team so they come in and we do all the packing and things but then I also contract movers and they’re contracted for me so that’s really important because they’re a representation of me and of the business right so it’s important that they have the same sort of guidelines because they’re coming into people’s homes and they’re representing the business and myself so it’s important that you know we build that relationship as well so I try to build that relationship with the movers that I use so that they’re comfortable, I’m comfortable, everybody’s comfortable with working together and making sure that the move goes smoothly.
What advantages have you seen establishing your business in Waterloo Region?
One of the advantages is that I’m local so I’ve been here for a long time so I know the area I know the community – it’s familiar for me so that’s I mean that’s a benefit for myself and for my clients is because I know the area well so I can speak to different locations, I can speak to different retirement homes, I’m building relationships with retirement homes and long-term care homes as well so I can speak to that with my clients and give them that direction.
I had a client that was moving from Elmira to Waterloo they were concerned about keeping their car and driving with roundabouts and we had a conversation about whether that was a smart idea but I because I knew where they were going and because I used to live on that side of town I knew exactly which roundabout they were talking about whether or not that was a smart way to go so it helps build again back to trust it builds that relationship with a client because if you’re familiar with your surroundings then you know they trust that you know what you’re talking about and the nice thing about Waterloo Region is it’s while we’re growing, it still has that small community feel right everybody’s really closely knit I find and the networking opportunities around Waterloo Region are huge because everybody seems to know everybody else and if you don’t you’re somehow connected and things like that so I think that’s great it’s nice to be working in a large region, but at the same time have it feel like a small community.
What inspires you?
I think I’m inspired by the opportunity to help people it’s something different every day. I just had a conversation with somebody about that today actually that you know my work is something different every day it’s there’s always something new going on and so it’s exciting because I wake up and there’s something different than what was happening yesterday right so even if I’m still working on the same project with a client it’s going to be a different day right there’s going to be something else going on that day so it’s exciting that way I’m inspired because my business provides me an opportunity that it might be something I can hand down to my kids in the future so that keeps me motivated you know it allows me to include them in the conversation to let them know they can see how I’m working they can see how the business is running I include them in those conversations you know as they grow there will be an opportunity that maybe they can help me with different parts of the business as well so that keeps me motivated and inspired to keep progressing and keep things moving is the opportunity to build the business and to potentially bring them on if they want to do that.
So hopefully we’ll see how that goes but being able to include my family in it is important to me as well.
What advice would you give to other female professionals and entrepreneurs?
For other women that are looking at you know entrepreneurship or starting some sort of business on their on their own or getting out there it’s you know I think it’s important to do the research you know do the market research is there a demand for the business, do you see a need that exists out there I think that’s important is to make sure that you’ve as a woman as a female we have a lot on the go between you know raising families and taking care of ourselves and taking care of our homes and you know just trying to get through life on the day-to-day you don’t want to waste your efforts right, so I think it’s important to make sure that you’ve that you’re doing your research and you’re putting your all your efforts in to make sure that it’s a viable opportunity.
I think making sure that you have a support system in place that you have those individuals that you can go to that you trust that you can ask questions of whether that be your network, whether it be family, whether it be friends, whether it’s a complete stranger but somebody that happens to show an interest then I think that’s important as well but you know having that that network of support around you is important especially as you’re working through the stages of starting your own business because there’s a lot, it’s a lot to do and when you’re trying to manage all things at all times it can be a lot so I think it’s important to have those people with you but yeah it’s exciting right and then the other thing is I think you know make sure to share your wins and put yourself out there because you never know who else is going to be able to want be able to support your business or want to support you and the business.
What are some of your future goals?
Obviously to continue to expand the business and bring on more clients that’s always the goal it’s you know big audacious goals are fun bringing on a team I’d love to be able to hire locally and you know support stay in in the region and but bring on teams that are that are available to help and potentially have you know more than one team on the road would be amazing you know growth is what I think most people want is to be able to expand, but also be make it manageable right I also want to make sure that I still have be able to deliver the service that we that our clients expect and that they deserve right so you know growth is great but if it gets out of hand and then the quality slips that’s not great so that’s important to me is making sure that we’re still delivering the best customer service that we can for our clients and that people are still you know appreciative and in the long run of the services that we’re providing so that’s important. I would love to expand the business, bring on the family and see where things go from there.
Where can viewers find out more about you?
They can visit my website at TailoredTransitions.com. They can also check us out on social media Facebook and Instagram.
