Golden opportunities to work with the best-managed agency


Cupid’s Escorts is an established female-owned and operated companionship agency that has built a solid reputation for being honest, reliable, and ethical. We understand what your needs are as a woman, and we will always make sure that you are comfortable working on our team. If this is your first time becoming a companion, if you’re looking to switch from another agency, or you want to return after an absence, we will guide you through the process to make sure this is the right choice for you.

Cupid’s Escorts is made up of a team of highly organized and professional women who believe in empowerment, education, and fun. We are here for you in every way possible. We are not just your agency sending you on calls; we are your support while you lay the foundation for your future.

Our business model is often copied by other other agencies, but they cannot compare with our unparalleled reputation and service.

At Cupid’s, we strive to help you build a better work/life balance and provide you with the full support you need to be financially independent, achieve your personal and professional goals, or find additional ways to enrich your life. Cupid’s Escorts strongly believes in achieving your best in everything that you do, we believe that every woman should have the power to make their lives better.

Joining Cupid’s Escorts agency can open up many doors for you; it’s up to you which one you choose to walk through.

Jillian Hollander

Jillian Hollander
Owner of Cupid’s Escorts

“All your dreams can come true if you have the courage to pursue them.”

Walt Disney


Women who work with Cupid’s Escorts enjoy their status as one of the most prestigious companions in the country. To see what Cupid’s can offer you in representation, we invite you to contact us directly and in confidence via email: hiring@cupidsescorts.ca

Please note that due to the high volume of applications we receive, we ask that you include a detailed description of yourself, your experience that is relative and non-relative to this industry, as well as some non-nude photographs for our consideration. Emails that do not contain the requested information will not be considered/responded to, so please be sure to include this. No phone calls, please.

All information is kept confidential.

Please note that we do not re-schedule interviews under any circumstance.

Perks of being a Cupid’s Escorts companion

Starting from day 1
  • A higher-than-average hourly wage, one of the highest in the industry
  • The flexibility of a schedule that you decide on; you decide on what hours you want to keep and how long you wish to be on schedule each day; you’re in charge!
  • We offer training for ladies who are new to escorting
  • Complimentary photo shoot by a female professional photographer in a proper studio with many perks like a gifted set of lingerie from high end brands for you to keep and a hair stylist on site, Cupid’s photoshoots standout more than other agencies because of our attention to detail
  • A safe and empowering environment that strives to be stress-free; we believe in work/life balance
  • The benefit of working with very experienced and organized all-female staff that understands your needs
  • Personal drivers that only drive one to two ladies at a time
  • We do not have an office that you are required to wait for your calls at, nor will you have to wait in a driver’s car all evening between calls
  • Full respect of your boundaries and limitations; with an understanding that these may change
  • Amazing Search Engine Optimization that has kept us on the front page of Google and other search engines for maximized exposure
  • A very loyal following of clientele who know who we are and what we represent, we have one of the most solid reputations in the industry and have been the leader in this industry for over two decades
  • Access to our exclusive library with dozens of titles about sex-work, relationships, money management and how to make the best of your time in and out of this industry
  • We offer complimentary self-defence workshops to our staff every quarter
  • Exclusive partnership with a highly regarded cosmetic clinic and spa that offers 30% off injectables and 50% off skin treatments to all employees
  • We are the “Fully Booked” agency; we are here to maximize your time and will book you as much as you are comfortable with
After 6 months of continuous employment
  • We will match your RRSP contribution by 25% at tax time
  • Should you be a student or wanting to return to an academic program, Cupid’s will do what we can to help build your future; we will pay 50% up to $3,000 toward your tuition per year
  • We will pay 50% of your plastic surgery (up to $2,000 per year), this includes breast implants, teeth whitening, Botox/fillers as well as most cosmetic procedures
  • Cupid’s Escorts will gift you $3,000 towards your purchase of a new home or investment property to help with overwhelming costs of buying in the Toronto area
  • Cupid’s is very proud to offer a Parental Benefit of $100 for your first child and $50 for each additional child per month to help with the of being a parent, this benefit is available immediately after you begin employment with Cupid’s

“There is no time like the present to change your life for the better.
We will be there to help along the way.”

Jillian Hollander
I just wanted to write a huge thank you, and wanted to let you know how working for Cupids has advanced me for the better. Aside from the fact that my ego is through the roof and I feel so much more empowered. In 2011, not only did I travel, but have taken care of most of my debt along with it! The most important thing, is that Cupid's is giving me the ability to look at further careers. I still maintain my current day job, but when I am ready to face the next step and change my career, Cupid's is able to carry me through without having to worry about where my money is coming from. Above all, it meant a lot that upon my return to Cupid's in August, the first thing you asked was if I was ok. No corporate company or employer shows that kind of consideration. Thanks Jillian for everything!

Compliments from Rachel
I'm having a lot of fun working at Cupid's :)

Compliments from Quinn
Like, I seriously think this is my favourite job of all time.

Compliments from Erica
I never had to opportunity to thank you before I left Toronto. YOU WERE THE BEST BOSS! HAVE THE BEST AGENCY! AND I WILL NEVER FORGET HOW YOU HELPED ME WHEN I NEEDED IT... and hands down from what I experienced at your agency, you guys have hands down the best operating agency in regards to service and dedication! YOU'RE AN AMAZING WOMAN! <3

Compliments from Isra
It seems as though it is time for 'Daria' to officially move on due to the recent positive events within my life. I wanted to take an opportunity to thank you for welcoming me to what I believe is the best agency out there, and for being so professional and supportive. I had an amazing experience and am sad to be leaving, but happy about what comes next for me :)

Compliments from Daria
Thank you very much for everything you have done for me. You've been very understanding and you are a great business woman.

Compliments from Claudia
I would like to say big THANK YOU for giving me the opportunity to work for Cupids! It has been a great experience.

Compliments from Nadya
I love you Jillian! You changed my life for the better, I want you to know that. Thank you!

Compliments from Berlin
Thank you so much for everything this year. Not only are an incredible boss and business woman, but truly and amazing friend. Your support and guidance has helped me become a better person within myself and set my goals beyond my dreams. Being a Cupid, a part of this team and being surrounded by a network of more amazing women in inspiring. It much than a Aussie girl could ask for.

Compliments from Bella
I can't thank you enough for taking me under your wing and giving me a chance to make money in this industry. I came to you with $100 in my bank account, and you immediately got me primped and fancied up for a fantastic photoshoot, you got me started working right away, and before I knew it for the first time in my life I didn't feel worried about money: I was paying rent, buying myself luxury items that I have never bought myself before, and I was finally having financial freedom and eliminating the debt I was in. Jillian, you truly do have a heart of gold, a wicked sense of humour and so much warmth. I really appreciate who you are as a person and as the businesswoman who runs Cupid's. You have always immediately gotten in touch with me whenever I have a question, a comment or a concern, and I have always felt valued and respected. I am still blown away that after six months of working at Cupid's that you honoured me with 50% of my tuition because I had earned over 85% in my final average. You have no idea how much that meant to me, and how touched I was that you were proud of me and were thrilled of my success. You have given me many luxuries since I've signed with Cupid's, and I have so many wonderful memories to be thankful for. You and your incredible team including Bridgitte and not to mention the wonderful drivers, have made my time at Cupid's easy, fun, enjoyable, and heartwarming. I will never forget how well I was treated, how sweet and understanding everyone has been, and how taken care of I felt. I thank you so much Jillian from the bottom of my heart, you're an absolute doll and a truly beautiful woman. Thank you for meeting me on that hot blistering day this past April, sitting me down with a glass of wine, giving me a chance, and saving me. :)

Compliments from Jerri

Get in touch


Cupid's Escorts
Toronto Escorts Cupid's Signature Angel
Office hours

352 Front Street West, Toronto M5V 0K3





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