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Tiffany Kaminsky: “Don’t be afraid to be vulnerable”

Don’t be afraid to be vulnerable. This does not come easy for me. Vulnerability does not equal weakness. Ask questions. Be upfront about what you don’t know, and you will be surprised by the lengths people will go to help you. As a part of our series about powerful women, I had the pleasure of interviewing […]

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Don’t be afraid to be vulnerable. This does not come easy for me. Vulnerability does not equal weakness. Ask questions. Be upfront about what you don’t know, and you will be surprised by the lengths people will go to help you.


As a part of our series about powerful women, I had the pleasure of interviewing Tiffany Kaminsky, Co-Founder & Chief Strategy Officer of Symend. Tiffany is a passionate entrepreneur and expert in data-driven business and consumer engagement, with over a decade of experience in marketing, strategy and leadership.

Tiffany leads marketing and strategy at Symend, where she brings together the cross-functional teams spanning data and behavioral sciences to empower at-risk customers and drive positive outcomes.

Tiffany has received numerous awards and recognition for her work with Symend, including being named as one of Canada’s Top 50 Women in FinTech by the Digital Finance Institute and a Metabridge Top 10 Founder in 2019. She placed in the top 10 in Canada in the Lazaridis Institute’s Women Founders Scale Up Program in 2019 and achieved second place in the global Female Founders in Fintech 2018 from Quesnay Inc. Symend was named CIBC FinTech Startup of the Year in 2019 by the Digital Finance Institute.

Prior to co-founding Symend, Tiffany led a successful consulting practice that focused on building business strategies and processes while applying LEAN practices for clients in EdTech, SaaS, oil and gas, manufacturing, and non-profit sectors. Tiffany launched her career as the National Director of School Relations for TinyEYE Therapy Services, where she focused on marketing and developing global partnerships. She grew the business over 1,000%, spanning 12 countries and five languages, during her tenure.

Tiffany is a frequent speaker and panelist on empowering women in technology, and she is passionate about implementing initiatives that focus on achieving social good.

Tiffany holds a Bachelor of Commerce in Marketing and Management degree, a certificate in Applied Behavioral Science, and a certificate in fintech from the Massachusetts Institute of Technology (MIT).


Can you tell us a bit about your “backstory”? What led you to this particular career path?

I come from a marketing background and have always found it very compelling to see how psychological and behavioral nudges can influence and drive action. My co-founder, Hanif, has come to me with many great business ideas in the past, but this was the first idea that resonated, as it creates a positive social change. Intrinsic motivation and personal connection have always been a major driver for me. It excited me to think about how my background could be applied to help drive positive behavior and empower at-risk customers.

We created Symend to help individuals who have fallen behind on payments and treat them with understanding and respect at a time when they need it most. When I was in college, I ran into problems with my first credit card. Being on the receiving end of collections agency tactics, I know first-hand how predatory and disrespectful they can be. Due to this experience, I understood that young people struggle with financial literacy and how this extends to new immigrants who have access to credit for the first time, as well as to people who face hardship like a lost job or loved one. I have been one of these people, as I’m sure many of you have been. I wish Symend would have been around to help me.

Can you share the most interesting story that happened to you since you began leading your company?

Thinking back, there have been a lot of interesting stories since starting Symend. The one that stands out in my mind is bringing our product MVP to market and launching our first client. We spent the first five months after starting Symend focused on the discovery and worked through the Strategyzer series (which I highly recommend) before developing anything. We were very vulnerable in reaching out to the industry and sharing our vision for the company and desire to learn from domain experts to ensure we built the right product to serve their needs. Our mission is to change at-risk customers from transactions into people, combining science and compassion to create lifelong relationships. Our measure of that effectiveness is our ability to increase cure rates, reduce bad debt, and reduce OPEX savings while increasing customer satisfaction. I can distinctly remember looking at these metrics and thinking, “Wow, it works!” So much work went into building our business and unique product offering that when we saw our first positive client results, our team was in awe and felt a sense of huge accomplishment.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I’ve made a lot of mistakes along my journey. Early in my career I recall coming out of meetings thinking I was the “stupidest person in the room.” It was real insecurity, and I saw it as a negative, often questioning the value I brought to the table. As I’ve grown throughout my career, I look at that statement completely differently. I hope that I am the “stupidest person in the room” because it means I’ve surrounded myself with a talented team that I can learn from, be challenged by, and collaborate with. I think that a foundational shift in mindset has truly helped me to build an incredible team and become a better leader.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. What is it about the position of CEO or executive that most attracted you to it?

I’ve always had a very entrepreneurial spirit, and the idea of founding a new company has always been very appealing. I wore a lot of hats as we got started and am our Chief Strategy Officer today. Our team is made up of behavioral scientists who fuel our strategic IP and work collectively with our data and computer science teams to transform customer engagement. This is an uncharted area where we are developing alongside multi-disciplinary experts, biometric capabilities, AI/ML algorithms, and cutting-edge solutions, which is extremely interesting. We do the cool shit. The ability to define a new space and drive data-first findings that have such a positive impact on the treatment of at-risk consumers is really rewarding.

Most of our readers — in fact, most people — think they have a pretty good idea of what an executive does. But in just a few words can you explain what an executive does that is different from the responsibilities of the other leaders?

Driving the mission and vision of the organization and building the strategy and team that can deliver on the company’s goals.

What is the one thing that you enjoy most about being an executive?

The ability to impact change. Strategic solutions, collaborating with clients to deliver positive outcomes, team coaching and mentoring, and being a catalyst for change. You have the ability to set the course for how to achieve your goals and can be creative in how you get there.

What are the downsides of being an executive?

It can be high stress. There are a ton of ups and downs, and the buck stops with you. There is a great amount of personal responsibility. For example, you are responsible for the careers of hundreds of employees who trust you.

What are the “myths” that you would like to dispel about being an executive? Can you explain what you mean?

One such myth is that executives make the decisions but don’t do the work. I have never had a role where this is true, and we have built a culture at Symend based on rolling up your sleeves. There is a big difference between a boss and a leader.

In your opinion, what are the biggest challenges faced by women executives that aren’t typically faced by their male counterparts?

One challenge I’ve personally faced is the gender divide when it comes to areas of negotiation. There are tons of studies on the topic, and one of my mentors pointed this out to me years ago when I was not going to pursue an opportunity I didn’t check every box for. I would have self-selected out, but, thanks to his advice, I was accepted. The idea that “more men ask” is something that we as women can directly control. Don’t be afraid to ask for what you want and need.

What is the most striking difference between your actual job and how you thought the job would be?

Given the speed we’re growing, my role has dramatically evolved over time, and I expect it will continue to. I am excited by our growth and the new challenges it brings as we rapidly scale. While I loved wearing every hat as we got started, I am excited to narrow in and strategically focus on our Science Department.

Certainly, not everyone is cut out to be an executive. In your opinion, which specific traits increase the likelihood that a person will be a successful executive, and what type of person should avoid aspiring to be an executive?

Every executive is different. I don’t think there’s a secret sauce.

Having been on both sides of the table, I think that executives who lead by example aren’t afraid to get their hands dirty and invest in the development of their people; they are the most successful.

The ability to make quick decisions is critical.

What advice would you give to other women leaders to help their team to thrive?

Make time for your high-performing team members. This means weekly 1-on-1s, coaching, mentorship, and career path planning. I’m a big proponent of the idea that every time you replace yourself, you give yourself a promotion, which encourages team members to build systems and processes that can be handed off to elevate themselves from tactics to focus on strategic initiatives.

Creating an environment where your team feels comfortable failing fast and learning is key to empowering each member to push the boundaries of what is possible while having the support to make mistakes along the way. Give your team a voice to challenge ideas.

None of us are able to achieve success without some help along the way. Is there a particular person to whom you are grateful for helping you get you to where you are? Can you share a story about that?

I have been very grateful to have had a tremendous amount of support to help get me where I am today.

I would not be the person I am today without the strong morals, drive, and work ethic my parents instilled in me from a young age. I am grateful for the unconditional support of my partner Cam, family, and friends throughout my career. They keep me grounded and authentic.

Secondly, my co-founder, Hanif, I can’t imagine being on this journey with anyone else. I value our executive team, investors, advisors, and each Symender, who continue to push me, challenge ideas and raise the bar. A startup is full of ups and downs, and we would not be where we are today without the passionate and dedicated team that jumped on the roller coaster ride we call Symend.

I was also very lucky to have incredible mentors, including Greg Sutton, who truly took me under his wing early in my career. Maor Amar and Mitchell Wasserman continuously challenge me and share their vast experience. I cannot emphasize more the importance of having strong business mentors.

How have you used your success to make the world a better place?

The need for what Symend does has become more pronounced than ever. At a time when the delinquency is being felt the most, we are helping people maintain their services and not face the hardship of negative credit impacts. We know times are hard, and we’re here to stand by you. It’s not about collecting every dollar; it’s about preserving lifetime value and working with at-risk customers to find a resolution that ensures that they keep their service and that their credit is not negatively impacted. Symend is currently on track to be one of the most innovative technology companies focused on social good.

What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

  1. Surround yourself with people who bring you up. You become like the five people you spend the most time with, so choose them wisely. Understanding where you bring the most value and filling your gaps is critical to success.
  2. Ruthlessly prioritize! Saying no to something means saying a bigger yes to something else. You can’t do it all. Wearing every hat in a startup does not scale and is not sustainable. Do it, delete it, delegate it, or defer it.
  3. Culture trumps strategy. We have been very lucky to have organically developed our culture at Symend, but as we grow, the need to formalize this has become very apparent. Developing your mission, vision, and values early will guide how you hire, fire, promote, and reward your team. Having a strong framework makes those decisions very clear.
  4. Get comfortable with the uncomfortable, and don’t be afraid to fail. Some of my best ideas and solutions have come from my failures. Create an environment where people are empowered to push the boundaries and try new ideas, fail fast, and learn from mistakes.
  5. Don’t be afraid to be vulnerable. This does not come easy for me. Vulnerability does not equal weakness. Ask questions. Be upfront about what you don’t know, and you will be surprised by the lengths people will go to help you.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.

I am doing that now through the work we are doing at Symend. I’m a passionate entrepreneur, and my vision is to create a force for social good. We created Symend to help individuals who have fallen behind on payments and treat them with understanding and compassion. Currently, I lead marketing and strategy at Symend, where I bring together the cross-functional teams spanning data and behavioral sciences to empower at-risk customers and drive positive outcomes. I believe it is very compelling to see how psychological and behavioral nudges can influence and drive action, particularly in collections, which is a relatively untouched market. Symend is not collections; we are in the business of helping consumers. Not only are we developing a world-class platform, but I’m proud to say that we are applying the sciences to support our mission of creating positive social change. At Symend our North Star has always been to save at risk-consumers from negative outcomes. We built this company to help individuals who face financial struggles. I will know we are successful when we can measure at an ecosystem level the number of people saved from this negative credit outcome, and we’re doing that now.

We are on track to be the most innovative company focused on social good in the AI space. We are creating hundreds of jobs across North America. At Symend we pride ourselves on hiring the best person for the job regardless of race, gender, or background and have an extensive process. As of August 27 (we’re growing weekly), I’m proud to say that our team is 38% women and highly culturally diverse, which is outstanding in the tech space.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“Comparison is the thief of joy” has always been one of my favorite quotes. I think it’s so applicable personally and professionally. It’s too easy to diminish your own accomplishments and miss the moment because you compare yourself to someone else. There will always be someone smarter, funnier, prettier, or further ahead or who seemingly has more. Rather than focusing on what you don’t have, focus on what you do have. Taking the time to find joy in your own successes, regardless of how big or small they are, is so important for mental well-being. I strive to raise the bar and compete to be the best version of myself every day.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

There are so many incredibly inspirational individuals that it’s hard to narrow it down. I love the work of Brene Brown and Simon Sinek and have applied their teachings both personally and professionally throughout my career.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

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