Inside Trolley – A conversation with Jordy Cohen, Sr Director of Sales

Our goal at Trolley is to build the payouts platform for the internet economy: a payouts ecosystem that allows businesses to send payments around the world as fast and effortlessly as email. Trolley’s payment and software pros take great pride in how we equip our users and their recipient partners with a seamless contractor payout experience. Whether we’re developing new customer-facing features, improving our banking collaborations, enhancing customer documentation, or optimizing our communications, we’re always striving to build a bigger and better Trolley for you: our users and customers.

This series of blogs sheds light on our exceptional team members and the work they do to make Trolley what it is today.

Sales is about problem-solving, building relationships, and connecting with people. Our Sr. Director of Sales, Jordy Cohen, has taken this approach to heart and has been instrumental in building a sales team that represents and supports the diverse communities we serve.

An experienced sales leader who is the architect of Trolley’s current sales team, Jordy has been committed to building an inclusive and empowering environment, particularly for women. He has implemented strategies to ensure that our sales team provides equal opportunities for all.

As a payout platform that helps automate the process of onboarding and sending payouts worldwide, Trolley is committed to opening up economic opportunities to those who’ve been underserved in the past. Jordy’s efforts to build a more inclusive sales team align with our values and vision to unlock the collective economic opportunity of the internet – for everyone.

Join us as we delve into Jordy’s journey at Trolley and his impact on our sales team. He shared his insights on building a sales organization, the challenges he has faced, the successes he has achieved, and the importance of representation in leadership positions.


  • Name: Jordan Cohen
  • Title: Sr Director of Sales
  • Years with Trolley: 2 Years
  • Superpower: Unleashing the sales ninja in people🥷

Q&A with Jordy

Let’s start with your background. How did you leverage it in your current sales career?

My background is primarily rooted in Athletics, which gives me a unique perspective on how people interact, collaborate, and reach their full potential. Through my experiences, I learned a lot about human motivation and group dynamics. 

This has translated into my current sales career, where I bring a fresh and motivated approach to sales. I understand the importance of teamwork and work with my sales team to find ways to motivate each other and bring out the best in everyone. 

Additionally, my entrepreneurial background and experience in business development have helped me understand the challenges and opportunities that come with building a successful sales team.

—  What was the sales team like when you first joined Trolley? What is it like now?

The sales team has undergone a remarkable transformation since its early days. When I first joined, the group was small; most team members wore multiple hats and had different career paths in mind. But as Trolley grew, we knew we wanted to build a strong sales team. Fast forward to now, and our sales team is well-established and thriving. 

We opened an important hub office in Halifax, Nova Scotia, to support this growth and maintain our commitment to building a well-rounded sales team.

The Halifax office has been a remarkable success! We’ve got some hard-working and empathetic team members. Their diverse experiences and backgrounds have added a valuable layer of diversity to our sales team, making us even stronger. The team members have quickly established themselves as key contributors, bringing their skills and energy to every aspect of our sales operations.

— What was your main goal as you built the sales team?

When building our sales team, I placed a strong emphasis on fostering diversity and inclusivity. My goal was to bring together a group of individuals with varying backgrounds and perspectives, with a particular focus on increasing female representation in sales. 

At Trolley, we believe that a diverse and inclusive workforce cultivates a positive workplace atmosphere and drives superior outcomes. By having a team that encompasses a broad range of perspectives and experiences, we are better equipped to connect and empathize with our clients. This diversity fuels innovative thinking and fresh ideas.

— What inspired you to focus on building a more inclusive and empowering sales team, particularly for women?

I believe that sales is a field that should be open to everyone, regardless of gender, and I wanted to build a team that reflected that. I have always been passionate about empowering women and creating a more equitable society, and this was a way for me to put those beliefs into action. I want to break down gender stereotypes and create equal opportunities for everyone. By building a diverse and inclusive sales team, I hope to show that anyone can succeed in sales and that it’s possible to create a positive and inclusive work environment.

— What challenges have you faced in building a more diverse and inclusive sales team?

One of the biggest challenges I faced was changing the perception that specific roles are only for certain groups of people. I feel there is still a gender stereotype in sales, particularly in financial services & SaaS — that it’s a man’s role — but I have worked hard to build a team that is diverse in all respects and gives equal opportunities to everyone. This can be a complex and ongoing battle, but it is one that Trolley is committed to fighting. Additionally, I have faced challenges in creating a safe and inclusive work environment where everyone feels comfortable discussing and resolving conflict. I have found that all difficulties can be overcome by fostering open communication and encouraging growth and development.

— Can you share a success story of someone on the sales team who, in your eye, has excelled in this environment? 

One person who stands out is Alex Sankey, who joined Trolley as an Account Executive responsible for new sales. She has since risen to a Management Role as a Sales Development Manager, directly responsible for our inbound and outbound sales efforts and managing our in-house BDR team.

Alex’s professional development is a testament to her tenacity and drive to learn. She quickly understood the dynamics of the sales environment and worked tirelessly to support the team. Her dedication paid off, and she has been instrumental in driving our sales growth. Alex’s commitment to her own personal and professional, combined with her leadership skills, has made her a valuable asset to the team and a source of inspiration for others. 

Alex’s journey is just one of many inspiring success stories within our sales team – every member brings unique qualities contributing to our overall success. Our team is poised for continued success and growth; there is so much potential and talent here, and I can’t wait to see what the future holds for everyone. 

Ready to level up in the world of sales and leadership? Whether you’re a seasoned pro or just starting out, there’s always room for growth and discovery. By getting a better grasp on the different styles and techniques, you can supercharge your success and tackle any obstacle with confidence. We invite you to contact Jordy; you might learn something that takes you to the next level!

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