Why Wisetack Favors Initiative Over Experience

The financial services company is dedicated to helping its employees make a lasting impact on the future of its business.

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Published on Oct. 21, 2022
Why Wisetack Favors Initiative Over Experience
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Shortly after joining Wisetack, a financial services company that facilitates buy-now, pay-later solutions for in-person businesses, Justin Coopersmith was in the woods of Colorado, reflecting on how to better do his job.

It was an excursion motivated by wonder and trepidation, he said. A former political researcher turned customer support associate, Coopersmith had a gnawing feeling that in his new role, he was missing the mark when fulfilling his responsibilities.

In fact, it wasn’t a suspicion at all. “The truth is that I wasn’t a very good support agent at the start. That’s because I love to sell people on ideas. I love to hear about their process and dig into the little details,” Coopersmith recalled.

Coopersmith had been hired for his conversational skills and inquisitive nature. But his enthusiasm was proving to be an obstacle: “It got to the point where people started saying, ‘Justin, you got to stop chatting with everyone,’” he laughed. 

It was that same enthusiasm that led Coopersmith to the woods, clutching a booklet of training materials he’d printed out to quiz himself during a hike. Wisetack had taken a chance on him, and he wanted to show the company that he was worthy of their investment.

“You look around, and you realize that everyone around you is so smart and so talented. You want to be a part of that team,” Coopersmith said. “That’s what fueled me to go above and beyond. It was the opportunity to work with people whom I really wanted to learn from.”



Through its suite of APIs, the fintech firm embeds financing options into software platforms that businesses are already using in their day-to-day operations.


Coopersmith may have recognized his good fortune. But he was far from undeserving of his role. His hiring belongs to a lineage of progressive practices at Wisetack that empower employees and support professional development — identifying promising candidates with the potential to help the business grow in conjunction with their own careers.

“At Wisetack, we’re intentional about providing structure and mentorship to give our employees meaningful and exciting work, as well as clearing a path for people to take on projects and responsibilities that they might not get somewhere else,” said Head of Growth and Marketing Iris Pfeifer, citing the company’s recent Series B fundraising of $45 million as a testament to its approach.

“The truth is that a growing company opens up a lot of career opportunities,” she continued. “Our employees have shown growth within the company, and they’ve shown a commitment that was motivated by the growth of the company as a whole.”

For Coopersmith, that commitment has translated into a fast-tracked career path that took him from customer support member to customer success associate. The new role better suits his skills and developments -- now his entire job is engaging in deep conversations and selling people on ideas.

“Feeling supported like that motivates your daily decisions,” Coopersmith said. “It’s really great knowing you have a network of people behind you who are rooting for you to succeed.”


Wisetack prides itself on not just hiring for the position, but for future roles within the organization as well. How has that approach to professional growth affected your tenure with the company? 

Kara Farkas, manager of decision analytics: My story is unique in that my title hasn’t really changed, but my role has grown to encompass so much more. I came into this role wanting to do more with data and analytics. But as the company grew, I felt like I was spending an increasing amount of time on tactical decisions. I needed more people to help with all of the operational work, so I hired two people from the customer support team who had a deep knowledge of our product and a deep understanding of our customer needs. This allowed people from within the company to take on more responsibility, while also freeing up time for our analysts to do more of the analytics work that needs to be done. To have a manager who hears your feedback and to have a leadership team who supports your feedback is really awesome.

Justin Coopersmith, customer success associate: Early on in my interview process, I made it very clear that I have a real passion for talking to people who come from a slightly different perspective than me. That’s what I did as a political researcher, and I think that’s what convinced Wisetack to hire me. I love having connections with people who I don’t normally get a chance to interact with. Most of my conversations these days are with small business owners such as plumbers, electricians and HVAC operators. And boy do I like to talk. I think it was these things put together that made me a good candidate. Even though I didn’t have the tech jargon or language in my back pocket, they were willing to teach me because I have the conversational skills that help me connect really well with our merchants.

Iris Pfeifer, head of growth and marketing: I remember discussing this with our CEO and COO pretty extensively. There was this question of, “Do we hire people who are really excellent at something and have a lot of domain knowledge, or should we push for people who are really smart and want to be at the company — and mold them from there?”

Across the board, I think every hiring manager would prefer to hire for trajectory rather than specific points on a resume. If there are two candidates, and one’s more experience but the other is more excited, hungry and curious, we tend to choose the person with less experience but more curiosity.

What does hiring for trajectory mean at Wisetack?

Pfeifer: I’ve been at companies where the intent to hire for trajectory exists, but the temptation to find someone externally who can immediately fill a role is so strong that you end up putting a ceiling on that original candidate. At Wisetack, though, we continue our investment beyond their initial onboarding. We don’t want people just hacking away, doing the best they can. We go out of our way to give real feedback for improving in those areas.



Wisetack offers customers a simple way to pay over time for a service or product. From home improvement projects to necessary vehicle repairs, Wisetack enables its users to break up the cost of a purchase into easy monthly payments. Businesses get paid directly when they provide the product or service, and the customer pays Wisetack over time. 


What has it been like to be on the receiving end of this support in your career?

Farkas: I joined this company for new challenges and to feel supported and cared about by a team, and I’ve seen it in practice in my own experience. That’s been great personally, and it also makes it easier to sell Wisetack to other people when interviewing or telling my team ways that they can grow and look for opportunities. I always want to hear their input and learn about what challenges they’re having and the solutions they have for solving those challenges. 


What kind of emphasis is there internally on branching out beyond your defined job description?

Pfeifer: I try to emphasize with my team that if there’s a business problem or an area for improvement and you have an idea for how to solve it, no one is going to stop you from trying to solve it — as long as you’re doing your actual job well.

Farkas: It’s about figuring out what the roles and responsibilities are. Specifically with the customer support team, every manager in the department is extremely supportive of having that team be a feeder for the rest of the organization. It takes extra work on their part, because they have to recruit and train more to backfill those roles, but they’re happy to take on that work because it means offering more career opportunities outside of the team. 

Coopersmith: My department recently moved to a different part of the organization. And when that happened, my manager’s manager immediately reached out to every member of the team to set up individual meetings in order to get a better understanding of where we want to go, what we want to do and what skills we want to learn. I really appreciated how she took time out of her busy schedule to meet with every associate. We came up with a distinct timeline and plan to actualize it, as opposed to just some vague gesture toward professional growth opportunities. 



Wisetack is a remote, distributed team living and working in the United States and abroad. While the financial services company is based in San Francisco and more employees live there than in any other location, most roles can be based anywhere in the U.S. 


How do you pay it forward and work to provide those you manage, and others on the team, with growth opportunities?

Pfeifer: I think of it a little bit as a puzzle. It’s important to think about how these unique interests and skill sets fit together. There was a time when a lot of our focus and energy was centered around recruiting, and that’s still very important. But now that the team has grown and scaled to a completely different size, it would be a huge mistake to dedicate that same focus to recruiting and not invest in the people who are here today. There’s a lot to do at Wisetack. You don’t have to feel like you’re confined to a narrow job.


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