Carving Out a Career Path as a Woman in FinTech

Yieldstreet’s Melanie Alese and Taylor Fishman are two leaders forging a path for women in fintech.
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April 11, 2023Updated: April 11, 2023

In her current role at Yieldstreet, Senior Manager, Investor Relations, Melanie Alese works at the intersection of two traditionally male-dominated fields: tech and finance. While this might deter some, Alese says thanks to mentors and ample resources, she’s felt supported and empowered, raising her hand when opportunities for leadership come up. And it’s paid off. 

During her time at the company, Alese has honed the skills necessary to transform into a supportive and skillful manager. Her career trajectory has involved learning to be a manager coach and an advocate for her team — as well as herself. 

It’s also meant having to temper her inclination to do everything.

“My manager has worked with me to change my mindset, reallocate my time from being in the weeds of the day to day, to coaching others on the team and helping them develop their areas of expertise and grow within the company,” Alese said.

Alese’s colleague, Investment Operations Manager Taylor Fishman, has had a similar experience transitioning from an individual contributor to management at the intersection of two traditionally male dominated fields. She credits supportive leadership and a willingness to advocate for herself as major factors in rapidly accelerating her career growth at Yieldstreet.  

“Everyone here has the opportunity to grow, but if you don’t ask for it, you won’t get it,” Fishman said. “I had only been here for a little over a year when I was first considered for a managerial position, and that was never something that I experienced in my previous roles.”


Another Way to Invest

Yieldstreet is an online platform that offers investors access to private market investments, enabling them to diversify and strengthen portfolios through stakes in commercial real estate, private business credit and even fine art. 

From a Team of One to a Leader of Many

Alese started with Yieldstreet in 2017, a time in which Yieldstreet was still very much in its infancy as a company. “I started in what you might call an analyst role — but we didn’t even have role distinctions back then,” Alese said. “And I had to ramp up really, really quickly because, after six months, I was the only person on my team.”

Alese had previously worked at a corporate finance firm. At Yieldstreet, she joined a scrappy team of two at the then two-year-old online investment platform. Within six months, though, her colleague moved to Boston, leaving the company and effectively making Alese a team of one. 

The learning curve was steep, but ultimately, skills Alese honed traversing that curve set her up to grow prolifically — as a both finance professional and a future leader. 


My manager’s support — and the support of other leaders, even senior management, giving me their guidance and validation — really gave me confidence in myself.”


“I was the one person who was directly client-facing or investor-facing,” Alese said. “I spoke to all the new members and current investors on the platform, and for a while, it was really a one-man show.” 

As Yieldstreet continued to grow, however, the company’s vision for Alese’s team expanded as well. The team was originally intended to be a Spartan group of two or three assisting self-servicing customers in a tech-centric onboarding process. But Yieldstreet realized that it would need a much larger team to stay abreast of the company’s prodigious growth, and Alese shifted from an individual contributor role into a managerial position where she could better leverage her hard-earned expertise.

Alese has had the opportunity to report to the CMO and the CPO. She was able to learn from leaders throughout the organization, including members of the company’s C-suite. “It’s really given me insight into different aspects of the business which I was able to learn from and leverage within the Investor Relations team,” Alese said. 

In her current role, Alese oversees a team of three direct reports — part of a larger team of 11. That team has also grown from a New York City-based department of one into a fully distributed org with members in Texas, Florida, and even Athens, Greece. 



In addition to management classes, bi-weekly coaching sessions through Sounding Board, company mentorship program, Alese cites a recent Yieldstreet book club selection with shaping her approach to management: Radical Candor by Kim Scott. “The book involves dealing with people on an individual basis and finding the sweet spot of what works for them in terms of feedback, encouragement, when to step up and how to navigate challenging situations in a professional manner.”


“You Deal With Imposter Syndrome” 

Fishman joined Yieldstreet as an investment operations associate. She had previously worked on the mutual fund reporting team of a global asset management firm.

“It was a different industry, a completely new job and a huge change for me,” Fishman said. 

As an associate at Yieldstreet, Fishman initially focused on firmwide liquidity and warehouse management. The team was very lean when I joined and I knew I had to roll my sleeves up and learn as much as possible. It was a job she characterized as “really in the weeds” of Yieldstreet’s day-to-day operations.

The opportunity to work on an important project, onboarding a large-scale credit facility, presented Fishman with a chance to demonstrate her leadership capabilities. “Working on this credit facility — and really owning that project — was the turning point when stepping into that role came about,” Fishman said.

Becoming a manager was so important to Fishman, she met with her direct manager, developed an action plan, and within a year and a half of coming onboard at Yieldstreet, was promoted into her current role. Now overseeing a team of three direct reports, Fishman works to train and support team members to do what she did: excel in the associate role. 

“It’s challenging, and it’s exciting to be in a situation where I can now train people to do what I was doing in a more efficient way,” Fishman said. “Being early on in my career, in a new industry and a new type of role, it was all a little overwhelming at first. You deal with imposter syndrome. But my manager’s support — and the support of other leaders, even senior management, giving me their guidance and validation — really gave me confidence in myself.”



“Everyone at Yieldstreet, even the leadership team and directors, is more than willing to spend time with anyone who’s looking for mentorship,” Alese said. “Developing those relationships over the last five years has definitely helped me come into my current role and be a better leader and a better manager who is able to lean on the opinions and experiences of others.”


Growing Leaders

Alese noted parallels between Fishman’s struggles with imposter syndrome and her own, noting that in an industry where you’re much more likely to see men in leadership roles, carving out a career path as a woman has its own distinct challenges. 

“Transitioning into a senior management position at Yieldstreet felt like a natural progression, but it was also something that needed to be earned and asked for,” Alese said. “I definitely raised my hand to move out of the day-to-day, to make a bigger impact at a higher, more strategic level and to coach, becoming more of a people manager than an individual contributor.”

For Fishman, one of the most impactful aspects of her work at Yieldstreet is the open-door culture of transparency and inclusivity. While operations is usually recognized as a “back office” role, Fishman has plenty of opportunities to interact with colleagues throughout the organization — including senior leadership.



“You’re not behind the scenes,” Fishman said. “I’m in meetings with cross-functional partners from marketing, sales, investor relations and product. We touch everything. And I can walk into any C-suite level office and they know who I am. Being one of the few women in a conference room is an opportunity to advocate for yourself and grow professionally and personally.”

Fishman and Alese have both cultivated relationships throughout Yieldstreet that are both self-empowering and serve the greater good of creating a more inclusive and open culture at the company.

It’s a testament to a two-way street —  a Yieldstreet culture that strives to celebrate and elevate women’s voices and a very talented and capable group of women leaders who are creating their own paths to leadership at the company.

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