(Image: Oleh Shkinder | LinkedIn)
Startups rarely begin with certainty. They start with curiosity, risk, and often, no playbook.
For Oleh Shkinder, that beginning came during a turbulent time, building a fintech platform from Ukraine as war loomed, and resources were stretched thin. What started as a side project eventually evolved into Investables, a platform for fractional ownership of physical collectibles, and ultimately became a startup acquired by U.S.-based fintech company Stockpile.
Today, Oleh serves as the Senior Product Manager at Stockpile, where he leads product development efforts for cryptotrading, membership billing, and platform features, impacting over 1 million families across the United States. His story is one of resourcefulness, resilience, and a sharp eye for scalable, user-centric product design.
From Ukraine to 0–1: Building Investables
In 2022, amid political uncertainty and personal risk, Oleh co-founded Investables, an investing platform giving users access to physical assets through fractional ownership. Initially launched as a retail platform, it quickly evolved into a B2B API, enabling partners to embed alternative investing into their own apps.
Working remotely under crisis, Oleh juggled multiple roles: product strategist, architect, vendor integrator, and investor liaison. The product’s value crystallized after several pivots. Oleh evolved it into a B2B infrastructure solution that enabled fintechs to introduce a new asset class to their end users seamlessly. Early pilot integrations verified the demand, leading to multiple active contract negotiations with established brokerages.
The startup’s growth caught the attention of Stockpile, a Series B fintech serving U.S. families. In 2023, Stockpile acquired Investables, a defining moment that validated not just the product but Oleh’s ability to lead under pressure.
Making an Enterprise Impact at Stockpile
After the acquisition, Oleh took the lead on key product areas at Stockpile, directly impacting user growth, engagement, and revenue.
In his first year, he delivered trading, crypto, and portfolio capabilities that boosted retention by over 23% and increased user satisfaction by 30%. Through disciplined, data-driven experimentation aligned with the company’s North Star Metric, he helped drive sustained increases in MAU and contributed materially to growing AUM.
He also introduced wallet-based billing and optimized the membership lifecycle, leading to a 23% increase in recurring revenue and stronger conversion rates across user cohorts.
By aligning engineering, design, and data teams, he consistently shipped on time through clear roadmaps and OKRs aligned with the company’s strategy.
Strength in Structure: The Power of Process
Despite his creative energy, Oleh’s approach to product management is rooted in discipline and clarity.
“Discipline and structure,” he says, “are the real foundations of creativity and progress.”
This philosophy sharpened during his time at Investables, where every day required fast decisions, constant adaptation, and focused execution under uncertainty.
This mindset now influences his approach at Stockpile, guided by three key principles. First, he maintains a strong user focus, beginning with customer problems and making decisions based on data and real behavior. Second, he clarifies ambiguity by breaking down complex issues and aligning teams around the most impactful goals. Third, he influences without formal authority, communicating effectively and building trust to ensure that teams work together in the same direction.
His work reflects a structured, fast-moving approach to building products with depth and intention.
Guiding the Next Generation at Beta University
Since mid-2025, Oleh has mentored early-stage founders at Beta University, a Palo Alto pre-acceleration program that focuses on validating ideas and preparing for fundraising.
(Image: Freepik)
His hands-on, data-driven approach helps teams define go-to-market strategies, spot product-market fit, and structure investor-ready metrics, grounded not in theory, but in his own journey from concept to acquisition.
Earlier Roles: Pattern Recognition Through Experience
Before founding Investables, Oleh built a deep foundation across fintech, SaaS, crypto, and AI.
At Changeblock, he worked as a product consultant, shipping an MVP in close collaboration with the Cardano Foundation to help tokenize carbon credits globally.
At Heureka, he led a logistics SaaS (Software as a Service) used by enterprise clients, including Siemens and DB Schenker. His focus was on AI-driven optimizations that significantly reduced operational inefficiencies. He recognized that to move faster, the organization needed a new operating model, which led him to drive an agile transformation across various teams.
Subsequently, he held roles at SoftServe, where he contributed to large-scale digital transformation projects, and at Magnise, where he helped fintech clients secure significant early funding by collaborating closely with engineering to deliver high-quality products.
Each of these roles enhanced his systems thinking, data intuition, and user empathy, foundations that continue to define his approach to product leadership today.
AI as a Strategic Advantage
Today, Oleh is leading the way in integrating AI into product development, not simply as a tool for automation, but as a creative and technical partner. He utilizes platforms like Lovable, Supabase, ChatGPT, and custom agent workflows to rapidly validate ideas, prototype comprehensive experiences, and explore new product directions. For him, AI isn’t just a shortcut; it’s a means to work more efficiently, discover new possibilities, and communicate solutions with much greater clarity.
(Image: AI and human touch | Freepik)
For him, AI is not about replacing product intuition; it’s about amplifying it. He envisions a future where product managers operate more like storytellers and strategists, leveraging AI to automate mundane tasks and allocate more time to user insights, vision, and experimentation.
This is part of his broader aspiration: to modernize product management into a craft that blends technology, human understanding, and business impact.
Build What Matters
Oleh’s personal north star isn’t velocity, it’s clarity.
“The goal,” he says, “is not to build fast, but to build what truly matters.”
That focus shows in every phase of his journey, from founder to product leader.
Living in the Bay Area has only reinforced that conviction. Surrounded by builders who think long-term and lead with depth, he’s drawn inspiration not just for work, but for life. As he says, the best builders don’t chase hype; they ship what matters.
One quote that grounds his mindset comes from Andrew Horowitz:
“The goal isn’t to predict the future. It’s to prepare for it with clarity and discipline.”
That lens, courage over cleverness, has shaped how he builds, leads, and mentors.
Looking Ahead
Oleh’s next chapter is already in motion. He’s doubling down on the intersection of AI and product strategy, working to simplify complex systems into user-friendly tools, and rethinking how teams ideate, validate, and scale.
But even as the tech evolves, his foundation holds: build with purpose, lead with clarity, and stay close to the user.
From a founder under fire to a leader shaping fintech for millions, Oleh Shkinder’s story reminds us: the best products start with vision, and survive on courage.
About the Author
Jake Bennett is a tech writer and startup strategist focused on product-led growth and founder storytelling. With a background in UX research and SaaS marketing, J. brings clarity and depth to complex product narratives. Outside of work, you’ll find him experimenting with sourdough recipes on slow weekends.