The founding story begins with pizza, as useful software stories sometimes do. In 2005, Rascal House Pizza near Case Western Reserve University needed a website and an online ordering system. Alex Yakubovich and two friends, Stan Garber and Oleg Fridman, built it. They were students, but not novice sellers. Their web-design shop had already sent them door-to-door around Cleveland wearing shirts and ties, pitching local businesses. The pizza assignment gave the trio a sharper problem: take an ordinary action that still required a phone call and make it work on a screen.
They tested the ordering system with students in a basement computer lab. Nearby Quizno's and Georgio's locations followed. Soon the web shop became ONOSYS, a restaurant-ordering company with national chains on its client list. By 2012, its customers operated at more than 4,000 locations, and the platform had handled more than $90 million in online orders during the prior year. LivingSocial bought the company for a reported $18 million.
This is the first useful pattern in Yakubovich's career. The market can look abstract from a distance. Up close, it is a person trying to order lunch, answer a spreadsheet or get a purchase approved. His companies tend to start at that uncomfortable point where necessary work becomes easier to avoid than to complete.
One pizza website grows into an online-ordering system.
LivingSocial acquires ONOSYS for a reported $18 million.
Four friends start Scout RFP around a Cleveland basement whiteboard.
Workday agrees to acquire Scout RFP for $540 million.
Yakubovich and longtime collaborators start Levelpath.
Levelpath's Series B takes total funding above $100 million.
The outsider's blank slate
Yakubovich was born in Moscow and came to the United States at six. He has recalled watching his parents pack frying pans and pillows and wondering, with a child's practical logic, why the destination apparently lacked both. His family settled near Cleveland. His parents, who had worked in electrical trades in Russia, took jobs in construction and restaurants. Yakubovich worked at McDonald's, caddied, cleaned pool furniture and did clerical work.
At Mayfield High School, he met Garber. They started a Future Business Leaders of America chapter and traded stocks on a teacher's computer during lunch. At Case Western Reserve, Yakubovich chose mechanical engineering. His parents had suggested the familiar trio of doctor, lawyer or engineer; he thought engineering would give a future entrepreneur enough technical fluency to build.
That blank slate mattered when ONOSYS exposed the founders to requests for proposals. The supplier side was filled with repetitive forms and spreadsheets. When Yakubovich, Garber, Chris Crane and Andrew Durlak began sketching Scout RFP in 2014, they knew the irritation but not the procurement professional's entire job. So they treated ignorance as a research plan. They set a goal of speaking with 200 procurement professionals and interviewed even more.
What they heard was less a demand for another feature catalog than an adoption failure. Companies bought strategic sourcing tools, yet many employees returned to email and Excel because the official systems were too complicated. Yakubovich described adoption around ten percent. The unused software was not neutral. It scattered supplier data, hid the status of projects and turned collaboration into follow-up.
Scout's answer was to make sourcing software usable without an instruction manual. It connected project intake, supplier communication, bidding, contracts and reporting. By 2017, Yakubovich said the company had more than 95 customers and 27,000 active users across 89 countries. By 2019, customers included businesses such as Netflix, Levi's, Hulu, Intuit and Best Buy. That year, Workday agreed to buy Scout for $540 million.
The buyer becomes the classroom
Acquisitions are often written as endings because a price produces a clean final sentence. For Yakubovich, Workday made the procurement problem messier and more interesting. He stayed, first as vice president of Scout RFP and then as general manager of Spend Management. He and Garber were now employees inside a large enterprise, experiencing routine buying from the other side.
The frictions were wonderfully mundane: finding the right person to approve a happy-hour budget, identifying an approved vendor for company swag, getting an NDA prepared and signed. Each request carried hidden dependencies across procurement, finance, legal, security and the business team. The person making the request mostly saw messages, delays and another system they might not know how to use.
Yakubovich left after more than seven years across Scout and Workday. In 2022, he and Garber co-founded Levelpath with Bryan Rosenstein and Raimonds Samofals, colleagues with experience across product, operations and engineering. The new company widened the frame from strategic sourcing to a unified procurement platform covering intake, suppliers, contracts and purchasing workflows.
Its declared mission, “make procurement delightful,” is deliberately dissonant. Procurement protects budgets, manages risk and coordinates suppliers; delight is not the word most employees attach to it. Yakubovich uses the contrast as a product requirement. If employees can begin a request without knowing every policy or preferred supplier, if the platform can retrieve the right context and route the work, the official process has a chance to become the convenient process.
AI with a job description
Levelpath announced a $14.5 million seed round and a $30 million Series A in 2023. In June 2025, it announced more than $55 million in Series B funding led by Battery Ventures, taking total capital raised above $100 million. The company's pitch had also shifted from adding artificial intelligence to procurement toward building an AI-native architecture around it.
That distinction can collapse into marketing language, so Yakubovich describes it in workflow terms. The system needs a shared layer of supplier, contract and policy context. Agents need permission to retrieve information, complete bounded tasks and coordinate steps while preserving governance. A useful agent is not merely a chat window. It knows which context applies at which point and where a person must judge the result.
The intended payoff is time. Procurement staff do not enter the profession to reformat spreadsheets, copy records between systems or chase approvals through email. Their harder work involves negotiation, supplier relationships, trade-offs and experience. Yakubovich's question is pointed: if an agent can handle a portion of the job, was that the portion the person loved?
The customer behind the decision
Across three companies, the technical domain has changed more than Yakubovich's management language. Scout's first value was to obsess over customers. Levelpath uses the same phrase. In product discussions, he likes to ask whether the person proposing a feature can name the specific customer it will serve better. A vague answer is a reason to edit or stop. A vivid customer response is permission to keep going.
That habit is more exacting than it sounds. Customer obsession can become a slogan broad enough to excuse any roadmap choice. Naming the customer forces a claim: this person has this problem, and this change should make their work materially better. It brings the product conversation back from market size and model capability to observed behavior.
It also helps explain why Yakubovich keeps building with familiar people. His collaboration with Garber reaches back to high school. Their ventures have included friends, university classmates and colleagues who carried operating knowledge from one company into the next. The continuity is not romantic evidence that startups among friends always work; Yakubovich and his first partners were warned that business might ruin the friendship. It is evidence that trust, when tested through years of difficult work, becomes reusable infrastructure.
The career looks different depending on where you stand. From far away, it is a sequence of acquisitions and funding rounds. From closer in, it is Rascal House Pizza, a basement focus group, an RFP spreadsheet, an unanswered approval and an employee looking for the approved swag vendor. Yakubovich keeps returning to the small blockage inside the large system.
That is the lesson worth stealing. Important software does not always announce itself through a futuristic behavior. Sometimes it begins with a familiar task that everyone already understands and nobody enjoys. The opportunity is not simply to automate it. The opportunity is to understand why people avoid it, preserve the judgment that matters, and remove enough friction that the better process becomes the natural one. Yakubovich's three-company arc makes the point patiently: begin with the actual transaction, stay close to the people inside it, and let their repeated resistance show where the product still has work to do.