The Big Shift - Episode 4 - Eugenio Ferrante

From Survival to Growth — How to Turn Around a Company That Nearly Ran Out of Cash

"We're growing faster than we've ever been able to grow — with much less resources."

Eugenio Ferrante is CEO of OSOME, an AI-enabled corporate services platform that's supported over 40,000 global startups & small and medium-sized businesses. In his career he has built, survived, and scaled businesses across consulting, co-living, and AI-powered software. After four years at Bain & Company and two software company stints, he founded Casa Mia — a co-living operator for young professional expats — the same day COVID hit Singapore. He built it to 500 rooms, turned the forced pause of lockdown into a product-building sprint that made the business more efficient than any competitor at the same scale, and sold it to one of Asia's largest co-living operators. 

He then stepped into Osome as it was approaching the edge of running out of cash. What he found when he arrived at Osome: multiple rounds of layoffs, depleted morale, senior talent gone, no clear direction, and an R&D team that had shrunk from over 120 people to 35. 

The strategic shift Eugenio made was both simple and direct: stop trying to serve everyone. Osome had been spreading resources across every business incorporated in Singapore. He narrowed the focus to two or three customer segments — tech startups and freelancers — where the data already showed stronger retention and higher satisfaction. Everything else followed. With half the marketing budget of pre-2023, the company started growing faster than it ever had.

The second shift was technological — but it had been waiting years to happen. Osome's founders had always intended to automate the trivial, repeatable work in accounting. What they hadn't been able to do was execute that vision with the technology available at the time. When Gen AI arrived, the groundwork was already laid: the accounting process had been broken into small sub-processes, which meant AI could be applied immediately at the task level. By 2026, everything related to bookkeeping, document processing, bank reconciliation, and first-draft reporting was fully automated. Accountants now focus entirely on advisory work — the conversations and decisions that actually require human judgment.

The conversation with host Moritz Kaffsack goes deep into the operational and cultural mechanics of the turnaround. How Eugenio managed the tension between exhausted long-serving employees and energetic new hires who kept proposing things that "had already been tried." How he rebuilt company-wide OKRs — previously siloed in the product team — into a live operating system tied directly to a four-year strategy. How he used open Slack channels to maintain transparency while pushing teams to make decisions faster rather than cycling through long discussions. And what it felt like to watch the first month of real growth become a quarter, and a quarter become a trend.

What you'll take from this episode:

• How to make strategic focus the primary tool of a turnaround — and why saying no to some of your customers can be the fastest path to growth

• What it takes to rebuild culture and direction in a team that has survived multiple rounds of layoffs

• How to manage the dynamic between battle-scarred veterans and fresh-energy new hires — and why you need both

• Why AI finally delivered on a vision that technology couldn't support for years — and what that means for any business that tried automation too early

• When fractional and independent operators create real leverage — and when they don't