Fundraising
Series B for Computer Vision Startup
$45M
Amount Raised
12
Investors
SG & US
Markets
6 weeks
Timeline
The Challenge
What Our Client Faced
VisionAI, a Singapore-incorporated computer vision startup with a Delaware subsidiary, was raising a $45M Series B led by a top-tier US venture fund. The round involved 12 investors across Singapore, the US, and Japan, each with different regulatory requirements and investment structures. The company had an existing cap table with three classes of preferred shares from prior rounds, outstanding SAFE instruments from angel investors that needed to convert, and an ESOP pool that required expansion. The lead investor required the company to flip its primary jurisdiction from Singapore to Delaware — a common but complex restructuring that needed to preserve the existing shareholders' rights and avoid triggering tax events under both Singapore and US law. Additionally, the company's core computer vision models were trained on a dataset that included images sourced from a European partner under a license that restricted transfer to third parties — a potential issue for investors conducting IP due diligence.
Our Approach
How We Handled It
We managed the legal execution across all workstreams simultaneously. For the corporate restructuring, we designed a tax-neutral flip structure using a share-for-share exchange that qualified for rollover relief under Singapore tax law and met the requirements for tax-free reorganization under US Internal Revenue Code Section 351. The restructuring preserved all existing shareholder rights, maintained the same economic terms, and was completed within the first two weeks — allowing the investment documentation to proceed on the Delaware entity. For the SAFE conversion, we worked through the mechanics for five outstanding SAFE instruments, each with different valuation caps and discount rates. We calculated the conversion prices, modeled the dilution impact, and ensured that the conversion terms were consistent with the Series B term sheet. Two SAFEs required amendment to correct Singapore-specific issues in the original drafting — a common problem when US templates are used without adaptation for Singapore law. For the ESOP expansion, we designed a new equity incentive plan under Delaware law with global sub-plans for Singapore employees (structured to qualify for tax deferral under Singapore's ESOP tax scheme) and Japanese employees. The pool was expanded from 10% to 15% of fully diluted share capital, with the dilution allocated to the pre-money capitalization as negotiated with the lead investor.
The Outcome
Results & Impact
The Series B closed at $45M on a $180M pre-money valuation — a 4x step-up from the Series A. All 12 investors signed within 6 weeks of term sheet execution. The corporate restructuring was completed without triggering any tax events for existing shareholders. The five SAFE instruments converted cleanly into Series B preferred shares. The new ESOP pool was fully implemented with jurisdiction-specific sub-plans that provided tax-efficient equity compensation for the company's 85 employees across three countries. The European data license issue was resolved by negotiating an amended license that permitted use by the post-restructuring entity, with a specific carve-out for AI model training — a precedent that the licensor has since adopted as standard language.
Key Takeaways
Lessons Learned
- Singapore-to-Delaware flips can be structured tax-neutrally, but require careful coordination between Singapore and US tax counsel.
- SAFE instruments drafted under US templates require Singapore-specific amendments to avoid conversion complications.
- Global ESOP sub-plans can provide tax-efficient equity compensation across jurisdictions but require early planning.
- Data licensing terms should be reviewed for transfer restrictions before any corporate restructuring.
- Managing 12 investors across three jurisdictions requires a structured communication protocol and a centralized document management system.