General Counsel & Head of Legal Operations (AI-First)

TL;DR

General Counsel & Head of Legal Operations (AI-First): Architect an AI-augmented legal and tax function enabling acquisition of 5+ SaaS companies per year with an accent on automation, due diligence, and structural efficiency. Focus on leading M&A execution, strategic tax structuring, global compliance, and debt facility management using LLMs and AI tools.

Location: 100% remote, work from wherever you like

Company

Delaware-incorporated, remote-first serial acquirer of SaaS companies across North America and Europe with a portfolio spanning 6+ jurisdictions, $100M debt facility, and 400-person global team.

What you will do

• Lead legal lifecycle of ~5 acquisitions per year, own SPAs, manage local counsel in Europe/NA, and drive deals to close.
• Model tax-efficient deal structures (Asset vs. Share) and maintain global transfer pricing framework using AI.
• Manage $100M debt facility, including drawdowns, covenant compliance, and lender relations.
• Oversee compliance for 400-person workforce (FTEs, contractors, EOR) across Germany, Austria, France, Finland, Canada, and US.
• Scale Stock Appreciation Rights (SARs) program globally.
• Build AI-driven tech stack for due diligence, entity management, CLM, and tax research.

Requirements

• 6–10 years experience (JD/LLM required), from top-tier Private Equity or M&A practice.
• AI-native: prompt-engineer workflows, build no-code legal stack.
• Tax-literate generalist: understand international tax geometry, use AI for research, know when to involve specialists.
• Operational mindset: prioritize deal velocity, quantify risk in dollars.

Nice to have

• Experience with OECD/Pillar Two and European tax changes.

Culture & Benefits

• Ultimate flexibility: 100% remote, work from anywhere, whenever.
• High-trust team with autonomy, minimal bureaucracy, efficient momentum.
• Small friendly team that helps each other, has fun, and shares knowledge.
• Flexible time off to recharge.
• Significant participation in SAR program.
• Network of entrepreneurial SaaS professionals.