Alpha Square Group
ASG is a New York–headquartered, SEC-registered investment firm with approximately $1.6 billion in assets under management. The firm invests in global innovation across public and private markets, applying institutional-grade rigor, disciplined underwriting, and proprietary data intelligence to identify and invest in category-defining companies.
The Opportunity
We’re looking for a Vice President, Investment, to join our investment team as a senior deal leader. This is a high-autonomy role for an investor who can own opportunities end-to-end — from sourcing and diligence through structuring and portfolio engagement — across the full investment spectrum and a range of sectors.
As a VP, you’ll serve as a primary deal lead: evaluating opportunities, building and validating financial models, structuring investments, and preparing clear, conviction-driven recommendations for senior leadership and the Investment Committee. Beyond individual deals, you’ll help shape firmwide investment strategy through thematic research, contribute to our standards for diligence and analytical rigor, and play an active role in developing junior team members.
This role suits an investor who thrives on ownership, holds a high analytical bar, and wants their judgment to matter — not just on their own deals, but in how the firm thinks and operates.
What You’ll Do
Deal Sourcing & Pipeline Development
- Source high-quality investment opportunities through deep market engagement and active network development
- Conduct rigorous first-pass evaluations spanning financial, competitive, and strategic dimensions
- Build and maintain strong relationships with founders, operators, syndicate partners, and co-investors
- Maintain disciplined pipeline documentation, rationale, and tracking
Due Diligence & Investment Execution
- Lead full diligence processes — risk assessment, financial model validation, and strategic fit — ahead of IC review
- Build financial models directly, and guide and challenge models built by junior team members
- Structure deals and lead term sheet negotiations in coordination with legal counsel
- Present investment opportunities to the IC with clear thesis, risk articulation, and valuation logic
- Own diligence decisions at the VP level, including founder engagement, expert calls, and competitive analysis
Portfolio Management & Value Creation
- Lead engagement with portfolio companies, supporting growth, capital strategy, and operational initiatives
- Monitor KPIs, financial performance, and strategic milestones, escalating concerns proactively
- Assess follow-on opportunities with clear, risk-adjusted recommendations
- Partner with founders on fundraising preparation, hiring, product/GTM strategy, and financial planning
Market Research & Thematic Development
- Lead thematic investment theses that shape firmwide sourcing direction
- Identify emerging market opportunities, competitive shifts, and sector inflections across stages
- Collaborate with senior leadership to refine investment frameworks
- Deliver structured, actionable research consistently across the team
External Engagement & Firm Development
- Represent ASG at conferences, industry events, and ecosystem forums to strengthen deal flow
- Support LP and co-investor conversations
- Contribute to internal process improvements, knowledge sharing, and talent development
What We’re Looking For
- 7–10+ years of investing experience at a VC, growth equity, private equity, or family office, with a track record of leading deals end-to-end
- Demonstrated ability to build and defend independent investment conviction
- Strong familiarity with the AI sector — where ASG concentrates much of its investment activity — including an understanding of the technology landscape, key players, and emerging market dynamics
- Strong financial modeling, valuation, and deal structuring capabilities
- Experience across multiple stages and/or sectors, with the adaptability to evaluate opportunities wherever they arise
- Excellent judgment, communication, and the ability to present persuasively to an Investment Committee
- A collaborative orientation — someone who raises the standard of the team around them
- Bachelor’s degree required; MBA, CFA, or equivalent a plus
ASG is an equal opportunity employer. We are committed to building a diverse team and welcome applicants from all backgrounds.
