AI-Powered Investment Associate: Portfolio & Growth

Headway Inc.; United States; Hybrid; USD 90,000 - 140,000; Full time

Benefits offered by this job

Two week-long paid corporate holidays

20 vacation days

Medical insurance

Personal development plan

Office amenities and wellness

Ukraine-focused generosity programs

Job summary

Headway Inc is seeking an Investment Associate to join the CEO Office, working closely with leadership to analyze performance, identify opportunities, and prepare insights that guide strategic portfolio decisions. You will help automate processes, build AI-driven tools, and collaborate with Finance, GMs and other teams to drive scalable growth.

You will contribute to portfolio management, M&A screening, and the development of clear, data-backed recommendations.

Qualifications

• 2+ years of experience in finance or strategy.
• Experience with financial modelling and business analysis.
• AI-native builder: built an agent, automation, dashboard or tool used by others.
• Take ownership and initiative to turn ambiguous requests into action plans.
• Think critically and communicate clearly with senior stakeholders.
• Fluent in Ukrainian and advanced English.
• Experience with CRM or data platforms (Attio, etc.) is a plus.

Responsibilities

• Portfolio monitoring and analysis; track performance and support capital allocation memos.
• Business development and M&A: build a pipeline of opportunities and evaluate targets.
• Organize internal boards; prepare materials and track follow-ups; automate processes.
• Develop AI automations; manage automation backlog and recurring workflows.
• Maintain data rooms and connect information across tools and workflows.
• Contribute to analytical projects like goal cascading and performance management.

Skills

Financial modelling

Business analysis

AI-native builder

Ownership and initiative

Critical thinking

Strategic execution

Ukrainian language

AI automation

Tools

SQL

Python

Amplitude

Tableau

Attio CRM

Job description

Headway Inc is seeking an Investment Associate to join the CEO Office, working closely with leadership to analyze performance, identify opportunities, and prepare insights that guide strategic portfolio decisions. You will help automate processes, build AI-driven tools, and collaborate with Finance, GMs and other teams to drive scalable growth.

You will contribute to portfolio management, M&A screening, and the development of clear, data-backed recommendations.