Investment Associate

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

At Headway Inc, we believe that sustainable growth comes from knowing where to invest, understanding what drives business performance and acting on the right opportunities. We're looking for an Investment Associate to work closely with our leadership team, bring analytical rigor to key business decisions and help us make the most of opportunities across our portfolio.

You'll work closely with the CEO Office, business GMs and Finance, analyzing business performance, evaluating new opportunities and preparing insights that inform strategic decisions. Alongside this, you'll improve the processes and tools behind this work, using automation and AI to make them more efficient and scalable.

About Headway Inc

Headway Inc is a global tech company building products that help people grow. Our apps have reached 170M+ downloads worldwide, and TIME ranked Headway Inc #4 among the World’s Top EdTech Companies.

Our achievements start with our people and the values we share. At Headway Inc, we believe in building strong teams around our SELECT values.

You'll join the CEO Office, a team working across our businesses on initiatives that shape the company's growth — from portfolio management and M&A to business development, investor relations and company-wide projects. This gives you exposure to different business models, strategic priorities and the people driving them.

Why join us?

• A view across the business. Get exposure to different products, business models and growth strategies, and understand how a portfolio of businesses operates.

• Room to build. Some of our tools and processes already exist, but there's plenty to rethink. You'll have the autonomy to improve what works, rebuild what doesn't and automate the rest.

• A broad scope early on. Work across portfolio management, BD and M&A, take ownership of varied projects and develop your own approaches with fast feedback.

What you'll do

• Portfolio monitoring and analysis: Track business performance across our portfolio, maintain portfolio reporting and the business leaderboard, and support capital allocation memos and bets tracking with Finance.

• Business development and M&A: Build a systematic pipeline of potential opportunities, assess inbound targets and contribute to M&A screening and evaluation.

• Internal Boards: Organize board meetings, prepare materials, document decisions and track follow-ups. Improve and automate the board preparation process.

• AI automation and process improvement: Build individual and shared AI automations, maintain the automation backlog and streamline recurring workflows across the CEO Office and other teams.

• Data and process management: Maintain relevant data room sections, document recurring processes and connect information across tools and workflows.

• Company-wide initiatives: Contribute to analytical projects such as goal cascading and performance management.

You'll report to Oleksandr Yaroshenko, Chief of Staff, and work closely with the core team, GMs of our businesses and Finance.

What success looks like

• Leadership has reliable, up-to-date insights into business performance and uses them to inform portfolio and investment decisions.

• Internal boards run smoothly, with clear materials, documented decisions and follow-ups tracked through to completion. Preparation requires significantly less manual effort.

• Our CRM and BD pipeline provide a structured, up-to-date view of potential opportunities and their progress.

• AI automations deliver measurable time savings and reduce repetitive manual work across the CEO Office and other teams.

• Recurring processes are documented, streamlined and can run consistently without depending on one person's involvement.

You'd be a great fit if you

• Have 2+ years of experience in finance or strategy, for example in investment banking, PE/VC, Big4 Deals, strategy consulting or corporate development at a tech company.

• Have hands-on experience with financial modelling and business analysis, including P&L, unit economics and preparing materials for senior leadership.

• Are an AI-native builder: you've built an agent, automation, dashboard or tool that others actually use, and can explain the problem it solves.

• Take ownership and initiative: turn ambiguous requests into action plans, manage multiple stakeholders and deadlines, flag risks early and bring recommendations.

• Think critically and communicate with candor: challenge existing approaches, explain your reasoning and feel comfortable disagreeing with senior stakeholders.

• Enjoy combining strategic analysis with hands-on execution, adapt to changing priorities and handle confidential information with discretion.

• Are fluent in Ukrainian, have advanced English and align with our SELECT values.

It would be a plus if you also have:

• Entrepreneurial experience: a startup, side project or initiative you launched and grew with few resources.

• Experience with consumer subscription or mobile apps, including CAC, LTV, ROAS and retention.

• Exposure to M&A, due diligence, fundraising or investor relations, or experience setting up a CRM such as Attio.

• SQL or Python, or tools such as Amplitude or Tableau.

• Experience with performance management or OKR frameworks.

• CFA progress, case championship wins or sports achievements.

What we offer

• Two week-long paid corporate holidays each year and 20 vacation days.

• Medical insurance, full sick leave compensation and access to a corporate doctor.

• A personal development plan, professional communities and a knowledge base.

• Compensation for English-language learning, external training and courses.

• An office with a reliable shelter, generators, satellite internet, and other amenities.

• Sports activities, including running, yoga, boxing and more.

• Supporting initiatives that help Ukraine. Find out more here.

We've created a Talent Guide to help you navigate our hiring process with clarity and confidence — and get the most out of each stage. Take a look here.