Strategy & AI Associate

Job Summary

The Strategy & AI Associate is both an analyst and a builder. The role exists to build and operate AI-enabled workflows that multiply throughput across the Chief Strategy Officer’s organization — Corporate Development, Content, Strategic Partnerships, and Government Affairs — while still delivering core transaction work, financial modeling, diligence, and executive materials. The Associate partners closely with executive leadership to generate insights, accelerate deal execution, and develop reusable analytical and operational systems that scale across the broader strategy team.

• Develop and maintain financial models for acquisitions, divestitures, joint ventures, and organic growth initiatives, including valuation analyses across DCF, public comparables, precedent transactions, and LBO frameworks.
• Support live transactions end-to-end: target evaluation, due diligence, management discussions, investment memoranda, and integration planning.
• Conduct market, competitive, and strategic research; prepare investment memos, board materials, and executive presentations that translate analysis into clear recommendations.

• Design, build, and maintain reusable AI-enabled workflows for diligence (data room ingestion, target profiling, CIM analysis), modeling (template generation, scenario and sensitivity runs), and document production (memos, decks, board materials).
• Productize prompts, agents, and automations so that other CSO team members can use them independently, without engineering support.
• Identify, pilot, and evaluate new AI tools and capabilities; maintain an informed working view of what is worth adopting.

• Partner with the Content team on programmer contract review, audit support, and lineup analysis; partner with Strategic Partnerships on joint venture modeling and partner diligence.
• Support Government Affairs and Corporate Governance with regulatory tracking, policy analysis, and related research as needed.
• Perform other duties as required or assigned.

• Bachelor’s degree in Finance, Accounting, Economics, or a related field.
• 2–5 years of experience in investment banking, private equity, strategy consulting, or corporate development, with demonstrated use of AI tools to increase output in prior roles.
• Strong financial modeling and valuation experience.
• Hands‑on experience using Claude, ChatGPT, or comparable large language models in a work setting.
• Working ability to write Python for automation and API integration — scripting and connecting systems, not full software engineering.
• Experience designing multi‑step AI workflows, agents, or automations.
• Excellent written and verbal communication skills, with experience presenting to senior stakeholders.
• Proven ability to manage multiple work streams in a fast‑paced, ambiguity‑tolerant environment.
• Proficiency in Microsoft Excel and PowerPoint (table stakes; the role will frequently use AI to accelerate work in both).

• Comprehensive Healthcare/Dental/Vision Plans
• 401K Retirement Plan with Company Match
• Paid Vacation, Sick Time, and Additional Holidays (including your Birthday!)
• Paid Volunteer Time
• Paid Parental Leave
• Hotwire Service Discounts – for employees who live on a property serviced by Hotwire. Discounted service offerings are provided for high‑speed internet, video service, phone, and security service
• Employee Referral Bonuses
• Exclusive Entertainment Discounts/Perks

Hotwire provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws.