AI Strategy - Analyst, Associate, or Vice President

Job description

About Hackberry Lane

Hackberry Lane is a vertically integrated student housing owner-operator with 2,265 beds and $330M in real estate assets nationwide, with a strong concentration in the Southeast. We are a small, tight-knit team that is growing rapidly.

The Opportunity

We are looking for a sharp, hands-on Head of AI to drive digital and AI innovation across our real estate investment platform — shaping capabilities that meaningfully influence investment performance, operations, and strategic decision-making. This is a builder's role. You will own AI strategy and implementation across acquisitions, underwriting, asset management, property management, and everything in between, and you will report directly to the firm's executive team.

This is a rare opportunity to build new solutions from the ground up while partnering closely with senior leaders who are actively transforming how technology enables value creation at Hackberry. If you are obsessed with AI and the ways it can make a business faster, smarter, and more efficient, this role was built for you.

What You'll Do:

AI Strategy & Implementation

• Lead digital transformation and AI adoption across the Hackberry platform — data management, digital workflows, and investment processes
• Identify high-impact problems across every function (acquisitions, underwriting, asset management, property management, accounting, marketing, and leasing) and shape product direction for AI-enabled solutions that support commercial outcomes
• Translate strategy into actionable roadmaps, prototype quickly, ship working solutions, and iterate based on real feedback from the field and the office
• Stay ahead of the curve on LLMs, agents, and vertical real estate tooling, and bring the best ideas back to Hackberry

Investments & Underwriting

• Build AI-powered workflows that sharpen deal screening, underwriting, market analysis, and comp work
• Help ownership pressure-test assumptions and pull insights from large data sets — rent rolls, T12s, market data, public records — faster and more reliably than our competition

Operations & Asset Management

• Partner with Market GMs and the asset management team to automate the grunt work — variance analysis, lease audits, vendor management, reporting, resident communications
• Build dashboards, agents, and internal tools that turn scattered data into decisions
• Drive adoption and change management so new tools actually get used and generate sustained impact across the team
• Serve as the go-to internal resource for anyone at Hackberry who wants to work smarter with AI — training, enablement, and day-to-day support

Who You Are

• Obsessed with AI. This is the single most important qualification. You experiment constantly, you follow the space closely, and you instinctively reach for AI to solve problems others still solve by hand
• Experience range is wide open — whether you're a recent college graduate, a self-taught builder, or someone with a few years under your belt at a startup, a fund, or a tech company, we want to hear from you. Hands-on work matters more than credentials or years
• Fluent (or rapidly becoming fluent) in modern AI tools — LLMs, agents, RAG, automation platforms — and have actually built things, not just read about them
• Strong structured problem-solving — you can walk into a messy workflow and figure out where AI earns its keep and where it doesn't
• Comfortable with ambiguity — we don't have a playbook for this role; you will help write it
• Solid Excel skills and genuine curiosity about real estate and finance (or the willingness to learn both fast)
• Strong verbal and written communication skills — comfortable interfacing with ownership, field teams, and vendors alike
• Self-sufficient and resourceful; you move fast and figure things out without needing hand-holding
• Low ego, team-first mentality — we are a small company and everyone pitches in

Compensation & Benefits

• Base salary: TBD, commensurate with experience
• Benefits: Comprehensive health and dental care, generous paid time off, and all travel expenses covered
• Upside: We are a young platform that is scaling rapidly. There is meaningful room to grow here — in responsibility, compensation, and involvement in the business — for someone who delivers

Hackberry Lane is an equal opportunity employer.