Director Of Development in Chicago, Illinois at Fairlawn

Fairlawn is a vertically integrated investment, development, and management platform. Based in Chicago and Champaign, Illinois, we have a more than 10-year track record across two distinct verticals: student housing and middle market multifamily, where we deploy both value-add acquisition strategies and ground-up development. With a portfolio of approximately 6,000 units and approximately $1 billion in assets under management, Fairlawn has established a strong presence across Illinois, Indianapolis, and Kentucky. We are actively expanding into additional Midwest markets.

The Opportunity

The Director of Development will report directly to the CIO and be charged with building Fairlawn’s ground-up development pipeline capable of supporting at least $100 million in annual starts, focused primarily on Midwest student housing markets, with select multifamily opportunities as the platform grows. This means sourcing the opportunities yourself, evaluating and underwriting the ones that fit, and driving them through entitlements, capitalization, and execution. This is a full-cycle role, and the pipeline you build is the one you run. You will inherit a small team and have the ability to grow it as the pipeline demands.

Our principals are hands-on and committed to supporting this role across day-to-day execution, capital markets, and everything in between. The firm has a demonstrated track record of capitalizing deals, an established and growing network of capital partners, and the appetite to scale those relationships alongside the development pipeline. This role owns the development function from sourcing to delivery, with the full support of Fairlawn’s principals and organizational platform.

Fairlawn is expanding its development platform into new markets, and we are looking for the person who wants to drive that expansion. If you are energized by an entrepreneurial environment, embrace AI and modern ways of working, and want to grow alongside a firm that rewards ownership and initiative, you will find a firm that is built for people like you.

What You Will Do

Pipeline Development & Market Presence

• Build and maintain a credible, well-screened development pipeline across target markets, sourcing and advancing ground-up opportunities aligned with Fairlawn’s strategic markets and return thresholds, with the ability to influence market selection as the platform evolves.
• Establish deep, sustained presence in target Midwest student housing markets, building the relationships that make Fairlawn a trusted market participant over time. Fairlawn wins through trust and presence, not data alone.
• Leverage AI-powered tools to accelerate market screening, site evaluation, and pipeline tracking, and help establish Fairlawn’s technology and AI toolkit for the development function.

Underwriting & Feasibility

• Own the development underwriting process end-to-end, including market analysis, zoning review, density assumptions, construction cost assumptions, and hard and soft cost budgets.
• Evaluate opportunities against Fairlawn’s capitalization capacity and LP expectations before advancing them internally, protecting organizational bandwidth and ensuring the pipeline stays focused on executable deals.
• Drive the underwriting process with the fluency to produce models yourself, the judgment to leverage your team effectively, and the instinct to use technology to stay lean and fast.
• Set and maintain the pace of underwriting on active opportunities. Speed matters: turning a development model in 24 to 48 hours on a live deal is a baseline expectation, not a stretch goal.
• Prepare and present development opportunities for Investment Committee approval, clearly articulating the business plan, risks, capital requirements, and capitalization strategy.
• Ensure ongoing alignment between underwriting assumptions, design development, and final construction documents as projects evolve.
• Partner with Fairlawn’s CIO and CFO to structure and capitalize deals, including active participation in sourcing debt and equity. This role co-owns the capitalization process, not just the development thesis.

Entitlements & Pre-Development

• Own zoning, entitlements, variances, PUDs, and municipal approvals.
• Manage external consultants including architects, engineers, and attorneys.
• Take ownership of development risks across every phase, including political, entitlement, cost, schedule, and execution, proactively identifying issues and driving them to resolution before they become problems.

Execution & Delivery

• Own the full project lifecycle from site identification through delivery, with accountability for outcomes at every phase.
• Own pre-development and construction budgets, schedules, and scopes, and deliver on time and on budget, every time. Fairlawn has built its reputation on execution, one delivery at a time, and protecting and extending that reputation rests entirely with this role; not the team, not the General Contractor, not third parties.
• Lead General Contractor selection and Construction Contract negotiation, bringing the discipline and market knowledge to structure construction contracts that protect Fairlawn’s budget and schedule from the start.
• Partner with Property Management and Asset Management to ensure operationally efficient designs and smooth transitions into operations.

Team & Operations

• Assess, develop, and build the development team to match the pipeline’s growth trajectory, including evaluating existing team members and presenting a clear business case to leadership before adding headcount.
• Lead Fairlawn’s thinking on how AI can reshape the development function, actively identifying opportunities to improve efficiency, rethink workflows, and build a team and process that reflects how the best development shops will operate going forward.
• Develop and refine Fairlawn’s student housing development playbook, codifying site selection criteria, design standards, cost benchmarks, and execution processes into a repeatable institutional framework.
• Standardize development processes, templates, and reporting to improve predictability and scalability across the pipeline.
• Set and deliver on quarterly goals, maintain performance scorecards, and provide clear, concise reporting to leadership on milestones, issues, and pipeline status.
• Participate on our Senior Leadership Team, collaborating with leaders across all functional areas to drive the company’s strategic and operational priorities forward
• Embody Fairlawn’s core values: Be Kind, Own It, Be Flexible, and Always Improve. Build a team that does the same.

Who You Are

We are looking for a principal-side developer with strong fundamentals, deep underwriting fluency, and the drive to build something from the ground up. What matters most is what you have done and how you think. Specifically:

• A track record of principal-side development experience, ideally 8 or more years, with direct ownership of deals from concept through completion. We are open to exceptional candidates who have done more with less time.
• A record of leading multiple projects with full accountability for budget, schedule, and execution.
• Proven ability to build ground-up development models from scratch, including land basis, hard and soft costs, financing assumptions, and return metrics, at the speed active deals demand.
• Experience in multifamily, student housing, or adjacent residential development types. Genuine interest in Midwest student housing markets is essential. You do not need to have worked in the sector, but you need to understand or be eager to learn what drives demand near a university campus and how to evaluate a site.
• Deep familiarity with entitlements and municipal approval processes, ideally in Midwest markets.
• A history of building and sustaining relationships in markets over time, with municipalities, landowners, universities, and the development community.
• Experience managing and building small teams, with the judgment to assess what you inherit and grow what the role requires.
• Fluency with, or genuine curiosity about, AI tools for market analysis, underwriting, reporting, and process management.
• Clear, direct communicator with internal teams, consultants, municipalities, the Investment Committee, and capital partners.
• High ownership mindset: you close the loop, flag issues early, and do not wait to be asked.
• Experience with EOS is a plus. More important is the willingness to operate within a structured, accountable system and embrace it fully.

Why Fairlawn

• The opportunity to build and lead Fairlawn’s development strategy from the ground up. A firm mandate, backed by engaged principals, with upside that reflects our shared commitment to what we build together.
• Direct access to Fairlawn’s Investment Committee, where your projects get approved and your voice shapes what gets built.
• The freedom to build the team, the process, and the pipeline your way, within a firm that runs with discipline and accountability.
• A firm with the balance sheet, track record, and capital relationships to turn the right opportunities into buildings you will be proud to have built.
• Chicago or Champaign base, with regular presence in the markets where Fairlawn is building its reputation.
• Promote participation on every deal you originate and advance.
• Base salary of $160,000 to $200,000 depending on experience
• Additional compensation includes promote participation in every deal you originate and advance, plus a performance bonus tied to development fees
• Full benefits package including medical, dental, vision, 401(k) with match, paid time off, and wellness days.

We are seeking candidates who demonstrate a strong alignment with the requirements listed above. While meeting all qualifications is preferred, we understand that exceptional candidates may bring comparable experience and skills to the table including prior experience at Fairlawn. We value diversity of thought and experience, and we are committed to considering all applicants [internal and external] and to identifying and selecting the most qualified applicant for the role.

Depending on the role requirements, offers of employment may be contingent upon one or more of the following: employment history verification, criminal background check, motor vehicle record check, education verification, or credit check.

Our company uses the Entrepreneurial Operating System (EOS) to run and help grow our business – the tools from EOS contribute to finding the right people and putting them in the right roles, effectively solving issues as they arise, and building a culture of accountability. In short, it gets everyone on the same page and working toward the same goals. If you have an ownership mindset and take pride in all the details, joining our team may be perfect for you!

We are an equal opportunity employer, and all qualified applicants will receive consideration for employment without regard to race, color, religion, national origin or ancestry, sex, age, physical or mental disability, veteran or military status, genetic information, sexual orientation, marital status, or any other characteristic protected by law.