Full-Time
Real Estate Asset Manager
Skydeck Capital
1-10 employees
Direct investments in lower-middle market assets
No salary listed
Chicago, IL, USA
In Person
Travel and non-business-hour commitments are required.
Bachelor's
 Real Estate (2) |
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- Five to eight years of real estate asset management experience.
- A Bachelor's Degree in real estate, business, finance, or accounting is a plus.
- Strong interpersonal skills and the ability to collaborate with others.
- Ability to manage several projects simultaneously.
- Strong organizational, time-management, and prioritization skills.
- Attention to detail, proactive self-starter behavior, and results-oriented execution.
- Excellent financial modeling skills and strong proficiency in Excel, Word, and PowerPoint.
- Travel and non-business-hour commitments are required.
- Oversee an existing portfolio of real property and development projects on a day-to-day basis.
- Assist in sourcing, evaluating, and closing new real estate investment opportunities and in the disposition of real property.
- Direct and coordinate asset management, ongoing operations, and administration of multiple multifamily, industrial, and office properties.
- Manage relationships with joint venture partners and track performance, capital inflows and outflows, and major decision rights.
- Review periodic financials and forecast distributions or potential capital injections across multiple properties, markets, and product types.
- Evaluate performance against business plans by reviewing budget-to-actual analyses, leases, occupancy, revenue, expenses, and capital expenditures.
- Work with external joint venture partners to drive asset and project performance and anticipate issues that may affect performance.
- Review and approve preliminary project business plans, capital projections, and annual budgets.
- Conduct routine site visits and update calls with operators.
- Participate in due diligence for acquisitions, dispositions, and recapitalizations.
- Source and evaluate new opportunities.
- Establish and evaluate leasing strategies and monitor property management teams for the outright-owned portfolio.
- Develop, measure, and refine investment strategies based on market conditions to maximize value and performance.
- Lead budget development for each property.
- Trigger distributions, approve financials, and maintain compliance with debt agreements, legal documents, and regulations.
- Read, document, interpret, and negotiate leases, loans, and operating or joint venture agreements.
- Represent the office in discussions with architects, contractors, engineers, leasing and sales brokers, and local community stakeholders.
- Oversee trade-contractor performance with development partners through routine site visits and meetings.
- Prepare monthly reports for the assigned portfolio.
- Manage real estate tax appeals and payment deadlines with the accounting team and other responsible parties.
- Lead financial closings for new projects and refinancing of portfolio assets.
- Provide analytical support through market research, review of property operating statements, cash-flow modeling, property valuation, and preparation of investment memoranda.
- Evaluate and lead property debt financing as needed.
- Manage residential and personal real estate projects as needed, including construction management, acquisition, and disposition.
- Experience in one or two additional property types, such as residential and industrial.
- Experience with Argus DCF/AE, Yardi, or AppFolio.
Skydeck Capital makes direct investments across three areas: lower-middle market companies, real estate, and venture capital opportunities. Its product is direct equity or debt investments in small- to mid-sized companies, property acquisitions or development projects, and participation in venture rounds. In practice, Skydeck identifies and evaluates potential opportunities, negotiates deal terms, and uses an active ownership approach to monitor and support portfolio companies and assets until exit. The firm differentiates itself by focusing on a three-asset-class strategy (operating companies, real estate, and venture investments) and taking a hands-on, value-add approach to help portfolio companies grow and real estate assets improve. The goal is to generate returns for investors through capital appreciation and income while managing risk across these three areas.
Company Size
1-10
Company Stage
N/A
Total Funding
$3.9M
Headquarters
Chicago, Illinois
Founded
2013
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Simplify's Take
What believers are saying
- On August 11, 2026, Skydeck showcased industrial, multifamily, and office assets.
- Its venture portfolio still includes FourKites, Aurora Solar, and Amira Learning.
- Skydeck added Allos AI and AAllos in January 2026, signaling fresh venture activity.
What critics are saying
- Skydeck publishes no recent fundraising, leaving the Polsky family exposed to concentration risk.
- Private-equity targets $3-7 million EBITDA companies, a narrow deal funnel that stalls deployment.
- Any weakness in Invenergy wealth threatens every check, making the firm existentially fragile.
What makes Skydeck Capital unique
- Michael Polsky family-office capital backs direct equity, real estate, and venture deals from Chicago.
- Skydeck writes 5-10 million checks and demands major decision rights in deals.
- The firm spans private equity, seed venture, and long-term real estate investments.
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