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Assistant Controller

Job in Chicago, Cook County, Illinois, 60290, USA
Listing for: Lessen
Full Time position
Listed on 2026-01-13
Job specializations:
  • Finance & Banking
    Accounting Manager, Financial Reporting
  • Accounting
    Accounting Manager, Financial Reporting
Salary/Wage Range or Industry Benchmark: 100000 - 125000 USD Yearly USD 100000.00 125000.00 YEAR
Job Description & How to Apply Below

Join to apply for the Assistant Controller role at Lessen
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Lessen is a tech-enabled, end-to-end property service provider that is transforming how commercial and residential real estate services are delivered and managed sen’s technology platform provides data‑driven insights that unlock key growth opportunities for the entire real estate ecosystem—including investors, owners, managers, and service providers. The company leverages a network of over 30,000 vetted, qualified vendors (Lessen Affiliates) serving clients with over 1 million properties and completing more than 3.5 million work orders annually across an expanding range of services.

Lessen, LLC is a venture‑backed, privately held company with offices in Scottsdale and Chicago.

Summary

The Assistant Controller is a hands‑on accounting leader who supports the Controller and Accounting organization by overseeing general ledger activities, driving month‑end close, supporting treasury and cash management, and managing equity compensation accounting and administration. This role partners cross‑functionally with HR, Legal, Operations and external auditors.

Responsibilities General Ledger & Financial Close
  • Oversee day‑to‑day GL operations and ensure the integrity of accounting records.
  • Prepare, review and post recurring and non‑recurring journal entries.
  • Own month‑end and quarter‑end close activities: lead schedules, reconciliations, and variance analyses.
  • Maintain and strengthen internal controls and accounting policies; drive SOX‑ready documentation where applicable.
  • Support preparation of management reporting and ad‑hoc financial analyses for leadership.
Treasury & Cash Management
  • Monitor daily cash balances and support short‑term liquidity planning.
  • Prepare cash flow forecasts and assist with monthly/quarterly cash reporting.
  • Execute and reconcile bank activity, including inter‑company and wire tracking.
  • Support banking relationships, signatory maintenance, and treasury documentation.
Equity Compensation Accounting & Administration
  • Administer equity plans in partnership with HR, Legal, and external equity vendor.
  • Maintain equity ledgers and cap table records; process grants, exercises, cancellations, and required adjustments.
  • Calculate, record and disclose equity‑based compensation (ASC 718) and prepare related journal entries and forecasts.
  • Support 409A, tax reporting, and audit requests; prepare schedules and footnote disclosures for equity awards.
Systems, ERP & Process Improvement
  • Act as Net Suite subject‑matter expert: maintain GL configuration, support module integrity, and manage accounting workflows.
  • Drive system improvements and automation initiatives to increase efficiency and scalability.
  • Own integrations and data integrity between payroll/equity/ERP systems and the GL.
Audit, Tax & Compliance
  • Support external audits and tax provision processes; provide schedules, explanations and reconciliations as requested.
  • Ensure compliance with US GAAP and company accounting policies.
Cross‑Functional Partnership & Ad‑hoc Projects
  • Partner with HR on payroll, benefits and equity administration.
  • Collaborate with Legal on contract accounting implications.
  • Lead and participate in ad‑hoc projects and business process implementations as assigned.
  • Ensure confidentiality of internal and external data.
Role Specific Skills
  • Equity compensation accounting and administration (ASC 718, cap table maintenance).
  • Treasury / cash management and forecasting.
  • Month‑end close ownership and GL oversight.
  • Net Suite (GL and accounting modules) — Advanced; proven experience implementing/configuring accounting workflows.
  • Excel — Advanced (pivot tables, complex formulas, reconciliations).
  • Familiarity with equity administration platforms (preferred: Carta, Share works)
People Management Skills
  • Proficient in all people management processes, including recruitment, performance management and reward.
  • Proficient in building, growing and developing a team; including department structure design and resourcing.
  • Proficient in coaching and developing individual team members to reach their potential.
  • Proficient in engaging a team through communication, processes, personal impact and influence.
Qualifications

Minimum…
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