Senior Controller+ / Director of Finance

Charlesgate•Boston, MA

12h•$180,000 - $240,000•Hybrid

About The Position

We're hiring for a Senior Controller+ / Director of Finance who has the talent, experience, and desire to lead CHARLESGATE to scale nationally across multiple operating subsidiaries. If you’re a whip-smart accounting/finance leader who wants real responsibility, real challenges to solve, and a real fast-track path to CFO… keep reading. Why work at CHARLESGATE? CHARLESGATE is a multi-entity real estate platform (HoldCo + operating subsidiaries + investment/SPV entities). We’re scaling quickly (5x Inc 5000 Winner!) and we expect finance to be an operating weapon - not a stogy back-office function. We need a leader to own the finance engine behind it. We’re growing into more entities, more revenue types, and more complexity. The business will not slow down so finance can “catch up.” The mission for this role is to build and run a lean Finance Operating System across the companies for clean close, cash predictability, intercompany discipline, and decision-grade reporting at speed.

Requirements

7 - 12+ years in accounting/finance; 3+ years leading teams
Proven multi-entity ownership: intercompany, eliminations, consolidation
Built/owned operating cadence: close + cash + forecast + KPI pack
Strong cash leadership experience: AR discipline + collections accountability
Ability to translate contribution margin + drivers into clear operator recommendations/actions
Systems and automations fluency: multi-entity accounting software + advanced spreadsheets/BI + AI-enabled workflows
Understanding of business operations + drivers: a model builder, not just a numbers jockey
Comfortable in ambiguity; know how to create structure without slowing the business

Nice To Haves

Industry adjacency: multifamily ownership/management, brokerage, agency/pro services, fund management, private equity
Allocation model design + implementation experience
Incentive comp administration (STIPs/LTIPs)
Fund/SPV/partnership accounting (capital calls, distributions, capital accounts)
CPA/audit background; M&A diligence/integration; forecast/BI models

Responsibilities

Accounting + Close Management (multi-entity)
Own close calendar, task checklist, and signoffs
Maintain balance sheet integrity and reconciliations
Standardize accounting policies and coding rules across entities
Cash + Treasury + Working Capital
Own weekly 13-week cash forecast and cash decision cadence
Lead AR aging, collections accountability, and billing discipline
Maintain AP runway and payment approval thresholds
Revenue Operations for Finance (Contract → Invoice → Collect → Recognize)
Ensure invoicing matches contract terms (retainers, projects, reimbursables, commissions)
Define and enforce revenue reporting and recognition practices by revenue type
Install process to reduce write-offs, billing lag, and margin leakage
Intercompany, Consolidation, and Allocations
Build intercompany agreements, billing, and eliminations
Improve shared services cost allocation model (simple, transparent drivers)
Produce consolidated financials with clear OpCo performance visibility
Administer STIP and LTI incentive comp plans
Management Reporting + Forecasting Cadence
Publish monthly KPI pack with margin bridges and key drivers
Lead monthly forecast roll-forward and variance analysis
Partner with OpCo leaders to build revenue and business models and make decisions from numbers (not just report)
Asset Management Reporting + LP/Fund Finance
Own capital accounts, calls, and distributions; maintain waterfall accuracy
Standardize quarterly lender + LP reporting packages and cadence
Controls + Governance + ERP
Implement Delegation of Authority (DoA), vendor onboarding, and spend controls
Build audit-ready documentation (without creating bureaucracy)
Maintain policy library and process SOPs
Own ERP/Accounting/Expense management software implementation