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.

What you'll own:

A) 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

B) 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

C) 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

D) 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

E) 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)

F) Asset Management Reporting + LP/Fund Finance

Own capital accounts, calls, and distributions; maintain waterfall accuracy

Standardize quarterly lender + LP reporting packages and cadence

G) 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

Outcomes we expect:

Close performance: Sustained T+10 close across entities with documented reconciliations/amortizations/signoffs

Balance sheet reliability: Reconciliations current; limited post-close adjustments

Cash forecast discipline: Weekly 13-week forecast delivered on time; meeting accuracy requirements

Working capital improvement: AR aging improves vs baseline with 50% reduced >60/90 day balances

Intercompany + consolidation governance system: Monthly intercompany billing/eliminations run cleanly; consolidated numbers trusted; allocation model is updated and implemented cleanly

Allocation model in production: Allocation Model v2 implemented

Decision-grade reporting: Strong, trusted KPI pack used in business reviews

Forecast cadence and driver models installed: Monthly rolling forecast with defined owners; forecast error improvements

Investor Relations: Institutional-grade asset reporting packages and on-time distribution workflows

STIP + LTIP Implementation: Upgraded compensation plans implemented and managed

AI enabled finance ops: Embed practical AI workflows to speed process and produce AI-ready finance data

Fast-Track Growth Opportunity

Opportunity to earn fast-track pathway to CFO. Upon demonstrated achievement of defined outcomes - including sustained close and cash discipline, trusted profitability and forecasting systems, mature intercompany and allocation frameworks, and executive-level decision support - the role may be eligible to be elevated to Chief Financial Officer, with expanded scope and compensation.

Required qualifications (must-haves)

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

Preferred qualifications (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

This role is NOT for you if...

You want a role that's mostly monthly close + compliance

You avoid cash forecasting, AR, or collections accountability

You need perfect clarity before acting

Your default move is adding approvals/process that slows operators

You don't have a growth mindset or are scared of change (growth = change, the messy middle is real)

You can't translate margin + driver math into simple recommendations

You avoid intercompany/allocations because they're "political"

You're uncomfortable with high standards and direct accountability

You haven't built robust forecast models

You're not fluent in multi-entity systems

You don't believe in implementing automation/AI workflows

A clear warning...

This is not a "join and coast" role. Reporting to the CEO, this is a demanding role with high standards, only a fit for someone who can prove they know how to do it and who gets excited by the pressure to dive in to execute at pace. It's a high-trust, high-reward environment for A+ talent on the way up.

We hire on proof, not stories or promises. Be ready to share detailed work history and work samples in the interview process (non-confidential/redacted as necessary).

Location

Boston-based candidates are preferred; highly qualified remote candidates will be considered, with an expectation of regular on-site presence to support leadership cadence and cross-functional collaboration.

CHARLESGATE

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