Senior Controller+ / Director of Finance

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).
Compensation + Benefits
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.
 

About CHARLESGATE

CHARLESGATE is a vertically integrated real estate platform based in Boston. We operate at the intersection of property management, brokerage, new development leasing & sales, and modern marketing, to help owners, residents, and partners drive winning results through disciplined execution, hospitality-led experiences, and systems that scale. We’re building a high-performance team that moves fast and owns outcomes as we expand nationwide. If you’re a strategic executor who wants real responsibility, clear standards, and the chance to challenge conventions in a legacy industry, you’ll fit in here.

Our Mission:
To inspire and empower our clients, our communities, and our team to live better and invest better through comprehensive real estate solutions.

Our Core Values:

MOVE MARKETS & WIN TOGETHER | We're not order takers. We're partners who drive transformative wins through critical thinking and aligned action.

SPEAK HARD TRUTHS | Seek first to understand the perspectives of others.

CHALLENGE CONVENTIONS | Status quo is the enemy of value. We mine the gap between what is and what could be to unlock more value.

OWN IT | Results matter more than effort. Accountability means rising above your circumstances. We commit fully to getting it done right.

PEOPLE > EVERYTHING | Creating better outcomes for the people we serve is our highest calling. Everything we do is delivered with genuine hospitality.

Equal Opportunity Statement

CHARLESGATE is committed to providing equal employment opportunities and complying with all applicable federal, state, and local laws. We strive to maintain a work environment free from harassment, discrimination, or retaliation based on age, race, color, national origin, ancestry, religion, sex, sexual orientation (including transgender status, gender identity or expression), pregnancy (including childbirth, lactation, and related medical conditions), physical or mental disability, genetic information, veteran status, uniformed service member status, or any other protected status.