Senior Controller+ / Director of Finance
Charlesgate Realty Group, LLC, Boston, Massachusetts, us, 02298
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 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 Base salary range: $180,000-$240,000 (based on qualifications & experience) Plus short and long-term performance bonus opportunities and industry-leading benefits package.
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.
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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 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 Base salary range: $180,000-$240,000 (based on qualifications & experience) Plus short and long-term performance bonus opportunities and industry-leading benefits package.
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.
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