Schedule a call →

<p>Interview fractional leaders this week for <strong>free</strong>!</p>

Asset Management

AI-Powered Investment Platform for Modern Wealth

Sales

Finance

Operations

Engineering

Real Estate

Entrepreneurship

Business Development

Information Technology

Media and Communication

United States

San Diego, CA

California, United States

San Diego Metropolitan Area

Milwaukee, WI

Greater Milwaukee

Salt Lake City, UT

Utah, United States

Wisconsin, United States

Salt Lake City Metropolitan Area

DiversyFund

DiversyFund is a fintech and private-market investing company on a mission to make wealth-building accessible. Backed by a proprietary technology platform — including a custom CRM, AI-driven communications and agents, and a growing suite of data and automation systems — we are scaling how everyday investors access institutional-quality opportunities. We have raised over $1B and serve tens of thousands of investors.

## The Opportunity

We are looking for a Fractional Chief Information Officer to lead the operational and strategic side of our technology function. The CIO is a senior executive responsible for our internal technology strategy, digital transformation, and technology-driven business operations. You will bridge business objectives and technology — overseeing systems, data security, and workflow efficiency — and turn our technology investments into dependable, scalable outcomes.

You will partner closely with a highly capable Chief Technology Officer who leads architecture and product engineering. Your focus is complementary: taking what is built and making it run reliably in production, driving adoption, building and structuring the technology team, and giving leadership clear visibility into delivery. This is a builder-of-systems-and-teams role, not an individual-contributor coding role.

## What You'll Own

**Technology delivery & program management**

- Own the technology roadmap, backlog, and delivery cadence — ensuring every workstream has a clear owner, estimate, committed date, and visible status.
- Sequence priorities, surface trade-offs, and keep leadership informed with accurate, low-effort reporting.
- Bring order and predictability to day-to-day operations across our tools and systems.

**Operationalizing technology (build to production)**

- Own the path from "built" to "live and adopted" — deployment, configuration, testing, monitoring, and end-user enablement.
- Establish release discipline: environment alignment, versioning of live workflows, pre-launch testing, and post-deploy verification.
- Drive adoption of platform capabilities (CRM campaigns, AI agents, reporting) by the teams they serve, and stand up observability so issues surface early.

**Team building & organizational design**

- Design the technology organization: define the roles needed, and recruit, onboard, and manage technical and operational staff and vendors.
- Build depth and resilience into the team so critical systems are well-supported and scalable.

**Business–technology bridge**

- Translate business objectives — capital raising, investor experience, marketing, and new product initiatives — into prioritized technology outcomes.
- Tie technology decisions to measurable business results and communicate them to leadership in business terms.

**Security, governance & risk**

- Own information security posture: access control, secrets management, endpoint auditing, and data-integrity controls.
- Establish IT governance appropriate to a regulated financial-services environment, in coordination with legal and compliance.
- Own business continuity, backups, and incident response for critical systems.

**Workflow efficiency & internal systems**

- Rationalize the internal application and automation stack, eliminate broken hand-offs, and reduce operational drag.
- Ensure investor-facing service needs surfaced by our systems are routed to the right operational owners quickly.

## Your First 90 Days

1. Days 1–30: Establish a single source of truth for technology status, owners, and target dates, and a lightweight weekly leadership readout.
2. Days 31–60: Get our highest-value built systems fully operational and adopted, proving a repeatable build-to-production pipeline.
3. Days 61–90: Publish the technology org design and hiring plan, a security and governance baseline, and a prioritized roadmap tied to business goals.

## What You Bring

- Senior technology leadership experience (CIO, VP Engineering, Head of Technology Operations, or similar) scaling systems and teams.
- A proven track record of operationalizing technology: release management, deployment discipline, QA, observability, and driving adoption.
- Strong program and project management skills, and experience with organizational design, hiring, and vendor management.
- Security and governance fluency; comfort operating in a regulated financial-services context.
- A business-minded approach — translating technology into commercial outcomes and communicating clearly with executive leadership.
- A collaborative, low-ego style, with the ability to partner closely with a talented technical team and earn trust quickly.

## Bonus points

- Fintech, proptech, or financial-services experience.
- Familiarity with modern web, data, and AI/automation stacks.
- Experience in a founder-led, fast-moving growth environment.

## Engagement

This is a fractional, part-time engagement designed to scale with the needs of the business, with the potential to expand over time. Compensation is competitive and commensurate with experience.

Co-Founder & Chief Investment Officer | Real Estate Private Equity

Alan Lewis

DiversyFund, Inc.

Co-Founder & Chief Investment Officer

Fractional Chief Information Officer

Information Security

Chief Information Officer

Program Management

Early Team

Ready to Elevate Your Business? The Craig Cecilio Brand delivers the strategic leadership and innovative thinking required to break through barriers and achieve ambitious goals. Follow us to gain insights and discover how we can help you reach the next level.

CraigCecilio.com

$1 Billion+ Raised. 40,000+ Investors. Now teaching you how. Building the future, one relentless move at a time. 

**About DiversyFund**

DiversyFund is a fintech and private-market investing company on a mission to make wealth-building accessible. Backed by a proprietary technology platform — including a custom CRM, AI-driven communications and agents, and a growing suite of data and automation systems — we are scaling how everyday investors access institutional-quality opportunities. We have raised over $1B and serve tens of thousands of investors.

**The Opportunity**

We are looking for a Fractional Chief Information Officer to lead the operational and strategic side of our technology function. The CIO is a senior executive responsible for our internal technology strategy, digital transformation, and technology-driven business operations. You will bridge business objectives and technology — overseeing systems, data security, and workflow efficiency — and turn our technology investments into dependable, scalable outcomes.

You will partner closely with a highly capable Chief Technology Officer who leads architecture and product engineering. Your focus is complementary: taking what is built and making it run reliably in production, driving adoption, building and structuring the technology team, and giving leadership clear visibility into delivery. This is a builder-of-systems-and-teams role, not an individual-contributor coding role.

**What You’ll Own**

Technology delivery & program management

- Own the technology roadmap, backlog, and delivery cadence — ensuring every workstream has a clear owner, estimate, committed date, and visible status.
- Sequence priorities, surface trade-offs, and keep leadership informed with accurate, low-effort reporting.
- Bring order and predictability to day-to-day operations across our tools and systems.

**Operationalizing technology (build to production)**

- Own the path from “built” to “live and adopted” — deployment, configuration, testing, monitoring, and end-user enablement.
- Establish release discipline: environment alignment, versioning of live workflows, pre-launch testing, and post-deploy verification.
- Drive adoption of platform capabilities (CRM campaigns, AI agents, reporting) by the teams they serve, and stand up observability so issues surface early.

**Team building & organizational design**

- Design the technology organization: define the roles needed, and recruit, onboard, and manage technical and operational staff and vendors.
- Build depth and resilience into the team so critical systems are well-supported and scalable.

**Business–technology bridge**

- Translate business objectives — capital raising, investor experience, marketing, and new product initiatives — into prioritized technology outcomes.
- Tie technology decisions to measurable business results and communicate them to leadership in business terms.

**Security, governance & risk**

- Own information security posture: access control, secrets management, endpoint auditing, and data-integrity controls.
- Establish IT governance appropriate to a regulated financial-services environment, in coordination with legal and compliance.
- Own business continuity, backups, and incident response for critical systems.

**Workflow efficiency & internal systems**

- Rationalize the internal application and automation stack, eliminate broken hand-offs, and reduce operational drag.
- Ensure investor-facing service needs surfaced by our systems are routed to the right operational owners quickly.

**Your First 90 Days**

1. Days 1–30: Establish a single source of truth for technology status, owners, and target dates, and a lightweight weekly leadership readout.
2. Days 31–60: Get our highest-value built systems fully operational and adopted, proving a repeatable build-to-production pipeline.
3. Days 61–90: Publish the technology org design and hiring plan, a security and governance baseline, and a prioritized roadmap tied to business goals.

**What You Bring**

- Senior technology leadership experience (CIO, VP Engineering, Head of Technology Operations, or similar) scaling systems and teams.
- A proven track record of operationalizing technology: release management, deployment discipline, QA, observability, and driving adoption.
- Strong program and project management skills, and experience with organizational design, hiring, and vendor management.
- Security and governance fluency; comfort operating in a regulated financial-services context.
- A business-minded approach — translating technology into commercial outcomes and communicating clearly with executive leadership.
- A collaborative, low-ego style, with the ability to partner closely with a talented technical team and earn trust quickly.

**Bonus points**

- Fintech, proptech, or financial-services experience.
- Familiarity with modern web, data, and AI/automation stacks.
- Experience in a founder-led, fast-moving growth environment.

**Engagement**

This is a fractional, part-time engagement designed to scale with the needs of the business, with the potential to expand over time. Compensation is competitive and commensurate with experience.

San Diego

Seeking a Fractional Chief Information Officer to lead technology strategy and operations at DiversyFund, focusing on digital transformation and technology-driven business operations.

DiversyFund is a fintech-enabled real estate investment company that makes institutional-quality real estate investing accessible to everyday investors. We manage multiple private real estate investment funds, special purpose entities (SPVs), investor capital accounts, and the regulatory reporting that surrounds them — all under one roof.

We are doing something unusual in our category: rather than stitching together off-the-shelf platforms, we are building our own CRM and finance back-end in-house, powered by AI. Our accounting system today is QuickBooks, and on top of it we are designing automated, AI-driven workflows for reconciliations, investor reporting, dashboards, and audit preparation. We believe a modern investment manager should run on software it controls — and finance is at the center of that vision.

## About the Role

This is not a traditional Controller role. We are hiring a Fractional Controller to act as the financial quarterback of the organization — someone who owns the integrity of our books today while helping architect the automated finance ecosystem we are building over the next 24 months.

You will combine deep controller and fund-accounting expertise with genuine systems thinking, process-automation experience, and an AI-adoption mindset. The ideal person is equally comfortable reviewing a journal entry, modeling a fund waterfall, walking an auditor through a workpaper, and designing an AI-assisted reconciliation workflow. You see automation as a force multiplier, not a threat, and you are excited to help shape the finance tooling we build in-house.

This is a fractional, contract engagement reporting directly to the CEO. It is ideal for a seasoned Controller who wants meaningful ownership and the chance to help build something, without a full-time commitment.

## What You'll Do

### Fund Accounting & Financial Oversight

- Own and oversee fund accounting, parent-company accounting, and SPV accounting across the organization.
- Manage monthly, quarterly, and year-end closes, ensuring general-ledger integrity and a well-designed chart of accounts.
- Prepare and review financial statements — balance sheets, income statements, and cash flow statements.
- Ensure accuracy of investor capital accounts, property-level reporting, and consolidated reporting across funds and the parent company.

### Cap Table & Investor Accounting

- Manage and oversee the parent-company cap table and individual fund cap tables.
- Maintain investor ownership records and subscription tracking; administer capital-call accounting.
- Calculate distributions, preferred returns, and waterfalls accurately and on schedule.
- Produce shareholder and investor reporting, and reconcile investor accounts.
- Apply a working command of corporate cap tables, equity issuance, SAFEs, preferred equity, and fund ownership structures.

### Financial Planning & Analysis

- Build and maintain company and department budgets, cash-flow forecasts, hiring and revenue models, capital-planning models, and fund-level projections.
- Translate the numbers into decisions through executive dashboards, variance analyses, scenario models, and board reporting packages.

### Audit, Tax & Regulatory Reporting

- Serve as primary coordinator for annual, fund, and parent-company audits, keeping everything audit-ready.
- Coordinate tax preparation and planning support, including K-1 and 1099 preparation.
- Oversee financial reporting tied to SEC requirements, fund financial statements, semi-annual reporting, investor reporting packages, and regulatory disclosures.
- Manage relationships with external auditors, tax advisors, fund administrators, legal counsel, and compliance consultants.

### AP, AR & Treasury

- Oversee accounts payable and receivable, vendor payments, and invoice approvals.
- Manage cash, treasury functions, banking relationships, and payroll coordination.
- Implement internal controls that ensure accuracy and scale with the business.

### Technology, Automation & AI-Driven Finance

This role is deliberately technology-forward. Our current accounting system is QuickBooks, and we are building our own CRM and finance back-end in-house, powered by AI. You will help architect and improve this stack by:

- Identifying manual processes and recommending automation opportunities across the finance function.
- Partnering with leadership and the AI team to deploy AI agents that automate reconciliations and reduce manual reporting work.
- Helping design AI-assisted workflows, real-time executive dashboards, and audit-ready documentation.
- Improving forecasting accuracy and reporting speed, and reducing spreadsheet dependency over time.
- Documenting finance operating procedures that scale as we grow.

### Strategic Finance Support

- Provide executive-level support to the CEO, CFO (if applicable), Investment Committee, and leadership team.
- Assist with fund launches, M&A and new-product analysis, capital-raising support, and investor due diligence.
- Serve as a trusted thought partner in strategic, data-driven decision-making.

## What You'll Bring

### Required Qualifications

- 10+ years of progressive accounting experience.
- 5+ years as a Controller, Assistant Controller, or equivalent.
- Hands-on real estate accounting experience.
- Fund accounting experience (private funds, SPVs, or similar structures).
- Audit experience and deep GAAP expertise.
- Strong proficiency in QuickBooks, Excel, and financial modeling.

### Preferred Qualifications

- CPA designation and/or a Big 4 background.
- Private equity and/or fund-administration experience.
- Fintech experience.
- Exposure to SQL, BI and data-warehouse tools, and investor reporting systems.
- Hands-on experience with AI and automation workflows (e.g., GPT- or Claude-based workflows).

*Because we build our own systems, day-to-day tooling is QuickBooks plus what we develop in-house — experience with other ERP or fund-accounting platforms is a plus but not required.*

## How You Operate

Detail-oriented, highly accountable, and process-driven — a systems thinker who is tech-forward, entrepreneurial, independent, low-ego, and solution-oriented. You move fluidly between reviewing journal entries, designing financial processes, speaking with auditors, building models, advising executives, and implementing AI-driven automation. You are genuinely curious about emerging AI tools and excited to put them to work.

## What Success Looks Like in Your First 12 Months

- Financial accuracy — clean audits, accurate monthly closes, and zero material financial errors.
- Operational efficiency — faster close cycles, reduced manual work, and improved reporting speed.
- Technology adoption — automation initiatives launched, AI-enabled workflows implemented, and reduced spreadsheet dependency.
- Executive visibility — real-time dashboards, improved forecasting accuracy, and stronger decision support.
- Compliance — on-time audits, tax coordination, and regulatory reporting.

## Engagement Details

**Title:** Fractional Controller

**Engagement type:** Fractional / Contract

**Commitment:** 20–30 hours per week (30–40 during audit, tax, and year-end close periods)

**Reports to:** Chief Executive Officer

**Location:** Remote (US) preferred, with occasional in-person executive meetings

**Compensation:** Market-based fractional executive compensation, depending on experience and qualifications

Fractional Controller

GAAP

Financial Reporting

Controller

Fund Accounting

**About DiversyFund**

DiversyFund is a fintech-enabled real estate investment company that makes institutional-quality real estate investing accessible to everyday investors. We manage multiple private real estate investment funds, special purpose entities (SPVs), investor capital accounts, and the regulatory reporting that surrounds them — all under one roof.

We are doing something unusual in our category: rather than stitching together off-the-shelf platforms, we are building our own CRM and finance back-end in-house, powered by AI. Our accounting system today is QuickBooks, and on top of it we are designing automated, AI-driven workflows for reconciliations, investor reporting, dashboards, and audit preparation. We believe a modern investment manager should run on software it controls — and finance is at the center of that vision.

**About the Role**

This is not a traditional Controller role. We are hiring a Fractional Controller to act as the financial quarterback of the organization — someone who owns the integrity of our books today while helping architect the automated finance ecosystem we are building over the next 24 months.

You will combine deep controller and fund-accounting expertise with genuine systems thinking, process-automation experience, and an AI-adoption mindset. The ideal person is equally comfortable reviewing a journal entry, modeling a fund waterfall, walking an auditor through a workpaper, and designing an AI-assisted reconciliation workflow. You see automation as a force multiplier, not a threat, and you are excited to help shape the finance tooling we build in-house.

This is a fractional, contract engagement reporting directly to the CEO. It is ideal for a seasoned Controller who wants meaningful ownership and the chance to help build something, without a full-time commitment.

**What You'll Do**

**Fund Accounting & Financial Oversight**

- Own and oversee fund accounting, parent-company accounting, and SPV accounting across the organization.
- Manage monthly, quarterly, and year-end closes, ensuring general-ledger integrity and a well-designed chart of accounts.
- Prepare and review financial statements — balance sheets, income statements, and cash flow statements.
- Ensure accuracy of investor capital accounts, property-level reporting, and consolidated reporting across funds and the parent company.

**Cap Table & Investor Accounting**

- Manage and oversee the parent-company cap table and individual fund cap tables.
- Maintain investor ownership records and subscription tracking; administer capital-call accounting.
- Calculate distributions, preferred returns, and waterfalls accurately and on schedule.
- Produce shareholder and investor reporting, and reconcile investor accounts.
- Apply a working command of corporate cap tables, equity issuance, SAFEs, preferred equity, and fund ownership structures.

**Financial Planning & Analysis**

- Build and maintain company and department budgets, cash-flow forecasts, hiring and revenue models, capital-planning models, and fund-level projections.
- Translate the numbers into decisions through executive dashboards, variance analyses, scenario models, and board reporting packages.
- Audit, Tax & Regulatory Reporting
- Serve as primary coordinator for annual, fund, and parent-company audits, keeping everything audit-ready.
- Coordinate tax preparation and planning support, including K-1 and 1099 preparation.
- Oversee financial reporting tied to SEC requirements, fund financial statements, semi-annual reporting, investor reporting packages, and regulatory disclosures.
- Manage relationships with external auditors, tax advisors, fund administrators, legal counsel, and compliance consultants.

**AP, AR & Treasury**

• Oversee accounts payable and receivable, vendor payments, and invoice approvals.

• Manage cash, treasury functions, banking relationships, and payroll coordination.

• Implement internal controls that ensure accuracy and scale with the business.

**Technology, Automation & AI-Driven Finance**

This role is deliberately technology-forward. Our current accounting system is QuickBooks, and we are building our own CRM and finance back-end in-house, powered by AI. You will help architect and improve this stack by:

- Identifying manual processes and recommending automation opportunities across the finance function.
- Partnering with leadership and the AI team to deploy AI agents that automate reconciliations and reduce manual reporting work.
- Helping design AI-assisted workflows, real-time executive dashboards, and audit-ready documentation.
- Improving forecasting accuracy and reporting speed, and reducing spreadsheet dependency over time.
- Documenting finance operating procedures that scale as we grow.



**Strategic Finance Support**

- Provide executive-level support to the CEO, CFO (if applicable), Investment Committee, and leadership team.
- Assist with fund launches, M&A and new-product analysis, capital-raising support, and investor due diligence.
- Serve as a trusted thought partner in strategic, data-driven decision-making.

**What You'll Bring**

**Required Qualifications**

- 10+ years of progressive accounting experience.
- 5+ years as a Controller, Assistant Controller, or equivalent.
- Hands-on real estate accounting experience.
- Fund accounting experience (private funds, SPVs, or similar structures).
- Audit experience and deep GAAP expertise.
- Strong proficiency in QuickBooks, Excel, and financial modeling.

**Preferred Qualification**
s

• CPA designation and/or a Big 4 background.

• Private equity and/or fund-administration experience.

• Fintech experience.

• Exposure to SQL, BI and data-warehouse tools, and investor reporting systems.

• Hands-on experience with AI and automation workflows (e.g., GPT- or Claude-based workflows).

*Because we build our own systems, day-to-day tooling is QuickBooks plus what we develop in-house — experience with other ERP or fund-accounting platforms is a plus but not required.*

**How You Operate**

Detail-oriented, highly accountable, and process-driven — a systems thinker who is tech-forward, entrepreneurial, independent, low-ego, and solution-oriented. You move fluidly between reviewing journal entries, designing financial processes, speaking with auditors, building models, advising executives, and implementing AI-driven automation. You are genuinely curious about emerging AI tools and excited to put them to work.

**What Success Looks Like in Your First 12 Months**

- Financial accuracy — clean audits, accurate monthly closes, and zero material financial errors.
- Operational efficiency — faster close cycles, reduced manual work, and improved reporting speed.
- Technology adoption — automation initiatives launched, AI-enabled workflows implemented, and reduced spreadsheet dependency.
- Executive visibility — real-time dashboards, improved forecasting accuracy, and stronger decision support.
- Compliance — on-time audits, tax coordination, and regulatory reporting.

**Engagement Details**

**Title**
Fractional Controller

**Engagement type**
: Fractional / Contract

**Commitment**
: 20–30 hours per week (30–40 during audit, tax, and year-end close periods)

**Reports to:**
Chief Executive Officer

**Location**
: Remote (US) preferred, with occasional in-person executive meetings

**Compensation**
: Market-based fractional executive compensation, depending on experience and qualifications

The role is for a Fractional Controller at DiversyFund, a fintech-enabled real estate investment company. The position involves overseeing fund accounting, financial planning, and automation initiatives, with a focus on AI-driven finance solutions. It requires 20-30 hours per week, with potential increases during peak periods.

DiversyFund

Growth signals

Headcount change

Team composition

By function

By region

Inside DiversyFund

Categories

Markets

Jobs

Past roles

About this page