Carole Crawford, CFA, Finance Expert in New York, NY, United States
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Carole Crawford, CFA

Verified Expert  in Finance

Finance Expert

New York, NY, United States
Toptal Member Since
August 14, 2017

At Morgan Stanley, Carole advised eight founders through exits totaling over $750 million and then founded her own practice to manage venture investments for family offices. A former tech CFO, she freelances to leverage her experience with capital raises, strategic pivots, and turnarounds. She enjoys helping innovators and entrepreneurs achieve financial success across many verticals, and has recently focused her efforts on fintech.

Career Highlights

CKI/ESP Software

Education Highlights

Bachelor's Degree
University of Michigan
Certified Investment Management Analyst
The Wharton School Executive Education

Certification Highlights

Case Studies

Work Experience

Founder | Managing Partner

2007 - PRESENT
fincap360, LLC
  • Designed and managed venture-direct and co-investment initiatives for family offices, often serving as the interim CFO for clients' portfolio companies.
  • Served as the interim CFO for a sports, media, and entertainment agency—leading a $52 million recapitalization and five acquisitions totaling $15 million.
  • Provided fundraising support and a go-to-market strategy for a seed capital fund in Silicon Valley who was looking to raise $50 million.
  • Served as the interim CFO for an edtech company, raising $8 million and rebuilding financial infrastructure for an incoming CEO, including KPIs, budgets, cash management, board reporting and capital budgeting for growth initiatives.
  • Worked as a fractional CFO for a rapidly growing business intelligence and alternative data firm focused on eCommerce platforms.
  • Developed a niche as a fintech expert, covering 750 startups for family office clients; sub-verticals include blockchain and distributed ledger technology, alternative data, AI-driven analysis methods, bitcoin/cryptocurrency, marketplace lending, capital markets, investing and crowdfunding.
  • Built financial models for internal projections and fundraising efforts for 12 companies.
Focus areas: Debt Restructuring, Mergers & Acquisitions (M&A), Pitch Decks, Financial Planning & Analysis (FP&A), Communication, Fundraising, Board Presentations, Family Office, Interim CFO

Senior Consultant, VP and Branch Head of Alternative Investments

1995 - 2005
Morgan Stanley
  • Significantly increased clients' post-sale assets on exits ranging from $20 to $350 million through pre-liquidity deal structure scenario analyses, and optimizing for post-liquidity wealth, tax and investment plans.
  • Added value to the firm's investment banking efforts, advising on and managing assets of executives pre- and post-IPO.
  • Outperformed relative benchmarks with smooth risk-adjusted returns, building custom portfolios with short-term tactical positioning using mean-variance optimization for strategic asset allocation.
  • Led the internal business development for alternative investments and separately managed accounts for Chicago and Washington, DC offices, ranking number one in the region for both offices.
  • Performed due diligence and analysis of over 75 professional investment managers (long-only, managed futures, private equity, and hedge funds).
Focus areas: Exit Planning, Due Diligence, Investment Monitoring, Comparable Company Analysis, Business Development, Investment Decision-making


1989 - 1992
CKI/ESP Software
  • Led a successful turnaround of an almost-defunct software development company which was subsequently listed on Washington Technology Fast 50.
  • Built a financial model for internal projections, instrumental in positioning the company for an eventual sale of $100 million in today's dollars.
  • Rebuilt, restructured, and automated the entire accounting and financial reporting process.
  • Collected $3 million in outstanding government receivables—leading to positive cash flow.
  • Charted a path to profitability by analyzing contract gross profit margins, developing pricing strategies, cutting costs, and identifying additional strategic opportunities.
Focus areas: Debtor & Creditor Management, Contract Negotiation, Turnaround, Cash Flow Management, Financial Planning & Analysis (FP&A)
1981 - 2015

Bachelor's Degree in Economics

University of Michigan - Ann Arbor, MI, USA

2000 - 2001

Certified Investment Management Analyst in Investment Management

The Wharton School Executive Education - Philadelphia, PA, USA


Chartered Financial Analyst (CFA)

CFA Institute


CFO, Fundraising, Three-statement Modeling, Startup Funding, Cash Flow, Corporate Finance, Financial Planning & Analysis (FP&A), Mergers & Acquisitions (M&A), Debt Restructuring, Investment Decision-making, Investment Monitoring, Debtor & Creditor Management, Recapitalization, Cash Flow Modeling, Asset-based Finance, Comparable Company Analysis, Due Diligence

Industry Expertise

Education Technology (Edtech), Financial Services, Technology, Venture Capital, Banking & Finance

Geographic Expertise

United States

Output Software

Microsoft Excel, Microsoft Word, Microsoft PowerPoint


Finance Product Manager, Family Office, Fintech, Family Office Management, Cash Flow Management, Business Consulting, Interim CFO, Fractional CFO, Finance Director, Managerial Finance, Virtual CFO, Consulting, Business Planning, Cash Flow Consultant, Fintech Consultant, Business Plan Consulting, SaaS, Software as a Service (SaaS), Accounting Software, Financial Analysis, Communication, Board Presentations, Business Development, Exit Planning, Turnaround, Contract Negotiation, Media, Pitch Decks, Turnaround Management, eCommerce, Communication Strategy, Investments, Exit Strategy, Investor Relations

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