Carole Crawford, CFA
Verified Expert in Management Consulting
Management Consulting Expert
New York, NY, United States
Toptal member since December 11, 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
Education Highlights
Certification Highlights
Case Studies
$52 Million Recapitalization Analysis
Industry Expertise
- Advertising & Marketing
- Education
- Finance
- Banking
- Investment Banking
- Venture Capital & Private Equity
- Media & Internet
- eCommerce
Software Expertise
- Microsoft Excel
Other Expertise
- Accounting Software
- CFO
- Family Office
- Fintech
- Fundraising
- Software as a Service (SaaS)
Work Experience
Founder | Managing Partner
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.
Senior Consultant, VP and Branch Head of Alternative Investments
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).
CFO
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.
Education
Bachelor's Degree in Economics
University of Michigan - Ann Arbor, MI, USA
Certified Investment Management Analyst in Investment Management
The Wharton School Executive Education - Philadelphia, PA, USA
Certifications
Chartered Financial Analyst (CFA)
CFA Institute
Skills
Finance
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
Other
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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