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Carole is available for hire
Hire CaroleCarole Crawford, CFA
Verified Expert in Finance
Finance Expert
Location
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.
FundraisingVenture CapitalFinancial Planning & Analysis (FP&A)Interim CFOFractional CFOVirtual CFOStartup Funding ConsultantCash Flow ConsultantFintech ConsultantBusiness Plan ConsultingExit StrategyComparable Company AnalysisBusiness DevelopmentMergers & Acquisitions (M&A)Financial PlanningFinancial Management ConsultingFinance ManagementCash Management ConsultingStart-up CFOsFinance DirectorPMI ConsultingPart-time CFOFinancial StrategiesOutsourced CFO
Career Highlights
Founder | Managing Partner
fincap360, LLC
CFO
CKI/ESP Software
Education Highlights
Bachelor's Degree
University of Michigan
Certified Investment Management Analyst
The Wharton School Executive Education
Certification Highlights
Chartered Financial Analyst (CFA)
CFA Institute
Case Studies
Industry Expertise
Software Expertise
Other Expertise
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
CFO
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)
Education
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
Certifications
AUGUST 2013 - PRESENT
Chartered Financial Analyst (CFA)
CFA Institute
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