Rich Smolen, Finance Expert in Plainfield, IL, United States
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Rich Smolen

Verified Expert  in Finance

Finance Expert

Plainfield, IL, United States
Toptal Member Since
October 26, 2018

Rich, an experienced CFO, has led $500 million in fundraising for three private equity-backed companies and helped sell two of the businesses. His engaging style and desire to learn is fueled by meeting people via freelancing. An expert in the financial services, telecommunications, and technology sectors, Rich has partnered with CEOs, investors, and lenders of companies ranging from early-stage startups to entities with $250+ million in revenue.

Career Highlights

Oasis Financial
Director, Corporate Finance
optionsXpress Holdings
Assistant Treasurer
Looking Glass Networks

Education Highlights

Bachelor's Degree
University of Illinois at Urbana-Champaign

Work Experience


2011 - 2017
Oasis Financial
  • Managed the sale of a business to a private equity firm with responsibilities including the selection of an investment bank, reviewing and creating all investor materials, coordinating due diligence responses, presenting in all investor and lender meetings, developing the financial model, evaluating the legal documents, and negotiating the debt facility utilized to finance the acquisition.
  • Oversaw due diligence and the refinancing of acquired debt for an acquisition that expanded the company's product offerings into adjacent space.
  • Led an increase in credit facilities of more than four times to over $100 million, enabling growth in the loan portfolio and revenue that resulted in EBITDA growth of more than 100%.
  • Partnered with operations and marketing teams to create dashboards that provided visibility into acquisition costs, conversion, pricing, margin, and operational performance.
  • Led a revenue-recognition-accounting project, including the development of the financial model reflecting the change and guided auditors and lenders to understand the change.
  • Negotiated decreased interest costs resulting in hundreds of thousands in interest savings, an expansion of the borrowing base availability, and relaxed financial covenants—ultimately increasing the profitability and growth in originations.
  • Navigated multiple junior debt refinancings and lender changes without any business disruptions.
  • Led an initiative to build an internal data analytics team—managing the resources and prioritizing projects to support sales expansion and weekly automated performance reporting.
  • Developed key metrics for the monthly board reporting after a private equity sale to provide visibility into critical operational and financial measures.
Focus areas: Valuation Modeling, Valuation Multiples, Valuation, Growth Capital Raising, Capital Raising, CFO, Investment Memoranda, Budgeting, Due Diligence, Management, Audits, Pricing Strategy, Financial Planning & Analysis (FP&A), Financial Modeling, Investor Presentations, Mergers & Acquisitions (M&A), Bank Debt Raises, Senior Secured Debt, Subordinated Debt, Debt Raises, Private Equity

VP, Finance

2010 - 2011
Telecom Transport Management
  • Raised $7 million in incremental debt financing from equity investors to support new revenue and customer growth.
  • Participated in strategic merger discussions, created acquisition models, and prepared and reviewed due diligence materials.
  • Oversaw the process to obtain equity commitments and worked with financial advisors and investors on facilitating an additional equity raise as well as strategic discussions.
  • Created and reviewed market-level forecasts, internal scenarios, and monthly financial results for quarterly and special board meetings to guide critical discussions.
Focus areas: Budgeting, Investor Presentations, Mergers & Acquisitions (M&A), Due Diligence, Financial Modeling, Debt Raises

Director, Corporate Finance

2008 - 2010
optionsXpress Holdings
  • Developed and modified acquisition models, coordinated the review of due diligence materials, and evaluated all legal documents for two completed acquisitions with a combined purchase price of $30 million.
  • Developed and updated earnings forecast model used to guide equity analysts.
  • Partnered with department heads to create and review annual budget for distribution to the board of directors.
  • Created SEC filings for distribution to public investors, including quarterly earnings, proxy statement, annual report, annual shareholder meeting, and monthly press releases.
  • Maintained primary responsibility for all board materials, monthly management reporting, and quarterly reviews with CEO and department heads.
Focus areas: Internal Financial Reporting, Investor Presentations, Financial Modeling, Budgeting, Mergers & Acquisitions (M&A)

VP, Planning and Analysis

2006 - 2007
Level 3 Communications
  • Created the annual divisional budget, monthly operating and capital expenditure forecast, and long-term strategic planning efforts for an 850-employee organization within Level 3.
  • Prepared the monthly reporting information for senior executives that summarized financial performance and provided measures of key performance indicators to evaluate the organization.
Focus areas: Internal Financial Reporting, Capital Expenditure Planning, Operational Finance, Budgeting, Financial Planning & Analysis (FP&A)

Assistant Treasurer

2000 - 2006
Looking Glass Networks
  • Managed all of the reporting requirements for a $275 million credit facility with seven lenders. Participated in negotiations related to the establishment, amendment, and recapitalization of the facility and managed all borrowings, maturities and interest payments.
  • Established bank accounts and maintained responsibility for daily cash management, vendor payments, and the issuance of letters of credit and surety bonds.
  • Created and revised operating and merger financial models including updating for actual performance, running sensitivities, monitoring compliance with financial covenants, creating short-term cash forecasts to monitor near-term liquidity, and leading synergy discussions.
  • Produced ad hoc financial analyses including segment reporting and budget versus actual comparisons. Created all PowerPoint presentations for board meetings, lender updates, investor presentations and general corporate overviews for senior management.
  • Sold the company to Level 3 Communications for $97 million in 2006.
Focus areas: Capital Raising, Insurance, Corporate, Financial Data, Financial Statements, Financial Planning & Analysis (FP&A), Financial Modeling, Debt Restructuring, Debt Raises, Due Diligence, Corporate Treasury


1999 - 2000
Paradigm Group
  • Evaluated and recommended investment opportunities.
  • Conducted comprehensive due diligence on management, business strategy and industry dynamics on both private and public companies.
  • Monitored the overall portfolio performance and provided a quarterly update to investors.
Focus areas: Discounted Cash Flow (DCF), Valuation, Investor Presentations, Financial Modeling, Due Diligence

Financial Analyst

1998 - 1999
Salomon Smith Barney
  • Prepared pitch books for potential clients including potential M&A targets, debt market overview, valuation metrics and discussion of strategic alternatives.
  • Drafted materials for $1.5 billion public debt offering and road show.
  • Developed financial models for potential M&A transactions.
Focus areas: DCF Valuation, Valuation Analysis, Valuation Multiples, Discounted Cash Flow (DCF), Financial Modeling, Debt Raises, Mergers & Acquisitions (M&A), Comparable Company Analysis, Pitch Books
1993 - 1997

Bachelor's Degree in Finance

University of Illinois at Urbana-Champaign - Urbana-Champaign, IL, USA


Fundraising, Valuation Multiples, Valuation Modeling, Discounted Cash Flow (DCF), Financial Modeling, Financial Planning & Analysis (FP&A), Debt Raises, Budgeting, M&A Modeling, Bank Covenants, Bank Debt Raises, Financial Reporting, Debt, Subordinated Debt, CFO, Pricing, Pricing Strategy, Capital Budgeting, Mergers & Acquisitions (M&A), Private Equity, Senior Secured Debt, Due Diligence, Investment Memoranda, Capital Raising, Growth Capital Raising, Valuation, Internal Financial Reporting, Operational Finance, Capital Expenditure Planning, Corporate Treasury, Debt Restructuring, Comparable Company Analysis, Valuation Analysis, DCF Valuation

Output Software

Microsoft PowerPoint, Microsoft Word, Microsoft Excel

Industry Expertise

Financial Services, Telecommunications, Technology, Insurance

Geographic Expertise

United States

Data & Analysis Software

Financial Data, Intuit QuickBooks, Bloomberg


Unit Economics, Ad-hoc Modeling, Pricing Models, Budget Modeling, Pitch Decks, Investor Reporting, P&C Insurance, FPA, Treasury Management, Key Performance Indicators (KPIs), Investor Presentations, Audits, Management, Financial Statements, Corporate, Pitch Books

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