Toby Clarence-Smith, Finance Expert in Milan, Metropolitan City of Milan, Italy
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Toby Clarence-Smith

Verified Expert  in Finance

Valuation Expert

Milan, Metropolitan City of Milan, Italy
Toptal Member Since
August 25, 2016

With over a decade of experience across private equity, venture capital, and banking, Toby founded and successfully sold a venture-backed eCommerce company, giving him a unique skill set that combines the financial/investment perspective with tangible operational expertise. His consulting work focuses on helping clients with diligence investment opportunities, as well as companies looking to raise capital and grow their businesses.

Career Highlights

Education Highlights

Master of Business Administration (MBA)
The Wharton School of the University of Pennsylvania
Bachelor of Science
London School of Economics and Political Science

Certification Highlights

GMAT: 760
Graduate Management Admission Council

Case Studies

Work Experience

Founder & Managing Partner

2019 - PRESENT
CS Investimenti
  • Focused efforts on deal origination, assessment, and due diligence to find one single SME to acquire and then actively manage.
  • Built detailed cashflow models for multiple investment opportunities to assess intrinsic cashflow generation through both up and down cycles.
  • Negotiated with business owners regarding the structure of acquisitions including earn-out mechanisms, seller note issuance, and layered financing structures.
  • Industry assessment and sector-focused macro predictions to choose specific verticals in which to focus the search.
Focus areas: Valuation, Financing, Small & Medium-sized Enterprises (SME), Mergers & Acquisitions (M&A), Due Diligence, Private Equity

Venture Capital Investor

2016 - 2017
Mountain Nazca
  • Acted as an entrepreneur-in-residence, assisting portfolio companies with operational issues and growth-related challenges.
  • Participated as a member of the investment team. I aided in the origination of new dealflow and assessment of investment opportunities.
  • Helped develop thesis-based investment strategies around global macro trends and sectors. Areas of focus; cryptocurrency, fintech, and online commerce and marketplaces.
  • Assisted with fundraising efforts for the new fund, helping put together the pitch and other fundraising-related documentation.
  • Spearheaded the development of a new investment strategy akin to "company building" but where the original focus was on the entrepreneur rather than the idea itself.
Focus areas: Venture Capital, Startups, Growth Capital Raising, Fundraising, Mergers & Acquisitions (M&A), Technology

Co-Founder | CEO

2013 - 2016
  • Launched one of the most respected and successful startups in the country, receiving multiple rounds of investment from the top venture capital funds in the country.
  • Built an extremely loyal customer base with incredibly high net promoter scores.
  • Oversaw an expansion from a three-person team to a 50+ person team.
  • Managed the entire development of the technology platform across web, mobile web, and native mobile applications.
  • Opened our first retail store to build out a full-service omni-channel retailer.
  • Built all the operating and financial models underlying three rounds of capital raise with Venture Capital funds as well as business plan approval at the board level.
Focus areas: Financial Reporting, Venture Capital, Fundraising, eCommerce, Business Intelligence (BI), Digital Strategy, Marketing, Technology, Retail & Wholesale

Founder Intern

2012 - 2012
  • Led the opening of a warehouse from which we were processing over 1,000 orders a day.
  • Led and managed a UX/UI review with clients and delivered several recommendations to the product team regarding improvements to the platform.
  • Modeled and proposed an optimized customer service team structure.
  • Managed an offline marketing strategy (below the line) for a project.
  • Offered a full-time founder position by the end of my time at Linio, but decided to turn it down to launch my own company.
Focus areas: Operations Analytics, eCommerce, Customer Service, Marketing, Retail & Wholesale

Investment Associate

2010 - 2010
Bridges Ventures
  • Helped prepare the investment memorandum for an investment in a chain of gyms.
  • Oversaw incoming business plan proposals and appraisals.
  • Built a detailed store rollout financial and execution model for one of the portfolio companies.
  • Helped develop the social impact assessment framework.
Focus areas: Entrepreneurship, Social, Venture Capital

Investment Banking Assistant Vice President

2007 - 2010
Barclays Capital
  • Prepared investment memorandums and credit memos for highly leveraged transactions.
  • Managed portfolios and assessments of loan book portfolios.
  • Created a pitch book for corporate finance and M&A deals.
  • Did extensive valuation and merger analysis.
  • Managed client responsibilities with some of the world's largest private equity funds.
  • Promoted six months early (a highly unusual occurrence).
Focus areas: Valuation, Financial Modeling, Mergers & Acquisitions (M&A), Corporate Finance, Debt Structuring, Leveraged Finance
2010 - 2012

Master of Business Administration (MBA) in Finance

The Wharton School of the University of Pennsylvania - Philadelphia, PA, USA

2004 - 2007

Bachelor of Science in Economic History (Economics)

London School of Economics and Political Science - London, England


Endeavor Entrepreneur



GMAT: 760

Graduate Management Admission Council


Financial Modeling, Valuation, Fundraising, Equity Research, Capital Structure Analysis, Market Research, Corporate Finance, Three-statement Modeling, Financial Planning & Analysis (FP&A), Private Equity, Mergers & Acquisitions (M&A), Business Intelligence (BI), Financial Reporting, Debt Structuring, Growth Capital Raising, Due Diligence, Data Analysis

Output Software

Microsoft PowerPoint, Microsoft Excel, Prezi

Industry Expertise

Venture Capital, Financial Services, Retail & Wholesale, Technology

Geographic Expertise

Europe, Mexico, United Kingdom, United States, Italy

Data & Analysis Software

Capital IQ, Bloomberg


Business Development, Communication, Email Marketing, eCommerce, Online Marketing, Investment Committee Advisory, Business Planning, Marketing Strategy, Digital Marketing Strategy, Interim CFO, Small Business Consultants, Search Fund Expert, Business Plan Consulting, Business Modeling, Business Strategy, Project Management, Operational Efficiency Improvement, Warehouse Operations, Marketing, Digital Strategy, Customer Service, Operations Analytics, Social, Entrepreneurship, Leveraged Finance, Startups, Small & Medium-sized Enterprises (SME), Financing, DCF Modeling, Customer Research, Business Models

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