Chris Sigala, Finance Expert in Los Angeles, CA, United States
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Chris Sigala

Verified Expert  in Finance

Finance Expert

Location
Los Angeles, CA, United States
Toptal Member Since
January 15, 2020

Chris has been active in the technology space (and B2B software in particular) for the last decade in differing roles and functions—from M&A and capital formation advisory to private equity investing to executive-level operations. He has extensive experience in working with founders/executives in early-to-late stage capital raising, M&A, integrations and strategic planning, business development, and go-to-market strategy and operations.

Financial Planning & Analysis (FP&A)Mergers & Acquisitions (M&A)FundraisingPrivate EquityEquity ResearchValuationFinancial Modeling

Career Highlights

Chief of Staff
Crownpeak
Associate
K1 Investment Management

Education Highlights

Bachelor's Degree
University of Southern California

Case Studies

Work Experience

Chief of Staff

2018 - PRESENT
Crownpeak
  • Served as the key member of the company’s executive leadership team, responsible for developing long-term business plans and identifying and executing key strategic initiatives.
  • Drove critical rhythm-of-the-business meetings such as business QBRs, weekly demand council, executive leadership discussions, and board meetings.
  • Served as a cross-functional partner between sales, marketing, customer success, and product functions to align the organization on long-term strategic direction, go-to-market positioning, and sales funnel management, utilizing a data-driven approach of ongoing monitoring, and analyzing and optimizing of key business metrics.
  • Partnered with the CFO and finance function to review and develop financial forecasts, examine underlying assumptions, and manage financing and investor partner relationships.
  • Held the interim CFO role from January 2018 – April 2018.
  • Led employee communications strategy and execution, including meeting agenda and scripts for all-hands meetings as well as partnering with the CEO to effectively communicate the vision and strategy of the management team.
  • Led two rounds of financing with prominent middle-market direct lenders—PNC and Monroe Capital—raising more than $75 million in capital (growth financing).
  • Served as an internal project leader working with management consulting firm Simon-Kucher Partners to develop and implement the company’s pricing and monetization strategy (pricing/monetization project).
  • Led the project team responsible for formulating in-depth market and competitive assessment, culminating in the long-term strategic vision for the company (go-to-market strategy development).
  • Oversaw all corporate development functions including evaluation of M&A opportunities and market landscape analysis; partner closely with the partner leader to drive new business development relationships (business & corporate development).
  • Implemented customer satisfaction initiative including planning, developing, and executing a biannual NPS survey and partnering with key business functions in sales, marketing, customer success, support, and engineering to implement customer experience improvement projects.
  • Led the project team responsible for formulating in-depth market and competitive assessment, culminating in the long-term strategic vision for the company (go-to-market strategy development).
Focus areas: Software Sales, Private Equity, Fundraising, Investor Presentations, Investor Relations, Corporate Development, Budgeting, Finance Strategy, Pricing Strategy, Sales Strategy, Strategy Planning, Financial Planning & Analysis (FP&A), Mergers & Acquisitions (M&A)

Associate

2015 - 2018
K1 Investment Management
  • Worked for K1, a private equity firm with over 70 investment professionals and approximately $5.0 billion in assets under management, investing exclusively in B2B software companies across growth equity and buyout strategies.
  • Led the execution of four acquisitions and one exit in the enterprise software industry, representing over $400 million in transaction value.
  • Executed a range of transactions across various investment strategies and structures, including growth equity, minority, and majority recaps, platform leveraged buyouts and add-on acquisitions.
  • Conducted significant due diligence, including developing analyses on customer acquisition costs, sales efficiency, customer retention and engagement models, detailed financial models, and investment returns analyses.
  • Served as a member of the firm’s Deal Captain Group, comprised of tenured, mid-level investment professionals, formed to lead firm operational, strategic and organizational initiatives.
  • Acted as a co-CFO as part of the exit transaction to a financial sponsor, playing a significant role in developing the company’s financial model and projections as well as managing a quality-of-earnings review with a Big Four accounting firm.
Focus areas: Capital Raising, Leveraged Buyout Modeling, Value Creation, Private Equity Valuation, Fundraising, Mergers & Acquisitions (M&A)

Associate

2010 - 2015
B. Riley & Co.
  • Served as a key revenue contributor by sourcing and executing three public capital raise transactions in the enterprise software space (was the first and only associate at the firm to personally source and close multiple transactions).
  • Executed a range of transactions including sell-side and buy-side M&A, private and public capital raises, debt and equity, capital markets including Dutch tenders/stock repurchase programs, and fairness opinions/valuation studies.
  • Gained significant transaction modeling and financial analysis experience, including public-to-public mergers, corporate divestitures, recapitalizations, leveraged buyout, accretion-dilution, and complex operational and restructuring analyses.
  • Acted as a senior analyst, covering public companies primarily in technology industries such as semiconductors, communications equipment, software, and media/telecom.
Focus areas: Equity Research, Equity Financing, Private Placement Structuring, Private Placement Memoranda, Private Placements, Capital Raising, M&A Modeling, M&A (Sell-side)
2004 - 2008

Bachelor's Degree in Accounting

University of Southern California - Los Angeles, CA, USA

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