HG Insights, Santa Barbara, California: Dr. Elizabeth Cholawsky, CEO

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Dr. Elizabeth Cholawsky is an award-winning executive leader, strategist, and visionary. With over 25 years of success in the technology industry, Cholawsky is known for creating market-leading offerings and growing SaaS/DaaS businesses through in-house talent, organic innovation, partnerships, and acquisitions. She is a seasoned board director, helping public companies and start-ups achieve their goals. Often requested as an industry events speaker, she is also frequently recognized for her business leadership. Her numerous accolades include: Comparably ‘Best CEO’ (2019), ‘Best CEOs for Women’ (2019, 2020), and ‘Best CEOs for Diversity’ (2020); recognized multiple times by the Pacific Coast Business Times as a ‘Top 50 Women in Business’ (2013-2014, 2020-22); South Coast Business & Technology ‘Executive of the Year’ Award (2023), and a four-time Stevie Award winner (2012, 2020-22)—in addition to the many awards HG Insights has received during her tenure. Cholawsky consistently strives to overcome the leadership gap for women and all underrepresented people. She has actively worked to remove hidden biases in businesses so that people of any background can have the same opportunities as others. Continuing her work beyond the office walls, Cholawsky works within the local community, from HG’s ongoing partnership with Santa Barbara Women in STEM and joining forces with UCSB’s Data Science Program to oversee student capstone projects—all in the name of promoting diversity and inclusion. 

Cholawsky has led HG Insights as CEO since 2018, growing revenue by 40% CAGR and leading the acquisition and integration of Pivotal iQ in 2019 and Intricately in 2022. In 2020 Cholawsky recapitalized HG Insights through a majority investment by Riverwood Capital, delivering a market-leading return to HG Insight’s original shareholders. Riverwood’s investment underscores HG Insights’ accelerated growth and its future massive opportunity in the global business intelligence market size which was valued at USD 29.22 billion in 2023. Jeff Parks, co-founder and managing partner of Riverwood Capital, said, “HG Insights represents a golden opportunity for Riverwood to continue to use our capital and expertise to accelerate the growth of innovative technology companies addressing demonstrated but unmet market needs. Elizabeth and her team have built an organization poised to disrupt the traditional Go-To-Market process for companies of virtually any size, and we’re very excited about the potential of this partnership.”

Before HG Insights, Cholawsky was president and CEO of Support.com. She joined this $77M, a 2,000-person public company (NASDAQ: SPRT) to market a ground-breaking SaaS-based contact center solution while transforming the legacy service-based business. Customers such as Cox Cable and Comcast adopted Support.com’s offerings to improve their customer experience materially.  Prior to Support.com, Cholawsky was an executive at Citrix’s SaaS Division. As GM of the IT Services business line, she grew the line’s annual revenue to $190M while the SaaS Division doubled its revenue to over $500M during her tenure. Cholawsky also held executive leadership roles at Move.com, Clarent, and ValueClick (now Conversant). While at ValueClick, she held a lead role in the acquisition of Commission Junction and subsequently joined ValueClick’s executive team. Throughout her career, Cholawsky has used her marketing acumen to position companies in large growth markets and align products and messaging for maximum effectiveness, while creating new revenue streams from both services and new products. 

Dr. Cholawsky holds a Ph.D. in Political Science with a concentration in Econometrics from the University of Minnesota, and a BA (Phi Beta Kappa, cum laude) from Franklin & Marshall College. She attended the Stanford Directors’ College in 2015 and 2022.

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Since the beginning of 2019, Elizabeth Cholawsky has:

• Successfully led the acquisition of Pivotal iQ by HG Data

  • The combined company (HG Insights) is the first in the market to deliver a unique blend of IT spend, IT install, and contract renewal intelligence. This is the industry’s highest quality Technology Intelligence that is relied upon by 9/10 Fortune 100 B2B technology companies

• Led HG Insights to 50% revenue growth from 2019-2020. 2020-2021 was another record year with 42% annual recurring revenue and profitability 

  • Sustained rapid growth throughout 2020, increasing employee count by 30% and meeting aggressive financial goals despite the pandemic and ensuing down economy

  • Placed for the first time ever on the Inc. 5000 of fastest-growing private companies in 2022

• Successfully led the acquisition of Pivotal iQ by HG Data

  • The combined company (HG Insights) is the first in the market to deliver a unique blend of IT spend, IT install, and contract renewal intelligence. This is the industry’s highest quality Technology Intelligence that is relied upon by 9/10 Fortune 100 B2B technology companies

• The HG Insights Platform is the first and best in the market at delivering a unique blend of IT spend, IT installations, and contract renewal intelligence. This is the industry’s highest-quality technology intelligence and is heavily relied upon by sales, marketing, and strategy teams. 

• Received multiple employee-voted rewards for Best CEO and Best CEO for Women (as enumerated above) 

• Built out a flexible, self-service, industry-leading platform and products to enable customers to use data-driven analysis to solve complex business problems throughout their organization.

• When Covid hit, Elizabeth quickly helped our customers by providing them with insights on where to prioritize their selling efforts. This included reports on

  • Identifying which companies were better equipped to weather the Covid storm (those with more mature cloud infrastructures, for example)

  • Top 1000 firms that were hiring during the Covid crisis

  • How much the banking and financial industries were spending on cloud technologies

• During the pandemic, in addition to running the business to ensure it was meeting it’s revenue goals, Elizabeth also worked extensively to motivate and inspire her employees to excel personally and professionally           

  • For the first six months, she kept employees’ spirits high while they were working from home by sending daily email updates. 

  • She strongly supported Mental Health Month by allowing employees to take mental health rest days and wrote informative blog articles 

  • Actively participates in a Back to the Office committee dedicated to listening and meeting employees' needs throughout the pandemic

• Overcame the leadership gap for women. Cholawsky is among the roughly 8% of female CEOs in the U.S. She has actively worked to remove hidden biases in businesses that may prevent women from getting the same promotion opportunities as others. 

  • As well as working with her community to do the same: 

    • Santa Barbara Women in STEM 

    • UCSB’s Data Science Program to oversee student capstone projects 

• The HG Insights Platform is the first and best in the market at delivering a unique blend of IT spend, IT install and contract renewal intelligence. This is the industry’s highest quality technology intelligence and is heavily relied upon by sales, marketing, and strategy teams. 

• In 2020, Cholawsky recapitalized HG Insights through a majority investment by Riverwood Capital, delivering a market-leading return to HG Insight’s original shareholders as well as employees. Riverwood’s investment underscores HG Insights’ accelerated growth and its future massive opportunity in the global business intelligence market size which was valued at USD 29.22 billion in 2023.