Cindy Padnos is an innovator and an advocate for all things entrepreneurial. She is a founder (both of a VC-backed tech startup and a VC firm), with a passion for enabling experimentation that can lead to the discovery of new business models and unique points of leverage. Cindy bleeds B2B/Enterprise Tech – gaining the moniker “Queen B2B” and a place at the table with the top institutional investors in the category.

Cindy has been working with enterprise technology startups for more than 20 years – as a founder, operating executive, adviser, or investor. She founded Illuminate Ventures, a seed and early-stage venture capital firm that invests exclusively in enterprise cloud and mobile software companies. Illuminate seeks entrepreneurs that are “re-inventing the enterprise” with products that deliver dramatic productivity and decision making improvements while leveraging better, faster, cheaper – cloud technologies and innovative business models.

Prior to her investing career, Cindy led several successful venture-backed entrepreneurial efforts. She was the founder/CEO of Vivant (now part of Oracle) an early Software as a Service (SaaS) company. She was CEO of Acumen, orchestrating a profitable M&A, and VP Marketing for Scopus, helping position this early CRM company for its successful IPO. Early in her career, Cindy served as a management consultant at Booz Allen and Arthur D Little.

Illuminate is particularly interested in companies delivering:

– B2B SaaS applications and infrastructure

– Application of AI and blockchain technologies to the Enterprise

– Enterprise mobile solutions

– Predictive and prescriptive analytics that improve business results

– Business model innovation enablers

– Industrial Internet of Things (IIoT)”

Cindy is also an investor at various companies, such as Jacobi, Cafe X Communications, Bedrock Analytics, Peerlyst, ChannelEyes, Pyze Inc., JetStream Software Inc. Influitive, Hoopla Software, Xoupang, Contentstack, BrightEdge, and Allocadia.

During this interview we cover:

00:00 – Intro

02:09 – Early SaaS Experience from Raising VC Capital to Acquisition

15:00 – The Decision Behind Illuminate Ventures and Transformation to what it is today (Metrics)

22:21 – Experience & Perspective on the Volatility of Deal Flow Investments with the COVID-19 Pandemic

24:10 The Value of a Dollar & Current Challenges in the COVID-19 Environment

26:18 How Founders Deal with the Slow Down in Decision to Buy or Renew Software from Customers and Some Strategies for the New Normal

31:34 What Illuminate Ventures Share with Startups Beyond Capital Support

38:46 What is a Founder Heroic & Why Any Founder Should Aim to Become One

40:54 Cindy’s Winner Startup Criteria for Investing

42:29 Cindy’s Turn Down Startup Criteria for not Investing

Mentions

Terms:

Shelfware

RRSP

People:

Jennifer Savage

Ken Goldman

Michael Stonebraker

Chris Cabrera

Gary Swart “The future of work Ep.”

Companies:

Illuminate VC

– Vivant Corp.

AWS

Oracle

Google

Azure

People Soft

SAP

– Evolve

Express Ventures

Ariba

Xactly

Vista

BrightEdge

Hoopla

Cafex

Get in touch with Cindy:

Cindy’s LinkedIn Profile

Cindy’s Twitter

Tag us & follow:

Facebook

LinkedIn

Instagram

YouTube

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