Challenges of Entering the Enterprise Software Market

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Entering the enterprise software market presents challenges such as the need to continuously improve and delight various end users within the organization, including those who make the purchase decisions, implement the software, and use it. In this competitive landscape, understanding the multiple buyers in enterprise software is crucial, as there are different stakeholders with varying needs and priorities. Additionally, competing with established incumbents in the market can lead to feature-by-feature battles that may not be in the best interest of the new entrants. Avoiding getting caught in this battle requires a strategic shift in the conversation and a focus on offering a comprehensive platform rather than a point solution. Building a robust platform over time is essential for success in a highly competitive and saturated enterprise software market.

This week, Tracy Young launched her second startup, TigerEye, from stealth mode. After selling PlanGrid to Autodesk for $875 million and working with YC for a couple of years, Tracy and her husband/co-founder decided to build the software they wished they’d had while building PlanGrid. In our conversation, Tracy unmasks her vision for TigerEye and shares everything she learned as a first time CEO that she’s bringing into her second company.

(00:00) Intro

(01:39) The Shift in Market Dynamics and PlanGrid's Response

(07:07) The Importance of Addressing Multiple Stakeholders in Product Development

(09:08) From PlanGrid to TigerEye: Tracy Young's New Venture

(11:39) The Significance of Organizational Structure and Team Dynamics

(15:03) The Evolution of Sales Strategy and Team Structure

(17:28) The Decision to Sell PlanGrid and Its Aftermath

(24:17) The Genesis of TigerEye and Its Mission

(31:09) Cultivating a Purposeful Company Culture at TigerEye

(39:29) Recruitment Strategies and the Value of Reference Calls

(45:42) Product Development Insights and Market Focus

(49:39) The Importance of Customer Tracking for Startups

(49:57) The Challenges of Scaling with CRM and ERP Systems

(51:55) Navigating the Tough Decisions of Firing Employees

(57:08) The Journey from Construction Engineering to Tech Entrepreneurship

(57:42) The Birth and Growth of PlanGrid

(01:01:24) Navigating Personal and Professional Growth

(01:05:50) The Emotional Journey of Losing a Co-Founder

(01:17:34) From Stealth Mode to Market Impact with Tiger Eye

(01:18:31) Embracing Remote Work and Building a Diverse Team

(01:30:15) Reflections on Fundraising and Board Meetings

(01:34:28) Finding Work-Life Balance in Startup Culture

Executive Producer: Rashad Assir

Producer: Leah Clapper

Mixing and editing: Justin Hrabovsky

Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA

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About the Show

Logan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode, Logan goes behind the scenes with world-class entrepreneurs and investors. If you're interested in the real inside baseball of tech, entrepreneurship, and start-up investing, tune in every Friday for new episodes.