RevOps and planning cycles, working with the board as CEO

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The speaker emphasized the importance of focusing on RevOps team to allow them to strategize and provide valuable insights instead of spending time on manual spreadsheet tasks. They highlighted the inefficiencies of traditional planning cycles, taking months to create plans on spreadsheets with multiple errors. The lack of suitable tools for planning and forecasting led to significant time and financial costs for the company. The use of AI and simulators can streamline the planning process, offering quicker and more accurate results. The speaker discussed the need for businesses to adopt modern tools to enhance efficiency and accuracy in planning, referencing the challenges faced at Plan Grid due to relying on outdated methods. They shared a personal anecdote about the difficulties in convincing the board to approve plans created through lengthy and error-prone spreadsheet processes, illustrating the need for more sophisticated planning solutions in the business world.

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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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.