LIVE: How AI is Reinventing Software Business Models ft. Bret Taylor of Sierra

LIVE: How AI is Reinventing Software Business Models ft. Bret Taylor of Sierra

May 14, 2025 34 min
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🤖 AI Summary

Overview

This episode features Brett Taylor, co-founder of Sierra and former co-CEO of Salesforce, in conversation with Ravi Gupta. They explore how AI is reshaping software business models, the rise of vertical-specific AI agents, and the challenges and opportunities for startups versus incumbents in this evolving landscape.

Notable Quotes

- Don't let something you're good at become who you are.Ravi Gupta, reflecting on lessons learned from Brett Taylor.

- Outcomes are valuable. Some outcomes are extremely valuable.Brett Taylor, on why selling outcomes rather than productivity tools is the future of enterprise software.

- It's more fun to be a pirate than it is to be in the Navy.Brett Taylor, on why startups are better positioned to innovate in AI-driven business models.

🧠 The Entrepreneurial Mindset

- Brett Taylor shared his journey from engineering to enterprise sales, emphasizing the importance of adaptability. He recounted a pivotal moment when Sheryl Sandberg advised him to stop trying to do everything himself and instead focus on scaling through his team.

- Entrepreneurs often regress to their comfort zones, whether it's product design or technical problem-solving. Success requires self-awareness and the ability to shift focus as the company grows.

- Ravi Gupta highlighted Brett’s philosophy: prioritize impact over personal preferences, and avoid letting your strengths define your identity.

🤖 The Rise of Vertical-Specific AI Agents

- Sierra’s vision is that every company will have a singular branded AI agent as their primary digital interface, akin to websites in the early internet era.

- Examples include AI agents for ADT Home Security and SiriusXM, tailored to specific customer needs like alarm troubleshooting or subscription management.

- Brett Taylor argued that vertical specialization is key in AI, as generic horizontal platforms often fail to deliver the depth of value required by enterprises.

📈 Outcomes-Based Pricing Models

- Sierra employs outcomes-based pricing, charging only when its AI agents autonomously resolve customer issues. This aligns incentives between Sierra and its clients.

- Brett Taylor noted that traditional subscription models are ill-suited for AI-driven solutions, as they fail to capture the value of completed tasks.

- Pricing strategies must account for the nuances of procurement processes in different industries, such as HR departments preferring subscription models due to budgeting constraints.

🏔 Opportunities for Startups in AI

- Startups have a significant advantage over incumbents because they are not constrained by legacy business models. Brett Taylor emphasized that adapting business models is often harder than closing technology gaps.

- AI is enabling structural changes in industries like customer service and legal operations, allowing companies to reinvest cost savings into growth.

- To stand out in a saturated AI market, startups must deeply understand their customers’ pain points and tailor their solutions accordingly. Research and preparation are critical for effective enterprise sales.

🌐 The Competitive Landscape for Foundation Models

- Brett Taylor predicted consolidation in the foundation model market due to its capital-intensive nature, likening it to the cloud infrastructure industry.

- Applied AI, particularly domain-specific agents, represents the most exciting opportunity. These agents shift the focus from productivity enhancement to delivering measurable outcomes, unlocking larger markets.

- He speculated that the next trillion-dollar software company will emerge from this applied AI space, as selling outcomes is inherently more valuable than selling tools.

AI-generated content may not be accurate or complete and should not be relied upon as a sole source of truth.

📋 Episode Description

Recorded live at Sequoia’s AI Ascent 2025: Sierra co-founder Bret Taylor discusses why AI is driving a fundamental shift from subscription-based pricing to outcomes-based models. Learn why this transition is harder for incumbents than startups, why applied AI and vertical specialization represent the biggest opportunities for entrepreneurs and how to position your AI company for success in this new paradigm.