How the CEO of a Billion Dollar Company Uses AI with Andrew Waitman of Assent

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In episode 4 of This New Way, Aydin sits down with Andrew Waitman, CEO of Assent, to explore how a billion-dollar B2B SaaS company is transforming operations, product development, and team productivity with AI. Andrew shares how Assent went from under $1M to nearly $200M ARR, became one of the earliest adopters of GitHub Copilot and ChatGPT Enterprise, and how they now embed AI-driven OKRs across every team.

You’ll hear real use cases: from summarizing messy trip reports, generating synthetic bills of materials for secure testing, and accelerating supplier document reviews — to measuring impact on productivity and profitability. Andrew also offers actionable insights on how to drive AI adoption across teams, how CEOs should personally lead the AI charge, and which tools he uses daily to stay ahead.

You’ll walk away knowing how to start small, scale fast, and turn AI into a measurable force multiplier across your org.

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TIMESTAMPS:

00:35 Andrew’s background and Assent’s growth journey

02:37 The scale: 18,000 suppliers, 200 compliance topics

05:07 The post-ChatGPT transformation and Vista Equity OKRs

06:09 Early adoption of GitHub Copilot & ChatGPT Enterprise

08:51 Trip report improvements using AI synthesis

09:35 Generating synthetic bills of materials for safe testing

12:26 Where AI drives efficiency: entity resolution, part matching, document validation

13:12 Measuring AI’s impact: productivity, quality, and profitability

17:32 Expanding customer success capacity without adding headcount

20:37 How to drive company-wide AI adoption (hackathons, Slack, evangelists)

24:10 Andrew’s personal AI workflows & deep research routines

TOOLS & RESOURCES MENTIONED:

AI Tools & Platforms

• GitHub Copilot (Microsoft) → adopted early for engineering

• ChatGPT (OpenAI, including Enterprise license) → used across teams for synthesis, rewriting, summarization

• Perplexity AI (Pro) → used for deep research reports
  

Internal AI Use Cases & Systems

• Synthetic bills of materials → generated using AI to safely test software without exposing sensitive customer data

• Automated document review → handling millions of supplier documents for compliance

• Entity resolution → using AI to match the right supplier or part across massive datasets

• Part resolution & document validation → automating complex checks in the supply chain
  

Company-Wide AI Adoption Tools & Methods

• OKRs (Objectives & Key Results) → embedded AI goals at company, team, and functional levels

• AI hackathons → internal competitions to inspire creative use cases

• Slack channels → for sharing, evangelizing, and discussing AI applications internally
  

Personal CEO Tools & Workflows

• Perplexity deep research → running 12–15 deep research reports per day

• AI summarization & rewriting → e.g., turning multi-page trip reports into professional one-page summaries