How the CEO of a Billion Dollar Company Uses AI with Andrew Waitman of Assent Compliance
Subscribe at www.thisnewway.com to get the step-by-step playbooks, tools, and workflows.In episode 4 of This New Way, Aydin sits down with Andrew Waitman, CEO of Assent Compliance, 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.Click here to check out the AI-generated timestamps, episode summary and transcript.. . .Like this episode? Be sure to leave a ⭐️⭐️⭐️⭐️⭐️ review and share the episode with someone who will benefit from listening.. . .TIMESTAMPS:00:35 Andrew’s background and Assent’s growth journey02:37 The scale: 18,000 suppliers, 200 compliance topics05:07 The post-ChatGPT transformation and Vista Equity OKRs06:09 Early adoption of GitHub Copilot & ChatGPT Enterprise08:51 Trip report improvements using AI synthesis09:35 Generating synthetic bills of materials for safe testing12:26 Where AI drives efficiency: entity resolution, part matching, document validation13:12 Measuring AI’s impact: productivity, quality, and profitability17:32 Expanding customer success capacity without adding headcount20:37 How to drive company-wide AI adoption (hackathons, Slack, evangelists)24:10 Andrew’s personal AI workflows & deep research routinesTOOLS & RESOURCES MENTIONED:AI Tools & PlatformsGitHub Copilot (Microsoft) → adopted early for engineeringChatGPT (OpenAI, including Enterprise license) → used across teams for synthesis, rewriting, summarizationPerplexity AI (Pro) → used for deep research reportsInternal AI Use Cases & SystemsSynthetic bills of materials → generated using AI to safely test software without exposing sensitive customer dataAutomated document review → handling millions of supplier documents for complianceEntity resolution → using AI to match the right supplier or part across massive datasetsPart resolution & document validation → automating complex checks in the supply chainCompany-Wide AI Adoption Tools & MethodsOKRs (Objectives & Key Results) → embedded AI goals at company, team, and functional levelsAI hackathons → internal competitions to inspire creative use casesSlack channels → for sharing, evangelizing, and discussing AI applications internallyPersonal CEO Tools & WorkflowsPerplexity deep research → running 12–15 deep research reports per dayAI summarization & rewriting → e.g., turning multi-page trip reports into professional one-page summaries