The AI Report Live with Liam Lawson

Shopify’s Sidekick Just Leveled Up: AI That Runs Your Store (Proactively)

How Shopify Is Building The Future of AI Commerce with Andrew McNamaraShopify's Director of Applied ML, Andrew McNamara, reveals how the new Sidekick Pulse and SimGym features are revolutionizing e-commerce for merchants of all sizes. With 15 years of experience building AI assistants—dating back to pre-Siri days—Andrew breaks down how Shopify is using "LLM as a judge" to ensure quality and why "vibe entrepreneurship" is the future of business.Andrew explains how Sidekick has evolved from a simple chatbot into a proactive "AI Co-founder" that can democratize data for small business owners. He shares behind-the-scenes details on Sidekick Pulse, which performs deep research to surface actionable insights (like finding shipping errors that cost sales), and Simgym, a powerful simulator that uses AI shoppers to A/B test store changes before they go live.We also dive into the technical side of how Shopify evaluates these models using statistical rigor and why the ability for merchants to build admin apps with a single prompt is a game-changer for productivity.---Topics Covered- The 15-year evolution of AI assistants from rule-based systems to LLMs- How Sidekick Pulse proactively finds and fixes business-critical errors- Simgym: Using AI shoppers to simulate A/B tests without risking live traffic- The "LLM as a Judge" framework Shopify uses for product quality control- "Vibe Entrepreneurship" and reducing technical barriers for founders- Building custom Admin Apps in seconds using natural language prompts- Real-world examples from Andrew's own maple syrup store- The difference between general chatbots (Copilot) and specialized agents (Sidekick)- How "App Gen" allows merchants to create custom workflows instantlyEpisode Timestamps00:03 - Introduction to Andrew McNamara and his 15-year history with AI01:01 - Comparing early AI assistants (BlackBerry/Samsung) to modern LLMs06:45 - How Sidekick democratizes data analytics for small merchants11:25 - Deep Dive: Sidekick Pulse and proactive business research15:43 - Using "LLM as a Judge" to replace human evaluation at scale18:41 - Generating custom Admin Apps with a single prompt ("App Gen")21:58 - Andrew's personal experience running a Shopify store25:31 - The concept of "Vibe Entrepreneurship" as a North Star26:30 - Using AI to edit online store themes and layouts in real-time37:39 - Simgym: Simulating buyer behavior to predict experiment results42:06 - Why simulation is critical for both small and large enterprise merchants48:04 - The culture of technical depth and passion at Shopify51:34 - Why Andrew has dedicated his entire career to building assistants---## About Andrew McNamaraAndrew McNamara is the Director of Applied Machine Learning at Shopify, where he leads the development of Sidekick and other intelligent merchant features. Previously the Director of the Montreal Research Lab at Microsoft and a key contributor to Bing Chat (Copilot), Andrew has over 15 years of experience building and deploying AI assistants at scale.Shopify is the leading global commerce company, providing trusted tools to start, grow, market, and manage a retail business of any size. It powers millions of businesses in more than 175 countries and offers a unified platform for physical and digital commerce.Resources Mentioned- Shopify Sidekick (AI Commerce Assistant)- Sidekick Pulse (Proactive Research Agent)- Simgym (AI Shopper Simulator)- Microsoft Copilot & Bing Chat- "LLM as a Judge" Evaluation Framework---Partner Links- Book Enterprise Training — https://www.upscaile.com/- Subscribe to our free newsletter — https://www.theaireport.ai/subscribe-theaireport-youtube

The $30M AI Sales Startup Replacing 15 GTM Tools Overnight | Jason Eubanks, Aurasell

Jason Eubanks on Building Oracel: Raising $30M in 28 Hours to Disrupt the $236B Go-To-Market Tooling Market with AI-Native Sales AutomationJason Eubanks, CEO and Co-founder of Oracel, discusses how the company raised $30 million in just 28 hours—oversubscribed at $40 million—by solving a critical problem in the go-to-market industry. With a $236 billion market opportunity and only a "desert of innovation" since the late 1990s, Aurasell is building an AI-native platform to intelligently automate sales workflows and consolidate the 12-15 fragmented tools that plague modern sales teams. Jason shares how his experience scaling revenue from $1M to $100M+ across five startups—including Twilio (IPO), Meraki (acquired by Cisco for $1.2B), and Harness—directly informed the founding vision of AurasellEpisode Timestamps- 00:00 - Introduction and Jason Eubanks joins the podcast- 00:26 - Why Oracel raised $30M in 28 hours despite initial $40M oversubscription- 01:24 - The "desert of innovation" in go-to-market tooling since the late 90s- 01:42 - History of CRM evolution from mainframe to cloud to niche products- 03:12 - Founding vision: One intelligent GTM sales platform to replace them all- 03:39 - How pain as a CRO across five startups led to Oracel's creation- 05:58 - The X-Ray productivity assessment revealing tool sprawl inefficiencies- 07:59 - Sellers spending 28% of time selling and 70% on manual tasks- 09:03 - First principles AI-native approach with whiteboards in the kitchen- 09:29 - Five key personas: SDR, seller, IC manager, executive, ops team- 12:18 - AI-native architecture: multimodal interface, lakehouse, and 10,000 agents- 14:39 - Unified data model importance for contextualized AI automation- 15:45 - Current hat wearing: product focus and 50% building go-to-market engine- 18:43 - Platform features and customer experience design philosophy- 19:05 - Three wow moments per persona as success metric- 20:39 - Onboarding experience: automatic territory building and customer choice- 21:40 - 10,000 agents discovering ICP, personas, and competitors automatically- 24:07 - Automated account research and value hypothesis creation- 25:34 - Outbound prospecting content generation with propensity scoring- 26:32 - Outbound sequencer integration and email platform plugins- 27:00 - AI voice dialer coming in three weeks with closed-loop automation- 28:47 - What's missing: deep marketing and customer success automation- 30:49 - Ideal customer profiles: startups and enterprises with tool sprawl- 31:30 - Solution for heavily customized legacy systems coming in December- 34:24 - Dynamic change detection layer solving technical debt- 36:23 - Jason's career arc from BMC Software through Harness- 37:09 - Why: helping go-to-market operators solve problems he experienced- 39:55 - Meraki's disruptive cloud-managed network architecture- 41:51 - Three constants: great product builders, important problems, massive markets- 43:22 - Intrinsic motivation as foundation for hiring and culture- 45:31 - Hiring from first job onward to assess character and values- 51:24 - Understanding why someone wanted to work at 14 years old- 53:21 - Importance of formative years for work ethic and intelligence- 55:46 - AI adoption culture: using own product and building agents internally- 56:36 - All employees use AI daily across PMs, engineers, and operations- 59:25 - Ask AI features: analytics dashboards, data enrichment, natural language-

The AI Behind Fortune 500 Risk: Anton Dam, AuditBoard

Discover how Anton, one of the most experienced AI and machine learning experts in the industry, discusses his evolution from building matching algorithms at Bright.com to navigating today's AI landscape. With over a decade of experience in large-scale recommendation systems and data processing, Anton reveals how the fundamentals of big data and embarrassingly parallel computing shaped modern AI applications, and why human-centered design is now more critical than ever in building AI-powered products.Episode Timestamps:- 00:00 - Introduction and welcome- 00:47 - Anton's experience at Bright.com and the recruitment matching problem- 03:23 - The big data era, Hadoop, and Spark in the web 2.0 world- 05:00 - Embarrassingly parallel computing and large-scale data processing- 10:00 - How recommendation algorithms work at scale in recruitment- 20:00 - Evolution of the data scientist role over time- 30:00 - Building intelligent matching systems- 40:00 - Understanding user needs and organizational workflows- 50:00 - The shift toward human-centered AI design- 57:30 - Providing pre-filled content and personalization- 58:02 - Anton's vision for the future and human values- 01:01:46 - Closing thoughts on humanity and technologyAbout Anton:Anton is a veteran machine learning and AI engineer with over a decade of experience building large-scale recommendation and matching systems. He played a key role at Bright.com, a two-sided recruitment platform that pioneered transparent scoring algorithms for candidate-job matching. His expertise spans big data infrastructure, recommendation systems, user experience optimization, and the human-centered approach to AI product development.Resources Mentioned:- Hadoop and Spark (big data processing frameworks)- Big data infrastructure and cloud computing platforms- Two-sided marketplace architectures- Recommendation algorithms and matching systems- User workflow analysis toolsPartner Links:- Book Enterprise Training — https://www.upscaile.com/- Subscribe to our free newsletter — https://www.theaireport.ai/subscribe-theaireport-youtubeHashtags:#AIAgents #MachineLearningSystems #RecruitmentTechnology #BigData #DataScience #RecommendationAlgorithms #HadoopSpark #AIProductDesign #HumanCenteredAI #LargeScaleML #CloudComputing #AIStrategy #FutureOfWork #TechLeadership #CareerDevelopment

The Slack Vision: Everyone Manages an AI Team from Day One | Ryan Gavin

Building Teams in the Age of AI: How Slack CMO Ryan Gavin is Reshaping the Future of Work In this episode, Ryan Gavin, Chief Marketing Officer at Slack, reveals how self-awareness in leadership and the convergence of marketing and product strategy are creating unprecedented opportunities in the agentic era. Learn why employee productivity through AI orchestration is poised to become the fastest accelerator for top line business growth companies have ever seen, and how Slack is positioning itself as the conversational work platform for this transformation. The conversation explores the critical shift from employees as doers to orchestrators, where every team member—from day-one interns to seasoned executives—will manage digital coworkers and AI agents. Discover the product principles driving Slack's approach to agent integration, the social dynamics of working alongside AI teammates, and why the traditional career ladder is being replaced by immediate access to capabilities across development, creative, analytics, and more. The discussion also covers practical frameworks for building exceptional teams, reducing AI adoption anxiety, and why picking the "right" career path matters less than crushing the job you're in. Ryan delivers actionable insights on leadership development through self-awareness, understanding how team members receive feedback and recognition differently, and connecting business opportunities with talent growth. You'll also hear his compelling argument for why marketing must sit between product and sales as a strategic amplifier, not just a message distributor, and what marketers need to do to earn their seat at product strategy and sales planning meetings. Key Topics Covered: * Self-awareness as the foundation of effective leadership and team development * Why marketing is product and product is marketing in modern B2B organizations * The shift from doers to orchestrators in the age of AI agents and digital coworkers * How every employee will manage AI teammates from day one across finance, HR, creative, and development * Employee productivity as the most underutilized growth lever for businesses * Slack's product principles for agent integration: don't make me think and be a great host * Reducing AI adoption fear by showcasing capability expansion rather than job displacement * Social dynamics of agent interaction in channels and preserving psychological safety * Why there is no "right" career path and how to multiply opportunities by crushing your current role * The changing consumer patterns of information seeking and their impact on business workflows Episode Timestamps: 00:00 - Introduction and setting the stage 02:16 - Knowing thyself: Ryan's journey to leadership self-awareness through family and life experience 05:19 - What makes an amazing marketer in 2026 and bridging the marketing-product divide 08:43 - From doers to orchestrators: how AI agents give every employee a team from day one 11:24 - Designing agents to work like teammates: Slack's approach to intuitive AI integration 14:55 - Addressing AI fear: why productivity gains lead to higher expectations rather than job loss 18:03 - Advice for the next generation entering an AI-transformed workforce 21:49 - Career lesson from delivering papers in 110-degree Chicago heat 24:30 - Final question: why Ryan does what he does and the importance of lasting market impact

Low Ego, High Grit: How Salesforce Lands MASSIVE AI Partnerships | Nick Johnston

Nick Johnston is the Senior Vice President of Strategic Partnerships & Business Development at Salesforce, where he leads strategic relationships with major technology companies including OpenAI, Anthropic, AWS, Google, IBM, and Workday. In this conversation recorded during Dreamforce 2025, Nick shares how Salesforce closed 12,500 Agentforce deals and navigated the complexities of announcing major partnerships like the expanded OpenAI integration that brings Salesforce's Agentforce 360 directly into ChatGPT. He reveals his unique approach to building win-win partnerships grounded in customer demand rather than competitive positioning. Key Topics Covered: * How Salesforce builds customer-driven partnerships with tech giants like OpenAI, Anthropic, AWS, and Google * The three core hiring values that create high-performing partnership teams: low ego, high curiosity, and grit * Why uncomfortable conversations are essential for building trust and creating impactful partnerships * Using AI tools to position partnership proposals and draft joint press releases with strategic clarity * The Dreamforce partnership strategy and how compelling events drive deal execution * Career lessons from coaching varsity football wide receivers and celebrating team achievement over personal wins * Living in Buenos Aires for six months and the value of full cultural immersion for partnership work * Why getting customer-facing experience early in your career is the best foundation for any role * The interview question that reveals hero culture versus team players in partnership roles * Balancing partnership work across multiple departments including product, marketing, operations, and sales * How human experience will become the ultimate competitive moat as AI automates routine tasks * The "be great" daily philosophy and applying the same standards to yourself that you set for your team Episode Timestamps: 03:07 - From college football to coaching varsity wide receivers at Torrey Pines High School in 2006 05:47 - The vibes and trust mentality: lessons from undersized teams that outperform expectations 07:26 - Three core hiring values: low ego, high curiosity, and grit in partnership teams 09:15 - Six months in Buenos Aires learning Spanish through full immersion with Spencer Stuart 12:49 - Customer-driven partnership strategy: building frameworks from market demand to product integration 16:15 - The customer-centric approach at Dreamforce and delivering the Agentforce agenda with partners 18:04 - Using AI to write joint press releases, position partnerships, and create mutually beneficial proposals 21:27 - Career advice for new graduates: get as close to the customer as possible in sales or customer success roles 24:56 - Why human experience and the arts will be the ultimate differentiator as AI automates work 28:02 - Parenting lessons and the "be great" daily motto for building confidence and pushing through challenges 29:06 - Why do you do what you do: achieving hard things in team settings and making family proud About Nick Johnston Nick Johnston is the Senior Vice President of Strategic Partnerships & Business Development at Salesforce, where he has spent over 12 years advancing from Customer Success Director to leading strategic technology partnerships. He holds an MBA from UC Berkeley Haas School of Business and a BA with honors in International Relations from UC Davis, where he also played college football. Nick has been instrumental in establishing major partnerships with OpenAI, Anthropic, AWS, Google, IBM, Workday, and other leading technology companies to deliver integrated customer experiences through Salesforce's Agentforce 360 platform. ransformation and agentic AI. Partner Links: Book Enterprise Training — ** [https://www.upscaile.com/]https://www.upscaile.com/** [https://www.upscaile.com/**] Subscribe to our free newsletter — ** [https://www.theaireport.ai/subscribe-theaireport-youtube]https://www.theaireport.ai/subscribe-theaireport-youtube** [https://www.theaireport.ai/subscribe-theaireport-youtube**]