In this episode of the Shift AI Podcast, Adam Alfano, Global Head of SMB at Salesforce, joins host Boaz Ashkenazy for a wide-ranging conversation on how AI agents are fundamentally reshaping small and medium-sized businesses.

Adam shares his unconventional career journey—from growing up in a steel town outside Toronto to building a global sales career and now leading Salesforce’s SMB organization. From there, the discussion dives deep into how today’s SMBs are navigating constant macro change with resilience, optimism, and an increasingly innovative mindset.

The conversation explores how agentic AI is enabling small teams to operate with enterprise-level reach—automating frontline sales development, customer service, onboarding, and even complex workflows traditionally reserved for large organizations. Adam explains why CRM platforms are becoming the operating system for human–AI collaboration, how structured data is the foundation for effective agents, and why managing AI agents increasingly looks like managing employees.

Boaz and Adam also examine the growing sense of overwhelm SMB founders feel around AI tooling, why “just help me set it up” is becoming the winning go-to-market strategy, and how natural-language interfaces are collapsing the technical barrier to adoption. The episode closes with a forward-looking discussion on avatars, workforce orchestration, and why the future of work is best described as “limitless potential.”

This episode is essential listening for founders, operators, and product leaders who want to understand how AI is moving beyond individual productivity gains to unlock entirely new operating models for small businesses.

Chapters

[00:00] From Steel Town to Salesforce: Adam’s Career Journey

[04:24] The State of SMBs: Resilience, Innovation, and Opportunity

[07:18] What Defines an SMB—and Why Size Matters Less Than Ever

[08:17] Agentic AI in Practice: Sales, Service, and Infinite Reach

[11:22] Why CRM Is Becoming the OS for Human–AI Collaboration

[14:44] Data as the Foundation: Structuring Information for AI Agents

[17:32] Lowering the Barrier: Natural Language, Vibe Coding, and Usability

[19:41] The AI Tool Overload—and How SMBs Actually Want Help

[21:31] Where AI Delivers the Biggest Near-Term Impact

[24:31] Avatars, AI Teammates, and New Interaction Models

[28:48] The Future of Work: Limitless Potential

Connect with Adam Alfano

LinkedIn: https://www.linkedin.com/in/adam-alfano-60ab329/

Connect with Boaz AshkenazyLinkedIn: https://www.linkedin.com/in/boazashkenazy/

Email: info@shiftai.fm

In this episode of the Shift AI Podcast, Arnab Bose, Chief Product Officer at Asana, joins host Boaz Ashkenazy to explore how artificial intelligence is transforming the way teams collaborate and get work done. Bose shares his journey to becoming CPO at Asana and the company's ambitious vision for human-AI collaboration, including their groundbreaking AI Teammates and AI Studio products.

From the early days of smartphones reshaping work behavior to today's AI agents that can automate the "toil aspects" of project management, Bose offers a compelling look at where workplace productivity is heading. The conversation dives into how Asana is building a structured approach to work that enables AI agents to seamlessly collaborate alongside human teammates, what customers are actually asking for when it comes to AI tools, and how to build defensible enterprise products through security, governance, and simplicity.

If you're interested in understanding how AI is moving beyond individual productivity gains to transform entire team workflows, what it takes to build competitive moats in enterprise software, and what the future holds for managing AI agents in the workplace, this episode offers invaluable insights from a product leader at the forefront of the AI-powered future of work.
Chapters

[00:00] Journey to Asana: Embracing AI Collaboration

[06:22] Transformations in Work: AI's Impact on Productivity

[11:50] Asana's Vision: Human and AI Collaboration

[17:26] Industry Insights: Customer Needs and AI Adoption

[22:25] Building a Moat: Strategies for Competitive Advantage[

25:26] Future Predictions: The Evolution of Work and AI
Connect with Arnab BoseLinkedIn: https://www.linkedin.com/in/abosesf/
Connect with Boaz AshkenazyLinkedIn: https://linkedin.com/in/boazashkenazyEmail: info@shiftai.fm

In this episode of the Shift AI Podcast, Eilon Reshef, Co-founder and Chief Product Officer at Gong, joins host Boaz Ashkenazy to explore how artificial intelligence is revolutionizing revenue operations and transforming the future of sales teams. Reshef shares the decade-long journey of building Gong from a data-driven conversation platform into what they call an "AI OS for Revenue Teams," serving Fortune 10 companies and pioneering the use of AI in go-to-market workflows.

From capturing customer conversations to deploying AI agents that can automate mundane tasks, Reshef offers a compelling vision of where sales productivity is heading. The conversation delves into how AI is making revenue teams more efficient and effective, the transformation of traditional sales roles, and why the biggest shift isn't just in technology but in how quickly organizations can execute and adapt. If you're interested in understanding how enterprise AI is moving beyond hype to deliver measurable productivity gains, how unstructured data creates competitive advantages, and what the future holds for revenue professionals in an AI-driven world, this episode offers invaluable insights from someone building the infrastructure that's reshaping B2B sales.

Chapters

[00:00] Introduction and Welcome

[02:15] Eilon's Background and Journey to Gong

[05:30] The Origin Story: Starting Gong 10 Years Ago

[08:45] First and Worst Jobs

[11:00] The ChatGPT Moment and AI Acceleration

[14:30] Gong's Unfair Advantage with Unstructured Data

[17:00] Three Pillars of AI Transformation

[21:15] The Rev Ops Revolution

[24:00] Enabling Sales Teams with AI

[27:30] What's Hype vs. Reality in AI for Revenue

[31:00] The Future of Sales Roles and Team Structure

[33:45] The Platform Strategy and Integrations

[36:30] Security and Trust in Enterprise AI

[39:00] Gong's Growth Trajectory and Future Plans

[41:30] Voice Agents and the Future of Customer Interaction

[45:00] Two Words for the Future: Efficient and Exciting

[48:00] Connecting with Eilon and Hiring at Gong

Connect with Eilon Reshef

LinkedIn: https://linkedin.com/in/eilonreshef

Connect with Boaz Ashkenazy

LinkedIn: https://linkedin.com/in/boazashkenazy

Email: info@shiftai.fm