Rich Nazzaro sits down with Beth Mastre, a 30-year sales veteran, to discuss why email marketing isn't dead—it's just being done wrong. Beth shares her framework for transforming sales outreach from pitchy, self-centered messages into relationship-building conversations that actually get meetings.

Beth Mastre — Sales strategist and creator of an AI-powered email tool that helps sales teams craft effective outreach. With three decades of sales experience, she specializes in teaching teams how to lower barriers and create genuine connections with prospects.

1. Email isn't for selling—it's for getting meetings. The only metric that matters is whether your outreach results in a conversation.
2. Stop pitching, start teaching. Instead of leading with "here's who we are and what we do," share insights about industry challenges, common mistakes, or questions prospects should be asking.
3. Create FOMO (Fear of Missing Out). Frame your outreach around what prospects don't know rather than what you offer.
4. Make relationship deposits. Every touchpoint should add value to the prospect, not extract it.
5. Sales teams don't have a prospecting problem—they have a fear problem. Fear of rejection, fear of saying the wrong thing, and fear of not hitting quota all contribute to ineffective outreach.
6. The "HVAC Guy" approach: The best salesperson doesn't just quote a price—they walk through your situation, identify problems you didn't know existed, and educate you before ever discussing solutions.

• "People are happy to be unhappy. They have containment around their unhappiness."
• "Email's not for selling. Your email is about getting a meeting."
• "You don't have a prospecting problem, you have a fear problem."
• "Your first meeting is kind of free. If you get the meeting but then you pitched, you might not get your second meeting."

When you reach out with insights about industry challenges, you'll get one of three answers:

• "We didn't know, so we don't have a plan" (easy opportunity)
• "We know, but don't have a plan" (they need help)
• "We already have a plan" (rare—ask what else they're working on)

• Never say "us," "me," "we," "our," or "they"—use "in the industry" or "other organizations" instead
• Subject lines matter more than you think (her best performer: "requesting discount")
• Keep it short and focused on one relationship deposit
• Always end with a simple ask: "When do you have 20 minutes?"

AI tools can help, but only when built on solid frameworks. Generic AI-written emails will "burn people so hard and so fast." The key is feeding AI with proven methodology and intellectual property—not just asking it to write cold emails.

• (00:00:00) - Business Uncomplicated: Email Is Dead
• (00:01:33) - Beth Mastry on Business Uncomplicated
• (00:02:44) - In the Elevator With Beth Mastry
• (00:04:13) - How to Build a Sales Team with AI
• (00:04:57) - Are You Ready to Make a Sales Decision?
• (00:07:18) - How to Sell to a Large Company
• (00:12:05) - How to Lead with Empathetic Focus
• (00:17:00) - Onboarding: The 3 Things We Don't Know
• (00:19:09) - How to Build a Strategic Plan in 2020
• (00:24:14) - How to Build a Successful Sales Email
• (00:28:36) - How to Coach Your Clients Through the Talk
• (00:29:40) - How to Get Your Pitch Heard
• (00:32:45) - How to Coach People on Authenticity
• (00:35:53) - How AI is Affecting Sales Communication
• (00:39:28) - What is the Importance of Frameworks in AI?
• (00:40:36) - The Inbox: The Framework
• (00:42:10) - Sales Whisperer: Poor Enabling and Training
• (00:47:40) - Onboarding With AI: From Onboarding to Sales

In this engaging conversation, industry leaders discuss the transformative impact of AI on customer success. They explore strategic priorities, the importance of data management, and the evolving roles within customer success teams. The discussion emphasizes the need for collaboration across departments and the significance of building trust in customer relationships. As organizations navigate the integration of AI, they highlight the importance of AI literacy and the potential for new roles that blend traditional account management with AI capabilities.

Guest:

John Durocher: https://www.linkedin.com/in/johndurocher/

Shane Hughes: https://www.linkedin.com/in/shanehughes/

Cesar Sanchez: https://www.linkedin.com/in/thebigc/

Takeaways

• AI is transforming customer success roles and strategies.
• Adoption of AI tools is crucial for enhancing productivity.
• Data management is foundational for effective AI implementation.
• Customer success must focus on relationship building and trust.
• Organizational silos hinder effective AI integration.
• The role of customer success managers is evolving with AI.
• AI can automate routine tasks but won't replace human interaction.
• Companies need to prioritize AI literacy across teams.
• Collaboration between departments is essential for AI success.
• Future roles in customer success will blend traditional account management with AI capabilities.

• (00:00:02) - Business Uncomplicated: AI and the Customer Relationship
• (00:01:59) - John Durocher, Shane Hughes and Cesar Sanchez
• (00:05:08) - Customer Service Executives: One Strategic Priority
• (00:07:56) - Tribble on the Application of AI in CS
• (00:12:08) - Does the CSM Have a Future?
• (00:15:58) - Sales and Customer Success: The Future of AI
• (00:20:48) - Top Executives: More Confusion Within the Organization
• (00:24:17) - WSJD. AI Acceleration
• (00:30:28) - CIO Network: How to Integrate AI into your Business
• (00:35:43) - AI Literacy and Fluency
• (00:37:28) - COO Network: Do We Need a Chief AI Officer?
• (00:40:31) - The Need for AI-related Upskilling
• (00:42:04) - Will AI Replace Human Jobs?
• (00:45:59) - Will AI Replace Human Interactions?
• (00:47:26) - December Brings Bold Predictions
• (00:47:51) - John, what percentage of customer interactions will be AI first by 20
• (00:49:34) - What CS Role Will Exist in 5 years?
• (00:51:22) - A.I. in 2028
• (00:52:17) - milo on EWTN

In this episode of Business Uncomplicated, Rich Nazzaro sits down with innovation strategist and author Steve Wunker, Managing Director at New Markets Advisors and author of AI and the Octopus Organization: Building the Super Intelligent Firm.

They explore how AI can do far more than automate tasks—it can fundamentally reshape how your organization thinks, decides, and acts. Using the octopus as a metaphor (nine brains, eight tentacles, three hearts), Steve explains what it really means to build a firm that’s fast, adaptive, and intelligent at every node, not just at the top.

Together, Rich, Steve, and co-host Andy Worobel dig into why so many AI efforts stall at “pilot theater,” how to move from tools to true transformation, and what this means for leaders, middle managers, and frontline teams.

Get your copy of: AI and the Octopus Organization: Building the Superintelligent Firm

• The Octopus Organization metaphor
  How nine brains and eight tentacles map to AI-enabled decision-making at the edge of your business.

• Why most AI initiatives fall flat
  Pilot overload, narrow thinking, and the trap of sprinkling AI across 17 steps instead of redesigning the process.

• Transformation vs. technology
  Why “buying the tool” (Salesforce, AI platforms, etc.) without a clear why leads to shallow change and wasted spend.

• Starting with the customer, not the model
  How reimagining growth, customer value, and competitive strategy should precede any AI deployment.

• Bottom-up autonomy and the new frontline
  How AI finally makes it possible to devolve authority—with real context, guardrails, and feedback loops.

• The reinvention of the middle manager
  Moving from admin and coordination to steward of the model, coach, and day-to-day change manager.

• Breaking silos without becoming a micromanager
  How AI-driven transparency can unite marketing, sales, ops, and IT—without turning leadership into “radio-era admirals” meddling in everything.

• The CIO’s once-in-a-generation moment
  Why this may be the best time in history for IT to lead organizational transformation—and what that partnership with the business should look like.

• Energy, infrastructure, and the real constraints on AI
  Why the current path of hyperscale models is unsustainable and how leaner, purpose-built models may shape the future.

• Democratizing data and tools
  From “everyone build a GPT” chaos to intentional productization and access to the right data sources with the right guardrails.

• Why most companies are terrible at experimentation
  Zombie projects, poor learning loops, and how to design AI experiments that actually move the needle.

If you’re an executive, CIO, or operator trying to move past AI hype and into real, structural change, this conversation gives you both the language and the lenses to start redesigning your organization.

• (00:00:00) - Business Uncomplicated: AI and the Octopus Organization
• (00:01:59) - Steve Wunkur on The AI Origins of Business Uncomplicated
• (00:02:32) - Disruptive Innovation: Rich Sulzanski
• (00:05:06) - AI and the Octopus Organization
• (00:06:44) - The Decoding of the Octopus
• (00:08:29) - Does AI Need a Transformative Impact?
• (00:10:56) - Reimagining Growth with AI: The Transformation
• (00:13:53) - Middle Manager: The End of the Boss
• (00:14:35) - In the Elevating the Marketing Job
• (00:15:24) - WSJDLive: Devolving Authority in the AI Era
• (00:17:17) - Re-Educating the Skills of the Future
• (00:19:42) - AI and the Breaking of the Silo
• (00:21:28) - Does AI Change the Middle Manager Role?
• (00:24:13) - Why are so many AI Projects Failing?
• (00:26:18) - Projects and the Future of AI
• (00:27:46) - Energy and the AI Race
• (00:30:57) - Does Data Decentralization Enhance Business?
• (00:37:18) - CIO Network: Who Owns the Transformation in a Company?
• (00:38:44) - Confirmating the Burning Platform for Change
• (00:42:09) - Steve Jobs on Becoming an Octopus Organization

• Jay is at the forefront of Salesforce's AI initiatives.
• The focus is on integrating AI into real business operations.
• Production-grade systems are essential for measurable improvements.
• AI can significantly enhance seller productivity.
• Customer experience is transformed through AI integration.
• Enterprise outcomes can be positively impacted by AI.
• The conversation emphasizes practical applications of AI.
• Innovative approaches are necessary to tackle enterprise challenges.
• Measurable metrics are crucial for assessing AI effectiveness.
• AI is not just a demo; it's a tool for real business success.

• (00:00:00) - Meet Jay Desai
• (00:02:19) - Interview With Rich Desai
• (00:02:53) - The Scariest Thing About AI
• (00:06:22) - What's The Future of Original Content?
• (00:07:14) - Talking About the Dot-Com
• (00:07:59) - Is AI Going to Replace Human Work?
• (00:12:54) - WSJD Live: What's My Role at Salesforce?
• (00:14:53) - WSJD Live: Starting with SMB and Moving Up
• (00:16:27) - Agents on the Company's Goals
• (00:17:45) - How to Build a Real-World Agent with Agentix
• (00:19:55) - Salesforce: Data is the fuel for AI
• (00:22:17) - What's the Challenge to Content Management?
• (00:24:32) - What are the big pillars for anybody's AI or agentic strategy
• (00:25:08) - WSJD Live: The People Factor in AI
• (00:29:35) - Salesforce Agents on the Human In the Loop
• (00:35:01) - What Should Your Agent Be Looking For in AI?
• (00:41:46) - Informatica Data Cloud: End-to-End Solution
• (00:43:46) - AI Agents: The Overhyped vs Underhyped
• (00:45:58) - Williams Sonoma CEO on E-Commerce
• (00:47:05) - Is AI Driving Salesforce's Transformation?
• (00:48:38) - Dissecting the Process of Technology
• (00:49:37) - In the Elevating the AI Challenge
• (00:50:41) - Punishment

Varun Jain shares his journey from Wall Street analyst to serial entrepreneur, revealing how he's been solving the same fundamental problem—making complex business processes actually work—for 15 years. Now at ComplyJet, he's tackling the "SOC 2 deal killer problem" where startups lose customers because they can't prove compliance quickly enough.

In this conversation, Varun discusses:

• The evolution of compliance from physical binders to AI-native solutions
• How ComplyJet reduces SOC 2 compliance from 50-60 hours to 10-15 hours
• The difference between AI-native and bolt-on AI products
• Why security and compliance is fundamentally about building trust
• Practical advice for founders on when to start the compliance journey
• The future of work and what skills matter in an AI-driven world

https://www.linkedin.com/in/varun-jain-stanford/
https://www.complyjet.com/

• (00:00:00) - Business Uncomplicated: How to Make Complex Business Processes Work
• (00:01:24) - Introducing Compliance Gen
• (00:03:20) - The Process of IT
• (00:10:42) - How Can We Automate Security & Compliance?
• (00:13:14) - CIO Network: Hold Up the Security Business
• (00:14:15) - Security and Compliance for Early Startups vs. Large Companies
• (00:17:41) - How To Get Ready for SOC2 Compliance in 7 Days?
• (00:20:13) - WSJDLive: The Security and Compliance Journey
• (00:22:48) - WSJDLive: What Is an AI-Native Software?
• (00:28:23) - Human in the Loop at ComplyJet
• (00:32:15) - What is the Right Skills to Hire for AI-based Teams
• (00:37:33) - Hiring Tech Pros and Cons
• (00:39:04) - How to Create Value in Your Company
• (00:41:03) - How to Tell Your Company's Story
• (00:43:15) - Top Tech Talk: The Big Hype Around AI

• 73% of CIOs face pressure to show measurable results.
• IT must transition from order takers to strategic partners.
• Building trust is essential for IT-business alignment.
• Self-service BI empowers business users and reduces IT bottlenecks.
• CIOs are responsible for business continuity and data security.
• ROI must be attached to all IT initiatives.
• Successful digital transformation requires clear success metrics.
• Understanding business needs is crucial for IT effectiveness.
• AI should enhance human potential, not replace it.
• Data quality is foundational for effective IT solutions.

• (00:00:02) - The Denver Broncos Just Lost
• (00:00:30) - CIO Network: The CIO Conversation
• (00:02:57) - Ryan Warble on His Couple's
• (00:04:18) - The CIO Role in Private Equity
• (00:09:48) - How Has the SaaS Revolution Changed Your Approach to Transformation?
• (00:11:35) - CIO Network: The Role of the CIO
• (00:19:45) - CIO Network: The Alliance with the Executive Team
• (00:21:53) - CIO vs Private Equity: How Do You Report to the Board
• (00:25:45) - CIO Network: The Role of Revops
• (00:28:57) - Is AI a Silver Bullet for Business?
• (00:31:44) - What are people Missing in the AI Transformation?
• (00:34:44) - The Human in the Loop
• (00:35:23) - Will the Human Element Survive in the AI Era?
• (00:39:53) - CIO Network: The CIO's role in tech deals
• (00:42:13) - CIO Network: The CIO's role in the AI revolution
• (00:43:39) - CIO Network: Training and Change Management
• (00:46:32) - Questions for the Presidential Candidate
• (00:46:55) - Favorite Overhyped Tech Trend
• (00:49:14) - College and the Future of Jobs

In this conversation, Cyndi Choung shares her extensive experience in consulting and industry roles, discussing the unique aspects of both environments. The discussion delves into the challenges of business silos, particularly between IT and business, and how AI can play a role in breaking these down. Cyndi emphasizes the importance of leadership in guiding AI adoption and setting a clear vision for its integration into business processes. The conversation also touches on the evolving nature of jobs in an AI-driven world and the critical need for data quality to ensure AI's success.

• (00:00:00) - Business Uncomplicated: AI, Leadership, Business Silos
• (00:01:08) - Cindy Knows Everything About Technology and Business Strategy
• (00:02:46) - Cindy Chung
• (00:05:51) - Working in Industry vs. Consulting
• (00:08:03) - Ex-Consultant on the Other Side
• (00:11:18) - Questions for Leaders in AI and Leadership
• (00:12:35) - Business Silos
• (00:13:37) - The Business vs. the Silo
• (00:17:43) - On Breaking the Silos
• (00:22:02) - CIO Network: The AI Silos
• (00:26:59) - Payroll Executive: AI Is Here to Stay
• (00:31:01) - Will AI Make More Jobs Vacant?
• (00:35:56) - How to Coach Your Salesperson
• (00:36:58) - What Makes a Good Salesperson?
• (00:38:25) - Leadership: Art vs. Science in the AI Era
• (00:42:20) - What's the Role of Leaders in AI?
• (00:45:31) - Does a Leader Need a Strategy?
• (00:47:19) - The Script is the Foundation of a Movie