Buy, Sell, Beware: Examining the Ethics of AI with Dianna Cappello

Today’s episode was recorded during Presales Collective’s AI-Powered Presales Summit on March 26th, 2025. In this episode, Jack Cochran (General Manager, Presales Collective) and co-host Matthew James discuss the ethics and trust issues surrounding AI in sales environments with guest Diana Capello, Director of Solutions Consulting for US and Demo Engineering at Eightfold. The discussion explores how AI is transforming the presales landscape, from creating demo environments to navigating AI buying committees and addressing hiring practices in tech. Diana shares insights from her 20-year journey in AI, offering valuable perspectives on maintaining customer trust while leveraging AI tools. To join the show live, follow the Presales Collective's LinkedIn page or join the PSC Slack community for updates. The show is bi-weekly on Tuesdays, 8AM PT / 11AM ET / 4PM GMT. Connect with Us Connect with Jack Cochran: https://www.linkedin.com/in/jackcochran/ Connect with Matthew James: https://www.linkedin.com/in/matthewyoungjames/ Connect with Diana Capello: https://www.linkedin.com/in/dianacappello/  Links and Resources Mentioned Join Presales Collective Slack: https://www.presalescollective.com/slack Presales Collective newsletter: https://www.presalescollective.com/newsletter Book Recommendation, "AI Superpowers" by Kai-Fu Lee: https://www.goodreads.com/book/show/38242135-ai-superpowers  Presales Collective's YouTube channel: https://www.youtube.com/c/PreSalesCollective Presales AI Summit recordings, available on the PSC YouTube channel: https://www.youtube.com/@presalescollective7795  Timestamps 00:00 - Introduction 01:27 - Welcome Diana Cappello 04:10 - Maintaining customer trust while using AI 06:50 - Explaining how AI works to customers 11:45 - Navigating AI councils in enterprise sales 20:34 - AI in hiring processes 27:43 - Book recommendation 31:10 - Q&A  

In this episode, Jack Cochran (General Manager, Presales Collective) and guest co-host Allison Macalik dive into the topic of "Presales People in Disguise" with Alex Nation. They explore the journey into presales roles, the importance of effective discovery techniques, the power of silence in customer interactions, and the unique relationship between presales professionals and sales teams. Alex shares valuable insights from her career transition from retail to tech, highlighting key skills that have made her successful in the presales world. To join the show live, follow the Presales Collective's LinkedIn page or join the PSC Slack community for updates. The show is bi-weekly on Tuesdays, 8AM PT/11AM ET/4PM GMT. Find us: Connect with Jack Cochran: https://www.linkedin.com/in/jackcochran/ Connect with Allison Macalik: https://www.linkedin.com/in/allisonmacalik/ Connect with Alex Nation: https://www.linkedin.com/in/alexandranation/  Links and Resources Mentioned Join Presales Collective Slack: https://www.presalescollective.com/slack Presales Collective newsletter: https://www.presalescollective.com/newsletter Timestamps 00:00 - Introduction 02:48 - Alex's background and journey into presales 08:59 - The importance of being a presenter pain point gatherer 10:40 - The power of effective discovery 14:24 - The art of silence in customer interactions 20:26 - Presales vs. Sales 26:20 - Advice to younger self 29:25 - How to find Alex Key Topics Covered Career Transitions into Presales Alex's journey from Nordstrom to tech Finding your strength as a "presenter pain point gatherer" The accidental path many take into presales roles Effective Discovery Techniques The importance of listening more than speaking How good discovery differentiates vendors Building trust with customers through purposeful questions The Power of Silence Using silence as a negotiation technique Training yourself to be comfortable with pauses Demonstrating confidence through patience Presales and Sales Dynamics Developing empathy for sales counterparts Understanding the complete customer lifecycle Working together for customer success Career Development The unique pressures and rewards of presales Developing flexibility and resilience Creating paths for women in presales  

In this episode, Jack Cochran and Matthew James are joined by Manisha Raisinghani, Founder and CEO of SiftHub, to discuss how AI is transforming the Presales landscape. They explore how SiftHub's AI sales engineer helps solutions teams consolidate tribal knowledge, automate repetitive tasks, and increase productivity. Manisha shares insights on leveraging AI for RFPs, POCs, and competitive intelligence, while emphasizing that AI serves as a sidekick to enhance SEs' strategic value rather than replace them. To join the show live, follow the Presales Collective's LinkedIn page or join the PSC Slack community for updates. The show is bi-weekly on Tuesdays, 8AM PT/11AM ET/4PM GMT. Follow the Hosts Connect with Jack Cochran: https://www.linkedin.com/in/jackcochran/  Connect with Matthew James: https://www.linkedin.com/in/matthewyoungjames/ Connect with Manisha Raisinghani: https://www.linkedin.com/in/manisharaisinghani/ Links and Resources Mentioned Join Presales Collective Slack: https://www.presalescollective.com/slack SiftHub: https://www.sifthub.io/  Timestamps 00:00 Welcome 03:34 Manisha's journey to founding SiftHub 08:12 SE to AE ratios in different organizations 13:10 The changing role of SEs in relationship building 15:06 Three main buckets of SE work and how AI can help 16:30 The evolution of tribal knowledge 20:40 SaaS proliferation and knowledge fragmentation 26:51 How SEs can leverage AI effectively 31:02 Using AI to analyze POCs and RFPs Key Topics Covered The Evolution of Tribal Knowledge From undocumented information to knowledge scattered across platforms How AI can consolidate knowledge from Slack, Salesforce, call recordings, and more Leveraging recorded conversations to preserve context and insights SE Challenges and AI Solutions Managing repetitive questions from sales teams and product managers Handling documentation tasks and RFP responses Creating custom solutions across different industries and regions The Changing SE Role Shift from technical support to relationship building Evolving buyer journeys requiring deeper technical engagement Balancing solutioning, question-answering, and demo responsibilities Measuring AI Impact Time savings on RFP responses and repetitive questions Using freed-up time for strategic activities and better customer engagement Supporting more deals simultaneously with AI assistance AI as a Teammate Using AI to enhance rather than replace SE capabilities How AI can work 24/7 across global teams The future of visual and diagram-based AI assistance

In this episode, Jack Cochran and Matthew James talk with Kalyan Ramkumar about his journey from novice to expert in the presales field. Kalyan shares his experience starting as an SDR at RSA Security with no technical background and how he worked his way up to become a skilled solutions engineer. He discusses the importance of domain knowledge in security, his framework for effective demos, and strategies for managing POCs and building your internal brand. To join the show live, follow the Presales Collective's LinkedIn page or join the PSC Slack community for updates. The show is bi-weekly on Tuesdays, 8AM PT/11AM ET/4PM GMT. Follow the Hosts Connect with Jack Cochran: https://www.linkedin.com/in/jackcochran/ Connect with Matthew James: https://www.linkedin.com/in/matthewyoungjames/ Connect with Kalyan Ramkumar: https://www.linkedin.com/in/kalyan-ramkumar-679927151/ Links and Resources Mentioned Join Presales Collective Slack: https://www.presalescollective.com/slack Presales Collective Linkedin: https://www.linkedin.com/company/presalescollective Presales Collective newsletter: https://www.presalescollective.com/newsletter CompTIA Security+ Certification: https://www.comptia.org/certifications/security CompTIA Network+ Certification: https://www.comptia.org/certifications/network Timestamps 00:00 Introduction 03:15 Kal’s Background 10:12 First Ever Demo 14:10 When did you know you’re an SC 19:40 The Four Do's of Demos 23:35 Challenging the challenger 27:02 Building your personal brand 29:35 POC strategies  Key Topics Covered Breaking into Presales Starting as an SDR and transitioning to SE Getting hired without technical background Importance of work ethic and eagerness to learn Building Domain Expertise Value of security certifications (Security+ and Network+) Moving from scripted to fluid demos Building trust with technical customers Demo Framework: The Four Do's Conducting your own discovery Framing every click and feature Evaluating specific customer KPIs Challenging difficult stakeholders POC and Success Strategies Customizing POC length to customer needs Collaborating with account executives Building internal relationships Creating workshop sequences for implementation

In today's episode, Jack Cochran and Matthew James sit down with David Yockelson, Distinguished VP and Gartner Fellow, to discuss the evolution of value realization in tech sales. They explore how buyer behaviors have changed, the importance of understanding customer needs before leading with technology, and practical approaches for pre-sales professionals to shift towards value-based selling. To join the show live, follow the PreSales Collective's LinkedIn page or join the PSC Slack community for updates. The show is bi-weekly on Tuesdays, 8AM PT/11AM ET/4PM GMT. Follow the Hosts and Guest Connect with Jack Cochran: https://www.linkedin.com/in/jackcochran/ Connect with Matthew James: https://www.linkedin.com/in/matthewyoungjames/ Connect with David Yockelson: https://www.linkedin.com/in/david-yockelson-452324/  Links and Resources Mentioned Join PreSales Collective Slack: https://www.presalescollective.com/slack PreSales Collective newsletter: https://www.presalescollective.com/newsletter Timestamps 00:00 Introduction 03:33 The current issues in tech 10:48 How to stop talking about your tech to focus on value 23:04 Understanding your customer’s business 27:55 The place of demos on the website 31:15 Practical approaches to shifting to value   Key Topics Covered Changes in B2B Tech Buying Diversification of buying teams Shift from technical to business-focused decisions Evolution of the buying process Increased financial scrutiny on deals Value-Based Selling Approaches Understanding buyer personas and value drivers Moving beyond technical features Building and defending business cases Articulating value to different stakeholders Pre-Sales and Marketing Collaboration Alignment between product marketing and SEs Value modeling and demonstration strategies Website demo effectiveness Data collection and buyer insights Interactive Demonstrations Role of self-service demos Converting website visitors Collecting valuable user interaction data Creating warmer sales conversations Practical Implementation Leveraging SE expertise across the sales cycle Demonstrating impact on revenue Supporting customer success and adoption Documenting value contribution  

Show Notes In today's episode, Dean Shu (CEO & Co-founder, Arphie) joins Jack Cochran and Matthew James to discuss AI agents in PreSales and the evolution of the industry. They explore the changing landscape of PreSales leadership, practical applications of AI, and strategies for evaluating AI solutions. Thank you to Arphie for sponsoring this episode. Arphie is the leading AI-powered platform for automating RFPs and security questionnaires. Arphie empowers teams — from the Fortune 500 to high-growth startups — to save time, improve accuracy, and deliver results faster than ever by combining your prior responses and company context with the latest AI agent capabilities. To join the show live, follow the PreSales Collective's LinkedIn page. PreSales LIVE airs bi-weekly on Tuesdays, 8AM PT/11AM ET/4PM GMT. Links and Resources Mentioned Join the Presales Collective Slack:https://presalescollective.com/slack Contact Dean Shu: [email protected] https://www.linkedin.com/in/dean-shu/  LE SSERAFIM, Crazy EP: https://open.spotify.com/album/538vEfAgLJ6g2I8ubuOlap?si=so9xz_qMQBatFqHMDTp5sw  Hidden Brain podcast episode with Brian Klass - https://open.spotify.com/episode/5MowfIBQdmQEIMYdDL3MYK?si=fff1b1731daa48ff  Timestamps  00:00 - Introduction 03:13 - What are you listening to 06:30 - Dean's background 09:20 - What's top of mind for presales leaders? 11:57 - How to make a presales tech purchase 20:13 - What are AI agents? 26:40 - How do you properly explore AI? 32:25 - Is AI going to replace people? 35:41 - Outro Key Topics Covered PreSales Leadership Evolution Elevating the sales engineering role Building stronger cross-functional partnerships Gaining executive-level presence Understanding AI in PreSales Different types of AI models and their applications AI agents vs. traditional AI tools Real-world implementation strategies Evaluating AI Solutions Key criteria for vendor selection Security considerations Proof of concept best practices  

In this episode, Jack Cochran (General Manager, PreSales Collective) and Matthew James discuss the human qualities of presales leadership with special guest Ron Whitson. Ron shares insights from his 30-year career in the industry, discusses his book "A Friendly Human in Presales," and explores how leaders can effectively transition from being top individual contributors to successful team leaders. To join the show live, follow the PreSales Collective's LinkedIn page. PreSales LIVE airs bi-weekly on Tuesdays, 8AM PT/11AM ET/4PM GMT. Links Follow the Hosts & Guest Connect with Jack Cochran: https://www.linkedin.com/in/jackcochran/ Connect with Matthew James: https://www.linkedin.com/in/matthewyoungjames/ Connect with Ron Whitson: https://www.linkedin.com/in/ronwhitsonse/ Links and Resources Mentioned PreSales Collective Slack: https://www.presalescollective.com/slack Ron's Book "A Friendly Human in Presales": https://a.co/d/gJIwWE7 She Means Biz Podcast:  https://open.spotify.com/show/3zx8BmZ9PrURuASJbAemDu?si=26772c8356854348 Talking Too Loud with Chris Savage Podcast:  https://open.spotify.com/show/21btwSaqoaF8SDxmwcLMIQ?si=37aa691ee80b4a0f  Timestamps 00:00 Welcome and Introductions   03:54 What are you Listening to?   07:23 Ron's Journey to PreSales Leadership   13:56 Transitioning from IC to Leader   16:12 Coaching vs. Telling 19:11 One Plus One is More than Two 21:17 Importance of One-To-Ones   26:02 Coaching your Team to be Different than You   31:15 Practice Humility Key Topics Covered 1. Leadership Transition Moving from individual contributor to leader Common challenges and mindset shifts IBM's leadership training program insights 2. Essential Leadership Qualities Empathy and humility in leadership Balancing directness with support Creating space for team growth Regular one-on-one communications 3. Effective Team Development Coaching approaches vs. direct instruction Building trust and relationships Removing roadblocks for team success Understanding personality types 4. Practicing Humility as a Leader Provide room for your team to take the spotlight Be open to different ways of doing things Listen more and speak less

In today’s episode, Jack Cochran (General Manager, PreSales Collective) and new co-host Matthew James discuss the evolution of PreSales Collective and key industry trends for 2025. They announce the expansion of local PSC chapters, tease upcoming leadership conferences, and explore controversial topics like AI in pre-sales and team structure debates. The episode offers insights into career development opportunities beyond traditional paths and emphasizes the importance of community involvement in shaping the future of pre-sales. To join the show live, follow the PreSales Collective’s LinkedIn page or join the PSC Slack community for updates. The show is bi-weekly on Tuesdays, 8AM PT/11AM ET/4PM GMT.   Follow the Hosts Connect with Jack Cochran: https://www.linkedin.com/in/jackcochran/  Connect with Matthew James: https://www.linkedin.com/in/matthewyoungjames/    Links and Resources Mentioned Follow the PreSales Collective's LinkedIn Page: https://www.linkedin.com/company/presalescollective Join PreSales Collective Slack: https://www.presalescollective.com/slack  PreSales Collective newsletter: https://www.presalescollective.com/newsletter Simon Sinek's "A Bit of Optimism" podcast episode with Trevor Noah: https://simonsinek.com/podcast/episodes/trevor-noah-makes-my-brain-hurt/  Jack's YouTube video on microphone quality: https://youtu.be/B6nl64Sv7pw?si=wtOud1fS27ryqavI    Timestamps 00:00 - Welcome 01:26 - PSC Unlimited 02:34 - Show Kickoff 05:20 - Regional Community Leader Launch 12:24 - In-Person Leadership Conference Teaser 16:12 - Changes to PreSales LIVE & PreSales Podcast 18:02 - What Have You Been Listening To? 22:03 - Topics for 2025 28:16 - How to Get Involved in the PSC   Key Topics Covered 1. PreSales Collective Updates Launch of PreSales Live show New regional community leader program Upcoming leadership conferences (announcement pending) Slack community surpasses 16,000 members 2. Industry Trends for 2025 Presales influence within organizations Career paths and organizational changes Moving beyond demo-centric roles AI and automation in presales Team structure debates (pre/postsales integration) 3. Getting Involved Regional Community Leader opportunities Content creation and speaking opportunities Local chapter participation Blog writing and podcast guest appearances

As 2025 approaches, the PreSales Podcast has some exciting changes coming! First and foremost, Matthew James is joining Jack Cochran as co-host of the podcast. Also, starting in January, the show will be recorded live on LinkedIn via the new show PreSales LIVE! Join Matthew and Jack as they talk to guests and answer a live Q&A at the end of each episode.  

Today on the PreSales Podcast we have an exciting announcement, we have the pleasure and opportunity to announce the next General Manager at PreSales Collective, Jack Cochran. We talk about this exciting new chapter for PreSales Collective, how we are expanding with a new PreSales Collective board of directors, the excitement of hitting the milestone of 50,000 members, and the community's future.  What I love most about Jack is that he is deeply rooted in this thing, he has experience running communities, content creation, like his podcasts, and a passion to drive the collective forward. We discussed Chris' proudest moments here, lessons learned over the past 17 months, and his transition into the board of directors.  Chris will still be extremely active in the community at large. This is a story between two humans, discussing our love and appreciation for this profession. I am thrilled to see this organization continue to help people worldwide, so let’s jump right in with Jack.  Thank you so much for tuning in. I hope you enjoyed as much as I did.