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

1. 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
2. Effective Discovery Techniques
   • The importance of listening more than speaking
   • How good discovery differentiates vendors
   • Building trust with customers through purposeful questions
3. The Power of Silence
   • Using silence as a negotiation technique
   • Training yourself to be comfortable with pauses
   • Demonstrating confidence through patience
4. Presales and Sales Dynamics
   • Developing empathy for sales counterparts
   • Understanding the complete customer lifecycle
   • Working together for customer success
5. 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

1. 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
2. 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
3. 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
4. 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
5. 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