The Unexpected Lever

Building a new sales motion from scratch—where do you start? 

In this episode, Jarod Greene sits down with Zach Miller, CRO of VanillaSoft, about the real challenges of creating an enterprise sales strategy without disrupting a successful SMB pipeline. Zach shares the hurdles of transitioning to long-cycle, multi-stage deals and the importance of surrounding yourself with the right team.

In this episode, you’ll learn:

1. Building an Enterprise Sales Motion from Scratch: Establishing an enterprise sales motion requires careful planning to maintain an existing SMB pipeline, balancing new processes with proven success in smaller markets.
2. The Power of Team Alignment: Having the right people with clear objectives allows for efficient scaling and helps tackle challenges as they arise.
3. Challenges of Long Sales Cycles: Staying focused on core priorities is essential to managing the complexity of multi-stage deals without being overwhelmed by details.
4. Filling Knowledge Gaps as a CRO: Broadening expertise beyond traditional sales, especially in marketing and SDR functions, can be crucial for a CRO stepping into an enterprise role.

Things to listen for:
(00:00) Zach Miller’s hot take on building an enterprise sales motion

(00:28) The challenge of balancing enterprise and SMB sales

(01:15) Tackling the hurdles of starting an outbound motion from scratch

(02:15) Keeping priorities straight while adapting to a constantly changing sales landscape

(02:41) The importance of team alignment and focusing on key outcomes

(04:07) Advice for first-time CROs on filling knowledge gaps beyond traditional sales

Most AI knows how to respond—but does it know how to solve real SE problems?

In this episode, CEO Matt Darrow sits down with Vivun’s Sr. Machine Learning Engineer, Chen Liang, to explore why most AI just isn’t cut out for sales engineering—yet.

While language models like ChatGPT are powerful, they lack the insider knowledge and finesse that make sales engineers irreplaceable. Matt and Chen dive into Vivun’s unique approach to building AI agents that don’t just predict answers but deliver reliable, actionable insights grounded in real-world experience.

Discover how structured knowledge framework and top-down procedural graph prevent AI hallucinations and keep AI agents aligned with SE needs.

In this episode, you’ll learn:

1. Structured Knowledge for Smarter AI: Crafting a reliable AI system begins with a structured approach to knowledge, ensuring AI agents operate with accuracy and industry insight.
2. Preventing AI Hallucinations: Large language models often generate misleading responses, but with domain-specific guidance, AI can deliver more trustworthy results.
3. Real-Time Improvement Through User Feedback: Tracking user interactions, like the “frustration index,” helps AI continuously evolve and meet real-world demands.
4. AI as a Collaborative Team Player: Rather than just a tool, AI can become a partner in sales engineering, supporting complex decision-making with structured, actionable insights.

Things to listen for:
(00:00) Why AI alone isn’t enough for sales engineering

(05:09) How structured knowledge reduces AI hallucinations

(07:44) Using a knowledge graph to keep AI on track

(10:28) The importance of evaluation for AI reliability

(13:25) Real-world examples of AI’s limitations without domain knowledge

(15:23) Quantitative vs. qualitative methods for AI evaluation

(16:36) Real-time feedback and the “frustration index”

(18:46) Human-in-the-loop and automated quality checks

(20:05) Enhancing AI with ongoing data and real-time adjustments

Is the future of inbound sales powered by AI SDRs?

In this episode, Jarod Greene sits down with Blue Bowen, Research Principal at G2, to explore the game-changing role of AI SDRs in inbound lead management. AI is reshaping the buyer experience, and if companies shift focus to inbound leads, it can provide immediate wins. Tune in to learn how companies can leverage AI tools to drive more meaningful connections with potential customers.

In this episode, you’ll learn:

1. How AI SDRs Can Enhance the Buyer Experience: Using AI-powered SDRs for inbound leads can streamline engagement, providing a timely, tailored experience for buyers, which boosts buyer enablement and ultimately drives success in a competitive market.
2. Balance AI and Human Interaction: For companies hesitant to adopt AI, Blue suggests starting with AI as a supportive tool rather than a replacement. This helps nurture and enrich inbound leads while maintaining a human touch.
3. Speed in Engagement Matters: Prompt responses are key—delays can push prospects toward competitors. AI SDRs can improve the chances of winning deals by responding swiftly and effectively.

For additional insights on 2025 Sales Trends, see Blue’s research in this G2 post.

Things to listen for: 

(00:00) Introduction

(00:27) Why inbound leads are the key focus for AI SDRs

(01:00) Differentiating between autonomous AI and co-piloting in sales

(01:31) The importance of nailing the basics for inbound lead management

(01:53) How AI SDRs can improve inbound processes

(02:36) The rise of AI tools and their impact on sales productivity

(03:15) How the buyer experience drives sales success

(03:52) Why timely responses and effective communication matters

Is hiding your pricing costing you more than you realize?

In this episode, Jarod Greene sits down with Mark Huber, VP of Marketing at UserEvidence, as he shares his candid thoughts on the frustration of hidden pricing in B2B SaaS. He unpacks why transparent pricing is needed to build trust with buyers and how outdated sales tactics waste time for both teams and customers.

In this episode, you’ll learn:

1. The Importance of Price Transparency: Openly sharing your pricing can build trust with buyers and lead to faster decision-making.
2. Avoid Time-Wasting Sales Tactics: Hidden pricing can frustrate potential customers and waste valuable time for both your sales team and prospects.
3. Weed Out the Wrong Leads Early: Transparent pricing helps qualify leads from the start, saving your team from chasing prospects who can’t afford your product.

Things to listen for:

(00:00) Missing pricing information on pricing pages

(01:15) The impact of hidden pricing on the buyer's journey

(01:53) Inefficient demo calls without pricing transparency

(02:25) Weeding out unqualified leads through transparent pricing

(03:49) Why signal-based selling practices are absurd

ChatGPT may excel in conversation, but it’s not equipped to tackle the complex challenges that sales engineers face.

In this episode, CEO Matt Darrow speaks with Vivun’s Product & AI Leader, Russell Witham, about the criteria for AI that actually “gets” sales engineering. 

Most existing models fail to appreciate the complexity and true value of SE work, resulting in outputs that fall short of what great sales engineers produce. 

Tune in to discover a new, innovative approach to empowering sales engineers with AI that understands them. 

In this episode, you’ll learn:

1. The Essence of Sales Engineering: The core role of a sales engineer lies in crafting tailored solutions that address customer needs rather than simply answering product questions or filling out RFPs. 
2. The Limitations of Current AI Models: While AI and large language models are gaining traction, they often lack the nuanced understanding required for effective sales engineering. Successful integration of AI requires structured data and a top-down approach to fully leverage its potential in sales processes.
3. The Four Core Benefits AI for PreSales: By focusing on the 60% of what SEs do, AI can free SEs from administrative burdens, collapse enablement times, improve agility to pursue new target markets, and increase operational efficiency.

Things to listen for:

(00:00) How companies are using AI in sales engineering
(04:42) The essence of a sales engineer's role
(08:48) Why Claude & ChatGPT isn’t good enough
(10:03) The importance of structured data for effective solutions in sales engineering
(11:53) The need for detailed knowledge representation in AI applications
(15:46) Why current AI approaches fall short for sales engineering

Time is a critical factor in B2B sales success.

In this episode, Jarod Greene sits down with Kyle Smith, Managing Partner at The Bridge Group, to discuss the impact of direct alignment between sales engineers and account executives on customer experiences. Kyle shares his insights from the Sales perspective on how avoiding pooled resources can lead to smoother interactions and stronger client relationships.

In this episode, you’ll learn:

1. The Dangers of Resource Pooling: Kyle explains why pooling sales engineers can create a disconnect in the sales process and how it can lead to a less personalized customer experience.
2. Enhancing AE-SE Collaboration: Fostering effective partnerships between account executives and sales engineers ensures seamless communication and efficiency.
3. The Importance of Customized Demos: Learn how a well-prepared and targeted demo can address customer pain points, ultimately leading to higher conversion rates.

Things to listen for:

(00:00) The value of direct alignment in sales
(00:35) Why pooled resources can create unnecessary challenges
(01:50) Best practices for AE-SE collaboration
(02:45) The role of preparation in customer interactions
(03:30) How personalized demos enhance the buyer's journey
(04:15) Navigating organizational complexities in sales

Are we truly listening to our buyers?

In this episode, Jarod Greene sits down with Natalie Marcotullio, Head of Growth  and Operations at Navattic, as she shares about the pitfalls of traditional sales approaches, the importance of empowering buyers with the information they need, and how shifting our mindset can lead to stronger, more effective sales relationships.

In this episode, you’ll learn:

1. Trust Your Buyers: Buyers often have a deeper understanding of their own problems than sales representatives do about the product. Respect and leverage buyer insights to your advantage.
2. Rethink Sales Interactions: BDRs should lead meaningful discussions about buyers' challenges and goals, enabling AEs to offer tailored solutions for more productive engagements.
3. Empower Buyers with Information: Instead of gatekeeping information, give buyers the resources they need to qualify themselves.

Things to listen for:

(00:00) B2B sales process should focus on the buyers, not on sales reps
(01:10) Why BDRs might not be the best first interaction
(02:42) How demo automation has enhanced buyer journeys at Navattic
(03:04) Advice for CROs resistant to sharing information early
(04:22) Research report on the buyer-friendliness of Top 100 SaaS companies

AI is transforming the way PreSales teams operate. 

In this episode, Jarod Greene sits down with Leah McTiernan, Global Vice President of PreSales at Docusign, as she shares her perspective on how AI is streamlining workflows, boosting team morale, and enabling more meaningful, strategic work. Learn how AI is enhancing the PreSales role to build stronger customer relationships and deliver greater value.

In this episode, you’ll learn:

• How AI Transforms PreSales Efficiency: Leah explains how AI automates time-consuming tasks like demo creation and research, allowing PreSales teams to focus on more strategic activities like consultative selling and personalized customer engagements.
• The Role of AI in Boosting Morale and Innovation: Discover how AI integration improves workflows and enhances team morale by fostering innovation, leading to more excitement and engagement within the team.
• Why AI Enhances, Not Replaces, PreSales Roles: Leah addresses the common concern of AI replacing jobs, showing how AI complements PreSales by allowing professionals to spend more time on meaningful, strategic work, making their roles more valuable and fulfilling.

Things to listen for:

(00:00) Incorporating AI into PreSales workflows
(01:49) Will AI replace PreSales roles?
(03:03) Boosting morale through AI-driven innovation
(04:20) AI-powered tools used by Docusign

Time is the most valuable commodity for pre-sales teams. 

In this episode, Jarod Greene sits down with David Yockelson, Distinguished Vice President and Gartner Fellow, as he shares his insights on how driving efficiency in collaborative efforts with account executives can lead to more effective business cases and stronger customer relationships.

In this episode, you’ll learn:

1. The Importance of Time in PreSales: David highlights how presales teams often struggle with managing their time effectively. Streamlining processes like demo automation and interactive demos can give them valuable hours to focus on higher-level tasks.
2. Collaborative Business Case Development: Learn how presales professionals can work more closely with account executives to build compelling, personalized business cases that resonate with customers and help drive sales.
3. Understanding Customer Needs: Discover how sales engineering teams can better understand and address individual customer needs, ensuring that solutions are relevant, impactful, and aligned with the customer’s unique goals.

Things to listen for:

(00:00) The most valuable commodity for pre-sales teams

(00:56) The challenges with time management

(02:13) How to effectively move prospects through the funnel

(03:13) The role of pre-sales in developing business cases

(04:23) The impact of demo automation on pre-sales efficiency

(05:51) Why ROI stories need to be personalized to the customer

Is discovery or demos the secret weapon in sales?

In this episode of V5, host Jarod Greene chats with Tom Josephson, Director of Solution Consulting at TCP Software, about a controversial take: demos aren’t as crucial as everyone believes. Find out how mastering discovery can lead to deeper customer connections and more successful deals.

In this episode, you’ll learn:

• The Power of Discovery: Tom explains why understanding your buyer’s needs through effective discovery can give you an edge over competitors, even when pricing becomes a factor.
• Shifting the Focus: Setting clear expectations for demos ensures they are laser-focused on what matters most to the customer.
• Value-Based Selling: Tom shares insights on how to sell capabilities during discovery, getting buyers excited and showing alignment long before the demo.

Things to listen for:

(00:00) Demos don’t matter, discovery does

(00:45) Lessons Tom learned from the deals he lost and won

(02:07) Why strong discovery sets up the demo for success

(03:02) What to do when a prospective client requests early demos

(03:53) Steps to secure buy-in on the importance of discovery