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Selling Intelligence (formerly Selling the Cloud)

Selling Intelligence (formerly Selling the Cloud)

Von: Mark Petruzzi Alan Rudolph
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Selling Intelligence is the evolution of Selling the Cloud and designed for revenue leaders who are navigating the AI era.

Hosted by Mark Petruzzi and Alan Rudolph, the show brings candid conversations with C-suite leaders across sales, marketing, and customer success on how AI is reshaping the way companies grow, sell, and compete.

From agentic GTM strategies to AI-powered pipeline and revenue execution, each episode focuses on what’s actually working and how leaders are turning intelligence into performance.

If you’re responsible for growth and trying to lead through the fastest shift in go-to-market we’ve ever seen, this podcast is for you.


© © 2026 Selling the Cloud Management & Leadership Ökonomie
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  • Ep. 150 - Building Trust, Networks, and Revenue Growth with Todd Cassler - Part 2

    Ep. 150 - Building Trust, Networks, and Revenue Growth with Todd Cassler - Part 2
    Oct 28 2026
    In Part 2 of Selling Intelligence, Todd Cassler, Chief Revenue Officer at Wilshire, rejoins Mark Petruzzi and KK Anderson to explore how revenue leaders build organizations that can execute across different buyers, channels, and levels of complexity.Todd shares his “future back” approach to revenue strategy, starting with the outcome the organization needs to achieve and working backward to align talent, priorities, reporting, and pipeline discipline. He also explains how leaders should approach third-party distribution as a true partnership, giving external sales teams the same support, resources, and accountability they would provide on their own.The conversation then turns to AI and its role in modern selling. Todd explains why experience, context, and the ability to ask great questions can dramatically increase the value sellers get from AI. He shares how AI can help identify signals and “money in motion” events, allowing salespeople to focus their limited time on relationships and opportunities where change may actually be happening.Todd also shares his approach to coaching the next generation of talent, why people need to take ownership of their careers, and how investing early in personal development can compound over time.What You’ll Learn:Building Revenue Strategy Backward: How a future back approach connects long-term goals with talent, priorities, KPIs, and pipeline execution.Selling Across Different Buyer Tiers: How team structure and specialization should evolve based on organizational size and buyer sophistication.Making Distribution a True Partnership: Why third-party sales teams need the same support, resources, communication, and accountability as internal teams.Using Leading Indicators to Measure Progress: How activity, pipeline movement, relationships, and business trends can reveal performance before revenue appears.Where AI Creates Sales Leverage: How experienced sellers can use AI, context, and better questions to identify signals and prioritize opportunities.Taking Ownership of Your Career: Why personal development is the career lever individuals can control and how early investments in learning can compound over time.Key Topics:Future back revenue strategyBuilding teams for multi-tiered buyersGeneralists versus technical specialistsChannel sales and third-party distributionPipeline hygiene and KPI measurementLeading indicators of sales performanceAI as a multiplier for experienced sellersIdentifying money in motion signalsAI and sales territory prioritizationCoaching and mentoring emerging talentPersonal, corporate, and compensation developmentHiring for attitude and driveCuriosity as a leadership skillGuest Spotlight: Todd CasslerTodd Cassler is Chief Revenue Officer at Wilshire, where he leads global growth and distribution across wealth management, retirement, alternatives, and data and analytics. With more than 20 years of experience across wealth management, asset management, and institutional advisory, Todd brings a practical perspective on building revenue organizations, developing talent, strengthening distribution partnerships, and using technology to improve sales execution.Resources & Mentions:Book: Never Eat AloneWilshireLinkedInAI for sales and opportunity identificationCareer development and mentorship🎧 Listen now and follow Selling Intelligence for more insights from revenue leaders on building stronger teams, using AI effectively, and creating sustainable revenue growth. Subscribe wherever you get your podcasts.Disclosures:Recording Date: August 10, 2026This does not constitute advice or a recommendation or offer to sell or a solicitation to deal in any security or financial product. Except where otherwise indicated, the information contained in this presentation is based on matters as they exist as of the date of preparation of such material and not as of the date of distribution or any future date.The views and opinions expressed are those of the speaker and do not represent Wilshire as a whole.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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    23 Min.
  • Ep. 149 - Building Trust, Networks, and Revenue Growth with Todd Cassler - Part 1

    Ep. 149 - Building Trust, Networks, and Revenue Growth with Todd Cassler - Part 1
    Oct 21 2026
    In this episode of Selling Intelligence, Todd Cassler, Chief Revenue Officer at Wilshire, joins Mark Petruzzi and KK Anderson to explore the fundamentals that drive trust, stronger relationships, and sustainable revenue growth.Todd explains the three questions every buyer is trying to answer: Can I trust you? Do you add value? Will you put my interests ahead of your own? He shares how preparation, thoughtful follow-up, and consistent execution help sellers earn that trust over time, especially in complex enterprise sales where relationships can take multiple interactions to develop.The conversation also introduces Todd’s concept of “Network Alpha,” the ability to activate the right relationships at the right time to create favorable outcomes. Todd explains why having a large network is not enough, how sellers can create “presence in their absence,” and why leaders should deliberately train teams to build and activate stronger professional networks.Todd also breaks down why sales teams need focus when managing a broad portfolio. Rather than expecting sellers to master everything, leaders should identify the few opportunities that are truly sellable while training their teams to recognize signals and uncover opportunities that may be hiding on the margins.What You’ll Learn:The Three Questions Every Buyer Asks: Why trust, value, and alignment of interests shape every sales relationship.Building Trust Through Execution: How preparation, responsiveness, and following through on commitments strengthen buyer confidence.Understanding Network Alpha: How activating the right relationships at the right time can create new opportunities and accelerate growth.Creating Presence in Your Absence: Why referrals, advocates, and strong professional relationships can extend your influence beyond direct conversations.Focusing on What Is Sellable: Why salespeople can only deeply focus on a few priorities and how leaders can distinguish between what is sellable and what is simply tellable.Finding Opportunities on the Margin: How curiosity, observation, preparation, and better questions help sellers uncover needs buyers may never state directly.Key Topics:Building buyer trust in complex salesTrust, value, and customer-first sellingNetwork Alpha and relationship-driven growthTurning professional networks into business opportunitiesCreating advocates and referral networksBuilding networking skills across a sales organizationSales preparation and follow-up disciplinePrioritizing three to four key sales opportunitiesSellable versus tellable products and solutionsAsking better questions and identifying hidden opportunitiesGuest Spotlight: Todd CasslerTodd Cassler is Chief Revenue Officer at Wilshire, where he leads global growth and distribution across wealth management, retirement, alternatives, and data and analytics. With more than 20 years of experience across wealth management, asset management, and institutional advisory, Todd brings a relationship-driven approach to building sales organizations, developing networks, and creating sustainable revenue growth.Resources & Mentions:Book: Never Eat AloneWilshireLinkedIn🎧 Listen now and follow Selling Intelligence for more insights from revenue leaders on building trust, strengthening sales organizations, and driving sustainable growth. Subscribe wherever you get your podcasts.Disclosures:Recording Date: August 10, 2026This does not constitute advice or a recommendation or offer to sell or a solicitation to deal in any security or financial product. Except where otherwise indicated, the information contained in this presentation is based on matters as they exist as of the date of preparation of such material and not as of the date of distribution or any future date.The views and opinions expressed are those of the speaker and do not represent Wilshire as a whole.Mark Petruzzi (00:29)Welcome to Selling Intelligence, the weekly conversation for chief revenue authors and the leaders who build revenue teams.I'm Mark Petruzzi here as always with my co host KK Anderson.KK Anderson (00:41)Thanks, Mark. Here's the number that frames today's conversation. It takes six to ten interactions to build trust with someone before you can sell them anything. Six to ten. Now think about how most teams are running outreach right now, and you can see the gap.Mark Petruzzi (00:58)Our guest today has spent more than 20 years building distribution across wealth management, asset management, and institutional advisory. He is the Chief Revenue Officer at Wilshire, a firm with more than one and a half trillion dollars under advisement. Todd, welcome to the show.Todd Cassler (01:17)Mark, hi KK.KK Anderson (01:19)All right. Well let's dig right in, Mark.Mark Petruzzi (01:21)Okay, let's start off with topic one, the three questions every buyer asks. Todd, you have sold in nearly every market and channel there is. Direct to consumer and enterprise, the US, EMEA, Latin America. You told us that ...
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    23 Min.
  • Ep. 148 - Building the Revenue Engine with Chris Kobus - Part 2

    Ep. 148 - Building the Revenue Engine with Chris Kobus - Part 2
    Oct 14 2026
    In Part 2 of Selling Intelligence, Chris Kobus, Chief Revenue Officer at Genlogs, joins Mark Petruzzi and KK Anderson to explore how revenue leaders can balance immediate sales performance with the strategic decisions that drive long-term growth. From forecasting pipeline requirements and planning future headcount to developing a disciplined approach to value selling, Chris shares how he connects day-to-day execution with the broader needs of a growing business.Chris explains why effective revenue planning requires more than setting bookings targets and calculating pipeline coverage. Leaders must understand conversion rates, average deal sizes, sales cycles, rep productivity, and onboarding timelines to determine when and where to invest in their teams. He also introduces a four-stage value selling framework designed to help customers understand the business impact of unfamiliar technology. By identifying customer challenges, connecting them to measurable business priorities, demonstrating differentiated capabilities, and quantifying financial outcomes, sales teams can build stronger business cases and create meaningful buying conversations.The conversation also examines the growing role of artificial intelligence in sales organizations. Chris discusses why AI adoption requires both urgency and discipline, emphasizing the importance of internal ownership, measurable value, and ongoing adoption. He highlights how AI tools can help revenue teams analyze customer interactions, identify missing information in sales opportunities, and improve execution across the sales process. For CROs, sales executives, and go-to-market leaders, this episode offers practical insights into building a revenue organization that can deliver results today while preparing for future growth.What You’ll Learn:Balancing Short-Term Execution with Long-Term Growth: How revenue leaders can support current-quarter opportunities while planning future pipeline requirements, headcount investments, and strategic business priorities.Building a Data-Driven Revenue Capacity Plan: Why pipeline conversion rates, average contract values, sales cycles, quota attainment, and rep ramp times are essential to determining the right hiring and investment strategy.Applying a Four-Stage Value Selling Framework: How to guide customers from identifying business challenges and understanding their importance to evaluating differentiated solutions and quantifying potential financial returns.Creating Better Discovery Conversations: Why understanding what motivated a prospect to engage can help sellers uncover business problems, evaluate existing solutions, and build a more relevant value proposition.Driving Meaningful AI Adoption in Sales: How organizations can evaluate AI investments, establish internal ownership, measure business impact, and use customer interaction data to improve sales execution.Key Topics:Balancing quarterly revenue execution with multiyear growth planningConnecting customer feedback with product development and future revenue opportunitiesPipeline forecasting, sales capacity modeling, and headcount planningSales onboarding, rep productivity, and quota attainment assumptionsBuilding financial business cases for emerging technology solutionsDiscovery strategies for identifying customer challenges and buying motivationsAI adoption, internal accountability, and measurable business valueUsing AI to analyze sales conversations, CRM data, and opportunity gapsGuest Spotlight: Chris KobusChris Kobus is the Chief Revenue Officer at Genlogs, where he leads revenue growth and go-to-market strategy for a company developing technology and data capabilities for transportation and logistics markets.With a professional background that includes consulting, technology implementation, and value engineering, Chris brings a practical perspective to revenue leadership. His experience includes developing business cases for technology investments, aligning solutions with customer priorities, and helping organizations understand the financial impact of adopting new capabilities.At Genlogs, Chris focuses on building scalable revenue operations, developing sales talent, supporting specialized go-to-market strategies, and connecting customer insights with broader business opportunities.In this conversation, he shares his approach to strategic revenue planning, value-based selling, and thoughtful AI adoption, offering lessons for leaders navigating growth in evolving markets.Resources & Mentions:Genlogs: Chris Kobus’s company, providing technology and data capabilities for transportation and logistics markets.AGS: The growth advisory organization associated with Selling Intelligence, focused on helping businesses build and improve their revenue engines.Battery Ventures: Investment firm mentioned during the conversation in connection with Chris’s professional mentorship.Bill Bench: Mentioned by Chris as a trusted mentor who has provided guidance and perspective...
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    19 Min.
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