The Top Five Errors When Buying Sales Technology, With Craig Rosenberg

Welcome to the “Great Sales Awakening.” In this episode of the Gartner Sales Podcast, host Betsy Gregory-Hosler and Dan Gottlieb explore this uniquely transformative era in B2B sales. Changes in labor, economics, resources and technology are driving a unique opportunity to chase a new revenue productivity frontier. Join us for a conversation about the three "big bets" sales leaders can take to lead this transformation: redefining leadership in the AI era, building the agentic sales organization and prioritizing future-fit talent over traditional experience.Dan Gottlieb is a vice president analyst in the Gartner for Sales practice. He writes about sales technology and covers a spectrum of topics related to AI for sales, generative AI, and seller/buyer engagement. Mr. Gottlieb combines over a decade of sales experience with creative thinking to collaborate with clients. His collaborative style invites clients to convert Gartner's research into actionable insights that yield scalable, repeatable growth. 

In the latest episode of the Gartner Sales Podcast, host Betsy Gregory Hosler talks with Gartner experts Kevin Hooper and Andy Clement to explore sales leadership in uncertain times. These seasoned executives share strategies for navigating volatile, uncertain, complex, and ambiguous (VUCA) environments, drawing lessons from their own leadership roles during past crises like the Great Recession and COVID-19 pandemic.Andy Clement is an Executive Partner with Gartner's Chief Sales Officer program, where he coaches, guides, and challenges sales leaders who are Gartner clients. He joined Gartner in August 2024.Andy retired from Kimberly-Clark in March 2024 after a distinguished 33-year career. During his tenure, he held various key roles, including chief customer officer, vice president of sales, general manager, strategy director, marketing director, and manufacturing director. Andy earned his executive MBA from Vanderbilt University and his undergraduate degree from Wake Forest University.Kevin Hooper is an Executive Partner at Gartner, where he leverages over three decades of experience in technology and sales to advise clients on strategic growth and operational excellence. Before joining Gartner, Kevin held leadership roles at companies including Oracle, NEC, Hewlett-Packard, IBM, and Lenovo, where he served as North America president and general manager of the Infrastructure Solutions Group. His extensive background encompasses expertise in cloud business analytics, enterprise solutions, sales operations and strategy. Kevin is dedicated to helping organizations optimize their strategies and achieve their business objectives.

CSOs grapple with two challenges: the relentless pressure to hit quarterly targets and the need to sustain competitiveness in the long term. Research shows that only 11% of organizations successfully do both.  In this installment of the Gartner Sales Podcast, Gartner expert Greg Hessong takes us through recent research into what those organizations do differently in order to thrive in turbulent times.Greg Hessong is a Sr. Director, Analyst in the Gartner sales practice, where he studies the drivers of top performing sales teams and revenue leaders. Greg helps clients apply Gartner's research to improve collaboration, specifically between sales and marketing leaders, to boost pipeline generation, and operationalize go-to-market strategies and channels, such as account-based and inside sales, to drive more efficient and predictable revenue. 

In this episode of the Gartner Sales Podcast, host Betsy Gregory-Hosler interviews Nacho Castroverde from Cisco about a groundbreaking AI-powered prospecting tool that is transforming their sales process. The discussion delves into how Cisco's virtual sales organization, managing over 100 customers per seller, leverages AI to prioritize customer interactions and enhance sales efficiency. Nacho shares insights into the development and implementation of this AI assistant, highlighting its impact on pipeline creation, territory penetration, and conversion rates. Sales leaders will find valuable lessons on integrating AI into sales processes to drive effectiveness and scalability, making this episode a must-listen for those looking to innovate their sales strategies.

As challenges arise, chief sales officers (CSOs) are often trapped between their desire to take action and the fear of hurting revenue growth. In this episode, Gartner Sales Podcast host, Betsy Gregory-Hosler, interviews Gartner expert and former chief revenue officer (CRO), Brendan Condon, to discuss the changes that CSOs can confidently make in 2025.Brendan Condon is a senior director analyst within Gartner’s CSO Strategy team covering go-to-market (GTM) strategy and CSO effectiveness. Prior to coming to Gartner, Brendan served as the global chief revenue officer of the martech firm, GDS Group. Previously, he was the CRO of Captify — the world’s leading independent provider of search intelligence for global marketers and their advertising agencies. In this role, Brendan took the company to new heights of sustainable and profitable revenue, resulting in a successful sale to a private equity (PE) firm. Prior to that, Brendan was the chief revenue officer for Comcast Advertising (Effectv). He was recruited to streamline and oversee $2.5 billion in advertising revenue streams across national, regional and local agencies and clients (>25K) covering cross-screen, addressable, audience-based, linear TV and digital video solutions. Prior leadership roles include the CEO of an advanced TV ad network and a fulfilling career holding numerous positions across Time Inc., Time Warner and AOL.

In this episode, we explore the Gartner Leadership Visions for 2025, highlighting recommendations tailored to chief sales officers, sales enablement leaders and sales operations leaders. Gartner experts Robert Blaisdell, Tyler Huguley and Shayne Jackson guide us through the trends, challenges and priorities for each sales leadership role.Robert Blaisdell is a vice president, analyst and chief of research in the Gartner Sales Research and Advisory practice. He covers all aspects of sales but with a primary focus on current customer management and growth via account planning best practices and strategic key account management.Tyler Huguley is a senior director, analyst in Gartner’s Sales practice. Tyler has 15 years of experience in sales and sale operations in the media, automotive and consumer goods (B2B) industries. He also has three years of experience practicing law in private practice and in-house with Cox Enterprises.Shayne Jackson is a senior director, analyst in Gartner’s Sales practice. Shayne covers enablement and talent management, advising and producing research for chief sales officers and sales enablement leaders. His extensive global experience leverages a programmatic approach to learning, content and tools that elevate sales teams’ effectiveness.

Sales development is an essential function for addressing pipeline challenges and driving business growth. However, CSOs are struggling to evolve the function and maximize SDRs’ impact on revenue. Gartner expert Shiela Rahimian joins the podcast to discuss the best practices sales leaders should consider when assessing and optimizing their sales development function, and how to measure that function’s impact.Shiela Rahimian is a Director Analyst in the Gartner for Sales Practice, where she covers all aspects of sales execution with an emphasis on pipeline generation and development, optimizing inside sales roles, launching key account programs, account planning, evolving sales processes, methodologies and playbooks within sales enablement functions. As a former Director of Sales Enablement and Sales Consultant, Mrs. Rahimian provides sales leaders with practical guidance on how to improve performance and results. 

The role of the chief sales officer (CSO) is evolving. The drive to align commercial functions is sparking growth and transformation in the CSO role itself. Podcast host Betsy Gregory-Hosler speaks with Graham Stringer, head of customer markets for Fujitsu North America, to discuss his commercial organization’s transformation, how his role has changed and what it’s like to be in a growing leadership position. “Even if you’re not in a position as a sales leader to drive a greater level of convergence, at least see how you can lean in and be closer to those parts of the business. Don’t just shrug your shoulders and say, well, that’s just the way we’re organized. And hey, best-case scenario, perhaps you can move the needle.” Graham Stringer is the head of customer markets for Fujitsu’s North America Region, where he oversees all sales of Fujitsu’s digital technology solutions and services. With over 25 years of experience in the IT industry, Graham has held key roles at DXC Technology, Oracle, Software AG, IBM and a global startup, managing teams across the U.S., Canada and Latin America. He holds a Bachelor of Math in computer science from the University of Waterloo and has completed management programs at Wharton and Queen’s University.  

Sales leaders prioritize meeting buyer expectations but often fail to account for the underlying element affecting most major purchases: emotions. In this episode, hosts Billy Luckey and Betsy Gregory-Hosler sit down with Gartner experts to discuss the B2B buyer experience, how buyers balance logic and emotion and what sales leaders can do about it.Alexandra Bellis, who has a doctorate in psychology, is a director of quantitative analytics and data science for Gartner for Marketers. She is responsible for survey data collection and analysis across a wide range of marketing and communications research, including marketing data and analytics, talent and collaboration, B2B buying behaviors, and communications leadership and strategy.Rick LaFond is a senior director analyst for Gartner for Marketers, based in Baltimore. He leads Gartner’s B2B customer acquisition and account growth research. As an analyst, he supports Gartner clients with insights and guidance on various marketing topics, including demand generation, digital marketing strategy, sales enablement, content marketing and account-based marketing. He is the lead analyst for Gartner research on marketing best practices in the manufacturing industry, as well as ongoing primary research studies on cross-industry B2B buying behaviors. Rick also serves as lead author for Gartner’s Magic Quadrant for B2B Marketing Automation Platforms.

Chief sales officers expect their enablement teams to drive seller productivity. Yet, sales enablement leaders struggle to demonstrate their influence on sellers and overall performance. In this episode, co-hosts Betsy Gregory-Hosler and Billy Luckey talk with Gartner expert Shayne Jackson about why enablement leaders struggle to show impact, why “random acts of enablement” are a problem and how a new approach can connect enablement to results. Shayne Jackson covers enablement and talent management for the Gartner for Sales practice. His research and advice help chief sales officers and sales enablement leaders solve critical business challenges. His extensive global experience leverages a programmatic approach to learning, content and tools that elevate sales teams’ effectiveness.