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Podcasts

E198 - What GTM Leaders Can Learn from the Innovation Ecosystem featuring Dave & Joe O'Callaghan
198
May 2, 2025

E198 - What GTM Leaders Can Learn from the Innovation Ecosystem featuring Dave & Joe O'Callaghan

In this episode of Tech Sales Insights, Randy Seidl is joined by Dave and Joe O'Callaghan, co-founders of Vation, about their journey and experiences as a father-son duo in the tech industry. They discuss the importance of go-to-market strategies and what leaders can learn from the innovation ecosystem. Sponsored by Sandler, a sales training provider, the discussion delves into the significance of sales training, especially for first-line managers, and explores the evolving roles of technology leaders. Joe and Dave share insights on the challenges emerging tech companies face, the importance of execution and humility, and the growing role of AI and data security. They also highlight the importance of cold calling, the shift in sales training needs, and the evolving skill sets required in the tech industry.KEY TAKEAWAYSFirst Father-Son Duo: Episode features Dave and Joe O’Callaghan, co-founders of Vation Ventures, discussing their father-son dynamic.Business Focus: Highlight on g…
E197 - IT Trends 2025: Insights from IDC's President on Market Direction and Essential Seller Knowledge
197
April 18, 2025

E197 - IT Trends 2025: Insights from IDC's President on Market Direction and Essential Seller Knowledge

In this episode of Tech Sales Insights, Randy Seidl is joined by Crawford Del Prete, President at IDC, to discuss IT trends for 2025 and what every seller should know about the market direction. The conversation covers Crawford's extensive career path, the role of AI in sales, infrastructure growth, and IDC's new Tech Match product. They delve into the importance of understanding customer needs, leveraging AI for sales preparation, and the transformation in application software businesses. Crawford shares insights on successful sales strategies, the significance of mentorship, and how IDC is positioning itself for future technological trends. The episode is sponsored by ZoomInfo and brought to you by the Sales Community.KEY TAKEAWAYSAI in Sales: Embrace AI tools for significant enhancements in preparedness and effectiveness in sales meetings. Lean into AI to stay competitive.Industry Growth: Infrastructure layer investments will continue growing, driven by AI advancements, with n…
E196 - Apply People-Based Data-Driven Learnings to Help Sellers Sell More, featuring Courtney McCashland
196
March 3, 2025

E196 - Apply People-Based Data-Driven Learnings to Help Sellers Sell More, featuring Courtney McCashland

In this episode of Tech Sales Insights, Randy Seidl is joined by Dr. Courtney McCashland, Chief Officer of Science and Strategy at AuctusIQ, to discuss data-driven strategies for improving sales performance. The conversation delves into the significance of understanding key attributes in top sales performers, the benefits of using talent assessments, and how AuctusIQ provides actionable insights to align talent with commercial success. Dr. McCashland shares her extensive background in positive business psychology and how it helps identify what drives success in individuals. Additionally, the episode touches on the unique challenges and opportunities for women in sales, as revealed by recent research.KEY TAKEAWAYSPositive Psychology in Sales: The importance of leveraging natural talents and behaviors for success in sales is emphasized, advocating for positive psychology approaches over trying to change inherent traits.Effective Talent Assessment: AuctusIQ's approach to sales perf…
E195 - Channel Leadership Best Practices featuring Denise Millard
195
Feb. 24, 2025

E195 - Channel Leadership Best Practices featuring Denise Millard

In this episode of Tech Sales Insights, Randy Seidl is joined by Denise Millard, Chief Partner Officer at Dell Technologies. They delve into the best practices for channel selling, the evolution of partnerships, and the importance of building strong, accountable relationships within the tech industry. Denise shares her incredible 27-year journey from EMC to Dell and her strategic role in fostering partner ecosystems. Learn how Dell embraces AI, marketplace dynamics, and the critical role of mentorship in career development. For anyone in tech sales, this episode is packed with valuable insights and real-life success stories.KEY TAKEAWAYSDenise Millard's Career: Denise has had an impressive career spanning 27 years between Dell and EMC, focused on partners and ecosystem roles.Channel Selling Best Practices: Simplicity and accountability are key—choose 2-3 focal points, align sponsorship, and hold teams accountable.Partner Relationships: Successful partnerships stem from mutual tr…
E194 - Startup Companies Biggest Issue: GTM featuring Richard Hegberg
194
Feb. 3, 2025

E194 - Startup Companies Biggest Issue: GTM featuring Richard Hegberg

In this episode of Tech Sales Insights, Randy Seidl is joined by Richard Hegberg, a notable figure in the semiconductor and entrepreneurial startup space, currently CEO of Aspinity. The main topic discussed is the biggest issue for startup companies, which is the go-to-market strategy. Richard shares his extensive career journey from starting at Motorola to leading various successful exits. Emphasizing the importance of early wins, he touches on the key considerations for product-market fit, the value of CEO-led sales in early stages, and strategic customer profiling. Richard also delves into effective lead generation tactics, the role of partnerships, and the significance of having a strong sales training program. The conversation offers rich insights on scaling startups, balancing compensation structures, and the essentials of building value-driven customer relationships.KEY TAKEAWAYSRick Hegberg is a renowned figure in the semiconductor industry and an entrepreneurial leader i…
E193 - Hard Work Pays Off: Lessons on Building GTM at a New Product Launch
193
Jan. 23, 2025

E193 - Hard Work Pays Off: Lessons on Building GTM at a New Product Launch

In this episode of Tech Sales Insights, Randy Seidl is joined by Dave Greenberger, VP and Head of North America at CHEQ, to discuss the intricacies of building effective go-to-market strategies for new product launches. Sponsored by Titan X, the episode delves into outbound sales effectiveness, customer engagement, and the role of culture in sales execution. Dave shares insights on leveraging sales ops, identifying product-market fit, and the importance of continuous learning and adaptation in sales. The episode also highlights tools like Gong and ZoomInfo that are instrumental in their sales processes. Together, Randy and Dave provide valuable lessons from Dave's extensive experience in tech sales and startup environmentsKEY TAKEAWAYSImportance of Hard Work and Culture: Emphasis on a culture of constant learning, adaptation, and hard work for successful product launches and enterprise sales.Sales Ops and Technology: Vital role of sales operations and leveraging technologies li…
E192 - Driving a Commit Culture featuring Steve Hershkowitz
192
Jan. 2, 2025

E192 - Driving a Commit Culture featuring Steve Hershkowitz

In this episode of Tech Sales Insights, Randy Seidl is joined by Steve Hershkowitz, the CRO of Rimini Street, to discuss the importance of building a committed culture in sales teams. Sponsored by Sandler, this conversation delves into the crucial role of sales training, the value of face-to-face meetings, and the challenges of leading a sales-driven transformation in a service-oriented company. Steve shares insights into his extensive industry experience, the significance of genuine relationships, and his goals for net new logo acquisitions. The episode also highlights tools like Clary and Zoom Info, alongside strategies such as Challenger Selling and the importance of continuous learning and training. Peppered with personal anecdotes and professional wisdom, this episode offers valuable lessons for sales leaders aiming to drive growth and accountability in their teams.KEY TAKEAWAYSCommit Culture: Emphasis on a commitment-driven sales culture where performance and accountability …
E191 - 5 in ’25 Leadership Wisdom featuring David Nour, Avnir
191
Dec. 20, 2024

E191 - 5 in ’25 Leadership Wisdom featuring David Nour, Avnir

In this episode of Tech Sales Insights, Randy Seidl is joined by David Nour, the founder and CEO of Avnir, and a 22-year founding partner of the Nour Group. David shares his expertise on leadership with five valuable tips for continued growth in the new year: 1) Executives in transition should ensure they truly belong; 2) In corporate dynamics, be a statesman; 3) Prioritize MEI (Merit, Excellence, and Intelligence) over mediocrity; 4) Revisit assumptions and zero-base everything; and 5) Leverage AI but humanize the last mile. David also discusses the development of Avnir, an AI platform to identify hidden relationship value, his journey in writing 12 books, and the importance of building meaningful relationships for long-term success.KEY TAKEAWAYSExecutive Due Diligence: Emphasize the importance of thorough due diligence and cultural fit when considering new roles.Statesmanship in Leadership: Advocate for a 'we’ mindset over 'me,' encouraging inclusive and discerning communicat…
E190 - Go-To-Market Practices from the CEO featuring Dave Donatelli, Riverbed
190
Dec. 13, 2024

E190 - Go-To-Market Practices from the CEO featuring Dave Donatelli, Riverbed

In this episode of Tech Sales Insights, Randy Seidl is joined by Dave Donatelli, CEO of Riverbed. They discuss go-to-market best practices from a CEO's perspective and delve into Dave's extensive career across various technology companies, including EMC, HP, and Oracle. Sponsored by ZoomInfo, the episode also touches upon sales strategies, leadership, and the importance of building strong relationships and delivering consistent value. Additionally, personal anecdotes and career advice underscore the importance of perseverance, focus, and ethical leadership in the tech sales industry.KEY TAKEAWAYSImportance of Relentless Customer Focus: Dave emphasized the critical need for maintaining strong customer relationships and how showing up consistently can make a significant difference.Value of Simplifying Sales Processes: Having straightforward and achievable comp plans can drive better sales performance.Impact of Organizational Changes: Dave's experience shows the importance of fo…
E189 - Enterprise Selling to CIO's & CTO's featuring Motti Finkelstein, Intel
189
Nov. 29, 2024

E189 - Enterprise Selling to CIO's & CTO's featuring Motti Finkelstein, Intel

In this episode of Tech Sales Insights, Randy Seidl is joined by Motti Finkelstein, Corporate Vice President and Chief Information Officer at Intel. Motti shares his career journey, starting from his early days in the Israeli Air Force computer unit to his current role at Intel. The discussion covers a range of topics, including the importance of understanding customer challenges in sales, leveraging AI at Intel, and the value of long-term business relationships. Motti also emphasizes the need for IT to align closely with business objectives and shares insights on effective sales strategies, including value selling and relationship building.KEY TAKEAWAYSIndustry Relationships: Long-term professional relationships are invaluable for navigating corporate roles and leveraging collective insights.AI Integration at Intel: The primary focus areas for AI at Intel include manufacturing, pre-silicon design, silicon testing, and software development.Importance of Client Understanding: Eff…
E188 - Sales Lessons Seen As CIO/COO at HSBC, HPE, Boeing, Verizon and more featuring John Hinshaw, Blackbird Vineyards
188
Nov. 21, 2024

E188 - Sales Lessons Seen As CIO/COO at HSBC, HPE, Boeing, Verizon and more featuring John Hinshaw, Blackbird Vineyards

In this episode of Tech Sales Insights, Randy Seidl is joined by John Hinshaw, owner of Blackbird Vineyards, and previously an executive at HSBC, HPE, Boeing, and Verizon. The discussion focuses on sales lessons, the importance of relationships and trust in business, and the strategic value of partnerships. John shares anecdotes from his career, insights on sales strategies, and the role of philanthropy in building strong relationships. The episode also highlights John's transition from corporate roles to acquiring and managing a vineyard.KEY TAKEAWAYSBuilding trust and relationships is essential in sales and partnerships. Effective communication and understanding of the customer's business needs are crucial.Collaborating with partners on product development and exploring joint market opportunities can enhance business growth.Philanthropy and doing good together can strengthen business relationships and create positive impacts.Combining technology expertise with business acumen…
E187 - Values Based Leadership featuring Kevin Guthrie, Alight Solutions
187
Nov. 16, 2024

E187 - Values Based Leadership featuring Kevin Guthrie, Alight Solutions

In this episode of Tech Sales Insights, Randy Seidl is joined by Kevin Guthrie, EVP of Sales at Alight Solutions. They discuss the importance of values-based leadership, sharing experiences from Kevin's illustrious career spanning companies like Oracle, Hyperion Solutions, and Tableau. Kevin highlights his leadership philosophy, the significance of fostering competitive camaraderie within teams, and the value of maintaining strong relationships. The episode also touches on the impact of mentors and peers in shaping Kevin's approach to leadership and sales success.KEY TAKEAWAYSValues-Based Leadership: Emphasizes the importance of clear values in leadership, fostering environments where employees align with company values.Customer Success: Prioritizing customer success creates loyal advocates and drives long-term business success.Mentorship and Development: Effective leadership involves mentoring, providing clear feedback, and fostering professional and personal growth.Rela…
E186 - GTM Tips featuring Chuck Smith, IBM
186
Nov. 8, 2024

E186 - GTM Tips featuring Chuck Smith, IBM

In this Tech Sales Insights episode, Randy Seidl is joined by Chuck Smith, VP of Business Development at IBM Infrastructure Group and Sales Community Advisory Board member. Chuck shares insights on IBM's infrastructure services, their pivot to 'as a service' models, and the importance of product-market fit and positioning. The discussion also covers Chuck's career trajectory, the role of sales engineers, and the evolving sales culture at IBM. Chuck emphasizes the value of networking, and maintaining personal relationships, and offers practical GTM tips for sales professionals. Sponsored by Sandler, this episode provides a deep dive into the strategies shaping IBM's market approach.KEY TAKEAWAYSIBM’s GTM Strategies: Discussions about IBM’s focus on modernizing through AI and Hybrid Cloud technologies with an emphasis on go-to-market (GTM) strategies.As-a-Service Model: Chuck details IBM’s transition towards offering flexible “as-a-service” models to meet modern business needs.I…
E185 - Generative AI for the Enterprise Business featuring Matt Horner, World Wide Technology
185
Nov. 1, 2024

E185 - Generative AI for the Enterprise Business featuring Matt Horner, World Wide Technology

In this episode of Tech Sales Insights, Randy Seidl is joined by Matt Horner, Executive Vice President of Global Enterprise Sales at Worldwide Technologies (WWT). They discuss the role and impact of generative AI in enterprise businesses, the importance of company culture at WWT, and the innovative ways WWT integrates new technology partners. The conversation also covers Matt's career journey, including his start in inside sales, his rise to leadership at WWT, and his approach to fostering enterprise relationships. Matt emphasizes the significance of preparation and adaptability in sales, and the ongoing need for training and development within teams. The episode highlights WWT's commitment to mentorship, community involvement, and the continuous pursuit of excellence in both innovation and customer engagement.KEY TAKEAWAYSGenerative AI's Impact: Compared to the industrial revolution, it can revolutionize modernization, profitability, and efficiency in enterprises.Enterprise Ado…
E184 - Leading Transformation featuring Greg Brown, Chairman and CEO of Motorola Solutions
184
Oct. 18, 2024

E184 - Leading Transformation featuring Greg Brown, Chairman and CEO of Motorola Solutions

In this episode of Tech Sales Insights, Randy Seidl is joined by Greg Brown, chairman and CEO of Motorola Solutions, to discuss his transformative leadership journey with host Randy. Greg shares his approach to decision-making, mentorship, and the critical role of clear communication. Reflecting on Motorola's significant growth through over 40 acquisitions and a 1400% increase in shareholder returns, he underscores the importance of customer engagement and listening over telling in sales. The episode also explores effective team dynamics, a meritocratic management approach, and the value of diverse perspectives. With insights on navigating Quarterly Business Reviews (QBRs), sales leadership, and genuine communication, Greg emphasizes resilience, adaptability, and the importance of continuous learning and authenticity in leadership. The discussion includes personal anecdotes, lessons from industry leaders, and the significance of integrating knowledge with wisdom for successful decisio…
E183 - Sales Tips from a Legend featuring Scott McNealy, Co-Founder of Curriki
183
Oct. 14, 2024

E183 - Sales Tips from a Legend featuring Scott McNealy, Co-Founder of Curriki

In this episode of Tech Sales Insights, Randy Seidl is joined by Scott McNealy, former CEO of Sun Microsystems, unfolds his vast career insights and personal anecdotes. The discussion, primarily focusing on sales tips, touches on various topics such as McNealy's parenting philosophy, experiences as a sales leader, and humorous personal stories from his life. The script highlights McNealy's sales strategies, the importance of leadership involvement in sales, and maintaining ethics in business. Also included are McNealy's ventures post-Sun, his involvement with his sons' careers, and the personal values that have guided his life and work.KEY TAKEAWAYSSales Tips: Emphasis on the importance of building strong relationships and being present.Leadership: McNealy's focus on ethical leadership and employee fulfillment.Parenting Wisdom: McNealy discusses his strict but loving approach to parenting.Company Culture: Sun Microsystems' culture fostered numerous future leaders.Innovatio…
E182 - Building a Winning Sales Culture with Steven Jow
182
Oct. 5, 2024

E182 - Building a Winning Sales Culture with Steven Jow

In this episode of Tech Sales Insights, Randy Seidl is joined by Steve Jow, EVP of Sales at TD SYNNEX, to discuss strategies for building a winning sales culture. Steven shares insights from his 34-year career at TD SYNNEX, emphasizing teamwork, customer focus, and leveraging partnerships. The role of culture in sales performance is highlighted, along with the integration of AI and technology for enhanced efficiency and solutions selling. Steve’s experiences and anecdotes provide a personal touch to his professional philosophy, underscoring the value of optimism and a service-oriented approach in the tech sales industry.KEY TAKEAWAYSCompany Profile: TD SYNNEX is a leading technology distributor, emphasizing a holistic approach that includes market planning, comp design, and channel setup.Sales Culture: A winning sales culture involves creating a team that celebrates wins, adapts to challenges, remains optimistic, and values customer experience.Team Synergy: Best team practices…
E181 - Outcome Based Selling featuring Scott Harvey
181
Sept. 30, 2024

E181 - Outcome Based Selling featuring Scott Harvey

In this episode of Tech Sales Insights, Randy Seidl is joined by Scott Harvey, Chief Customer Officer of Sprinkler. They delve into Scott's career journey, from broadcast journalism major to tech sales leader. They explore the importance of outcome-based selling and value creation in the sales process, emphasizing the critical role of customer relationships and consultative selling. Scott shares insights on transitioning strategies at major companies like VMware, ServiceNow, and Stripe, highlighting the significance of personalized engagement and value selling in post-sales and customer success. The conversation underscores the need for continuous sales training and the collaborative effort of teams in achieving success. Sponsored by Octus IQ, the episode offers a deep dive into modern sales strategies and leadership in a rapidly changing market.KEY TAKEAWAYSOutcome-Based Selling: Focus on understanding customer priorities and aligning your product capabilities to drive specific b…
E180 -  Sales, Leadership and Delivering an Exceptional Customer Experience featuring Frank Hauck
180
Sept. 20, 2024

E180 - Sales, Leadership and Delivering an Exceptional Customer Experience featuring Frank Hauck

In this episode of Tech Sales Insights, Randy Seidl is joined by his longtime friend and esteemed guest, Frank Hauck, a retired executive with an impressive career spanning DEC, EMC, and NCR. The conversation touches on commemorating 9/11, the importance of sales training, and Frank's journey from a finance manager at Digital Equipment Corporation to becoming a key figure at EMC. Frank discusses his methodologies for maintaining high standards in sales, the significance of leadership working for the sales team, and the relentless commitment required to deliver exceptional customer experiences. Personal anecdotes about learning from mentors like Mike Ruettgers, Jack Egan, and Joe Tucci highlight the importance of humility, accountability, and continuous learning. The episode also explores the evolving role of technology in sales, with a specific focus on the impact of AI and prospecting in a post-COVID world. With contributions from industry peers such as Eric Mann and insights into th…
E179 - Finding the Balance: Trust & Relationships vs. AI featuring Berk Mesta
179
Sept. 16, 2024

E179 - Finding the Balance: Trust & Relationships vs. AI featuring Berk Mesta

In this episode of Tech Sales Insights, Randy Seidl is joined by Burke Mesta, founder of Belsa Inc., to discuss the importance of balancing trust and relationships versus the role of AI in sales. Burke shares his extensive career journey, including his experiences in engineering, sales, and management at renowned firms like PTC, Bicis, and Temenos. The conversation delves into the critical role of trust and personal relationships in business, the evolving landscape of revenue intelligence and performance management, and the necessity for effective leadership over mere management. Burke also highlights the value of mentorship, drawing from his own experiences and insights from industry veterans like John McMahon and Tom Mendoza. The episode concludes with a light-hearted anecdote about a skiing adventure, reinforcing the theme of personal connection throughout the conversation.KEY TAKEAWAYSImportance of Relationships: Highlight the importance of building and maintaining relationshi…
E178 - GTM Best Practices featuring Scott Barker and Paul Irving at GTM Fund
178
Sept. 3, 2024

E178 - GTM Best Practices featuring Scott Barker and Paul Irving at GTM Fund

In this episode of Tech Sales Insights, Randy Seidl is joined by Paul Irving and Scott Barker from GTM Fund to delve into the dynamics of go-to-market (GTM) strategies and best practices. Scott, who also runs the GTM podcast and newsletter, along with Paul, the Platform Director, share their extensive experience and insights from investing in B2B SaaS companies. They discuss the evolution of outbound sales, leveraging relationships for warm introductions, and the impact of AI on sales tactics. Additionally, they touch upon the importance of personalized communication, the value of data-driven strategies, and the significance of marquee hires. With humorous anecdotes and practical advice, this episode offers a comprehensive overview for anyone looking to enhance their GTM approach.KEY TAKEAWAYSThe Power of Relationships: Leveraging your network and warm introductions is key to successful outbound sales, especially in the competitive B2B SaaS space.Outbound Sales are Alive and Thri…
E177 - Getting Maximum ROI from your Events featuring Tom Boccard
177
Aug. 30, 2024

E177 - Getting Maximum ROI from your Events featuring Tom Boccard

In this episode of Tech Sales Insights, Randy Seidl is joined by Tom Boccard, EVP of Sales at SmartSource, to discuss strategies for achieving maximum ROI from events and tips for selling to new accounts and markets. Tom shares his career journey, provides an overview of SmartSource's services, and delves into best practices for event planning, including cost control, leveraging technology, and proactive engagement with potential customers. He highlights the importance of relationship-building, utilizing sales tech stack tools like ZoomInfo and Outreach, and the advantages of collaborating closely with marketing teams. The conversation also touches on hiring new sales talent, training, and fostering a collaborative company culture focused on continuous improvement.KEY TAKEAWAYSMaximizing Event ROI: Learn practical steps to improve your return on investment from events, focusing on aligning marketing and sales efforts, understanding your audience, and leveraging technology to creat…
E176 - Building Teams Internationally featuring Dave Cronk
176
Aug. 19, 2024

E176 - Building Teams Internationally featuring Dave Cronk

In this episode of Tech Sales Insights, Randy Seidl is joined with Dave Cronk, SVP of Sales for EMEA at Tricentis, about his extensive experience in building and managing international sales teams. The discussion covers a wide range of topics including the importance of cultural understanding in international sales, effective sales strategies, tech stacks, and the pivotal role of sales ops and rev ops. Dave shares insights from his career journey, including his time at HP, SolarWinds, and Tricentis, and emphasizes the significance of relationships and authenticity in sales. The episode also touches on personal anecdotes, career advice, and the value of mentorship.KEY TAKEAWAYSBuilding Resilient Teams: The importance of investing in people and nurturing talent to create a strong, cohesive team, especially in diverse international markets.Crisis Management: How transparency, communication, and proactive customer engagement can turn a challenging situation, like a security breach, …
E175 - Coaching Sales Skills featuring Paul Salamanca
175
Aug. 15, 2024

E175 - Coaching Sales Skills featuring Paul Salamanca

In this episode of Tech Sales Insights, Randy Seidl is joined by Paul Salamanca, co-founder and CEO of the Top 1 Percenter Academy. They discuss the importance and challenges of sales coaching, share insights on leveraging tools like Gong and Clary, and emphasize the role of resilience, mindset, and discipline in achieving sales success. Paul's journey from door-to-door sales to creating a successful coaching business is highlighted, along with his focus on the top 1% performers. They also touch upon the evolution of sales practices, the impact of COVID on coaching cultures, and the importance of maintaining strong relationships in the sales process.KEY TAKEAWAYSSales Coaching Culture: Creating a true coaching culture goes beyond occasional feedback; it requires structured, consistent, and scalable approaches.Coaching at Scale: Effective sales coaching must be continuous and integrate with existing sales methodologies to drive better performance across the board.Maximizing Top P…