E94: Navigating AI Challenges in Established Tech Companies

Hiring a CRO is one of the most high-stakes decisions a founder can make—especially when a company is transitioning from SMB to enterprise sales. In this episode of Topline Spotlight, Shensi Ding, Co-Founder of Merge, shares her experience navigating the search for a stage-appropriate revenue leader after raising their Series B in 2022. She breaks down the challenges of finding a CRO who wasn’t just impressive on paper but could actually build a disciplined enterprise sales motion, adapt to Merge’s intense culture, and help scale the company upmarket.   Catch new episodes of Topline Spotlight every Thursday and full episodes of Topline every Sunday.   Want more from Pavilion?   Subscribe to Topline Newsletter written and edited by Asad Zaman.   Join the free public Topline Slack channel to engage with hosts, guests, and other listeners.   Listen to The Revenue Leadership Podcast with Kyle Norton every Wednesday.  

In this episode, Sam Jacobs, Asad Zaman, and AJ Bruno break down a viral LinkedIn post that sparked a heated debate about the role of B2B marketing in go-to-market strategy. Has marketing become too focused on pipeline at the expense of brand? Are CMOs being pushed out in favor of CROs? The team explores how marketing’s role is evolving, the tension between short-term revenue goals and long-term brand building, and what leaders can do to prove marketing’s strategic value.   Are you being paid what you’re worth? Help us refresh Pavilion’s industry-standard compensation report for 2025 by taking our anonymous survey at joinpavilion.com/comp and get early access to the results! Want more Topline by Pavilion? Join the Topline Slack channel to engage with hosts, guests, and other listeners and subscribe to Topline Newsletter.

Fundraising isn’t just sales—something Josh Guttman, co-founder and CEO of SELLIT9, learned the hard way. After spending years in SaaS sales and leadership, including a 12-year run at Salesforce, Josh thought his natural ability to pitch and build relationships would give him an edge in raising capital. But he quickly discovered that VCs don’t want to be sold—they want to believe.   In this episode of Topline Spotlight, Josh shares his journey from seasoned sales leader to first-time founder, the unexpected feedback that forced him to rethink his approach, and how he ultimately closed his pre-seed round by striking the right balance between confidence, storytelling, and authenticity.   Catch new episodes of Topline Spotlight every Thursday and full episodes of Topline every Sunday.   Want more from Pavilion?   Subscribe to Topline Newsletter written and edited by Asad Zaman.   Join the free public Topline Slack channel to engage with hosts, guests, and other listeners.   Listen to The Revenue Leadership Podcast with Kyle Norton every Wednesday.  

In this episode, hosts Sam, AJ, and Asad dive into the strategic choices behind building teams in Latin America, focusing on compensation arbitrage and offshoring. They offer guidance for junior talent in North America, who now face competition from equally skilled and cost-effective professionals abroad, all while navigating the impact of AI on traditional roles. The conversation also tackles the challenge of hiring sales reps for complex deals and whether AI can handle routine tasks, freeing up sales talent to focus on creativity and strategic deal-making. Finally, the hosts discuss OpenAI's Deep Research release, exploring how it might be integrated into products and the operational benefits it could bring to businesses.   Are you being paid what you’re worth? Help us refresh Pavilion’s industry-standard compensation report for 2025 by taking our anonymous survey at joinpavilion.com/comp and get early access to the results!   Want more Topline by Pavilion? Join the Topline Slack channel to engage with hosts, guests, and other listeners and subscribe to Topline Newsletter.  

In this episode of Topline Spotlight, hosts Sam Jacobs and Asad Zaman sit down with Alina Vandenberg, co-CEO of Chili Piper, to discuss the significant challenges she faced and overcame in her dual role as acting CMO. Alina delves into the complexities of scaling a rapidly growing company while maintaining a cohesive marketing strategy. She shares how she tackled the challenge of aligning data-driven marketing efforts with business goals, utilizing tools like Snowflake to enhance targeted outreach. Alina also addresses the creative hurdles of standing out in a saturated market, revealing how she employs humor and provocation to engage audiences effectively.   Catch new episodes of Topline Spotlight every Thursday and full episodes of Topline every Sunday.   Want more from Pavilion?   Subscribe to Topline Newsletter written and edited by Asad Zaman.   Join the free public Topline Slack channel to engage with hosts, guests, and other listeners.   Listen to The Revenue Leadership Podcast with Kyle Norton every Wednesday.  

In this episode of Topline, Sam Jacobs, AJ Bruno, and Asad Zaman explore AI’s growing influence on go-to-market strategy, growth, and operations. They break down the difference between AI-first and AI-enabled companies, why some integrate AI seamlessly while others fall behind, and the operational roadblocks leaders face. The conversation covers the rise of AI Ops roles, legal pushback on AI-driven data usage, and how outdated go-to-market strategies are being disrupted. They also discuss why incentive compensation should extend beyond sales teams and why companies that resist AI risk being left behind.   Are you being paid what you’re worth? Help us refresh Pavilion’s industry-standard compensation report for 2025 by taking our anonymous survey at joinpavilion.com/comp and get early access to the results! Want more Topline by Pavilion? Join the Topline Slack channel to engage with hosts, guests, and other listeners and subscribe to Topline Newsletter.

In this episode of Topline Spotlight, hosts Sam Jacobs, AJ Bruno, and Asad Zaman speak with Keith Frankel, Chief Product Officer at Totango, to explore the intricacies of merging company cultures post-acquisition. Keith shares his journey from founding enterprise AI companies to leading product teams at Totango, highlighting the challenges of integrating distinct cultures and product lines. The discussion delves into strategies for addressing cultural divides, emphasizing the importance of confronting uncomfortable issues to foster a unified company identity. Keith also outlines operational changes that blend teams across regions and enforce consistent processes.   Catch new episodes of Topline Spotlight every Thursday and full episodes of Topline every Sunday.   Want more from Pavilion?   Subscribe to Topline Newsletter written and edited by Asad Zaman.   Join the free public Topline Slack channel to engage with hosts, guests, and other listeners.   Listen to The Revenue Leadership Podcast with Kyle Norton every Wednesday.  

In this episode of Topline, hosts Sam Jacobs, AJ Bruno, and Asad Zaman review insights from Carta’s State of Startups 2024 report. They explore the rise of down rounds in 2023 and 2024, highlighting the financial challenges many startups face today. The conversation shifts to the increasing prevalence of solo founders, noting a significant rise from 17% in 2017 to 36% in 2024. The trio also examines AI's transformative impact on business decision-making, sharing personal experiences with tools like ChatGPT. Finally, they delve into shifting company cultures and management practices, offering insights into how leaders can navigate these changes while focusing on personal development strategies.   View Carta State of Startups 2024 report.   Want more Topline by Pavilion? Join the Topline Slack channel to engage with hosts, guests, and other listeners and subscribe to Topline Newsletter.  

Topline is excited to introduce our newest segment – Topline Spotlight. In this series, our hosts sit down with top B2B tech leaders to explore the biggest challenges they’ve faced and how they conquered them.   In this episode of Topline Spotlight, our hosts sit down with Tom McCarty, CEO of Org Chart, to discuss a pivotal challenge he faced: narrowing the total addressable market (TAM) to drive better growth. As a first-time CEO of a private equity-backed company, Tom shares his strategic approach to refining market focus, which led to more effective growth strategies. He also provides insights for aspiring CEOs, highlighting the value of selecting the right partners and viewing challenges as avenues for personal and professional development.   Want more from Topline?   Subscribe to Topline Newsletter written and edited by Asad Zaman.   Join the free public Topline Slack channel to engage with hosts, guests, and other listeners.   Listen to The Revenue Leadership Podcast with Kyle Norton every Wednesday.  

In this episode of Topline, Asad and AJ are joined by Kyle Norton, CRO of Owner.com and Host of The Revenue Leadership Podcast. They explore the evolving role of the CRO, highlighting the diverse characteristics of successful leaders in this position. The conversation also delves into the transformative impact of AI advancements, particularly the implications of GPT-3 and GPT-4 models on business operations and workforce dynamics. Kyle shares insights on how AI might reduce the need for middle management, prompting companies to rethink growth strategies.   Attention CEOs and Founders! Join Pavilion at the CEO Summit on January 23rd in vibrant New Orleans. Don’t miss out—reserve your spot today! Want more Topline? Join the Topline Slack channel to engage with hosts, guests, and other listeners and subscribe to Topline Newsletter.