Pillar Talk: Building Sales Leadership with Rick Smolen

We explore how a solo Camino de Santiago pilgrimage reset attention, then translate those lessons into a pragmatic playbook for fixing stalled revenue. We walk through segmentation, ICP, LTV:CAC, methodology, enablement, culture, and the myth that “it’s all talent.” • solo travel as a reset for presence and purpose • inch pebbles as a tactic for motivation and change • myth-busting the talent-firs...

We sit down with Erich Walters, VP of Enterprise Sales at Loopio, to dig into hiring for mindset over process, measuring clock speed under pressure, and making decisive calls when the quarter is on the line. We also explore AI handoffs, long-game recruiting, and why relationships still matter. • Erich’s path from Gartner mentorship to team-building philosophy • hiring great talent as the leader’s...

We trade super-rep heroics for scalable leadership with CRO Sean Munafo, unpacking credible swagger, the 1-3-1 framework, and how AI is splitting teams into catalysts and crutches. We share the systems, signals, and sincerity that sustain performance in hybrid work. • credible swagger as preparation, belief, and feedback loops • hiring to close your gaps, not mirror your strengths • shift from dep...

Sales expert Ash Khalek reveals how to identify and address the emotional factors driving buyer decisions that exist "below the waterline." His approach distinguishes between the logical elements prospects discuss openly and the personal motivations that actually move deals forward. • Pipeline coverage at quarter start often looks promising but deals stall without addressing emotional dr...

Andrea Kayal, a seasoned go-to-market leader with experience as both a CMO and CRO, shares her unique perspective on bridging the gap between marketing and sales functions while making the transition to C-Suite leadership. Having worked across some of the fastest-growing B2B SaaS companies, Andrea reveals the critical mindset shifts that separate functional VPs from true C-level executives. • Appr...

Colin Specter, SVP of Sales at Orum, shares his leadership philosophy centered on building people first, believing those people will then build successful businesses. His approach balances high standards with genuine care for team wellbeing, recognizing that sales is fundamentally about energy transference. • Zig Ziglar's principle: "You don't build businesses, you build people and...

Chris Orlob, Founder and CEO of pclub.io, shares his journey from product marketing to sales leadership and discusses how to effectively develop sales teams in today's challenging environment. He offers a practical framework for setting clear expectations and explains why systematic skill development is now a strategic necessity rather than just a nice-to-have. • Chris developed his "thr...

Leif O'Leary, CEO of Alegeus and veteran sales leader, shares how strong leadership skills can translate into executive success through communication, consistency, and a commitment to developing talent. Leif explains how strong sales leadership requires both consistency and positive communication Leif emphasizes building connections with team members is essential for motivating performance Co...

Wade Callison, CRO of Files.com, shares his journey from product leadership to sales and reveals how technical domain expertise creates credibility that transforms selling relationships from transactional to consultative. Curiosity, coachability, growth mindset, and self-awareness form Wade's core framework for identifying and developing sales talent. Wade details creating a culture of contin...

Thurman Sneed, COO of Marigold, shares leadership insights focusing on staying calm under pressure, creating organizational alignment through shared data, and building effective cross-functional relationships. Thurman tells how to stay poised during tense situations enables objective thinking and decision-making Thurman advocates for creating a "single source of truth" for data is crucia...

Shane Evans, Chief Revenue Officer at Gong, brings decades of executive leadership experience to this illuminating conversation about what truly drives sales leadership success.  Shane shares the frameworks and approaches that have allowed him to navigate increasingly complex leadership challenges throughout his career. Shane advocates for embracing a growth mindset and remaining open to opportuni...

In this episode of "Pillar Talk," Rick Smolen chats with Justin Griffin, SVP of Sales at Computacenter, exploring the resilience required in sales leadership, the journey from individual contributor to leader, and the delicate balance between professional and personal success. Episode Highlights: Justin Griffin shares his experience dealing with the demanding schedule of a sales leader a...

The Pillars of Sales Leadership with Ed McDonnell In this enlightening episode of Pillar Talk, Rick Smolen dives into the intricacies of sales leadership with the remarkable Ed McDonnell, the current CRO of Asana. With a friendship and professional relationship spanning over two decades, Rick and Ed explore Ed's impressive journey from his early days at Thomson Financial to leading organizati...

In this episode, Rick Smolen chats with Jonathan Pollack about his journey from an individual contributor to a leader in sales at companies like Intralinks, Shibumi, and Augury. They discuss the nuances of building a strong sales team, fostering a positive work culture, and maintaining team motivation in remote settings. Key Points: Career Growth: Jonathan's progression from hands-on sales ro...

Welcome to another episode of Pillar Talk, where we delve deep into the foundations of sales leadership success. In this episode, we're honored to have Brian Walsh from Force Management join us to share invaluable insights into the art and science of sales coaching. Key Takeaways:  Behavioral Influence of Senior Leadership : Senior leaders set the tone for the organization's coaching cul...

In this episode of Pillar Talk, Rick Smolen is joined by Dave Kennett, the founder and CEO of ReplayzIQ, a pioneering sales call intelligence platform.  With a rich background in sales leadership and a profound emphasis on coaching, Dave shares his extensive experience and invaluable lessons on building a robust coaching culture within sales teams. Key Highlights: Journey to Sales Coaching: Dave r...

Welcome to another episode of Pillar Talk with Rick Smolen, where we dive deep into the realms of sales leadership and uncover the strategies that define success. This episode features Dan Head, the accomplished CEO of Phrasee, sharing his insights that guided from from a seasoned sales leader to CRO, and now CEO. About Our Guest: Dan Head has an impressive career trajectory, evolving from senior...

Welcome to this episode of the Pillar Talk Podcast, where we delve into the intricacies of sales strategies, business planning, and the importance of P&L fluency with our guest, Sam Jacobs, the CEO of Pavilion.  Discover invaluable insights on navigating high-growth environments, the pitfalls of revenue-driven models, and the transformative power of understanding unit economics. Key Highlights...

In this episode of Pillar Talk, Rick Smolen chats with Kyle Norton, the CRO of owner.com, to explore operating rhythms in sales leadership. Kyle, with his rich background in sales leadership roles across companies like Shopify, League, and now Owner.com, delves into how establishing a robust operating rhythm is crucial for sales teams to achieve targets today and in the future. The discussion navi...

Welcome to Pillar Talk, where we dive into the foundations of sales leadership success. In this episode, we're thrilled to have Mark Kosoglow, a renowned figure in sales leadership, share his wealth of knowledge and experience. Mark delves into the intricacies of hiring a high-performing sales team, focusing on talent identification, innovative interviewing techniques, and fostering a culture...

In this edition of "Pillar Talk," Rick Smolen converses with Brian McDowell about instilling consistent sales process, adherence, and customer verifiable outcomes connected to forecasting. With his rich experience in sales, including his role as CRO, Brian shares invaluable insights on enhancing sales processes and team dynamics. Key Topics Discussed: Revisiting Sales Leadership Roles: B...

In this insightful episode of "Pillar Talk," Rick Smolen engages with Christina Brady in a deep dive into the essential role of communication in sales leadership. Christina, with her extensive background in sales leadership and unique experience as an artist and musician, brings a fresh perspective on how effective communication can drive success in sales teams. Key Topics Discussed: The...

Join Rick Smolen and other seasoned B2B sales leaders on the quest for defining great sales leadership. Learn the pillars of successful leadership, hear stories about what works and what doesn’t, learn lessons, and come away with specific tactics you can apply to your job or career. Music by Ben Cina & Ayler Young