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  • Entrepreneurship, Risk, and the Next Generation of Leaders

    Entrepreneurship, Risk, and the Next Generation of Leaders
    2026/06/30
    In this episode of Sales & Cigars, Walter Crosby sits down with Reed Nyffeler to talk about entrepreneurship, leadership, discipline, and what it takes to build opportunity for the next generation. Reed shares how entrepreneurship runs through his family history—from his great-great-grandfather immigrating to America and farming land in Nebraska, to his own early experiences selling gum in school and building lofts for college dorm rooms. The conversation explores why entrepreneurs are essential to the American economy, why self-discipline matters more than ideas, and why the next generation needs new models of ownership that match how they want to work and live. Reed also breaks down his approach to franchising, leadership development, and identifying the people who have the language, focus, and courage to become successful entrepreneurs. Episode Highlights Why entrepreneurship is deeply connected to America's growthReed's family history of immigration, farming, ownership, and opportunityThe early lessons Reed learned from selling gum and building dorm loftsWhy owning your job comes before owning a businessHow coming alongside an owner teaches entrepreneurial thinkingWhy the next generation wants autonomy before opportunityReed's vision for building app-driven franchise opportunitiesWhy fear and lack of focus are the two biggest threats to entrepreneursHow language reveals whether someone is ready to own a businessWhy small bets matter before taking big risks Key Themes & Takeaways Entrepreneurship starts with ownership. Before someone owns a company, they need to learn how to own their work.Value gets noticed. When people create value, the right leaders recognize it and reward it.Autonomy is changing entrepreneurship. Younger generations want control over how, where, and when they work.Fear and focus determine success. Entrepreneurs either get stuck because they are too afraid to move forward, or because they cannot focus long enough to win.Language reveals mindset. How people talk about responsibility, blame, and opportunity often reveals whether they are ready to lead.Risk should be calculated. Entrepreneurs do not avoid risk. They make smaller bets first and learn before firing the cannonball.Letting people go can create opportunity. Keeping the wrong person in a role can hold back both the company and the person who could thrive somewhere else. Who Should Listen This episode is especially valuable for: Entrepreneurs thinking about the next generation of ownershipYoung professionals who want to build something of their ownBusiness owners hiring or developing future leadersFranchise leaders looking for better ways to evaluate candidatesSalespeople who want to think more like ownersAnyone interested in discipline, risk, and entrepreneurial growth Links & Resources The Next in Leadership https://thenextinleadership.com Reed Nyffeler Transform Through Purpose by Reed Nyffeler Lead Exponentially by Reed Nyffeler Continue the Conversation If this episode made you think differently about ownership, discipline, sales, or what it really takes to build something, join the Sales Integrator Community. It's built exclusively for salespeople and sales managers who are looking for an edge—and for professionals who want support getting their questions answered by someone who has learned the hard way over 40 years. Free forever. Special founding member badges are available for the first 250 members. Join here: https://helix-community.circle.so/join?invitation_token=8b6622d942c852339d856b2af3504123cf9476e2-8b78b151-d94f-46df-a26b-ec4a6df24460 Subscribe & Follow Sales & Cigars is hosted by Walter Crosby of Helix Sales Development. The only smoke we blow is from cigars. Subscribe on Apple Podcasts, Spotify, YouTube, or wherever you listen.
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    37 分
  • Accountability, Visionaries, and the Right-Hand Seat

    Accountability, Visionaries, and the Right-Hand Seat
    2026/06/16
    In this episode of Sales & Cigars, Walter Crosby sits down with Matt Haney, fractional COO and integrator, to talk about accountability, visionary entrepreneurs, and what really keeps businesses from scaling. Matt works with founders who have built strong companies but have reached the point where they need help turning vision into execution. The conversation digs into the tension between visionaries and operators, why accountability often breaks down, and how leaders can create clearer expectations without slipping into micromanagement. Matt also explains why many business problems are really people problems—and why having a trusted right hand can help founders get out of seats they should no longer be sitting in. If you are a visionary leader trying to scale, this episode is worth your time. Episode Highlights Why founders often struggle to move from doing to leadingHow accountability breaks down when expectations are unclearWhy working sessions can become necessary when execution stallsThe danger of visionaries staying one or two levels too deep in the businessHow sales leaders can work better with founder-led organizationsWhy trust between a visionary and sales leader is criticalThe role of a fractional COO as operator, advisor, and accountability partnerWhy third-party perspective can help resolve leadership tensionHow to identify when your business needs a trusted right hand Key Themes & Takeaways Accountability starts with clear expectations. People cannot execute against vague direction. Leaders must define what success looks like.Visionaries often need help getting out of the way. Founders built the business by doing everything, but scaling requires them to release control in the right places.Execution problems are often people problems. Missed targets, stalled growth, and lack of follow-through usually connect back to communication, clarity, or accountability.Trust must be intentionally built. When founders bring in sales leaders or operators, information flow and role clarity are essential.A strong right hand creates leverage. The right operator helps translate vision into action, hold people accountable, and reduce chaos inside the business.Outside perspective can reduce friction. Sometimes a neutral third party helps leaders hear each other more clearly and move through tension faster. Who Should Listen This episode is especially valuable for: Visionary entrepreneurs who feel stuck in the weedsFounders looking for a trusted right hand or integratorSales leaders working inside founder-led businessesCEOs struggling with accountability across the teamService-based businesses trying to scale operationsLeaders who know the company needs structure but are unsure where to start Links & Resources Sinclair Ventures https://sinclairventures.com Matt Haney matt@sinclairventures.com Matt Haney on LinkedIn Continue the Conversation If this episode made you think differently about accountability, leadership, or how to build a business that can scale without everything running through you, join the Sales Integrator Community. It's built exclusively for salespeople and sales managers who are looking for an edge—and for professionals who want support getting their questions answered by someone who has learned the hard way over 40 years. Free forever. Special founding member badges are available for the first 250 members. Join here: https://helix-community.circle.so/join?invitation_token=8b6622d942c852339d856b2af3504123cf9476e2-8b78b151-d94f-46df-a26b-ec4a6df24460 Subscribe & Follow Sales & Cigars is hosted by Walter Crosby of Helix Sales Development. The only smoke we blow is from cigars. Subscribe on Apple Podcasts, Spotify, YouTube, or wherever you listen.
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    35 分
  • Invest in Yourself Before You Blame the Company

    Invest in Yourself Before You Blame the Company
    2026/06/02
    In this episode of Sales & Cigars, Walter Crosby sits down with John Golden, Chief Marketing Strategy Officer at Pipeliner CRM and host of Sales Pop, for a sharp conversation about sales leadership, self-development, business acumen, and what it really takes to stay valuable in sales. John shares why SPIN Selling remains one of the most important sales books ever written and why great salespeople are still defined by their ability to ask better questions, listen deeply, and resist the urge to jump into solution mode too quickly. The conversation also dives into one of John's biggest pieces of advice for sales professionals: invest in yourself. Don't wait for your company to train you. Don't complain that no one is developing you. Your career is your responsibility. From coaching and mentorship to business acumen and sales-marketing alignment, this episode is a reminder that the best salespeople never stop learning. Episode Highlights Why SPIN Selling still matters in modern salesThe difference between hearing and active listeningWhy silence after a good question is powerfulHow salespeople can stop rushing into solution modeWhy every salesperson should learn a sales methodologyJohn's advice to invest in yourself before blaming your companyThe ROI of hiring a coach or finding a mentorWhy sales, sales leadership, and CEO roles can feel lonelyThe importance of business acumen in today's sales environmentHow salespeople can bring value through insight, not just productsWhy a great sales call should be valuable enough to pay for Key Themes & Takeaways Great salespeople ask better questions. The best reps do not rush to pitch. They slow down, listen, and dig deeper.Silence is part of the process. When a prospect pauses after a strong question, don't interrupt. Let them think.Your career is your responsibility. If your company is not investing in your development, invest in yourself.Coaching pays for itself. A good coach or mentor can challenge your thinking, expand your goals, and accelerate growth.Sales can be lonely. Whether you are carrying a bag, leading a team, or running a company, you need people who can challenge and support you.Business acumen matters more than ever. Salespeople need to understand how businesses operate, how decisions get made, and how their solution impacts the whole organization.Value starts before the deal closes. A sales conversation should help the buyer think differently, even before they buy anything. Who Should Listen This episode is especially valuable for: Salespeople who want to take ownership of their careerSales leaders trying to develop stronger, more independent repsCEOs and entrepreneurs who want better sales conversationsTeams looking to improve discovery and active listeningRevenue leaders focused on sales and marketing alignmentAnyone who wants to become more valuable in every business conversation Links & Resources SPIN Selling by Neil Rackham Pipeliner CRM https://pipelinersales.com Sales Pop https://salespop.net John Golden on LinkedIn Continue the Conversation If this episode made you think differently about sales, leadership, or how to take ownership of your career, join the Sales Integrator Community. It's built exclusively for salespeople and sales managers who are looking for an edge—and for professionals who want support getting their questions answered by someone who has learned the hard way over 40 years. Free forever. Special founding member badges are available for the first 250 members. Join here: https://helix-community.circle.so/join?invitation_token=8b6622d942c852339d856b2af3504123cf9476e2-8b78b151-d94f-46df-a26b-ec4a6df24460 Subscribe & Follow Sales & Cigars is hosted by Walter Crosby of Helix Sales Development. The only smoke we blow is from cigars. Subscribe on Apple Podcasts, Spotify, YouTube, or wherever you listen.
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    34 分
  • Mike Chaput: Core Values Are Not Wall Art

    Mike Chaput: Core Values Are Not Wall Art
    2026/05/19

    Mike Chaput returns to Sales & Cigars to continue the conversation around leadership, culture, and why core values must go far beyond posters on the wall.

    In this episode, Walter Crosby and Mike dig into the real role values play inside a growing company—and what happens when leaders unintentionally create behaviors they never meant to encourage.

    Mike shares how nSight's early values around humor and fun sounded positive on paper, but eventually created fear, embarrassment, and resistance to admitting mistakes. The discussion explores why values should align with strategy, how culture impacts operational performance, and why leaders must actively model the behaviors they expect from their teams.

    This conversation is practical, honest, and highly relevant for leaders trying to build healthy accountability without losing connection and trust.

    Episode Highlights

    • Why many companies misunderstand core values
    • Mike's early "life raft exercise" for defining values
    • How humor unintentionally created unhealthy cultural behaviors
    • The rubber chicken story and the impact of public embarrassment
    • Lessons from lean thinking and Edwards Deming
    • Why fear destroys operational improvement
    • How respect became foundational to nSight's strategy
    • Why core values should evolve as the business evolves
    • The importance of making values memorable and teachable
    • nSight's RSVP framework:
      • Respect and Connect
      • Servant's Heart
      • Value Value
      • Progress Over Comfort
    • Why leaders must adapt to the values first
    • The difference between a workplace family and a high-performing team
    • Why accountability and connection must coexist

    Key Takeaways

    Core values should support strategy

    Values are not just words that sound good. They should reinforce the behaviors required for the business to succeed.

    Culture can create unintended consequences

    Even positive-sounding values can create fear, avoidance, or unhealthy team dynamics if they are not examined honestly.

    Fear prevents improvement

    Organizations cannot solve problems when employees feel unsafe admitting mistakes or identifying issues.

    Respect must come before humor

    Fun cultures work best when people first feel respected, safe, and valued.

    Leaders must model the values

    Core values are not just expectations for employees. Leaders must demonstrate them consistently themselves.

    Accountability and connection belong together

    Strong cultures balance caring deeply about people while still maintaining standards and honest feedback.

    Who Should Listen

    • CEOs and founders refining company culture
    • Leaders implementing EOS or operational frameworks
    • Managers trying to improve accountability and trust
    • Entrepreneurs building teams through growth and change
    • Sales leaders focused on culture-driven performance

    The Sales Integrator Community Invite

    Exclusively for salespeople and sales managers who are looking for an edge.

    For those sales professionals who want support in getting their questions answered by someone who has learned the hard way over 40 years.

    Free forever. Special badges created for the first 250 founding members.

    Join the Sales Integrator Community

    Subscribe to Sales & Cigars

    If you want real conversations about entrepreneurship, leadership, culture, and building companies with intention, subscribe to Sales & Cigars on Apple Podcasts, Spotify, or YouTube.

    The only smoke we blow is from cigars.
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    46 分
  • Culture Starts With the CEO

    Culture Starts With the CEO
    2026/05/05

    Culture Starts With the CEO

    Episode Description

    In this episode of Sales & Cigars, Walter Crosby sits down with Mike Chaput of nSight for part one of a three-part conversation on culture, core values, and leadership.

    Mike shares his entrepreneurial journey—from buying an IT services company at 24, surviving the dot-com crash, navigating bankruptcy, and rebuilding from scratch—to growing nSight into a $35 million managed IT services business with more than 140 employees.

    The conversation digs into one of the most important responsibilities of a CEO: strategy and culture. Mike explains why culture is not a vague company concept, but the behavioral operating system that shapes every decision inside the business.

    This episode is for business owners who have core values on paper—but want to understand whether those values are actually helping the company grow.

    Episode Highlights

    • Mike's journey from a failed first business to building nSight
    • The hard lessons learned from bad deals, bad leases, and misplaced trust
    • Why entrepreneurship often teaches through painful experience
    • How CEOs shape culture whether they realize it or not
    • Why strategy and culture are the CEO's two biggest responsibilities
    • The "Becker rudder" analogy for leadership and organizational direction
    • Why a business reflects the actions and beliefs of its leader
    • How old motivations can help you grow—then eventually hold you back
    • Why personal growth is required for business growth

    Key Themes & Takeaways

    • Your business reflects your leadership.
      The company you have today is a result of the actions, beliefs, and behaviors that created it.
    • Culture is not accidental.
      It is shaped by what leaders tolerate, reward, repeat, and reinforce.
    • The CEO has the greatest impact on strategy and culture.
      Those two responsibilities cannot be fully delegated.
    • Growth requires personal honesty.
      What helped you get to one stage may not help you reach the next.
    • Core values must connect to behavior.
      Values only matter if the team can understand them, remember them, and live them inside the business.
    • Entrepreneurial pain can become wisdom.
      Mike's early failures became the foundation for better leadership, better decisions, and a stronger company.

    Who Should Listen

    This episode is especially valuable for:

    • Business owners with core values that feel disconnected from daily operations
    • CEOs trying to scale without losing culture
    • Entrepreneurs who feel like the company has hit a ceiling
    • Leaders who want to better understand their role in shaping behavior
    • Teams preparing to revisit or redefine their company values

    Links & Resources

    nSight
    https://www.nsight.com

    Subscribe & Follow

    Sales & Cigars is hosted by Walter Crosby of Helix Sales Development.

    The only smoke we blow is from cigars.

    Subscribe on Apple Podcasts, Spotify, YouTube, or wherever you listen.
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    30 分
  • The Sales Problem You Can't See: Storytelling, Positioning, and False Momentum

    The Sales Problem You Can't See: Storytelling, Positioning, and False Momentum
    2026/04/21

    Most CEOs think they have a sales hiring problem, a sales performance problem, or a pipeline problem.

    But often, the real issue is deeper—and harder to see.

    In this solo episode of Sales & Cigars, Walter Crosby breaks down one of the most expensive hidden problems in growing companies: a lack of shared sales story and positioning clarity.

    This is not usually a problem caused by bad salespeople. In fact, it often shows up inside experienced sales teams. Reps sound confident. Conversations seem productive. Deals appear to move forward. But underneath the surface, the team is defaulting to pitching instead of guiding buyers through a clear story.

    Walter explains why pitching is often a coping mechanism, how false momentum shows up in the pipeline, and why this issue compounds as companies grow.

    Episode Highlights

    • Why many sales leaders misdiagnose messaging problems as hiring or performance problems
    • How experienced sales teams can still create confusion in the buying process
    • Why pitching feels productive—even when it is actually damaging deals
    • The hidden cost of collapsing context in sales conversations
    • How false momentum creates misleading pipeline and forecasting confidence
    • Why this issue gets worse as companies scale and add new people
    • The difference between a people problem and a visibility problem
    • Why you cannot coach alignment into existence—you have to extract it
    • How a shared sales story gives leadership more control over language, promises, and buyer expectations
    • The practical questions leaders should ask to evaluate whether this problem exists in their business

    Key Takeaways

    Pitching is often a symptom, not the root cause.
    When salespeople default to pitching, it is not always because they are lazy, untrained, or ineffective. Often, they are filling a gap. Without a shared sales story to anchor them, they rely on explanation, compression, and persuasion.

    False momentum is dangerous.
    Deals can look like they are moving when they are really just drifting. The pipeline feels active, forecasts appear reasonable, and leadership assumes progress is happening—until deals suddenly stall or disappear.

    The real issue is often visibility.
    The founder usually holds the origin story. Leadership holds the strategy. Marketing holds the brand language. Sales holds the buyer friction. But no one person sees the full picture clearly, which makes alignment difficult.

    This problem compounds as a company grows.
    New reps interpret the company differently. Marketing evolves. Strategy shifts. Language starts to drift. The result is not always immediate failure—it is inconsistency that becomes more expensive over time.

    You cannot solve this with surface-level fixes alone.
    More training, more scripting, or another sales hire will not fix the core issue if the underlying story is still unclear. Companies need to extract the real story already living inside the business and make it usable for the team.

    A shared story improves more than messaging.
    When sales teams know exactly what they are carrying into buyer conversations, deals become more grounded, forecasts become more trustworthy, and leadership regains control over promises, expectations, and positioning.

    Who Should Listen

    • Founders who feel like sales should be working better than it is
    • CEOs frustrated by stalled deals and inconsistent pipeline movement
    • Sales leaders trying to understand why experienced reps still default to pitching
    • Companies struggling with messaging drift as they scale
    • Anyone trying to improve sales clarity, consistency, and predictability

    Links & Resources

    • Free storytelling and positioning resource mentioned in the episode
    • Helix Sales Development

    Subscribe to Sales & Cigars

    If you want real conversations about selling, leadership, and the hidden issues that impact growth, subscribe to Sales & Cigars on Apple Podcasts, Spotify, or YouTube.

    The only smoke we blow is from cigars.
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    8 分
  • Your Story Is a Sales Advantage: A Conversation with Bill Blankschaen

    Your Story Is a Sales Advantage: A Conversation with Bill Blankschaen
    2026/04/07
    Bill Blankschaen joins Sales & Cigars to explain why entrepreneurs need a clear origin story, how storytelling builds trust, and why consistent messaging gives companies a real sales advantage. Episode Overview Most companies already have a story. The problem is they are not telling it clearly, consistently, or in a way that actually connects with customers. In this episode of Sales & Cigars, Walter Crosby sits down with Bill Blankschaen, author of Your Story Advantage, to talk about why storytelling is not just a marketing tool — it is a business and sales advantage. Bill shares his own journey from leading a private school to taking a major entrepreneurial risk in order to become a writer and storyteller. That decision eventually led to building Story Builders, where he now helps entrepreneurs, authors, and businesses clarify their messaging and tell stories that stick. The conversation explores the difference between an origin story and a brand story, why sales teams need a consistent narrative, and how leaders can create messaging their teams can actually use. Episode Highlights Bill's transition from school leader to entrepreneur, writer, and storytellerThe risk of leaving stable work to pursue a callingWhy every entrepreneur's breakthrough begins with understanding their own storyThe difference between a company's origin story and its broader brand storyWhy inconsistent storytelling creates friction for sales and marketing teamsThe importance of helping the whole company "sing from the same hymnal"Bill's five-part storytelling structure: attention, tension, connection, solution, and actionWhy salespeople often jump to the solution too earlyHow strong storytelling helps buyers feel understood before they ever hear the pitchWhy storytelling should be customer-centered, not company-centered Key Takeaways Your story matters more than you think. Many founders and entrepreneurs downplay their own story because it feels normal to them. But your story is often the very thing that helps customers trust you, relate to you, and understand why your company exists. An origin story creates context. A strong origin story explains where the business came from, why it was started, and what problem or calling led to its creation. It gives customers and employees a deeper understanding of the mission behind the company. Your story is about you — but it is not for you. One of Bill's most important points is that while your story may start with you, it must be framed for the customer. The goal is not self-expression for its own sake. The goal is connection. Sales teams need a shared story. When every salesperson tells a slightly different version of the company story, trust erodes and the message gets diluted. Clear storytelling gives the team a shared framework they can deliver in their own voice without drifting off-message. Storytelling should start with the customer, not the product. Too many companies jump straight to features, benefits, and solutions. But buyers care first about their own goals, problems, and frustrations. The best storytelling starts there. A simple structure makes storytelling usable. Bill's five-part framework gives companies a practical way to shape their messaging: Attention — what the customer wantsTension — what is getting in the wayConnection — why you understand and can helpSolution — what you offerAction — what they should do next Good storytelling makes scaling easier. When the founder is the only one who can tell the company story well, growth gets stuck. A clear story helps the whole team communicate consistently across sales, marketing, and leadership. Who Should Listen Entrepreneurs trying to clarify their company messagingFounders who know their story but struggle to get it out of their headSales leaders who want their team speaking more consistentlyCompanies where sales and marketing are not aligned on the messageAnyone who wants to turn their story into a real business advantage Links & Resources Your Story Advantage by Bill BlankschaenStory BuildersBill Blankschaenyourstoryadvantage.com Subscribe to Sales & Cigars If you want real conversations about selling, leadership, and building a message that actually connects, subscribe to Sales & Cigars on Apple Podcasts, Spotify, or YouTube. The only smoke we blow is from cigars.
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    32 分
  • Short-Term Pressure Is Killing Great Sales Leadership

    Short-Term Pressure Is Killing Great Sales Leadership
    2026/03/24

    In this episode of Sales & Cigars, Walter Crosby sits down with Darren Mitchell, host of the Exceptional Sales Leader podcast, for a sharp conversation about sales leadership, short-term thinking, and what it really takes to build sustainable sales teams.

    Darren shares his path from engineering to telecommunications sales to sales leadership, and explains why too many organizations still confuse high-performing salespeople with high-potential leaders. The conversation digs into the pressure sales leaders face to hit short-term numbers, the damage that comes from product-first selling, and why the best leaders focus on building teams that can succeed without them.

    From The Infinite Game to Atomic Habits, this episode is packed with practical leadership wisdom for anyone trying to build a stronger sales culture—one rooted in service, discipline, and long-term thinking.

    Episode Highlights

    • Why The Infinite Game is a must-read for sales leaders under quarterly pressure
    • How short-termism damages customer relationships and long-term revenue
    • Why Atomic Habits matters for sales teams and leadership development
    • Darren's transition from engineer to salesperson to sales leader
    • The danger of promoting top reps into leadership without proper development
    • The powerful lesson Darren's manager gave him on his very first day as a sales leader
    • Why the goal of great leadership is to make yourself unnecessary
    • How sales leaders accidentally train customers to bypass their salespeople
    • Why product training is not enough to create great sales teams
    • The importance of understanding buyer psychology instead of pushing product

    Key Themes & Takeaways

    • Great sales leaders play the long game.
      Organizations obsessed with quarter-to-quarter results often sacrifice trust, relationships, and sustainable growth.
    • Leadership is not the same as top performance.
      Being a great salesperson does not automatically prepare someone to lead, coach, and develop others.
    • The best leaders build teams that can thrive without them.
      Sales leadership is not about being the hero in every deal. It is about creating an environment where the team can perform independently.
    • Habits drive long-term success.
      Small daily disciplines compound over time and create the consistency great sales teams need.
    • Customers do not care about your product first.
      They care about their problems, their priorities, and what happens if those problems remain unsolved.
    • Sales is service when done correctly.
      The role of the salesperson is not to push product, but to help a customer recognize a problem and evaluate a solution.
    • Coaching and mentoring are essential.
      Without guidance, many new sales leaders default to control, ego, or problem-solving for their team instead of developing them.

    Who Should Listen

    This episode is especially valuable for:

    • Sales leaders feeling trapped by short-term revenue pressure
    • Founders and executives trying to build stronger sales leadership
    • Organizations promoting top reps into management roles
    • Sales teams that rely too heavily on senior leaders to close deals
    • Anyone who wants to build a more sustainable, service-driven sales culture

    Links & Resources

    The Infinite Game by Simon Sinek
    Atomic Habits by James Clear

    Exceptional Sales Leader
    https://exceptionalsalesleader.com

    Darren Mitchell on LinkedIn

    Exceptional Sales Leader Podcast

    Subscribe & Follow

    Sales & Cigars is hosted by Walter Crosby of Helix Sales Development.

    The only smoke we blow is from cigars.

    Subscribe on Apple Podcasts, Spotify, YouTube, or wherever you listen.
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    54 分