Coach2Scale: How Modern Leaders Build A Coaching Culture

After more than 100 episodes, #Coach2Scale wraps with a powerful closing message from host Matt Benelli, one that goes far beyond sales tactics. In this final episode, Matt shares four hard-earned truths from hundreds of conversations with CROs, enablement leaders, and frontline managers. He challenges the myth of the “super rep turned manager,” breaks down the true ROI of coaching (7–8X when done right), and reminds us that one-on-ones aren’t just a task, they’re the operating system for growth.Matt also reflects on why performance loops aren’t enough without practice loops, and how great teams aren’t built on pressure, but on preparation. This episode connects the dots between personal development and business outcomes; it’s a call for CROs and GTM leaders to stop managing through dashboards and start developing their people with purpose. If you're serious about building a high-performing team that lasts, this episode is your blueprint.Top Takeaways1. The human side of coaching is non-negotiable.Vulnerability-based trust isn’t soft; it’s the foundation for accountability, belief, and long-term performance.2. Properly equipped managers deliver 7–8X ROI.Coaching isn’t a “nice to have”; consistent, structured 1:1s lead to higher engagement, lower attrition, and stronger pipeline performance.3. Stop promoting super reps into management without support.Selling and coaching are completely different skills; without systems and training, you set managers (and their teams) up to fail.4. Practice beats performance.Top teams don’t just execute, they review, adapt, and improve with immediate, behavior-focused feedback that drives lasting change.5. Coaching isn’t a tool; it’s a behavior change engine.Technology alone doesn’t drive growth; tying behavior improvement directly to outcomes is what makes a coaching culture truly effective.6. One-on-ones are not optional; they’re the operating system.When coaching becomes the standard cadence, it shifts manager behavior from reactive firefighting to proactive development.7. Performance grows when reps feel developed, not just measured.The best leaders strike a balance between empathy and accountability, investing in long-term careers rather than just meeting short-term quotas.8. Coaching is how you scale without breaking your team.Growth doesn’t come from dashboards or pressure; it comes from developing people who are confident, capable, and aligned.

In this replay episode of Coach to Scale, host Matt Bonelli sits down with Josh Allen, a veteran sales leader from LogMeIn, CarGurus, Drift, and other notable companies, to unpack what it truly takes to elevate sales performance. Together, they explore the myths of sales leadership, why “what worked for you” won’t always work for your team, and how curiosity, drive, and resilience shape top performers. Josh shares hard-earned lessons from building high-performing teams, along with strategies for identifying intrinsic traits during hiring and coaching salespeople with diverse motivations.Listeners will walk away with practical insights on connecting personal and professional goals, developing consistent coaching rhythms, and sustaining quota attainment without falling into the trap of “growth at all costs.” From nurturing top performers who are often overlooked, to coaching through adversity and building cultures of accountability, this conversation is packed with actionable takeaways for frontline managers, VPs, and anyone passionate about building resilient sales teams.Top Takeaways1. What worked for you won’t work for everyone.Great sales leaders learn quickly that their personal playbook can’t simply be copied and pasted onto their team.2. Hire for intrinsic traits, train for skills.Curiosity, drive, and resilience are largely unteachable, whereas sales processes and methodologies can always be refined and developed.3. Connect personal goals to professional performance.Helping reps tie career milestones to life goals (like paying off debt or buying a home) builds deeper motivation and accountability.4. Don’t overlook your top performers.High achievers also need coaching and career development, not just attention to struggling representatives.5. Toxic performance is never worth it.Even the highest producers can’t be allowed to undermine team trust or culture.6. Coaching is non-negotiable.Leaders who claim they “don’t have time to coach” are missing the very activity that drives quota attainment.7. Focus on one change at a time.Like a golf swing, coaching is most effective when managers help reps improve one skill consistently before moving to the next.8. Long-term consistency beats short-term intensity.Sustainable sales success stems from steady development and efficient growth, rather than hiring sprees and short-lived pushes.

In this replay episode of Coach to Scale, host Matt Bonelli sits down with Ben Johnson, VP at Zendesk, seasoned sales leader, and longtime CrossFit coach, to explore what it really takes to build a thriving sales career. Drawing on more than 25 years of experience at companies like Dell, Oracle, Workday, and Zuora, Ben challenges the myth that sales success is measured only by the quarter. Instead, he shares why the true differentiator is consistent coaching, a culture of accountability, and the willingness to sharpen your sword through personal development.Listeners will walk away with actionable insights on transforming performance improvement plans into coaching opportunities, creating cultures where vulnerability is strength, and distinguishing between “must-dos” and “how-tos” in sales leadership. From rebranding coaching as a growth engine to embracing “deeds, not words,” this conversation delivers timeless lessons for sales reps, managers, and leaders who want to play the long game and win.Key Takeaways1. Coach to the career, not the quota – Long-term success comes from developing people beyond just hitting short-term numbers.2. Performance Improvement Plans can be growth tools – When used correctly, PIPs should guide reps toward improvement, not serve as a punishment.3. Coachability is the key to success – The most successful reps are those open to feedback, willing to adapt, and eager to learn.4. Culture starts at the top – A strong coaching culture must be modeled by leadership and reinforced consistently across the organization.5. Preparation and debriefing matter as much as the meeting – Success comes from doing the pre-work, running the meeting, and reflecting afterward to continually improve.6. Focus on “must-dos” vs. “how-tos” – Clear expectations around the basics (like CRM hygiene) free up time to coach on higher-value selling skills.7. Deeds, not words – Accountability is proven through consistent actions, not promises.8. Get the bad news early – Addressing risks and challenges upfront allows teams to respond effectively instead of scrambling at the last minute.9. Invest in personal development – Ongoing learning, mentorship, and self-improvement are essential to staying sharp and thriving in sales.10. Find mentors and be one – Having someone to guide you (and paying it forward to others) accelerates growth and resilience in a sales career.

In this episode of Coach2Scale, author, professor, and board advisor Rachel Pacheco joins host Matt Bonelli to unpack one of the most overlooked drivers of sales performance: meaning. Drawing from her research and experience working with fast-scaling startups and MBA students alike, Rachel challenges the myth that salespeople are only motivated by money or perks. Instead, she shows why helping reps find purpose in their day-to-day work leads to deeper engagement, higher productivity, and better retention, and why frontline managers have the greatest influence over that outcome.You’ll hear practical ways to coach for meaning, how to deliver feedback that builds self-awareness and performance, and why micromanagement isn’t the real problem, meaninglessness is. Rachel shares coaching tactics for time-strapped managers, explains the risks of cookie-cutter motivation strategies, and outlines how structured 1:1s can become high-trust development conversations. Whether you're a CRO, frontline manager, or enablement leader, this episode will help you rethink how to build a culture where performance and purpose go hand-in-hand.Key Takeaways1. Meaning is a daily experience, not a grand purpose.Most employees aren't searching for their “life’s purpose” at work; they’re looking for day-to-day meaning in their tasks, interactions, and progress.2. Managers play a central role in helping reps find meaning.It's a myth that meaning is personal and out of a manager’s scope; the way managers structure work, give feedback, and coach reps directly influences how meaningful their work feels.3. Productivity increases when reps experience more meaning.Research, including studies by Adam Grant, shows that employees who understand the why behind their work are not only more engaged but also more productive and resilient.4. Motivation is personal and needs to be customized.Not all reps are driven by competition or money; some value connection, stability, or mastery, and managers must learn what uniquely drives each individual.5. Great coaching starts with structured autonomy.Managers should set clear expectations and outcomes, then give reps the space to figure out the “how”; this autonomy fosters ownership, trust, and greater meaning.6. Effective feedback is specific, timely, and impact-driven.Generic praise (“Great job!”) is forgettable; meaningful feedback highlights what was done well, why it mattered, and how it helped the team or business.7. Constructive feedback is a growth opportunity, not a threat.Most employees want more feedback, even the tough kind, but managers often avoid it due to discomfort, missing critical chances to drive behavior change.8. Curiosity is a manager’s superpower.Asking thoughtful questions helps uncover what motivates each rep, what’s holding them back, and how to connect daily work to a more profound sense of purpose.9. Coaching isn’t about giving answers; it’s about guiding reflection.Coaching helps reps build self-awareness, clarify decisions, and reflect on their growth; it’s less about solving problems and more about building capability.10. Don’t wait for better managers; teach your current ones how to coach.Many frontline managers were promoted without training; they don’t lack intent, they lack tools. Organizations must invest in teaching them how to lead through coaching.

In this episode, Sean Harvey, CRO at RocketRez, shares a practical framework for building coaching cultures that actually stick. He explains why trust, not tactics, is the starting point for real performance, and how coaching must move beyond pipeline reviews and into intentional skill development. From his early Oracle training to leading teams through hypergrowth and private equity scale-ups, Sean outlines the lessons that shaped his belief in coaching as both a performance lever and a retention strategy.If you’re still coaching “on the fly” or stuck playing super-rep, this conversation will challenge your assumptions. Sean covers the link between psychological safety and rep engagement, how vulnerability-based trust unlocks real development, and why sustainable growth demands coaching at every level from C-suite to the frontlines. You’ll walk away with a clearer understanding of what coaching is, what it’s not, and how to build a team that stays, grows, and performs.Key Takeaways1. Coaching must start at the top to stick long-termIf the C-suite doesn’t model and prioritize coaching, it gets deprioritized the moment short-term pressure hits.2. Trust is the foundation of any real coaching cultureReps won't grow unless they believe their manager has their long-term development, not just this quarter’s numbers, in mind.3. Vulnerability-based trust drives engagement and learning.Creating psychologically safe spaces where reps can fail and learn openly is what unlocks real skill development.4. Great managers coach people, not just deals.Coaching isn’t about saving deals; it’s about building reps who can consistently win without constant intervention.5. Consistency matters more than intensity.A lightweight but regular coaching rhythm beats sporadic “inspiration bursts” that vanish under pressure.6. You can’t scale if you’re only hiring more reps.Scalability means increasing productivity per rep, which only happens when you build coaching into the operating system.7. Coaching drives retention, especially in high-talent environmentsReps stay where they feel invested in, especially when they’re being challenged to grow with structure and support.8. Managers are overwhelmed and under-equipped to coachMost FLMs were promoted as top reps but were never taught how to develop others; tools and frameworks help close this gap.9. The best leaders have coaching “trees”Just like in sports, great coaches produce other great coaches; mentoring others to lead is a force multiplier.10. Success is compounding when coaching becomes cultureWhen coaching becomes normalized, teams get better, faster, improving not just results, but predictability.