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.
What separates the good sales leaders from the truly great ones?
It’s not just hitting quota. It’s not just building big teams. It’s the ability to coach people in a way that transforms performance for the long haul.
In this replay episode of Coach to Scale, I sat down with Josh Allen, a sales leader who has built and scaled teams at companies such as LogMeIn, CarGurus, Drift, and others. Our conversation hit on a truth that every CRO needs to hear: motivating your sales team is not enough. To drive consistent performance, you need to build a culture of coaching that aligns individual strengths, personal goals, and company outcomes.
Lesson 1: You Can’t Copy and Paste Your Playbook
Josh shared one of the biggest myths in sales leadership: the belief that because something worked for you as a top rep, it will automatically work for everyone else. The reality? Every rep is wired differently. As leaders, we need to coach individuals, not based on our own past successes.
Lesson 2: Hire for Traits, Train for Skills
The unteachable factors drive, curiosity, and grit are what separate high performers from the pack. Skills and methodologies can be learned. If you’re serious about building a resilient team, prioritize those intrinsic traits in your hiring process and invest in training the rest.
Lesson 3: Connect Personal Goals to Performance
One of the most powerful insights from Josh was the importance of linking personal goals to professional targets. Whether it’s paying off student loans or buying a first home, when a rep can clearly see how quota attainment connects to their life, motivation skyrockets. As CROs, it’s our responsibility to ensure those conversations aren’t one-offs; they need to be built into our one-on-ones and coaching rhythm.
Lesson 4: Don’t Neglect Your Top Performers
Too often, managers spend all their energy on struggling reps and onboarding new hires while leaving their A-players to fend for themselves. Josh made it clear: your top performers need just as much coaching and development. Ignoring them risks burnout, disengagement, or even losing them to competitors.
Lesson 5: Culture Eats Numbers for Breakfast
High performance can’t excuse toxic behavior. Josh shared stories of top reps who delivered results but undermined trust and fairness. The lesson for CROs: numbers can’t come at the expense of culture. If someone is poisoning the well, the cost to the team outweighs the revenue they bring in.
Lesson 6: Coaching Is Non-Negotiable
When leaders say, “I don’t have time to coach,” what they’re really saying is, “I don’t have time to improve performance.” Coaching is the job. And effective coaching isn’t about fixing everything at once; it’s about finding one key area for each rep, focusing on it with consistency, and moving the needle step by step.
Lesson 7: Long-Term Consistency Wins
We closed with a reminder from Josh that’s worth putting on every CRO’s wall: long-term consistency beats short-term intensity. In a market that no longer rewards “growth at all costs,” sustainable coaching cultures will be the competitive advantage that separates thriving teams from those that churn.
Final Word
If you’re leading a sales organization today, the question isn’t whether you’re motivating your team; it’s whether you’re coaching them for long-term success. This episode is packed with strategies and stories that will challenge how you lead and inspire how you grow.
Listen to the full conversation with Josh Allen here — and remember: coach ’em if you want to keep ’em.
