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 Takeaways

1. 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 Takeaways

1. Coaching must start at the top to stick long-term
If 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 culture
Reps 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 environments
Reps 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 coach
Most 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 culture
When coaching becomes normalized, teams get better, faster, improving not just results, but predictability.

In this special episode of Coach to Scale, host Matt Benelli takes on a bold challenge: a live cold-call role play with Hyperbound’s AI-powered prospecting bot one of the “rudest bots on the planet.” Joined by Hyperbound co-founder and CEO Sriharsha Guduguntla, Matt puts his skills to the test, showcasing how sales reps can practice real-world scenarios, handle objections, and refine their pitch with real-time coaching. The result? A raw, unfiltered look at what happens when the pressure is on and every word counts.

Listeners will walk away with insights into effective prospecting, the power of permission-based openers, handling resistance with confidence, and how instant AI feedback can accelerate coaching and skill development. Whether you’re a sales leader, manager, or rep looking to sharpen your edge, this episode delivers a front-row seat to practical techniques, lessons learned, and a clear takeaway: you don’t have to love cold calling you just need to practice, improve, and get better every time.

Key Takeaways

1. Practice under pressure matters – Putting yourself in tough role plays with AI bots helps reps simulate real-world challenges and improve faster than passive learning.

2. Instant feedback accelerates growth – AI delivers coaching in real time with detailed scoring criteria, so reps don’t have to wait for a manager’s one-on-one to learn what to improve.

3. Consistency beats comfort – You don’t need to love cold calling, but consistent practice builds confidence and competence over time

4. Three types of prospectors – Some salespeople thrive on cold calls, some avoid them but claim they do, and managers often love them because they don’t have to make them anymore, recognizing this helps leaders coach more effectively

5. Objection handling is a teachable skill – With structured practice and coaching, reps can learn to confidently navigate push back and still secure meetings

6. AI empowers both reps and managers – By offloading repetitive role plays and providing objective coaching, managers can spend more time on strategy while reps still get valuable development.

7. Anyone can try it – Hyperbound makes its prospecting bots publicly available so sales professionals can test themselves, practice as often as they want, and benchmark improvement

Scaling teams inside matrixed organizations is rarely about speed alone. Shane Hughes, Head of Customer Success at LinkedIn and former Salesforce executive, argues that real growth comes from slowing down to coach with intention, aligning stakeholders early, and focusing relentlessly on customer value. In this conversation, he shares how leaders can avoid the trap of “chasing renewals” and instead build advocacy from the start by connecting adoption to measurable business outcomes.

Shane also pulls from his experience leading teams that grew revenue from millions to billions to highlight what separates managers from true coaches. He explains why curiosity is the foundation of influence, how consistency compounds impact, and why high performers act more like consultants than communicators. Whether you’re a CRO, frontline manager, or rep aiming to lead, his lessons offer a clear path to scaling without losing your edge.

Key Takeaways

1. Renewals are won early, not saved late – Retention isn’t about heroics at the end of a contract; it’s about shaping value in the first months after a deal closes.

2. Adoption does not equal value – Usage is necessary but meaningless unless it connects to the customer’s defined business outcomes.

3. Curiosity drives advocacy – The best customer success leaders don’t just communicate; they ask sharp questions that reframe problems and uncover hidden opportunities.

4. Coaching beats chasing – Managers who focus on coaching their teams to think like consultants create consistent impact, while those who chase activity confuse motion with progress.

5. Slow down to speed up – Scaling in matrixed organizations requires alignment and influence across stakeholders; patient lobbying accelerates outcomes later.

6. Consistency compounds – Small, repeatable practices in coaching and customer engagement build long-term trust and measurable growth.

7. Leaders must coach across, not just down – True leadership requires influencing peers and executives in addition to managing direct reports.

Too many frontline managers are promoted for hitting quota, then left to figure out leadership on their own. In this episode, Jeff Cummings, COO at LLC Attorney, shares a battle-tested coaching playbook built through 20+ years of leading high-growth teams. He challenges the “leadership lie” that there's no time for 1:1s and lays out a structured, repeatable framework that transforms one-on-ones from status updates into high-impact coaching sessions.

Jeff walks through how to coach top performers without coddling them, how to use AI to scale personalized development, and why being a good manager has nothing to do with being in the deals. This episode is packed with practical guidance for CROs, RevOps, and enablement leaders looking to build durable revenue teams, starting with better coaching habits at the frontline.

Key Takeaways

1. The “Leadership Lie” is that there's no time for 1:1s.
Jeff calls out the myth that leaders are too busy to coach; if you're too busy for your people, you're too busy to lead.

2. One-on-ones should be structured, consistent, and focused on development, not deals.
Effective 1:1s follow a repeatable process that goes beyond pipeline reviews to drive skill growth and accountability.

3. Coaching should start with reflection by the rep.
Asking “what went well?” first gives the rep ownership and builds a coaching culture grounded in self-awareness.

4. Top performers need coaching, too, especially around behavior and professionalism.
Being a high producer doesn’t exempt someone from expectations; true leaders help reps round out their game.

5. Managers must separate being in the action from building the team that drives the action.
If you're still acting like a super rep, you're not creating leverage, and you're stunting team growth.

6. Missed 1:1s should be rescheduled immediately, not skipped.
Treat coaching like a customer meeting; canceling without rescheduling signals that people aren’t the priority.

7. AI can be used to scale coaching, not replace it.
Jeff uses AI to track commitments, organize feedback, and personalize development, but the human connection stays central.

8. Be fully present, no Slack, no inbox, no distractions.
Undivided attention during coaching moments signals to reps that their development matters.

9. Coaching isn’t a task; it’s a leadership mindset.
Great leaders don’t wait for permission to coach or train; they take ownership of their team’s growth trajectory.

10. Pay mentorship forward, build a legacy through people.
Jeff credits his early mentors and reinforces that the best ROI in leadership comes from investing in others and teaching them to do the same.

LinkedIn profile: https://www.linkedin.com/in/jeffcummings/

In this episode of Coach to Scale, we sit down with Sriharsha "Sai" Guduguntla, co-founder of Hyperbound, to unpack one of the most pressing challenges in revenue leadership: the coaching crisis. Despite billions invested in enablement tools, most frontline managers still spend less than 5% of their time actually coaching, and it's costing teams deals, confidence, and retention. Sai shares how Hyperbound is redefining sales practice by enabling reps to roleplay high-stakes calls, objections, and negotiations using AI before they ever speak to a real prospect.

Sai and host Matt Benelli explore why traditional training doesn’t stick, how to coach the iPhone generation, and why AI-driven feedback is the key to scalable performance improvement. From building reps’ confidence to reducing CAC, shortening ramp time, and even coaching managers themselves, this conversation delivers practical insight for CROs and GTM leaders committed to leveling up their teams. If you think having Gong means you’re coaching, think again.

Key Takeaways

1. Coaching is broken, and leaders know it.
Most frontline managers spend less than 5% of their time coaching, and even if they admit it's not enough, despite having tools like Gong or Chorus.

2. Owning tools doesn’t mean using them.
Just because you’ve bought sales tech doesn’t mean your team is getting value from it; usage and enablement are two different things.

3. Reps are practicing on real prospects, and that’s a problem.
Without structured practice environments, reps learn in live selling situations, losing deals and confidence in the process.

4. AI enables real, scalable practice.
Hyperbound uses AI to let reps roleplay discovery, objections, and negotiations with instant feedback, so they improve before going live.

5. Training decay is real 87% is forgotten in a month.
Sai shares how Hyperbound clients are replacing costly SKOs and one-off trainings with ongoing practice that reinforces key skills year-round.

6. Feedback should be immediate, not delayed.
Instead of waiting weeks for one-on-one feedback, reps using AI tools can instantly iterate and refine their performance after each session.

7. AI coaching is objective and data-backed.
AI removes bias by evaluating reps consistently, benchmarking them against top performers, and identifying real improvement areas.

8. Confidence is often the root blocker to performance.
A lack of confidence, not skill, is what holds many reps back from picking up the phone; Hyperbound helps reps build that confidence safely.

9. Managers need coaching too.
Hyperbound doesn’t just coach reps, it also trains managers by simulating coaching conversations and giving feedback on their effectiveness.

10. Culture matters more than tools.
Without leadership buy-in and a true coaching culture, even the best tools won’t lead to behavior change; some orgs just aren’t ready.

What happens when a top-performing rep becomes a people-first leader in one of the most demanding roles in tech? In this episode of Coach2Scale, Jeff Perry, CRO at Carta, shares his leadership journey from his early days at Oracle to building high-performing, diverse teams at Carta. He unpacks the misconceptions that still hold sales leaders back, like the idea that only hard-charging, deal-focused managers succeed, or that considerable company experience doesn't translate to startup growth. Jeff challenges these myths with candor, offering lessons for anyone navigating their evolution as a leader.

The conversation tackles why being a “nice leader” isn’t a liability, how to hire from non-obvious backgrounds, and why no one should ever lose a deal alone. Matt and Jeff also dig into the most challenging job in sales, the frontline manager, and why equipping them with the right mindset and tools is the only way to scale performance sustainably. Whether you're a rep, manager, or CRO, this episode will help you rethink how leadership, culture, and coaching intersect to drive lasting results.

Key Takeaways

1. Lean into who you are as a leader
Stop trying to fit someone else’s mold, own your style, values, and story to build authentic credibility.

2. Prominent company leaders can thrive in startups.
Success in enterprise sales doesn’t disqualify you from excelling in high-growth, early-stage environments if you can translate your experience.

3. Empathy and accountability are not mutually exclusive
Being a “nice” leader doesn’t mean being soft; it means building trust so you can challenge and develop your people effectively.

4. Hiring for diversity improves team performance.
Creating teams with varied backgrounds and experiences, not just résumés, leads to more resilience, learning, and results.

5. Balanced team performance is more sustainable than star-centric models
Hitting 115% with everyone contributing beats 130% with a few carrying the load, especially when building culture and scale.

7. Managers should never lose a deal alone.
The best AEs use the entire team, from executives to product, to win; lone-wolf selling is inefficient and risky.

8. Coaching should focus beyond the deal.
Too many 1:1s revolve around the pipeline; great leaders use coaching to build reps’ long-term skills and confidence.

9. Sales leadership is about consistency through volatility
In unpredictable markets, reps need leaders who are steady, transparent, and focused on what can be controlled.

10. High growth creates opportunity, but only for those who embrace it
Carta’s rapid evolution has opened new career paths, but leaders must stay close to the people and remain hands-on to unlock them.

11. Frontline managers need structure and support to succeed
The FLM role is the most overloaded in the org; without tools, coaching frameworks, and clarity, they default to dealing with triage and burnout.

Consistency beats charisma in frontline sales leadership. In this episode of Coach2Scale, VMware Carbon Black’s Head of Sales Development, Victoria Abeling, shared what it takes to build a high-performance team when everyone’s overworked and every 1:1 is at risk of being replaced by a pipeline review. She unpacks why many reps view coaching as punitive, how that culture was unintentionally built over decades, and the mindset shift required to make coaching a trusted, productive habit, not a compliance exercise.

Victoria offers a pragmatic breakdown of how she uses quarterly operating cadences, individualized development plans, and coaching conversations grounded in deal inspection to uncover skill gaps, not just red flags. You'll hear how to coach for discovery, disqualify with confidence, and push back on the myth that high performers don’t need help. If you're a sales leader tired of playing firefighter, or a CRO wondering why the pipeline isn't growing with headcount, this conversation will reframe how you think about performance management and the role cadence plays in building trust, accountability, and results.

Top Takeaways

1. Coaching is not punitive; it’s a performance multiplier.
Many reps assume coaching signals underperformance, but reframing it as a skill-development tool builds trust and accountability.

2. Consistency in 1:1s is non-negotiable.
Coaching only drives behavior change when it follows a predictable cadence; skipping sessions sends the message that development is optional.

3. Top performers need coaching too.
Even the best reps have blind spots, and coaching them to sharpen specific skills is how you go from 100% to 130% of quota.

4. Quarterly operating rhythms help leaders avoid reactive management.
Structuring the year into coaching and development cycles keeps leaders proactive, not just in-the-weeds on deals.

5. Coaching must go beyond the deal to address the “how,” not just the “what.”
Managers who only review pipelines miss opportunities to build long-term skills like discovery, negotiation, and qualification.

6. Disqualification is as valuable as closing.
Teaching reps to say “no” to the wrong opportunities frees them to invest time in the right ones and protects forecast accuracy.

7. Modern buyers are informed; sellers must be sharper in discovery.
With buyers doing most of the research on their own, reps must master early discovery to stay relevant and competitive.

8. Leaders must learn to receive feedback without defensiveness.
Victoria shares how this mindset shift helped her grow as a leader and foster stronger coaching relationships.

9. How you show up matters, even on Zoom.
From attire to preparation, professionalism in remote settings still signals credibility and respect.

10. Coach the individual, not the scoreboard.
Coaching should focus on skills that compound over time, not just pressing for this month’s number.