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.

Matt Benelli sat down with Mark Roberge last year, former CRO at HubSpot, Harvard Business School professor, and co-founder of Stage 2 Capital, to challenge some of the most persistent myths in sales leadership. From debunking the idea that top reps make the best managers to exposing why shadowing high performers can actually backfire, this conversation delivers a candid look at why most coaching programs fail to scale and what to do instead.

Mark lays out a structured, repeatable approach to frontline coaching that not only boosts individual rep performance but transforms how entire sales organizations operate. He shares why focusing on team attainment is less useful than tracking the percentage of reps hitting quota, how managers can move from reactive fire drills to proactive coaching cycles, and why self-diagnosis is the new sales superpower. If you're a sales leader still stuck on the hamster wheel, this episode offers a way off.

Key Takeaways

1. Top reps don't make the best managers
The traits that drive individual quota success, such as assertiveness or autonomy, often conflict with the empathy and patience required to coach others effectively.

2. Shadowing high performers is not an onboarding strategy
New reps pick up bad habits and unteachable skills when learning only by imitation; structured onboarding with a defined process is more effective.

3. Coaching can (and must) scale.
A consistent, top-down cadence of rep-by-rep skill diagnosis, action planning, and metric tracking creates scalable coaching across large sales orgs.

4. Reps rarely know why they’re underperforming
Without data, reps and managers often misdiagnose performance gaps; combining call data and funnel metrics helps uncover the true root causes.

5. Managers must move from reactive to proactive
Time-blocked 1:1s tied to skill development, not just deal triage shift coaching from “fire drills” to intentional growth plans.

6. Quota attainment by rep is the real health metric.
Overall team attainment hides unhealthy reliance on a few stars; the percentage of reps hitting quota shows true team performance and scalability.

In this episode of Coach2Scale, CoachEm CEO and co-founder Colum Lundt joins host Matt Benelli to unpack a critical but often overlooked reality in sales leadership: frontline managers are the linchpin to scalable growth, yet they’re routinely undertrained, overwhelmed, and underleveraged. Colum shares firsthand insights on why simply promoting great reps into management roles isn’t working and how the right tools, data, and AI-powered systems can transform managers from reactive deal chasers into proactive skill builders.

Listeners will walk away with a clearer understanding of how AI should act as a copilot, not a crutch; the compounding impact of consistent developmental coaching over deal coaching; and how to drive real behavior change in reps without adding more to a manager’s plate. If you’re a CRO thinking about enablement, productivity, and long-term performance, this episode offers a sharp, no-nonsense look at what’s broken and what you can do to fix it.

Key Takeaway

1. Frontline Managers Are the Most Underdeveloped Yet Most Critical Role in Sales
Managers get the least training and the most pressure, yet their influence has the highest ROI, up to 7–8x for every dollar invested.

2. AI Should Be a Copilot, Not a Replacement
The future of sales management lies in AI that augments human leadership by handling prep, surfacing insights, and reducing cognitive overload, not replacing empathy and accountability.

3. Developmental Coaching Is What Scales, Not Deal Coaching
Skills coaching “between the games” has far more long-term value than reactive deal coaching, which often reinforces short-term thinking.

4. Manager Span of Control Has Exploded
The average frontline manager is managing too many reps with too many tools and no time to coach; CoachEm helps them scale themselves without sacrificing quality.

5. Change Fatigue and Tech Overload Are Crushing Sales Teams
Especially in mid-market, reps and managers are drowning in tools and new initiatives without a clear structure or prioritization, which undermines focus and execution.

6. AI-Powered Role Play Is a Breakthrough for Enablement at Scale
CoachEm’s integration with Hyperbound lets companies simulate real conversations—both for reps and for managers dramatically improving readiness without needing live trainers.

7. CoachEm Makes Performance Coaching Measurable and Repeatable
The platform uses CRM, call transcripts, and behavioral data to show exactly what’s working and what’s not, down to missed calendar invites that slow deal velocity.

8. The Best Reps Still Need Coaching, They Need Different Coaching
Even top performers benefit from sharpening specific skills; the right system gives managers the data to coach everyone, not just the squeaky wheels.

9. Customer Success Is the Next Frontier for Coaching Execution
As more CSMs are pulled into revenue roles, CoachEm is expanding to support upsell, cross-sell, and relationship-building motions as rigorously as sales.

10. If You Want to Fix Sales Productivity, Start by Fixing the Manager Experience
Sales cultures that prioritize manager development first see better rep retention, stronger pipelines, and more consistent execution across teams.

Welcome to Episode 100 of the Coach2Scale Podcast! In this milestone edition, host Matt Benelli delivers a no-nonsense Q2 debrief packed with hard-earned lessons, powerful guest stories, and leadership truths that cut through the noise. From blind spots that sink careers to the non-negotiables of trust, culture, and coaching, this episode distills what it really takes to scale teams and drive meaningful results. Hear firsthand from Kevin McCarthy on self-inflicted downfall, from John Walston on building mental resilience, and from Neil Wood on solving, not selling, your way to a billion-dollar success.

This episode is more than a recap; it’s a call to action. Matt shares five brutally honest themes that every sales leader, coach, and executive needs to hear: coaching is about asking questions, not issuing commands; culture is defined by what you tolerate, not what you say; inconsistency erodes trust; and enablement isn’t optional; it’s your competitive edge. Whether you're leading a team or trying to level up, this episode will challenge your assumptions and light a fire under your Q3 game plan. Let’s get after it, and as always, CoachEm if you want to keep ‘em.

Key Takeaways

1. Adversity Doesn’t Build Character; It Exposes It
2. Stop Pitching. Start Solving. Or Step Aside.
3. Coaching Is a Skill; And Most Managers Suck At It
4. Culture Isn’t a Slogan; It’s What You Tolerate

Guests
1. Kevin McCarthy -  https://www.linkedin.com/in/kevinmccarthycsp/
2. John Walston- https://www.linkedin.com/in/john-walston-63a042206/
3. Neil Wood -  ⁨https://www.linkedin.com/in/neilwoodconsulting/
4. Michael Muhlfelder -  https://www.linkedin.com/in/mikemuhlfelder/
5. Tom Young - https://www.linkedin.com/in/tom-young-7aba11/
6. Mike Montague -  https://www.linkedin.com/in/mikedmontague/
7. Jeff Keplar - https://www.linkedin.com/in/jeffrey-keplar-63a2b86/
8. Mark Kosoglow - https://www.linkedin.com/in/mkosoglow/
9. Kevin Gaither -  ⁨https://www.linkedin.com/in/kevingaither/
10. Tony Burnside - https://www.linkedin.com/in/tonyburnside/
11. Pam Dake - https://www.linkedin.com/in/pamela-dake-1152483/

What happens when a founder-led sales strategy hits its limits? In this episode of Coach to Scale, Ken Grasso, veteran CRO, advisor, and founder of Catalyst Peak Ventures, pulls back the curtain on the messy, mission-critical transition from instinct-driven selling to structured, scalable revenue operations. With experience leading global go-to-market teams and helping companies grow from zero to IPO, Ken shares unfiltered insights on why founders often struggle to let go of sales, the costly myth of the “natural-born” sales leader, and how process, not personality, is the real growth engine.

Packed with real talk for CROs, revenue leaders, and founders alike, this conversation explores the pivotal role of coaching cultures, how to hire for system-fit over resume flash, and the urgent need to professionalize sales before seeking investment or exit. You’ll also hear Ken’s candid reflections on career reinvention, building credibility as a fractional exec, and why planning for the next chapter before you need to is essential for long-term impact. Whether you’re scaling your first team or rethinking what makes sales truly sustainable, this episode is a playbook in disguise.

Top Takeaways

1. Founder-led selling becomes a liability as you scale
Early-stage founders may be the best sellers at first, but their instinctive, unstructured style can block repeatability and growth.

2. Great sales reps don’t automatically make great managers
Promoting top performers without leadership skills or process discipline can stall team performance and create chaos.

3. The sales process is the foundation, not a nice-to-have
A defined, teachable sales process enables forecastable growth, efficient onboarding, and higher valuations.

4. CROs must earn trust and re-educate founders on go-to-market
Transitioning founder-led orgs to scalable operations requires a blend of credibility, patience, and strategic coaching.

5. Hiring should prioritize system-fit and coachability.
The best candidates align with your GTM model and are eager to operate within a defined system, not just shine as individual contributors.

6. You can’t outrun a broken foundation with short-term wins
Heroics might save a quarter, but without an operational structure, you’ll eventually burn out or break the model.

7. Fractional leadership can unlock massive value for growth-stage teams
Bringing in experienced operators part-time can help companies avoid costly misfires and build maturity without overextending budgets.

8. Plan your career pivot before the market makes you do it
Ken urges seasoned leaders to proactively define their “Plan B,” emphasizing personal reinvention and long-term career resilience.

9. Strong systems beat star power—ask the NFL.
Drawing on sports analogies, Ken explains why team performance relies more on consistent playbooks than flashy individuals.

10. Valuation depends on your GTM maturity.
Investors and acquirers don’t just buy your product they buy your ability to sell it repeatedly, predictably, and without founder involvement

What happens when your top-performing rep becomes a struggling front-line manager? In this episode, Dan Freund, Chief Sales Officer at Invoice Cloud and former Oracle sales leader, unpacks the leadership gap plaguing high-growth sales orgs. From rethinking territory design to balancing equity with accountability, Dan shares how he transformed underperforming teams into consistent winners, without clinging to sales superstars or status quo assumptions.

This episode offers a candid look at the hard decisions CROs and sales leaders must make to scale performance without sacrificing culture. You'll hear why conviction matters more than consensus, how to spot reps ready for more than just promotion, and why internal networks can fast-track productivity. If you’re tired of recycling the same top 10% and ready to build a coaching culture where every position matters, this conversation will shift how you lead.

Top Takeaways

1. Don't fear reassigning key accounts.
Even top performers can adapt; keeping all the best accounts with senior reps creates a revolving door for new hires and stalls team growth.

2. Break the “greenfield trap” for new reps.
Reps in undeveloped territories often fail not from lack of talent, but from poor territory design and lack of enablement.

3. Promotion isn’t leadership readiness.
Great reps often struggle as managers unless they’re taught how to coach, hold people accountable, and operate strategically.

4. Coaching must go beyond deal reviews.
Most managers default to pipeline triage; real coaching means developing skills that affect every deal, not just the current quarter.

5. Internal networks matter as much as external ones.
High-performing reps build relationships across legal, finance, and other internal teams early, compressing ramp time and increasing deal velocity.

6. The best leaders make ideas that help the business, not themselves.
Dan’s biggest promotions came from pitching business-first ideas with no personal gain attached; conviction creates opportunity.

7. Equitable territories create stronger teams.
Giving everyone a real shot at success, rather than over-rewarding tenure, builds momentum and reduces attrition.

8. Friendship and accountability can coexist.
Strong relationships within the team don’t weaken performance; they create the trust needed for tough conversations and high standards.

9. Ask: Are you making the news or reporting it?
Reps who lead the sales process proactively outperform those who simply react to buyer-driven next steps.

10. You can build momentum and hit the number.
It’s not either-or; with the right structure, you can build long-term capability while executing in the short term.

When sales targets are missed, most leaders look at the pipeline, process, or personnel. But what if the real issue is a lack of psychological safety? In this episode of Coach to Scale, host Matt Benelli sits down with John Walston, author, entrepreneur, and founder of the Keep On Movement, to explore how vulnerability, empathy, and consistency in leadership can transform sales outcomes. Walston shares how personal adversity reshaped his leadership style, making him a more effective coach and culture builder.

This episode is a must-listen for CROs, VPs of Sales, and frontline managers navigating burnout, underperformance, or high turnover. You’ll walk away with tactical ways to shift from transactional management to human-centered leadership, without sacrificing accountability. Topics include managing anxiety in high-pressure environments, turning 1:1s into developmental moments, and why “get over it” is the fastest way to lose trust and performance. If you lead teams, this conversation will challenge how you measure success and show how culture is a quota strategy.

Takeaways 
1. “Just stop it” doesn’t work, especially in sales leadership.
Telling someone to push through stress or anxiety without support not only fails, but it also damages trust and culture.

2. You can’t lead people effectively if you don’t understand what they’re carrying.
Empathy isn’t a soft skill; it’s a leadership multiplier that directly impacts motivation and consistency.

3. Physical movement drives mental clarity and performance.
Exercise helped Walston recover from a personal crisis, and research shows it’s as effective as medication for many mental health issues.

4. Positivity isn’t the same as being happy.
Leaders can model resilience by moving forward with optimism, even while acknowledging discomfort or hardship.

5. Your team won’t grow if your 1:1s are just pipeline inspections.
Coaching conversations should go beyond deal reviews to include skill development and personal connection.

6. Culture is built in the moments between numbers.
Asking your reps about their weekend and remembering what they said builds trust that translates into accountability.

7. Positive self-talk is a skill leaders must model and teach.
Verbalizing functional thoughts (especially out loud) has a 10x psychological effect compared to internal dialogue.

8. Gratitude changes how you lead and how people follow.
Being grateful for struggle, not just outcomes, shifts the mindset and allows leaders to better support their teams.

9. Even one moment of connection can shift someone’s trajectory.
Whether it’s a smile, a T-shirt slogan, or a question at the right time, leaders have the power to influence more than they realize.

10. “Easy is not best,” and your reps need to hear that.
High standards, not hand-holding, are what help people rise. But they must be delivered with belief and support.

Can Sales Managers Be Friends with Their Reps? The Ultimate Sales Leadership Debate

Should leaders be friendly or firm? In this epic live debate from CoachEm’s inaugural Closing Arguments series, two powerhouse sales veterans, Mark Kosoglow (Co-founder & CEO at Operator, former Outreach leader) and Kevin "KG" Gaither (CEO of InsideSalesExpert.com, former ZipRecruiter exec), go head-to-head on one of the most controversial questions in sales leadership:

“Can, should, or would you be friends with your sales reps?”

Moderated by Matt Benelli, host of the Coach to Scale podcast, this unscripted, no-holds-barred session dives into real stories, polarizing philosophies, and battle-tested experiences on the fine line between empathy and authority.

What you'll learn:

When friendship enhances performance, and when it kills accountability

Why sales managers struggle with tough conversations

The hidden career risks of blurred boundaries

How modern leaders navigate connection, trust, and coaching culture

Get actionable takeaways for building high-performing sales teams while balancing trust, professionalism, and results.

This is not your average webinar. It’s honest. It’s engaging. It’s real sales talk for real sales leaders.

Sponsored by CoachEm: The world’s first AI coaching execution platform, built to scale sales success through data, coaching, and culture.

COMMENT below: Can you be friends with your reps? Where do YOU draw the line?

📥 Subscribe to the Coach to Scale podcast and never miss a real-world sales leadership discussion.