Blog to excel in sales conversations

Rolling out AI in traditional industries like insurance faces one major hurdle: resistance from the people who need to use it. Learn Bryan Dinklenburg's 6-step framework that transformed skeptical managers and veteran agents into AI advocates, delivering measurable results in weeks without forcing change or threatening jobs.

October 31, 2025

Most enablement teams struggle to prove their impact on revenue, leaving them vulnerable when budgets tighten. Jordan Timothy, Head of Enablement at Semrush, reveals the three critical metrics every enablement professional must own to transform from a support function into a strategic revenue driver: ramp time, pipeline generation, and deal velocity.

October 29, 2025

Insurance agents hear the same objections over and over: "too expensive," "found it cheaper," "let me think about it." Learn how top agents handle the 10 most common pushbacks and turn skeptical prospects into closed deals.

October 24, 2025

Buyers spend only 5-6% of their time talking to sellers—the other 95% happens through emails and documents you'll never see. Learn Lawrence Wayne O'Connor's proven framework for turning your sales team into strategic writers who influence decisions even when they're not in the room.

October 22, 2025

Most new sales leaders rush to fix problems without understanding the full picture. Learn Meredith Chandler's proven 90-day framework that helped two newer AEs hit 150% and 180% of quota by listening first, gathering the right data, and building systematic onboarding processes.

October 17, 2025

Most sales teams waste millions chasing the wrong customers because their ICP is based on outdated gut feelings, not data. Learn how to transform your ICP into a living, data-driven system that updates quarterly, integrates AI insights, and helps your reps prioritize high-fit accounts that close 6.3x more often and 21% faster.

October 14, 2025

Traditional sales training fails because reps forget 80% of what they learn within a month. AI sales roleplay tools solve this by offering on-demand, judgment-free practice that accelerates onboarding and scales quality coaching across entire teams.

October 10, 2025

Learn why the best sales coaches borrow from dog rescue psychology—creating safe spaces where vulnerability is welcomed, and discover four weekly activities that build trust before demanding performance.

October 8, 2025

Stop treating sales enablement like compliance training. Discover 5 strategies from Meganne Brezina, Head of Enablement at Zylo, to align enablement with business objectives and drive measurable revenue growth.

October 1, 2025

Master 15 powerful active listening techniques that transform sales conversations from product pitches into trust-building consultations. When prospects feel genuinely heard and understood, they're more likely to share their real challenges and choose your solution over competitors who talk more than they listen.

September 26, 2025

While 98% of business leaders believe AI will transform their industry, half have done zero formal AI training. Learn Julie Holmes' 3-step framework that transforms sales teams from AI skeptics into AI-powered revenue generators.

September 24, 2025

Discover 10 proven AI prompts that transform 4-hour prospect research into 30-second deep analyses. Learn how top-performing salespeople are using AI to conduct smarter research, build detailed buyer personas, and prepare for executive conversations while reclaiming hours to focus on closing deals.

September 19, 2025

When faced with aggressive sales targets, most leaders panic and start hiring more reps, but Ned Arick has a smarter approach. Learn his 5-step data-driven framework that turns "impossible" targets into achievable goals through strategic analysis and cross-departmental collaboration.

September 16, 2025

Discover why AI will never fully replace enterprise salespeople, despite transforming the sales landscape and explore how Human-AI collaboration through tools like AI coaching and roleplay is creating the optimal future for sales performance.

September 12, 2025

While everyone debates iPhone 17 features, smart sales leaders invest in AI coaching platforms that boost team performance. Discover why AI sales coaching delivers better ROI than hardware upgrades and transforms average reps into revenue generators.

September 10, 2025

Discover how to transform AI from a threat into your sales superpower with 4 practical strategies from John Barrows, who's trained over 100,000 reps at companies like Google and Salesforce. Learn to use AI as a curiosity engine, automate obvious tasks, and deploy AI-powered coaching to stay ahead in the rapidly evolving sales landscape.

September 3, 2025

Every word matters in sales, and certain phrases can instantly kill promising deals. Learn the 15 most damaging phrases that destroy credibility, like "just checking in" and "we offer competitive pricing", plus the powerful alternatives that build trust and keep prospects engaged.

August 29, 2025

Most sales leaders make a critical mistake: jumping into coaching without building trust first. Learn Mo'men Amin's four-step framework that transforms resistant teams into high-performers by earning trust before providing feedback, ensuring your coaching is welcomed rather than resisted.

August 27, 2025

While ChatGPT helps with content creation and basic sales tasks, it can't provide the real-time coaching and interactive roleplay that sales teams need to excel. Discover why specialized AI sales coaching platforms like SellMeThisPen deliver superior results for revenue teams through tailored training.

August 22, 2025

Discover how Phil Rapisardo transformed his struggling sales team using his "Film Review Method" - a group coaching approach where teams analyze real sales call recordings together every two weeks.

August 20, 2025

Discover 6 powerful features of GPT-5 that can make AI coaching essential for modern sales professionals, from practicing objection handling to analyzing presentations with unprecedented accuracy.

August 14, 2025

Laura Wheeler, who helped grow Tableau's federal business from $5M to $250M, reveals her four-layer pipeline health framework that transforms reactive pipeline management into a proactive system that spots warning signs before they become deal-killers.

August 13, 2025

Discover 9 game-changing AI prompts that top sales performers use to transform hours of research into 30-second insights, from deep account analysis to competitive intelligence. Learn Marcus Chan's proven frameworks for leveraging AI to enhance discovery calls, craft relevant outreach, and position yourself as a strategic advisor.

August 7, 2025

Learn how 3X CRO Joey Nalevka built winning sales cultures at Square, Houzz, and Groupon using his three-pillar framework: transparency, strategic communication, and staying connected to frontline details. Discover why traditional sales management fails with modern teams and how to create self-managing sales organizations that deliver consistent results.

August 6, 2025

Recent analysis of 655k opportunities reveals that well-qualified deals win 6.3x more often and close 21.6% faster than poorly qualified ones. Learn why rigorous qualification isn't about screening buyers out, it's the most buyer-centric move in sales, helping prospects gain clarity on their challenges and decision process.

August 1, 2025

Learn proven 5-step system for succeeding as a new sales leader inheriting an existing team, a challenge that's actually harder than building from scratch. Discover why focusing on people first, identifying real roadblocks, and having the courage to remove detractors can transform your team's performance in just 90 days.

July 30, 2025

Most companies make a costly mistake when hiring sales enablement leaders - they prioritize quota-carrying experience over the traits that actually drive success. Learn the 5 core traits that separate exceptional enablement leaders from the rest.

July 23, 2025

Most AI sales tools fail not because of technology limitations, but because of human psychology and poor implementation strategies. Learn Venkat Nagaswamy's proven 5-step framework that flips resistance into organic adoption.

July 18, 2025

Most sales enablement programs fail because they treat all sellers the same, but Edward Cannon's framework reveals three distinct seller personas. Learn how to tailor your enablement approach to each persona for maximum impact and results.

July 16, 2025

Elon Musk's Grok chatbot crisis, reveal critical risks that sales teams must address when implementing AI tools. Learn how to protect your brand reputation, maintain customer trust, and avoid compliance disasters while still leveraging AI's transformative potential through strategic risk management frameworks and proper safeguards.

July 10, 2025

With 78% of sellers missing quota and top performers now outselling peers by 11x, Guy Rubin from Ebsta reveals how to systematically close this performance gap by decoding what A-players actually do differently.

July 9, 2025

While Amazon's CEO warns that AI will replace workers, we believe this fear-driven approach misses AI's true potential in sales. Smart sales teams should embrace AI as a collaborative partner that handles administrative tasks, freeing up salespeople to focus on building authentic relationships and creative problem-solving.

July 2, 2025

Transform your sales coaching from dreaded feedback sessions into collaborative growth conversations with Kieran Smith's proven 4-question framework. Learn how asking the right questions instead of giving answers creates psychological safety, builds ownership, and drives real performance improvement.

June 26, 2025

SellMeThisPen earns four G2 High Performer badges in Spring 2025, proving that AI-powered sales coaching drives real results for teams worldwide. This recognition validates our core belief: AI doesn't replace salespeople, it empowers them to have better conversations and close more deals.

June 25, 2025

Sales organizations are implementing AI tools faster than teams can adapt, creating chaos instead of competitive advantage. Crystal Nikosey, a 2023 Enablement Legend, shares her proven 6-step framework for managing change in AI-driven sales enablement - from understanding company culture to measuring behavioral changes.

June 20, 2025

Apple's iOS 26 Call Screening is revolutionizing cold calling by requiring salespeople to justify their call before prospects even answer. Learn the 5 essential steps to adapt: craft compelling screening messages, maintain clean phone numbers, and turn this challenge into your competitive advantage by focusing on quality over quantity.

June 18, 2025

Master the art of transforming every sales objection into a deal-advancing opportunity with proven frameworks that top performers use to uncover the why behind the most common prospect concerns. Learn the four-step process for addressing objections about change, budget, trust, and timing.

June 12, 2025

Learn the 4 pillars of authentic leadership that prevent costly mistakes like the $1.5 million sales methodology failure Teri Long witnessed - where leaders invested heavily without understanding what was actually broken. Discover how transparency, active listening, root cause analysis, and getting into the trenches can transform your sales organization and build teams that actually perform.

June 11, 2025

70% of B2B buyers would rather avoid salespeople entirely, yet they still need help with complex purchases. Steve Reid, who scaled a company from $10M to $40M in 18 months, reveals the four critical skills that transform sales reps from product-pushers into trusted advisors. Master these skills at the right moments in the buyer's journey, and you'll become the kind of salesperson buyers actually want to work with.

June 4, 2025

Most sales teams struggle not because of poor training, but because of bad hires that started with flawed recruitment processes. Matt Schalsey, CEO of Perfect Hire, reveals how treating recruiters like sales professionals—with structured pipelines, targeted training, and quality-focused metrics—can eliminate the "enablement trap" where companies waste resources trying to fix fundamentally mismatched hires.

May 28, 2025

Change management in sales is about people, not just processes. Learn a powerful 3-step approach from Nate Joseph, VP of Sales & Partnerships at Twenty5, who reveals why starting with WHY before explaining WHAT and HOW creates buy-in instead of resistance, transforming uncertainty into opportunity for your entire sales organization.

May 21, 2025

In today's market where 75% of buyers prefer a seller-free experience, traditional sales approaches are failing. Discover four powerful buyer enablement tactics from Gal Aga, a veteran B2B SaaS sales leader who scaled companies from $1M to $100M in ARR, teaching how to shift from "selling" to offering "buying process as a service" that facilitates your customers' internal tasks.

May 14, 2025

One-on-ones aren't just another meeting on your calendar—they're the cornerstone of trust-building in sales teams, where "trust can't be built in a crowd." Discover Yusuf Ongel's proven 4-step framework for transformative coaching sessions that prioritize the human element first, then business outcomes.

May 7, 2025

Transform your sales kickoff from an expensive company party into a strategic enablement opportunity that actually drives revenue growth. Learn Ashton Williams' proven blueprint for creating successful SKOs with a before-during-after approach that maximizes face-to-face time, enables real-time action, and ensures lasting impact on sales productivity.

April 30, 2025

Sales role plays are crucial for preparation, yet most fail due to poor structure and unsafe environments. Learn the proven 20-minute framework from Sandler Trainer Hamish Knox that has leaders model behaviors first, implement rep feedback immediately, and focus on specific scenarios—creating psychological safety and measurable improvement in conversion ratios across every stage of the sales funnel.

April 23, 2025

Discover the crucial leadership formula for successful internal promotions in sales from Eric Stavola, VP at Visual Edge IT. Learn why top performers don't always make great leaders and how to identify true leadership potential through four key traits: leadership maturity, people-smart skills, problem-solving abilities, and executive presence.

April 15, 2025

Discover the 5-step framework for effective sales coaching from Jackelyn Skudra, VP of Sales at Xello with 20+ years of experience. Learn why being good at sales doesn't automatically make you a good coach, and how to transform your one-on-ones from overwhelming criticism to collaborative growth through focused improvement.

April 2, 2025

Discover how Auth0 achieved an incredible 90% quota attainment rate through a strategic approach to sales roleplays. Sales Enablement Leader, Taylor Jurgens, reveals the five-step formula that transformed their sales onboarding process, focusing on pure enablement and discovery mastery that got new reps fully ramped in just 60 days.

March 25, 2025

Discover the 4-step framework for successful AI sales tool implementation from a 17-year enterprise sales enablement veteran who's rolled out AI to thousands of sellers. Learn why most organizations fail by overlooking their most critical stakeholder and how to avoid the common pitfalls that doom AI initiatives before they begin.

March 18, 2025

Discover the five critical hiring mistakes that damage startup growth from Ryan Ing, a fractional sales leader who's sold for IBM, Oracle, and Shopify. Learn why hiring too senior, too junior, or sales reps with the wrong experience can waste precious time and resources—and get a practical framework for building a sales team that actually drives revenue.

March 10, 2025

Learn why proper discovery is the foundation of effective sales enablement with Jared Balzer, who shares a practical seven-step framework for gaining sales team buy-in. Learn how to avoid common pitfalls like building programs in isolation and instead create enablement initiatives that address real pain points, involve stakeholders at every level, and deliver measurable results.

March 5, 2025

Discover how Jake Hollis, "Most Impactful Leader" at OpenText, transforms struggling SDR teams by shifting focus from booking meetings to selling conversations, and implementing "everboarding" for sustained success. Jake reveals how these two fundamental changes create lasting results that turn teams into consistent high performers.

February 26, 2025

Discover how toxic leadership can silently destroy sales organizations, as revealed in a powerful discussion with Darren Hall, who scaled Avalara from $1M to $30M ARR. Learn how fear-based management crushes trust and coaching effectiveness, and explore practical strategies for building a high-trust sales culture where teams naturally evolve into communities of coaches.

February 19, 2025

The gap between sales enablement and sales teams often creates friction that holds back performance, but it doesn't have to be this way. Learn how Nicole Plant, who has led BDR teams at Float, Loopio, and Relay, breaks down the practical strategies for transforming enablement from "just the training team" into a strategic partner that drives real sales success through data-driven approaches and meaningful partnerships with both reps and management.

February 12, 2025

Learn how to successfully navigate the AI revolution in sales from Alexander Matyushenko, a Sales Enablement leader who has trained thousands of sellers at Google Cloud, AWS, and Microsoft. Discover his practical framework for integrating AI into sales organizations while retaining valuable talent, overcoming resistance, and measuring success through tangible metrics.

February 5, 2025

Discover 6 powerful frameworks that transform everyday sales challenges into opportunities for sustainable success. These resilience strategies are tested by a sales veteran Michael D’Angelo and go beyond simply "bouncing back" to help you develop a systematic approach for converting setbacks into growth, combining emotional intelligence with practical action steps to maintain high performance even during difficult times.

January 28, 2025

Transform your sales coaching approach from directive to developmental with insights from LinkedIn's Senior Leadership Development expert Nikki Schanzer. Explore how structured coaching sessions, powerful questioning techniques, and a simple mindset shift can transform underperforming sales teams into high achievers and discover the three pillars of effective coaching that led one team to achieve 57% average performance growth across 4 quarters.

January 22, 2025

Discover why the next 6-12 months are critical for adapting to AI in go-to-market strategies, as explained by AI Performance & Strategy Executive Jonathan Kvarfordt. Learn about the multi-agent future of sales, where specialized AI will handle everything from research to negotiation, while paradoxically driving a resurgence in face-to-face interactions.

January 15, 2025

When market leadership is threatened by aggressive competitors, having the best product isn't enough - you need a systematic approach to competitive enablement. Discover a proven 6-step framework that helped one company boost their win rates from 40% to 60%+ in a single quarter, along with four essential tools to empower your sales team for consistent wins against tough competition.

January 8, 2025

Sales is a performance-based career, and the truth is, without regular practice, you can't come close to success. Mastery comes through consistent effort. Let's explore why practice is so important—and why it’s crucial to practice the right things.

October 31, 2024

Learn the 3 key components to building a successful sales career from Ben Stokes, a seasoned VP of Sales who scaled his company to over $60M in revenue, led teams of 200+ reps, and coached hundreds—if not thousands—of sales professionals throughout his career.

October 23, 2024

When hiring new employees in the sales department, many companies step on the same rake. They overload newcomers with excessive information, forget about regular training and expect quick results. What result does this strategy lead to? Beginners get lost and do not show the expected results.

October 22, 2024

Learn how Ergeon leveraged AI roleplays to get 90% onboarding graduation rate for the new hires with SellMeThisPen AI

March 5, 2024

Access AI sales prompts for prospecting and AI role-play practices, and discover how to create your own tailored prompts to boost your sales efficiency.

February 23, 2024

Debunking the notion that “Practice makes perfect,”. Introducing AI roleplay as a solution for effective sales training, offering personalized, immediate feedback to ensure practice leads to improvement, filling the gap left by inadequate traditional training methods.

February 16, 2024

Learn essential advice for those starting in sales: from engaging in everyday conversations to building communication skills, to being selective and informed about your first sales job, and focusing on training and growth opportunities.

February 4, 2024

Learn how to have fun on a call, be genuine, when to share a story, and when to say nothing - all to build a connection that gets you to the next call.

January 14, 2024

Let's cook up your cold-calling game! Learn how to make your cold calls less awkward and more effective.

January 8, 2024