Transform Your Sales Team: Strategic Compensation Adjustments for Year-End Momentum

Transform Your Sales Team: Strategic Compensation Adjustments for Year-End Momentum

By Sean O'Shaughnessey

Autumn is the time of year for sales leaders, managers, and CEOs to begin laying the groundwork for next year’s success. Have you considered how your current sales compensation plans impact your team’s motivation and productivity? Now is the ideal moment to evaluate, adjust, and deliver these plans, preferably by December 1st. Doing so can significantly influence your team’s drive to close deals in December and build momentum heading into the next fiscal year.

Sales compensation should be motivating and rewarding for employees. It directly shapes your sales team’s behaviors and priorities. An effective plan incentivizes the right actions and deters the wrong ones.

Consider a common pitfall: salespeople holding back deals to inflate their numbers for the following year. Does your current compensation structure inadvertently reward this practice? If so, you’re unintentionally harming your year-end results.

To counter this, strategically incorporate compensation escalators and cliffs into your plan. Escalators progressively reward increased sales performance throughout the year. Higher performance equals higher commission rates, driving your sales team to push forward continually. 

Commission cliffs reset commission rates at the beginning of each year, creating a sense of urgency to close deals before the end of December. Communicating these compensation details clearly by early December ensures your team understands what’s at stake.

Don’t hold your team back!

Another critical compensation consideration is eliminating commission caps. While some organizations cap commissions to control expenses, this practice can backfire dramatically. Caps tell your top-performing salespeople that their exceptional efforts are neither valued nor rewarded appropriately. This demotivates your top talent and encourages them to seek opportunities elsewhere that offer uncapped rewards. 

Removing commission caps signals that the organization fully supports and rewards outstanding performance. Have you considered how much growth your company might achieve if artificial constraints didn’t limit your sales team?

When evaluating compensation, look beyond simple cost containment. Consider the true profitability of incentivizing increased sales volume. Once salespeople reach their targets and enter accelerators, each additional dollar earned typically comes at a lower incremental cost to your organization. 

Sales transactions earlier in the year have already covered the salesperson’s base salary once they have met their annual quota. In fact, at 100% of quota, the salesperson should have covered all their costs and their share of the overall company’s revenue needs. Thus, every extra sale at escalated commission rates still contributes positively to your overall profitability. 

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Hiring for Growth: How to Build a Sales Team That Drives Long-Term Success

Hiring for Growth: How to Build a Sales Team That Drives Long-Term Success

By Sean O'Shaughnessey

Building a successful sales team requires more than just filling open seats with available candidates. Company leadership must strategically align its hiring process with business objectives, market needs, and long-term goals. 

Whether you’re a solopreneur transitioning to a team-based approach or a CEO managing a growing sales force, the principles of intentional recruitment and onboarding remain the same. Hiring the right people is an investment in the future of your business.

One of the most common pitfalls in sales hiring is a lack of intentionality. Too often, small businesses hire out of convenience, choosing candidates from their immediate network or taking the first person who seems interested. While this approach may solve an immediate need, it rarely leads to long-term success. 

Hiring a salesperson means selecting someone who can actively drive growth and represent your brand with competence and integrity. The stakes are even higher when you’re working with a lean team; every hire matters, and mediocrity is not an option.

To avoid these missteps, it’s essential to approach hiring with the same rigor you apply to your sales process. Think of recruiting as a parallel to securing a high-value client. Just as you wouldn’t sell your product without qualifying leads or understanding their needs, you shouldn’t hire without a structured process to evaluate candidates. 

Begin by defining what success looks like for the role. What skills and attributes are non-negotiable? What specific outcomes do you expect this person to achieve within their first 90 days? A clear job description and measurable KPIs set the foundation for finding the right fit.

Cultural alignment is another critical factor. Your salespeople are the face of your business to prospects and customers. Their ability to embody your company’s values and mission can make or break the customer experience. A candidate might have a stellar track record, but if their approach clashes with your team’s culture, the partnership is unlikely to succeed. At the same time, skills and experience must align with the specific demands of the role. For instance, if your goal is aggressive market penetration, you need a hunter mentality, someone skilled in building relationships from scratch and closing deals in uncharted territory.

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Mastering Sales Channels: How to Align Your Strategy for Maximum Impact

Mastering Sales Channels: How to Align Your Strategy for Maximum Impact

By Sean O'Shaughnessey

Understanding the dynamics of sales channels can transform how businesses approach their markets. Many sales professionals, whether they are salespeople, managers, or CEOs, often miss a critical distinction: the difference between the product they are selling and the value it provides. 

This gap in understanding can lead to suboptimal sales performance, particularly in environments where products are sold through intermediaries, such as distributors, referral partners, or dealer networks. The challenge is not just about knowing your product, but also about understanding how to position it in a way that resonates with every player in the sales chain.

Sales success starts with recognizing who your true customer is. In sales management or channel sales, the end customer is often not the person you interact with directly. Instead, your “customer” might be the intermediary, your distributor, reseller, or even your own sales team. These intermediaries are the ones who ultimately connect your product to its final user. If you don’t understand their challenges, motivations, and context, you risk failing to equip them with the necessary tools to succeed. Are you selling a product’s features, or are you helping them understand how to sell it effectively? This distinction is vital.

When selling through intermediaries, the emphasis should shift from “what the product does” to “how the product can be sold.” Your distributors or referral partners don’t need every technical detail of your product. They need clarity on how it solves problems for their customers, how it fits into their existing offerings, and how they can position it to drive sales. 

The goal is not to overwhelm your partners with information but to provide actionable insights that align with their specific needs. If you’re focusing solely on product features, you’re likely missing the mark.

Salespeople and sales managers must also recognize the game they are playing. Are you selling a commodity, a widely available product, or an exclusive offering? Each scenario demands a different strategy. 

Commodities often compete on price, necessitating bulk sales or value-added services to differentiate themselves. Widely available products often rely on relationships, service quality, or unique add-ons to differentiate themselves. Exclusive products, on the other hand, can often avoid price wars by emphasizing their uniqueness and superior quality. Knowing which game you’re in allows you to tailor your approach and avoid misaligned strategies.

For small businesses and solopreneurs, the challenge lies in effectively managing referral partners. Referral partnerships are a powerful way to generate leads, but they require careful management and oversight. 

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AI Isn’t Replacing Salespeople, It’s Giving Them a Competitive Edge

AI Isn’t Replacing Salespeople, It’s Giving Them a Competitive Edge

By Sean O'Shaughnessey

AI isn’t replacing salespeople, it’s making them more effective. The real risk isn’t losing your job to AI; it’s losing to a competitor who uses AI better than you do. Sales professionals who integrate AI into their workflow will outperform those who don’t. 

It’s not about technology taking over but about using technology to gain an edge. The market is becoming increasingly competitive, and the most efficient salespeople will emerge victorious.

Time is a salesperson’s most valuable asset. 

Every minute spent on administrative tasks is a minute not spent selling. AI helps reclaim those lost hours. Tools that automate writing, scheduling, and research allow salespeople to focus on what matters: building relationships and closing deals. If you’re not leveraging AI to increase productivity, you’re leaving opportunities on the table.

Sales emails need to be clear and professional. AI-powered writing assistants ensure your messages are polished and effective. A poorly written email can cost you a deal. AI tools catch grammatical mistakes, improve clarity, and even suggest more effective phrasing. This isn’t just about looking professional; it’s about being understood. 

If your message isn’t clear, it won’t convert.

Presentations are another time-consuming task. AI can generate professional decks in minutes. Instead of spending hours designing slides, salespeople can focus on developing effective strategies. AI-powered tools create branded, structured presentations based on simple inputs. This ensures consistency while saving time. Sales professionals who utilize AI for presentations can focus on delivering insights rather than formatting slides.

CRM systems are the backbone of sales operations. AI enhances CRM by automating data entry, tracking customer interactions, and suggesting next steps. Salespeople often struggle with keeping CRM data updated. AI reduces this friction by automatically capturing and organizing information. A well-maintained CRM leads to better forecasting and stronger customer relationships. 

If your CRM doesn’t have AI capabilities, it’s time to upgrade.

AI-driven insights enable sales managers to make more informed decisions, rather than relying on instinct. Managers can use AI to analyze performance trends, identify coaching opportunities, and predict revenue outcomes. AI doesn’t replace leadership; it enhances it. 

Sales managers who adopt AI can build stronger teams and achieve better results. Ignoring AI in sales management is a strategic mistake.

Lead generation is another area where AI adds value. AI-powered tools can analyze vast amounts of data to identify high-potential prospects. Instead of spending hours researching leads, salespeople can receive AI-generated recommendations. This allows for more targeted outreach and higher conversion rates. AI doesn’t just find leads, it finds the right leads.

Sales follow-up is often inconsistent. AI ensures follow-ups happen at the right time with the right message. Automated reminders and AI-generated responses keep deals moving forward. 

A well-timed follow-up can be the difference between closing a deal and losing it. AI helps salespeople stay on top of their pipeline without relying on memory.

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Transforming Quota-Setting: Strategies for Sales Leaders to Optimize Performance and Revenue

Transforming Quota-Setting: Strategies for Sales Leaders to Optimize Performance and Revenue

By Sean O'Shaughnessey

Quota-setting is one of the most misunderstood elements of sales leadership. Too often, it’s treated as a spreadsheet exercise or a top-down directive, rather than a strategic lever that drives behavior, performance, and growth.

Whether you’re leading a team of 20 or you’re the founder managing three reps, how you define quotas has a direct impact on your revenue trajectory and your team’s motivation.

So, where do you start?

With timing. If you’re not delivering quotas to your team until February or March, you’re already behind. Salespeople need clarity by December. That gives them runway to plan, prioritize, and hit the ground running in January. Delayed quotas create confusion and stall momentum. To achieve a strong Q1, you need to equip your team early.

Quota-setting varies depending on the size of your company. Larger teams offer more flexibility. With 10 or more reps, you can spread risk, balance performance, and model averages. You’ll have top performers who consistently overdeliver, alongside newer reps who are still ramping up. The law of averages works in your favor. You can afford some variance. Smaller teams don’t have that luxury.

When you’re running a small team, maybe two or three reps or founder-led sales, every individual matters. One person missing quota can tank your number.

You can’t rely on averages. You need precision.

That means tying quotas to actual relationships, known opportunities, and real probability. It’s not about slicing up a target evenly. It’s about assigning numbers based on what’s realistically achievable in each territory or account list.

Territory design plays a big role here. Whether it’s geographic, vertical, or named accounts, quota must reflect the market potential. You can’t expect equal performance from unequal opportunity. If Rep A has 500 viable accounts and Rep B has 50, their quotas shouldn’t look the same unless you have data that says Rep B’s accounts are closer to your Ideal Client Profile. Use available market data to inform the number. Don’t assign quotas in a vacuum. 

In larger organizations, quotas often originate from the top down, typically from finance. The CEO and CFO commit a growth number to the board, investors, or in public filings to the SEC. They have no choice but to pass it down. It’s not uncommon for the sales team to receive the number without context. That’s a problem. If you’re in a leadership role, you need to pressure test that number. Can your team realistically hit it? If not, what additional resources are required?

  • More headcount?
  • Better enablement?
  • Marketing support?

In large organizations where the quota is driven by investor expectations, the VP of Sales must establish an organization well before the new year that achieves this year’s goal, while also meeting the expectation of growth for the next year. Planning ahead, sometimes years in advance, is part of the job.

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Two Tall Guys Talking Sales – Why Consistent Sales Strategies Win: Forecasting, Messaging, and Revenue Management – Episode 151

Two Tall Guys Talking Sales – Why Consistent Sales Strategies Win: Forecasting, Messaging, and Revenue Management – Episode 151

By Sean O'Shaughnessey

In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey delve into the crucial role of deal qualification in driving sales success. From simple frameworks like BANT to advanced methodologies such as MEDDIC and MEDDPICCC, Kevin and Sean explain how consistent sales processes, value selling, and business acumen can sharpen forecasting, strengthen messaging, and ultimately accelerate revenue generation. Whether you’re managing a sales team or selling solo, this discussion will help you refine your sales strategies and improve your revenue management outcomes.

Key Topics Discussed

  • The cooking analogy for sales qualification – how preparing a meal mirrors building consistent sales processes 
  • Why full qualification matters – reducing forecast slippage, aligning solutions to customer needs, and driving predictable revenue generation.
  • BANT explained – Budget, Authority, Need, and Timeline as a simple framework for qualifying deals 
  • Beyond BANT – an overview of advanced methodologies such as SPIN, SPICED, and NEAT for value selling in complex deals 
  • Deep dive into MEDDIC and MEDDPICCC – why metrics, the economic buyer, and champions are essential for enterprise-level sales success 
  • The importance of sales management consistency – ensuring every salesperson in an organization qualifies deals with the same discipline 

Key Quotes

  • Kevin Lawson : “When you close things better, when you have more deal intelligence or customer intelligence or relationship intelligence gained through a qualifying methodology, you end up being better able to serve a customer.”
  • Sean O’Shaughnessey : “If you have five salespeople trying to qualify deals, you want them to qualify them the same way—consistency matters because it creates repeatable sales success.”
  • Sean O’Shaughnessey : “Every deal needs a champion. If you can get a champion to sell for you when you’re not there, you are far more likely to win.”

Additional Resources

  • HubSpot Blog: A Guide to Sales Qualification Frameworkshttps://blog.hubspot.com/sales/6-popular-sales-methodologies-summarized
  • The Qualified Sales Leader by John McMahon is an essential read on MEDDIC from one of the most successful sales leaders in software history. https://a.co/d/76089W7
  • Join the B2B Sales Lab for 90 days free and access practical community discussions on sales strategies, revenue management, and messaging. https://b2b-sales-lab.com

A Significant Actionable Item from this Podcast

Select and consistently implement one sales qualification framework across all your deals.
Whether you adopt BANT for simplicity or MEDDPICCC for enterprise-level selling, consistency in qualification builds stronger forecasts, improves customer alignment, and accelerates revenue generation. Decide on one methodology, train your team, and hold yourself accountable to using it every time.

Why You Should Listen

This episode is packed with practical insights for salespeople, managers, and business leaders committed to improving revenue management and sales success. Kevin and Sean take you from everyday analogies to advanced enterprise strategies, showing why consistent qualification is the backbone of predictable growth. If you want sharper sales processes, better forecasting, and stronger messaging that supports value selling, you won’t want to miss this conversation. Download now and start applying these proven sales strategies to your own pipeline.

From Reporting to Coaching: Elevate Your One-on-One Sales Meetings to Drive Performance and Trust

From Reporting to Coaching: Elevate Your One-on-One Sales Meetings to Drive Performance and Trust

By Sean O'Shaughnessey

A one-on-one sales meeting is not a reporting meeting. It’s not about reviewing what already happened. And it’s definitely not about the manager doing most of the talking. The purpose of a one-on-one pipeline review is to develop the salesperson, surface challenges, and accelerate opportunities. If your one-on-ones are anything less, you’re leaving performance on the table.

Sales leaders often default to micromanagement. 

Especially when the rep is new or struggling. But that approach backfires. It creates dependency and stifles problem-solving. The goal is to coach your reps into leading the meeting. That shift changes everything. When reps own the agenda and bring forward deal-level insights, they’re forced to think critically. That’s where growth happens.

If you’re leading a sales team or are a CEO playing the role of sales manager, you need to establish a clear structure. But the rep does the prep. You define the meeting cadence and format. Weekly or bi-weekly, depending on your velocity. You outline the sections: committed deals, stalled deals, and at-risk deals. 

But the rep fills in the content. They come to the meeting ready to walk you through each opportunity, with specific updates and clear asks.

Preparation is non-negotiable. For both sides. 

The salesperson should have updated their CRM before the meeting. The manager should have reviewed that data in advance. If either party shows up unprepared, the meeting becomes reactive. 

A waste of time. And it erodes trust quickly. 

Reps notice when you haven’t read the notes. They know when you’re winging it. And if they feel their effort isn’t valued, they’ll stop putting in the effort.

You want to create a culture where preparation is expected and rewarded. 

The fastest way to management failure is to ask questions that could have been answered by reading the CRM. Instead, use that time: 

  • To probe deeper. 
  • Ask about the deal strategy. 
  • Challenge assumptions. 
  • Help salespeople spot gaps they missed. 

That’s where your experience has real value.

It’s tempting to jump in and solve the problem. Especially when you see the red flags before the rep does. But resist the urge. Let them talk it through. Coach them toward the insight. Your job isn’t to close the deal; it’s to build someone who can. That means teaching them how to identify weak spots, how to pressure test a deal, and how to re-engage a stalled buyer. The real value of one-on-ones is in that development.

Think about how you coach. 

Are you diagnosing for them? Or are you helping them diagnose for themselves? When a rep says “this deal is solid, no issues,” that’s a red flag. Every deal has risk. Your job is to help them uncover it. Ask: “What’s the biggest thing that could derail this?” Or “What’s the last thing the buyer said that gave you pause?” These questions surface the truth. And they teach reps to self-assess more effectively.

There’s a fine line between coaching and grading. You want reps to be honest about their pipeline without fear of judgment. 

If a deal is weak, that’s not a character flaw. It’s a coaching moment. 

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Two Tall Guys Talking Sales – No Leads, No Problem: Sales Strategies to Reignite Momentum – Episode 148

Two Tall Guys Talking Sales – No Leads, No Problem: Sales Strategies to Reignite Momentum – Episode 148

By Sean O'Shaughnessey

When your sales pipeline hits a wall—or worse, goes completely flat—it can feel like you’re spinning your wheels. In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey dive deep into what to do when your sales team is facing a revenue generation stall. This is a fast-paced, actionable conversation focused entirely on what sales leaders can do to recharge a stalled pipeline—without relying on marketing. Whether you’re in B2B tech, manufacturing, or professional services, this episode will equip you with practical, high-impact tactics to get your sales process moving forward again.

Key Topics Discussed

  • The “Flat Tire” Sales Pipeline Analogy (00:00)
    Why pipelines go flat—even after big wins—and how leaders can reframe the issue.
  • The Power of Referrals and Networking (03:00)
    Sean’s method for turning satisfied customers into a referral engine—complete with a ready-to-send intro letter.
  • Expanding Through Customer Proximity and Chambers of Commerce (05:00)
    Leveraging existing accounts and local business events to rapidly refill the funnel.
  • Using PESTEL for Industry-Relevant Messaging (07:00)
    Kevin shares a practical framework for creating insightful sales conversations that show business acumen and relevance.
  • Requalifying Open Deals with the Right Buyers (08:00)
    How to use sales processes and CRMs to validate opportunities—and why “access to power” is non-negotiable.
  • Getting to the Economic Buyer—and Asking for the Order (11:00)
    A breakdown of how to engage decision-makers, handle their buying criteria, and close with confidence.

Key Quotes

  • “I don’t care what you sell—coolants, software, promotional gear—if you’re not prospecting today, your pipeline will let you down tomorrow.”
    — Sean O’Shaughnessey (01:07)
  • “We’re not a demo organization. If the demo alone sold your product, you wouldn’t need a salesperson.”
    — Kevin Lawson (10:00)
  • “If your salespeople can’t tell you who the economic buyer is, it’s time for you to get in the car and go meet them yourself.”
    — Sean O’Shaughnessey (12:00)

Additional Resources Mentioned

  • B2B Sales Lab Community – A peer-led space for sales professionals and leaders to grow, collaborate, and share sales strategies. (Free 90-day trial with credit card to keep out spammers.) www.b2b-sales-lab.com
  • PESTEL Framework – A structured approach for bringing value to sales conversations by focusing on Political, Economic, Social, Technological, Environmental, and Legal issues impacting buyers.

A Significant Actionable Item from this Podcast

Requalify Every Deal in Your Pipeline This Week

Sales leaders: pull your team into a pipeline review and ask a simple, high-stakes question about every open opportunity—“If you walked in with a PO today, could your contact sign it?” If the answer is “no,” that deal is not qualified. Use this exercise to reinforce accountability, focus on real economic buyers, and prioritize deals that can convert into revenue. Don’t just forecast—verify.

Why You Should Listen Now

If you’ve ever looked at your pipeline and felt that creeping sense of panic, this episode is your emergency roadside kit. Sean and Kevin don’t waste time with fluff—they deliver real sales strategies rooted in decades of experience with sales management, business acumen, and revenue generation. From value selling tactics to reengaging your best customers, this conversation is loaded with sales success insights you can implement today. Plug in, take notes, and start patching your pipeline with purpose.

AI in B2B Sales Isn’t Optional Anymore

AI in B2B Sales Isn’t Optional Anymore

By Sean O'Shaughnessey

Several months ago, I was serving as a fractional VP of Sales for a $50 million manufacturing company. Their top salesperson was a 15-year veteran who knew the industry inside and out. Yet he was consistently being outsold by a competitor’s much newer hire. At first, it didn’t make sense until we discovered the reason.

The competitor’s rep wasn’t just more energetic or aggressive. They were AI-enabled. While my client’s rep was manually scrolling LinkedIn and drafting emails from scratch, the competitor’s rep was using AI tools to research prospects, craft personalized outreach, and prepare for meetings. In other words, the competitor had a partner working 24/7—freeing them to focus on what humans do best: building trust and closing deals.

That was the turning point. I realized we weren’t just competing against other salespeople anymore. We were competing against AI-enhanced sales teams.

The Most Urgent Technology Wave in Sales

Throughout my career, I’ve watched new technology waves disrupt the sales profession. Robotics transformed manufacturing in the 1980s. Solid modeling replaced drafting tables in the 1990s. Cloud computing reshaped IT in the 2000s.

Each time, early adopters gained the edge while laggards struggled to catch up. The AI wave is different for two reasons:

  1. It’s broader: touching every aspect of sales, from prospecting to forecasting.
  2. It’s faster: companies have months, not years, to adapt before the competitive gap becomes overwhelming.

AI in sales isn’t coming. It’s already here.

The Four Pillars of AI Sales Transformation

To make sense of AI’s role in sales, I use a framework I call the Four Pillars of AI Sales Transformation.

1. Efficiency Amplification

Salespeople lose hours each week on research, data entry, and administrative tasks. AI automates these repetitive activities, turning wasted time into revenue-generating capacity. If a rep with a $2 million quota spends 40% of their time on admin work, reclaiming even half of that time can translate into hundreds of thousands of dollars in additional revenue potential.

2. Personalization at Scale

Buyers expect relevance. AI enables sales teams to tailor outreach at a scale that was previously impossible. One client of mine went from producing 10 personalized emails per day to 500, each one referencing company news, industry pain points, or competitive dynamics. The result: higher engagement and faster response times.

3. Predictive Intelligence

AI spots patterns humans miss. It identifies which deals are at risk, when prospects are most likely to respond, and which leads are worth pursuing first. For one client, simply shifting demos to Tuesday afternoons increased conversion rates by 40%. When your competitors are guessing, AI gives you confidence.

4. Continuous Learning & Optimization

Unlike static playbooks, AI evolves. It analyzes win/loss data, tests messaging, and provides real-time coaching insights. One client discovered that pricing discussions were their biggest choke point. AI flagged the pattern, we built automated battlecards, and close rates improved by 18%.

Real-World Results

These aren’t theoretical benefits. In my own client work:

  • An AI-powered prospecting rollout increased appointment-setting rates from 8% to 23% in just six weeks.
  • A lost-deal analysis uncovered patterns that helped recover $2 million in the pipeline.

The reality is clear: companies already experimenting with AI are pulling ahead. Those who delay are watching the gap widen daily.

Three Things You Can Do This Month

If you’re ready to start, here are three immediate steps:

  1. Audit your workflow. Identify one repetitive task you can automate—prospect research, meeting prep, or follow-up emails.
  2. Pilot an AI tool. Start small with an affordable, no-code platform. Many cost less than $200/month.
  3. Learn with others. Don’t navigate this change alone. Surround yourself with peers who are experimenting, learning, and winning with AI.

Join the B2B Sales Lab

The best way to accelerate your adoption is to connect with others on the same journey. That’s why we built the B2B Sales Lab, a private, member-led community for sales professionals who want actionable insights, not theory. It’s where strategy meets execution.

In the Lab, you can:

  • Ask real questions about sales challenges.
  • Share proven best practices.
  • Learn from other sales professionals and veteran leaders.

Your first 90 days are free. Join us today at b2b-sales-lab.com.

The future of B2B sales isn’t about choosing between humans and AI. It’s about humans amplified by AI. Those who adapt now will thrive. Those who wait may not get the chance to catch up.

To learn more, listen to this podcast on the subject.