The AI Sales Process Map: The Ten-Stage Sales Process Framework

The AI Sales Process Map: The Ten-Stage Sales Process Framework

By Sean O'Shaughnessey

Sales leaders today often fall into the trap of using artificial intelligence tools randomly rather than systematically. This sporadic usage is like owning a Swiss Army knife but only using the bottle opener; you miss out on ninety percent of the available value. AI’s real power comes not from isolated tools but from integrating capabilities across every stage of your sales processes. When mapped correctly, AI accelerates every interaction, shortens sales cycles, and makes revenue generation more predictable.

Random AI adoption leads to inconsistent results. Some reps use it effectively, while others revert to manual methods under pressure, resulting in uneven performance. Systematic AI integration, however, compounds improvements across the entire sales cycle. Data captured at one stage strengthens the next, creating a virtuous cycle of sales success that is scalable, measurable, and sustainable. The outcome is not just faster deals, but stronger business acumen and more consistent revenue management.

The ten-stage AI sales process framework provides a structured way to apply AI:

  1. Prospecting,
  2. Outreach,
  3. Qualification,
  4. Scoping,
  5. Presentation,
  6. Economic Buyer meetings,
  7. Validation Events,
  8. Proposals,
  9. Closing,
  10. Onboarding/expansion.

Each stage leverages AI differently, from intent data analysis in prospecting to AI-driven customer success monitoring post-close. Integration ensures that research informs outreach, discovery guides scoping, and validation improves proposals. By connecting the entire workflow, sales teams gain predictable processes and continuous optimization opportunities.

Process-based implementation builds competitive advantage. Competitors can replicate isolated AI tools, but systematic integration across sales strategies and sales management creates a differentiated approach that scales with growth. Consistency across the team reduces dependency on individual skill differences, enhances messaging, and strengthens value selling.

The measurement framework behind this approach ensures continuous improvement. Stage-specific conversion rates, velocity metrics, and data quality indicators guide refinements. Weekly reviews, monthly AI effectiveness assessments, and quarterly adjustments keep teams aligned while maximizing ROI from AI investments. Over time, these optimizations compound, creating a performance engine that drives long-term revenue generation.

The future of B2B sales isn’t choosing between humans and AI. It’s humans amplified by AI. Let’s build that future together.

If you’d like to explore this topic in more depth, there’s a podcast episode that covers all of this information and more. You can find the link to the episode here and consider subscribing to the podcast AI Tools for Sales Pros on your favorite podcast player.

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.

Read the rest of the article…
ChatGPT vs. Claude vs. Gemini vs. Copilot: Which AI Wins in Sales?

ChatGPT vs. Claude vs. Gemini vs. Copilot: Which AI Wins in Sales?

By Sean O'Shaughnessey

A few days ago, a sales manager asked me which AI platform to use for writing cold emails. I told him it depends on what kind of emails he’s writing, and he looked confused. That confusion is common and costly. ChatGPT, Claude, Gemini, and Copilot all look similar at first glance, but in reality, they serve very different purposes depending on your sales workflow.

Choosing the right platform matters because the wrong choice drains time, creates change fatigue, and erodes ROI. Companies that align platform strengths to sales use cases are seeing dramatic results: 40% higher email response rates, 60% faster proposal generation, and triple the efficiency in call preparation. The stakes are high, and the decision deserves more than guesswork.

ChatGPT: The Versatile Performer
ChatGPT shines when creativity and personality are critical. It’s excellent for cold emails with humor, social selling posts, objection-handling scripts, and meeting prep. The downside? It can be verbose and sometimes casual for executive communication. If your team thrives on creativity and prospecting with personality, ChatGPT is a strong choice.

Claude: The Professional Communicator
Claude specializes in polished, business-appropriate communication. It’s strong for executive proposals, deal analysis, contract prep, and professional email sequences. While less creative than ChatGPT, it’s ideal for enterprise and strategic sales where tone, nuance, and professionalism are paramount.

Gemini: The Integrated Researcher
Google’s Gemini offers real-time research, market intelligence, and smooth integration with Google Workspace. It’s especially powerful for sales teams who rely heavily on spreadsheets, Gmail, and real-time prospect research. However, it may produce generic copy and come with potential data privacy concerns.

Copilot: The Enterprise Integrator
Microsoft Copilot excels in environments already standardized on Microsoft tools. Its strength lies in Outlook automation, PowerPoint proposals, Teams prep, and CRM integrations. While it can feel corporate and less creative, it’s perfect for organizations that value compliance, governance, and seamless integration across Microsoft 365.

Making the Right Choice
The best AI platform isn’t the one with the flashiest marketing; it’s the one your team will consistently use. Start by mapping your use cases: creative outreach, professional communication, research, or enterprise integration. Then run pilot programs, measure results, and refine your approach. Many sales teams find value in using more than one platform, each aligned to a different stage of the sales cycle.

The future of B2B sales isn’t about choosing between humans and AI. It’s about humans amplified by AI. Let’s build that future together.

If you’d like to explore this topic in more depth, there’s a podcast episode that covers all of this information and more. You can find the link below and consider subscribing to the podcast AI Tool for Sales Pros on your favorite podcast player.

B2B Sales in the Age of AI: Why Top Salespeople Will Thrive While the Repetitive Roles Disappear

B2B Sales in the Age of AI: Why Top Salespeople Will Thrive While the Repetitive Roles Disappear

By Sean O'Shaughnessey

The buzz surrounding artificial intelligence has left many professionals wondering about the future of their careers. For B2B sales professionals, the rise of AI presents a fundamental question: Will AI replace salespeople?

The short answer is no, but it will replace some of their work. More accurately, AI will redefine the B2B sales landscape by eliminating lower-value activities, consolidating support roles, and enhancing the capabilities of top performers. In doing so, it will widen the gap between average and great salespeople.

Several years ago, I wrote a similar explanation about the fear that “the internet” would replace salespeople. That didn’t happen. You can find that article on the blog that supports my first sales book. Are salespeople necessary in the Internet age?

This blog post explores how B2B sales is positioned relative to AI disruption, referencing key insights from Benjamin Todd’s article, “How Not to Lose Your Job to AI” (80,000 Hours, 2025). Todd’s framework on skill types that increase in value in the age of AI helps us understand how high-functioning sales teams should evolve and how sales professionals can future-proof their careers.

Understanding AI’s True Impact: Augmentation, Not Replacement

A common misconception about AI is that it simply replaces humans. This isn’t true. AI devalues tasks it can perform while increasing the importance of the skills it cannot. Todd explains this dynamic through examples like the ATM: while the ATM reduced the need for transactional teller tasks, it actually increased demand for bank branch workers by allowing banks to open more branches. AI follows a similar pattern.

In B2B sales, AI will handle the most automatable tasks, such as data entry, follow-ups, list-building, and basic prospecting emails. However, this doesn’t eliminate the sales role; it sharpens its focus.

Instead of dialing hundreds of prospects daily, sales professionals will focus more on strategic engagement, account planning, and using AI-generated insights to elevate conversations. The result? Sales has become a more thoughtful, human, and strategic discipline for those who can keep up.

Four Categories of Skills That AI Will Make More Valuable

In Todd’s excellent article, he identifies four skill types that increase in value in an AI-enhanced workplace:

  1. Hard-to-automate skills
  2. Deployment-related skills
  3. Scarce, high-utility skills
  4. Skills hard for others to learn or replicate

Each of these aligns tightly with the demands of modern B2B sales.

Read the rest of the article…
Two Tall Guys Talking Sales – Elevate Your Sales Game with B2B Sales Lab: A New Resource for Revenue Growth – Episode 141

Two Tall Guys Talking Sales – Elevate Your Sales Game with B2B Sales Lab: A New Resource for Revenue Growth – Episode 141

By Sean O'Shaughnessey

When sales professionals hit a roadblock, where do they turn? In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O’Shaughnessey unveil an exciting new initiative: B2B Sales Lab, a private peer networking community designed to support salespeople, sales managers, and business owners in their journey toward revenue generation excellence. This isn’t just a conversation; rather, we are offering an invitation to join something powerful. If you’ve ever felt alone in a tough sales challenge or wished for experienced advice on your messaging, sales processes, or strategy, this episode is for you.

Key Topics Discussed

  • (00:00) Why selling isn’t easy and how sales professionals can benefit from a support network
  • (00:39) The creation and mission of the B2B Sales Lab community
  • (01:42) How the platform fosters peer-to-peer learning without judgment or pressure
  • (02:58) The importance of community in developing strong sales strategies and business acumen
  • (03:54) Guardrails that make this space safer and more effective than LinkedIn or Facebook groups
  • (05:00) Why there’s a membership fee—and why the first three months are free

Key Quotes

  • Sean O’Shaughnessey (00:01:00): “We’re creating a community where people can get together, bounce ideas off each other without fear—just designed to help.”
  • Kevin Lawson (00:02:58): “It’s unreasonable to think your small sales team has all the answers. But it’s completely reasonable to find a community that does.”
  • Sean O’Shaughnessey (00:04:16): “If you’re not a salesperson or sales leader, you’re not getting in. This isn’t about selling to each other. It’s about growing together.”

Additional Resources

  • B2B Sales Lab Information & Registration: https://newsales.expert/b2b-sales-lab
    (Free for the first three months with no obligation.)

A Significant Actionable Item from this Podcast

Join the B2B Sales Lab.
If you’ve ever wished you had a sounding board for a tough sales call, a creative partner to work through messaging, or a peer to validate your sales strategy, this is your moment. Visit the link in the show notes and apply to join the B2B Sales Lab. The first three months are free, giving you access to experienced sales minds, curated content on value selling and revenue management, and a judgment-free environment to grow your sales acumen. Don’t wait for your next deal to fall through; build your support system today.

Why You Should Listen

This episode is a call to action for sales professionals serious about growth. If you’re navigating complex sales cycles, seeking stronger messaging, or simply want a community that understands your world, the B2B Sales Lab might be the resource you’ve been missing. Kevin and Sean, both seasoned in sales leadership and sales management, offer not just insights but an entire framework to elevate your career. Listen now to learn how to take the next step toward sustainable sales success—and connect with others on the same journey.

The Key to Profitable Sales Organizations: Understanding and Adhering to the Sales Process

The Key to Profitable Sales Organizations: Understanding and Adhering to the Sales Process

By Sean O'Shaughnessey

Many salespeople, sales managers, and CEOs face a unique problem. This issue concerns the sales process, particularly when specific steps are skipped. The challenge is common among sales teams across various industries, and there are different perspectives on its causes and solutions.

This issue is concerning since, according to Harvard Business Review, 28% of companies that master at least three stages of their sales process will see an increase in revenue growth. (https://hbr.org/2015/01/companies-with-a-formal-sales-process-generate-more-revenue). That same study states that companies that had trained their sales managers to manage their pipelines saw their revenue grow 9% faster than those that didn’t. But not just any training will do. Sales managers need targeted training to address specific pipeline management challenges.

Sometimes, the sales process might seem tedious, and salespeople may skip steps out of impatience or eagerness to close a deal. However, skipping these steps can lead to further complications down the line. When a sales team is not following the process that has been identified, it can disrupt the team’s rhythm and efficiency. Some might argue that this is a sign that the process needs to change or that more training is required.

This issue extends beyond the sales team. When a company hires a fractional VP of sales, it brings an outside perspective to evaluate its sales process. The fractional VP will often encounter resistance from the existing team, who may feel their industry is unique. While every business has its distinctive elements, the fundamentals of a sales process are universal.

Read the rest of the article…
Why Cold Calling is Dead: The Shift to Relationship-Based Selling

Why Cold Calling is Dead: The Shift to Relationship-Based Selling

By Sean O'Shaughnessey

Building an effective sales pipeline requires a shift in strategy. Traditional cold calling has become increasingly ineffective, with decision-makers ignoring unsolicited calls and emails.

In the spring of 2021, Bank of America Corp.’s Merrill Lynch Wealth Management unit banned trainee brokers from making cold calls. According to the Wall Street Journal, it is hard to succeed with cold phone calls in an era when no one picks up. Merrill executives said personal referrals lead to a response around 40% of the time, but less than 2% of people who are cold-called even answer the phone.

Sales teams must adopt a more strategic approach, focusing on relationships rather than volume-based outreach. The key is leveraging existing networks to create warm introductions, significantly improving engagement rates and overall success.

Cold outreach has become expensive and inefficient, and the time spent dialing numbers, leaving voicemails, and sending emails that never get opened results in diminishing returns. Many executives no longer answer unknown calls, and email filters automatically sort cold outreach into spam. Even when messages get through, recipients are skeptical, assuming they are generated by automation rather than a genuine human connection. In reality, sales professionals must find a better way to reach their target audience.

Relationship-based selling offers a more effective alternative. Salespeople should focus on leveraging their connections instead of reaching out to strangers. This approach involves identifying key contacts who can provide warm introductions to potential prospects. These “super connectors” are individuals with strong networks and the ability to facilitate meaningful introductions. By tapping into these relationships, sales teams can bypass the skepticism associated with cold outreach and start conversations with credibility.

Read the rest of the article…
Two Tall Guys Talking Sales – Measuring Marketing Success with Amy Connor of CMO OnLoan – E126

Two Tall Guys Talking Sales – Measuring Marketing Success with Amy Connor of CMO OnLoan – E126

By Sean O'Shaughnessey

Welcome back to another episode of Two Tall Guys Talking Sales with Kevin Lawson and Sean O’Shaughnessey! This week, we’re diving deep into measuring marketing effectiveness with special guest Amy Connor, founder of CMO OnLoan. If you’ve ever struggled to connect marketing strategies to real business results, this episode is for you. Grab your marketing colleague and tune in—understanding what’s working (and what’s not) in your marketing is the key to driving sales growth.

Key Topics Discussed:

  • The Importance of Measuring Marketing Performance (01:08)
    Many companies don’t effectively track their marketing impact. Amy shares how focusing on key metrics—without overwhelming dashboards—can create a direct path to success.
  • Sales and Marketing Must Be Aligned (02:09)
    Customers don’t see marketing and sales as separate—they see one company. Amy explains why integrating both functions is crucial for a seamless customer journey.
  • Why Vanity Metrics Don’t Matter (02:55)
    Impressions, clicks, and leads may look impressive, but if they don’t translate to business results, they don’t matter. Learn how to focus on meaningful data that connects to revenue.
  • The Billboard Advertising Myth (03:12)
    Can a billboard drive B2B sales? Amy and Sean discuss the realities of traditional advertising and why small businesses should think critically about marketing spend.
  • Aligning Sales Messaging with Marketing Content (05:57)
    Sales teams shouldn’t be the only ones communicating key messages. Amy shares why marketing content must reinforce what salespeople say to build trust and shorten sales cycles.
  • Tactical vs. Strategic Marketing – What’s the Right Balance? (08:29)
    Should your marketing focus on brand awareness or immediate sales action? Amy explains the difference and how to measure each effectively.

Key Quotes:

Amy Connor: “Marketing and sales are part of the customer’s journey in a united way. The customer doesn’t see ‘marketing did this and sales did that’—they see the company as a whole.” (01:45)

Sean O’Shaughnessey: “Salespeople start at a disadvantage because buyers inherently don’t trust them. That’s why marketing must reinforce their message to build credibility.” (05:40)

Kevin Lawson: “Up to 70% of the buyer’s journey happens before they talk to sales. If marketing isn’t working ahead of time, you’re already losing.” (07:52)

Additional Resources:

  • Visit CMO OnLoan for free marketing resources: www.cmo-onloan.com
  • Connect with Amy Connor on LinkedIn: Amy Connor LinkedIn
  • Listen to the first episode featuring Amy: Last Week’s Podcast: https://podcasts.apple.com/us/podcast/amy-connor-discusses-salespeople-vs-lead-generation/id1668686029?i=1000693738159

A Significant Actionable Item from this Podcast:

Audit Your Marketing Metrics
Take 30 minutes this week to assess what marketing data your company is tracking. Are you focusing on impressions and clicks or lead conversion and revenue impact? Identify one metric that directly connects marketing activity to business growth and make it your priority.

Why You Should Listen to This Episode

Marketing is more than just branding—it’s a revenue-driving function. In this conversation, Amy Connor unpacks how B2B companies can measure what truly matters, align sales and marketing, and ensure every dollar spent on marketing contributes to the bottom line. If you want your marketing efforts to drive real sales results, don’t miss this insightful discussion. Tune in now!

Building Winning Sales Teams for the Future: Insights for CEOs and Sales Leaders

Building Winning Sales Teams for the Future: Insights for CEOs and Sales Leaders

By Sean O'Shaughnessey

What are the key moves that CEOs and sales leaders must make to prepare their teams for success in 2025? That’s exactly what we explored in a recent episode of the Art and Science of Complex Sales podcast hosted by Paul Fuller of Membrain. I had the pleasure of joining Kevin Lawson, President of Lighthouse Sales Advisors, for a deep dive into the strategies defining high-performing sales organizations in the year ahead.

You may recognize Kevin’s name. He is my co-host on the Two Tall Guys Talking Sales podcast. Paul titled our interview with him “Building Winning Sales Teams for the Future with Two Tall Guys.”

In the episode, we uncover the real-world tactics and leadership insights that can help CEOs transform their sales organizations—from defining who to sell to building processes that deliver consistent results. If you’re serious about leading a sales team that thrives amid complexity, I highly encourage you to listen to the full conversation. The link is below—don’t miss it.

Driving Growth Through Data-Driven Leadership

One of the central themes we cover is the role of data in guiding strategic decisions. Successful sales leadership today hinges on the ability to read the right signals—metrics like call volumes, deal velocity, customer life cycles, and attrition rates. We discuss how to turn that data into insights that refine your ideal customer profile (ICP) and strengthen your sales and marketing efforts.

We also discuss how a CEO’s dashboard isn’t static. It must evolve based on the business environment, market pressures, and geopolitical events. Paul Fuller helps steer the conversation into practical territory, where we explore how CEOs can stay ahead by making data-informed decisions and leading their teams with clarity and focus.

This podcast episode will be particularly valuable if you’re a CEO or revenue leader aiming to refine your strategic lens. Be sure to check it out through the link below.

Coaching for Consistent Performance Improvement

Data might show you where to focus, but coaching is what gets you results. Kevin and I discuss the importance of coaching for incremental gains—not just pushing reps to hit more numbers but helping them level up in ability and mindset.

We show how leaders can move salespeople from C-level to B-level performers and beyond through relatable sports analogies and real-world examples. These small, steady improvements compound over time and create a team of confident, capable sellers who know how to win.

We also touch on the need for structured coaching frameworks and repeatable systems, which we provide through website resources. If you lead a team that could benefit from a morale, performance, or accountability boost, this is a conversation you won’t want to miss.

Building a Repeatable, Scalable Sales Process

We close the episode with a focused discussion on sales process discipline. By taking a structured approach to evaluating leads—based on product fit, probability, and alignment with your ICP—leaders can drive better forecasting and higher win rates.

Even modest improvements in key areas like win rate, deal size, and sales cycle length can produce exponential results. We explore how a 7% uptick in core metrics could double your revenue. The message is clear: Clarity, consistency, and customer focus are non-negotiable in 2025.

If you’re looking to future-proof your sales organization, this podcast episode is packed with strategies and examples that can serve as a roadmap. Listen to the full episode and learn how to apply these concepts to your company.

Listen to the Full Episode

This is a powerful episode for CEOs, sales leaders, and anyone responsible for building and leading high-performance sales teams. If you’re ready to equip your team for 2025 and beyond, don’t miss this conversation on the Art and Science of Complex Sales podcast.

🎧 Episode: Building Winning Sales Teams for the Future with Two Tall Guys
🎙 Host: Paul Fuller of Membrain
🔗 https://podcasts.apple.com/us/podcast/building-winning-sales-teams-for-the-future-with-two/id1723340327?i=1000684372709

Click the link to listen now—you’ll walk away with actionable ideas to implement immediately.