How I Built an AI-Driven Sales System in 5 Years

Purpose is the New Performance Technology drives speed. AI drives insight. But only purpose drives commitment. I’ve seen every kind of transformation — digital, cultural, structural — and one pattern always stands out. Without a clear why, everything eventually stalls. Purpose is the compass that keeps transformation on course. It connects leadership with meaning, people with progress, and data with direction. In sales, CRM and AI give us incredible visibility. But it’s purpose that gives those insights power. When teams understand the “why,” they bring the energy, belief, and ownership that no algorithm can replace. As Marc Benioff, CEO of Salesforce , said: “Doing well by doing good is no longer just a competitive advantage. It’s becoming a business imperative.” The most successful leaders I’ve worked with don’t just deliver performance. They create purposeful performance — where numbers reflect meaning, not just metrics. Technology builds capability. Purpose builds culture. Together, they build momentum. How do you keep purpose alive in the middle of transformation — when pressure and data start to take over? #Leadership #Purpose #Transformation #SalesEnablement #AI #CRM #Culture #MarcBenioff #JonRyley

Stop Letting Products Define Your Projects Too many companies start with a shiny new tool - CRM, AI (you name it) - and then struggle to reshape teams, workflows, and strategy around it. The result? Misalignment, wasted time, and frustrated teams. The real question isn’t “Which product should we buy?”. It’s “Which business problem are we trying to solve?” At InvestMatch, we see this play out often: ✤ CRM systems rolled out before customer strategy is clear ✤ AI pilots launched without metrics for impact ✤ Teams adjusting to products instead of products serving the team The truth: tech doesn’t drive growth - clarity does. Products should serve your goals, not set them. We put together a simple checklist to help leaders spot when a project is being driven by a product (instead of business needs) before it becomes a costly detour. 🔗 Read the full article here: https://lnkd.in/gQEXqSr3 At InvestMatch, we help leaders cut through the noise, separate hype from real opportunity, and match with partners that unlock measurable growth. Because clarity always beats chasing the next tool. #BusinessGrowth #Leadership #DigitalTransformation #AI #CRM #Strategy #InvestMatch

In every conversation I'm having with sales leaders about AI, there's a pattern emerging. Some are deep in the technical weeds — understanding every algorithm, every data model, every automation trigger. Others barely know what features their CRM has turned on. And here's what surprised me: Technical knowledge isn't the differentiator. The leaders whose teams are thriving with AI aren't the leaders who understand it best. They're the ones asking the best questions: "What pattern is this showing us that we weren't looking for?" "Why might this recommendation be right even though it contradicts my gut?" "What would we try if we believed this insight instead of dismissed it?" They're not AI experts. They're professionally curious. And their teams feel permission to be curious too. Because here's the truth: AI doesn't need you to be smarter. It needs you to be more open. It doesn't need your certainty. It needs your willingness to explore. The technical skills you can learn later. The curiosity? That's the leadership skill you need now. Are you asking better questions, or just looking for better answers? #SalesLeadership #B2BSales #LeadershipSkills #SalesTransformation #AIAdoption

Traditional sales enablement does not exist anymore. It’s devolved into a "massive filing cabinet of stuff" — a reactionary function that’s overwhelmed sellers  and left leaders guessing. I'm so excited that "Ignite Your GTM with AI," a book I contributed to, is coming November 5th and available now for pre-order! I’m incredibly honored to be one of the 25+ leaders contributing to this. A massive congratulations to Ashley Hock, Santiago Suarez Ordoñez, Moiz Virani, and Jonathan M K., and the entire Momentum.io team for architecting this critical conversation. I was thrilled to contribute to "Chapter 9: Coaching & Enablement: AI-Driven Skills Development". In it, we confront the "diagnostic crisis" plaguing our teams. Reps don't really know their skill gaps, and managers often aren't trained to coach them. We're stuck assuming "completion equals competency"... until a deal is lost. This chapter is the playbook for Predictive Enablement. We’re moving from the old, reactive model to a new, proactive architecture. We explore how to build systems that train AI on "what good looks like" for your company. This allows AI to objectively diagnose skill gaps and predict "revenue impacting mistakes" before they happen. But AI doesn't replace the human. It orchestrates it. AI is great for identifying gaps, but it can't remove the human element of true coaching and empathy. Here's a small preview from the chapter: “AI is great for identifying gaps, but it can’t remove the human element. Salespeople are best managed and best coached human to human because you can get inflection." This is how enablement stops being a "filing cabinet" and becomes the strategic architect of a team that is measurably ready to win. I can't wait for you to read it. Preorder your copy here: https://lnkd.in/gD8Sp54R #IgniteYourGTM #AI #GTM #BookLaunch #Momentum #SalesEnablement #Coaching #SalesLeadership #LMS #Readiness

“This will be the last generation to ever just manage humans.” - Marc Benioff Are you ready to manage a hybrid team of AI agents and humans? That is what’s coming, and most leaders aren’t ready. You can’t lead the next era of sales teams with yesterday’s skill set. The future of leadership looks more like RevOps, meets GTM engineer, meets psychology, meets accountability boot camp. You’ll need to: ➡️ Understand and react to prospect and customer signals, not just read a CRM dashboard. ➡️ Evaluate and implement AI-native tools that will appear out of nowhere and change everything your team is doing overnight. ➡️ Keep your humans motivated while half their teammates don’t sleep, take vacations, and double results in half the time. ➡️ Build trust in a world where technology is doing more of the heavy lifting. ➡️ Make hard calls about what stays human and what becomes agentic. It’s not just about being tech-savvy. It’s about being leadership-savvy in a completely new environment. The next generation of sales leaders won’t just manage people. They will manage change. How are you preparing?

Every GTM team needs an AI strategy. But here’s the problem—too many leaders are just throwing shiny tools at the wall to see what sticks. I’m seeing these trends across the industry: → Sales gets five new “AI copilots.” → CS gets a “productivity suite” that adds more clicks than it removes. → Marketing gets a dozen dashboards nobody opens. And everyone’s still drowning in the same meetings, the same decks, the same chaos. Before you deploy another bot or workflow, go talk to your trench warriors. The CSM who lives in QBR hell. The rep who actually carries the quota. The marketer trying to write content while juggling 12 Slack threads. Ask them: 🧠 What slows you down every day? ⚙️ What task do you dread most? 🚀 What would make you unstoppable? That’s where your AI strategy starts—not in a boardroom, not in a demo. It starts in the trenches. Because when you understand the job deeply, you stop building for “what’s possible” …and start building for what’s useful. #CustomerSuccess #Sales #AIGoToMarket #Leadership

Stepping outside the box means more than just getting a CRM. It's about leveraging tools that provide automated insights and summaries, which can be integrated into a vector store. This creates an agent capable of answering questions like, "Where are we with this project?" This is especially useful as teams grow and direct oversight becomes challenging. Instead of interrupting colleagues, leaders can leverage technology to gain a quick understanding of project status and team progress. #AI #Productivity #ProjectManagement #Innovation #Leadership

🚨 𝗖𝗼𝗺𝗽𝗲𝘁𝗶𝘁𝗼𝗿𝘀 𝗔𝗿𝗲 𝗦𝗵𝗶𝗽𝗽𝗶𝗻𝗴 𝗔𝗜. 𝗬𝗼𝘂’𝗿𝗲 𝗦𝘁𝗶𝗹𝗹 𝗜𝗻 𝗖𝗼𝗺𝗺𝗶𝘁𝘁𝗲𝗲. The gap is widening faster than you think. I'm hearing the same thing from founders and CEOs: "𝘞𝘦 𝘬𝘯𝘰𝘸 𝘈𝘐 𝘪𝘴 𝘤𝘳𝘪𝘵𝘪𝘤𝘢𝘭, 𝘣𝘶𝘵 𝘸𝘦'𝘳𝘦 𝘮𝘢𝘱𝘱𝘪𝘯𝘨 𝘰𝘶𝘵 𝘵𝘩𝘦 18-𝘮𝘰𝘯𝘵𝘩, 𝘰𝘳𝘨𝘢𝘯𝘪𝘻𝘢𝘵𝘪𝘰𝘯𝘢𝘭-𝘸𝘪𝘥𝘦 𝘴𝘵𝘳𝘢𝘵𝘦𝘨𝘺 𝘧𝘪𝘳𝘴𝘵." This is the biggest mistake of 2025. You are applying the heavy, monolithic, multi-quarter implementation logic of past ERP or CRM projects to a technology that thrives on rapid, iterative deployment. While you're building the 'army' to plan the 'war,' your competitors are running skirmishes and taking ground today. Here are 𝟯 𝗖𝗿𝗶𝘁𝗶𝗰𝗮𝗹 𝗠𝗶𝘀𝘁𝗮𝗸𝗲𝘀 𝗹𝗲𝗮𝗱𝗲𝗿𝘀 𝗺𝗮𝗸𝗲 𝘄𝗵𝗲𝗻 𝗳𝗮𝗰𝗶𝗻𝗴 𝗔𝗜 𝗮𝗱𝗼𝗽𝘁𝗶𝗼𝗻: 𝟭. 𝗧𝗵𝗲 '𝗔𝗹𝗹-𝗼𝗿-𝗡𝗼𝘁𝗵𝗶𝗻𝗴' 𝗧𝗿𝗮𝗽: Believing an AI strategy must be a holistic, enterprise-wide deployment before you can see a single ROI. This leads to analysis paralysis. 𝟮. 𝗧𝗵𝗲 𝗦𝗰𝗮𝗹𝗲 𝗣𝗲𝗿𝗰𝗲𝗽𝘁𝗶𝗼𝗻 𝗙𝗮𝗶𝗹: Assuming an AI implementation requires months of planning and an army of engineers. The reality? Many high-leverage process improvements can be deployed within weeks with a small, focused team. 𝟯. 𝗧𝗵𝗲 𝗣𝗿𝗼𝗰𝗲𝘀𝘀 𝗢𝘃𝗲𝗿 𝗣𝗿𝗼𝗱𝘂𝗰𝘁 𝗗𝗲𝗹𝗮𝘆: Focusing on governance and compliance before demonstrating tangible value. This trades market speed for administrative comfort, a fatal error in a competitive landscape. Every single process in your organization, from customer service intake to internal code review, can benefit from an incremental AI layer right now. You should develop the organizational AI strategy, BUT that cannot be the excuse for inaction. The most successful companies are treating AI as a series of high-ROI, two-week sprints focused on immediate productivity gains. Start with one team, one process, and one undeniable metric. Get a win. Build momentum. The choice isn't between planning and doing. The right approach is Strategic Planning alongside Rapid Implementation. 💭 What is one process your team could automate with AI in the next 14 days if the only goal was a single, measurable win? 👉 If this perspective resonated, please like, comment, share and follow. It helps spread the conversation. #AIStrategy #ProductLeadership #CompetitiveAdvantage #DigitalTransformation #CEOInsights

The ground under revenue teams is changing quickly. The sales leaders who will succeed in 2026 won’t be those who avoid AI; they’ll be the ones who understand it well enough to lead through it and with it. Over the past year, I’ve looked deeper than surface level adoption. I’ve been studying AI from the ground up:   > How machine learning systems make predictions.   > How LLMs process context and reasoning.   > How to translate that understanding into systems teams can trust. This hasnt been out of academic curiosity; it’s been preparation. The data shows this shift is already here. Here’s three lessons that have changed how I am leading: 1. From pipeline inspection to pattern recognition   We used to review deals one by one. Now we coach around AI identified patterns. > Gong's 2025 State of Revenue Growth shows that managers using AI scorecards spot risks before they appear on the dashboard. This turns coaching from reactive to proactive. 2. From data collection to orchestration   More tools didn’t make us better; cleaner data and tighter feedback loops did.  > Forrester's 2024 Revenue Orchestration Wave confirms it: RevOps has changed from a reporting layer to orchestration. It now serves as the central system where technology and human intuition work together. 3. From activity to impact   Top performers aren’t the busiest; they’re the most intentional. They use AI for 80% of tasks, like research, admin work, and follow-up, which allows them to focus completely on the 20% that matters most. This includes building trust, asking sharper questions, and closing deals effectively. As I move toward 2026, my focus is clear:   - Build teams that forecast with over 95% accuracy.   - Create AI augmented processes where coaching drives metrics, not dashboards.   - Foster a culture where data enhances intuition, rather than replaces it. If you’re leading a team right now, the question is:   Are you simply using the tools, or are you learning how they really work? Because the leaders who grasp both the technology and the human aspect will shape the next era of growth.

𝗪𝗲 𝗮𝗿𝗺𝗲𝗱 𝘁𝗵𝗲 𝗯𝘂𝘆𝗲𝗿 𝘄𝗶𝘁𝗵 𝗚𝗼𝗼𝗴𝗹𝗲 𝗠𝗮𝗽𝘀... 𝗯𝘂𝘁 𝘁𝗵𝗲 𝗿𝗲𝗽 𝗶𝘀 𝘀𝘁𝗶𝗹𝗹 𝗱𝗿𝗶𝘃𝗶𝗻𝗴 𝗯𝘆 𝗿𝗼𝗮𝗱 𝘀𝗶𝗴𝗻𝘀. Sales is a two-sided game. On one side - the customer. On the other - the rep. At the center - the product. For decades, we’ve obsessed over one side of the equation - the customer. Mapped their journey. Built personas. Personalized every touchpoint. Rightfully so. But somewhere along the way, the rep got left behind. We gave them dashboards, tools, and enablement - but not vision. We stopped asking: What does the rep need to truly grow? 𝗔𝘁 𝗣𝗲𝗼𝗽𝗹𝗲𝗟𝗲𝗻𝘀, 𝘄𝗲’𝗿𝗲 𝗵𝗲𝗹𝗽𝗶𝗻𝗴 𝗹𝗲𝗮𝗱𝗲𝗿𝘀 𝘀𝗲𝗲 𝘁𝗵𝗲𝗶𝗿 𝗿𝗲𝗽𝘀 𝘁𝗵𝗿𝗼𝘂𝗴𝗵 𝗮 𝗰𝗹𝗲𝗮𝗿𝗲𝗿 𝗹𝗲𝗻𝘀: ✅ Putting reps back in the equation - by diagnosing what’s driving performance ✅ Equipping managers with AI coaching agents - no expert analysis required ✅ Empowering reps with action-level insights and nudges to grow Because when you can see your reps clearly, you can coach them precisely. 𝗪𝗵𝗮𝘁’𝘀 𝗴𝘂𝗶𝗱𝗶𝗻𝗴 𝘆𝗼𝘂𝗿 𝘁𝗲𝗮𝗺 - 𝗼𝘂𝘁𝗱𝗮𝘁𝗲𝗱 𝘀𝗶𝗴𝗻𝗽𝗼𝘀𝘁𝘀 𝗼𝗿 𝗮 𝗰𝗹𝗲𝗮𝗿𝗲𝗿 𝗹𝗲𝗻𝘀? #RepPerformance #SalesCoaching PeopleLens #SalesAI