Complex AI Deals Require New Sales Strategies

If you're leading a team selling AI solutions, this topic is already top of mind. Make sure you listen into John Kaplan next Thursday: https://hubs.li/Q046z6mT #SellingAI #TechSales #BeElite

Underwhelming results usually trace back to vague prompts. When AI gets surface-level direction, it delivers surface-level performance. When you train AI strategically with context and constraints, it starts driving measurable outcomes. Most teams might type: “Write a post about our services.” That won’t increase revenue. It just fills space. If you want GenAI to extend your team, give it the clarity you’d give a new hire: 👉🏽Who we serve 👉🏽The exact pain point 👉🏽What makes our approach different 👉🏽The goal of this asset (pipeline, demos, retention, etc.) Here are better prompt examples. 👇 Instead of: “Help me pitch AI adoption to leadership.” Try: “Act as a CMO presenting to a C-suite leadership team. Build a concise executive briefing that explains why AI adoption in marketing operations is worth investing in this year. Include projected productivity gains, potential cost savings, realistic implementation risks, and a phased rollout plan. The goal is to secure leadership approval and budget for an initial pilot.” Instead of: “Create an email campaign.” Try: “Outline a 4-email campaign announcing a new product feature to our existing customer base and prospects. The goal is to generate demo requests and product adoption. Include the positioning angle for each email, subject line ideas, and how the messaging should evolve from awareness → consideration → action.“ Clear inputs drive stronger outputs. That’s how a team of 3 starts operating like a team of 10. #aiformarketing #marketingai #aiforbusiness

Most AI programs don’t fail because of bad technology. They fail because nobody wanted to talk about the hard stuff. I call them Big Rocks. The elephants in the room that everyone sees but nobody names out loud. Here’s what I’ve learned leading AI programs for some of the biggest companies in the world: Every level of strategy has its own Big Rock. And if you don’t deal with it head-on, the whole program stalls. At the top — Corporate Strategy The Big Rock here is fear of commitment. Leaders love talking about AI. They hate signing up for what it actually takes. The fix? Stop treating AI like an experiment. Decide what kind of company you want to be — and say it out loud. Your people are waiting for permission to go all in. One level down — Business Strategy The Big Rock here is competing the same way you always have. Agents don’t just make old processes faster. They change how you win. If your business leaders are still thinking about AI as a cost-cutting tool, you haven’t had the right conversation yet. Middle of the pyramid — Functional Strategy The Big Rock here is everyone thinking someone else owns it. Marketing thinks Sales is leading it. Sales thinks IT is leading it. IT thinks the business is leading it. Name an owner in every function. No owner, no progress. At the base — Operational Strategy This is where most programs go to die. And the Big Rock here is the biggest one of all — people don’t change how they actually work. New tools sitting on top of old habits don’t transform anything. You have to redesign the daily work, not just add a new button to click. The secret I share with every team I work with? Don’t wait until the rocks pile up. Name them early. Deal with them directly. Keep moving. The path to becoming a high-performing agentic enterprise isn’t a straight line. It’s a series of hard conversations that most teams keep postponing. The ones who have those conversations early? They win. #AgenticEnterprise #AITransformation #Leadership #ChangeManagement #Agentforce #Salesforce #BigRocks

Most AI for sales pitches talk about rep productivity. But leadership has a different question. What becomes more predictable this quarter? Because management does not need more activity. Management needs governance. The gap in most GTM teams is not effort. It is variance. - Different reps qualify differently. - Different follow up cadences. - Different definitions of a good lead. - Different reasons for deals stalling. AI is valuable only if it reduces that variance. So execution becomes consistent without leaders riding reps. Let me know in the comments below- If you could make one thing predictable in your funnel, what would it be? Pipeline velocity Qualification quality Forecast confidence #UnderstandingWithRaisn #AIForSales #GTMStrategy #RevenueOps #PipelineManagement #Forecasting #SalesLeadership

Most teams know who they want to target. Far fewer know who is actually in market right now. That gap is where a lot of pipeline goes to die. A good GTM motion should be able to answer 3 things: 1. Why this account? Do they fit the ICP? 2. Why this group of stakeholders? Do they live in the problem and have they got sign off authority? 3. Why now? What has changed in their world that makes action more likely? That third question matters most. At Clave, we think “why now” is usually hidden inside live triggers: - leadership changes - expansion plans - restructuring - new product launches - AI rollout - cost pressure - hiring shifts Those signals tell you where pressure exists.Then context tells you what it means. Then execution turns that into outreach, campaigns, and plays. That’s the difference between: sequencing at scale and engaging when it actually matters The goal isn’t more accounts. It’s knowing which accounts are moving, and why. Clave’s positioning is built around combining context, triggers, and automated plays so teams can engage the right accounts at the right time. Its ICP and persona framework also centers on live buying signals such as leadership changes, expansion, restructuring, AI adoption, and hiring shifts.

You don’t need another “AI workshop.” You need your team to show up to real calls prepared, consistent, and coachable. That’s why I’m running the AI-Powered Sales Enablement Program for teams of about 5–10 sellers. It’s built for leaders who have real targets, but no dedicated enablement function and are tired of reps operating on instinct instead of a system. In this program, your team will: Use AI prompts to prep smarter for calls (not just wing it) Practice with AI tools in a safe, guided way so they build confidence Turn real conversations into coaching moments, instead of letting insights die in call recordings The outcome: fewer “random good calls,” more consistent execution across the team, and a repeatable coaching rhythm you can keep running long after the program ends. If you’re leading a lean sales team and want structure, coaching, and AI support without hiring a full-time enablement leader yet, this is for you. DM me for more.

Over the last decade working across sales, partnerships, and commercial strategy, one thing has become very clear: AI will not replace great sales leaders, but sales leaders who use AI will outperform those who don’t. For years, commercial teams have relied on instinct, relationships, and experience. Those will always matter. But today, AI is introducing a new layer of intelligence into how growth happens. Imagine being able to: • Identify high-probability opportunities before competitors do • Predict client needs before the conversation even starts • Personalize outreach at scale without losing authenticity • Use data to strengthen partnership decisions and market expansion The real opportunity is not automation. It is augmentation. AI allows commercial leaders to spend less time on administrative tasks and more time on what truly drives growth: strategy, relationships, and value creation. In my view, the next generation of commercial leadership will sit at the intersection of: Sales + Partnerships + Strategy + AI-driven insight. Organizations that understand this shift early will build a significant competitive advantage. As I continue exploring broader leadership opportunities across commercial strategy, partnerships, and enterprise growth, I’m particularly interested in how forward-thinking companies are embedding AI into their revenue engines. Curious to hear from others: How are you seeing AI reshape sales and partnership strategy in your organization? #AI #SalesLeadership #BusinessDevelopment #Partnerships #CommercialStrategy

$280K in AI tools. Zero adoption. That is not a horror story. That is a Tuesday for most sales teams right now. I talked to 11 sales leaders in the last 60 days. Every single one had bought AI tools. Only 3 had teams actually using them. The pattern was almost identical every time. Leadership gets excited. Buys 3 to 5 tools in one quarter. Sends a launch email. Nobody assigns an owner. Reps try it once and go back to what they know. Six months later the contracts are sitting on a shelf. Untouched. This is not a technology problem. It is a leadership problem. I mapped the entire cycle in the carousel below. Four stages of failure and three steps to escape it. Swipe through. You will probably recognize exactly where your team is right now.

🚀 𝗘𝘅𝗰𝗶𝘁𝗲𝗱 𝘁𝗼 𝘀𝗽𝗼𝘁𝗹𝗶𝗴𝗵𝘁 𝗮𝗻 𝘂𝗽𝗰𝗼𝗺𝗶𝗻𝗴 𝗲𝘃𝗲𝗻𝘁 𝗳𝗿𝗼𝗺 𝗼𝗻𝗲 𝗼𝗳 𝗺𝘆 𝘁𝗿𝘂𝘀𝘁𝗲𝗱 𝗻𝗲𝘁𝘄𝗼𝗿𝗸𝗶𝗻𝗴 𝗽𝗮𝗿𝘁𝗻𝗲𝗿𝘀 𝗮𝘁 𝗣𝗶𝘃𝗼𝘁𝗮𝗹 𝗔𝗱𝘃𝗶𝘀𝗼𝗿𝘀, 𝗠𝗮𝘁𝘁 𝗛𝗮𝗹𝗹. 𝗧𝗵𝗲𝗶𝗿 𝘂𝗽𝗰𝗼𝗺𝗶𝗻𝗴 𝘀𝗲𝘀𝘀𝗶𝗼𝗻, “𝗣𝗿𝗮𝗰𝘁𝗶𝗰𝗮𝗹 𝗪𝗮𝘆𝘀 𝗦𝗮𝗹𝗲𝘀 𝗟𝗲𝗮𝗱𝗲𝗿𝘀 𝗔𝗿𝗲 𝗣𝘂𝗹𝗹𝗶𝗻𝗴 𝗔𝗵𝗲𝗮𝗱 𝗼𝗳 𝘁𝗵𝗲 𝗖𝗼𝗺𝗽𝗲𝘁𝗶𝘁𝗶𝗼𝗻,* 𝗶𝘀 𝗽𝗮𝗰𝗸𝗲𝗱 𝘄𝗶𝘁𝗵 𝗶𝗻𝘀𝗶𝗴𝗵𝘁𝘀 𝗳𝗼𝗿 𝗮𝗻𝘆𝗼𝗻𝗲 𝗹𝗼𝗼𝗸𝗶𝗻𝗴 𝘁𝗼 𝘀𝘁𝗿𝗲𝗻𝗴𝘁𝗵𝗲𝗻 𝘁𝗵𝗲𝗶𝗿 𝘀𝗮𝗹𝗲𝘀 𝗹𝗲𝗮𝗱𝗲𝗿𝘀𝗵𝗶𝗽 𝗮𝗻𝗱 𝘀𝘁𝗮𝘆 𝗰𝗼𝗺𝗽𝗲𝘁𝗶𝘁𝗶𝘃𝗲 𝗶𝗻 𝗮 𝘀𝗵𝗶𝗳𝘁𝗶𝗻𝗴 𝗺𝗮𝗿𝗸𝗲𝘁. Details are below 👇 AI for sales leaders is quickly moving from experimentation to competitive advantage. While some companies are using AI for basic tasks like drafting emails or proposals, others are integrating it into lead generation, prospect qualification, account research, and opportunity strategy. The difference in results creates a measurable competitive advantage. In this virtual session, Gary Braun of Pivotal Advisors joins Drew Schwartz of MPI to explore how sales leaders and business owners can move beyond experimentation and begin using AI as a strategic growth tool. 𝗬𝗼𝘂 𝘄𝗶𝗹𝗹 𝗹𝗲𝗮𝗿𝗻: ✔️Practical AI applications that can have an immediate impact on revenue ✔️Where to start and how to prioritize implementation ✔️The executive’s role in driving AI adoption across the sales organization ✔️How leading companies are using AI to improve qualification and deal health If you are a business owner, CEO, VP of Sales, or sales leader looking to integrate AI into your sales process in a practical and measurable way, this session will provide clarity and direction. 𝗜𝗳 𝘆𝗼𝘂’𝗿𝗲 𝗳𝗼𝗰𝘂𝘀𝗲𝗱 𝗼𝗻 𝗴𝗿𝗼𝘄𝘁𝗵, 𝗹𝗲𝗮𝗱𝗲𝗿𝘀𝗵𝗶𝗽, 𝗼𝗿 𝘀𝗵𝗮𝗿𝗽𝗲𝗻𝗶𝗻𝗴 𝘆𝗼𝘂𝗿 𝘀𝗮𝗹𝗲𝘀 𝘀𝘁𝗿𝗮𝘁𝗲𝗴𝘆, 𝘁𝗵𝗶𝘀 𝗶𝘀 𝗼𝗻𝗲 𝘄𝗼𝗿𝘁𝗵 𝗮𝘁𝘁𝗲𝗻𝗱𝗶𝗻𝗴. 🔗 𝗥𝗲𝗴𝗶𝘀𝘁𝗲𝗿 𝗵𝗲𝗿𝗲: https://lnkd.in/gXbGeubq #SalesLeadership #AIGrowth #SalesStrategy #BusinessDevelopment #CompetitiveAdvantage

🚀 𝗘𝘅𝗰𝗶𝘁𝗲𝗱 𝘁𝗼 𝘀𝗽𝗼𝘁𝗹𝗶𝗴𝗵𝘁 𝗮𝗻 𝘂𝗽𝗰𝗼𝗺𝗶𝗻𝗴 𝗲𝘃𝗲𝗻𝘁 𝗳𝗿𝗼𝗺 𝗼𝗻𝗲 𝗼𝗳 𝗺𝘆 𝘁𝗿𝘂𝘀𝘁𝗲𝗱 𝗻𝗲𝘁𝘄𝗼𝗿𝗸𝗶𝗻𝗴 𝗽𝗮𝗿𝘁𝗻𝗲𝗿𝘀 𝗮𝘁 𝗣𝗶𝘃𝗼𝘁𝗮𝗹 𝗔𝗱𝘃𝗶𝘀𝗼𝗿𝘀, 𝗠𝗮𝘁𝘁 𝗛𝗮𝗹𝗹. 𝗧𝗵𝗲𝗶𝗿 𝘂𝗽𝗰𝗼𝗺𝗶𝗻𝗴 𝘀𝗲𝘀𝘀𝗶𝗼𝗻, “𝗣𝗿𝗮𝗰𝘁𝗶𝗰𝗮𝗹 𝗪𝗮𝘆𝘀 𝗦𝗮𝗹𝗲𝘀 𝗟𝗲𝗮𝗱𝗲𝗿𝘀 𝗔𝗿𝗲 𝗣𝘂𝗹𝗹𝗶𝗻𝗴 𝗔𝗵𝗲𝗮𝗱 𝗼𝗳 𝘁𝗵𝗲 𝗖𝗼𝗺𝗽𝗲𝘁𝗶𝘁𝗶𝗼𝗻,* 𝗶𝘀 𝗽𝗮𝗰𝗸𝗲𝗱 𝘄𝗶𝘁𝗵 𝗶𝗻𝘀𝗶𝗴𝗵𝘁𝘀 𝗳𝗼𝗿 𝗮𝗻𝘆𝗼𝗻𝗲 𝗹𝗼𝗼𝗸𝗶𝗻𝗴 𝘁𝗼 𝘀𝘁𝗿𝗲𝗻𝗴𝘁𝗵𝗲𝗻 𝘁𝗵𝗲𝗶𝗿 𝘀𝗮𝗹𝗲𝘀 𝗹𝗲𝗮𝗱𝗲𝗿𝘀𝗵𝗶𝗽 𝗮𝗻𝗱 𝘀𝘁𝗮𝘆 𝗰𝗼𝗺𝗽𝗲𝘁𝗶𝘁𝗶𝘃𝗲 𝗶𝗻 𝗮 𝘀𝗵𝗶𝗳𝘁𝗶𝗻𝗴 𝗺𝗮𝗿𝗸𝗲𝘁. Details are below 👇 AI for sales leaders is quickly moving from experimentation to competitive advantage. While some companies are using AI for basic tasks like drafting emails or proposals, others are integrating it into lead generation, prospect qualification, account research, and opportunity strategy. The difference in results creates a measurable competitive advantage. In this virtual session, Gary Braun of Pivotal Advisors joins Drew Schwartz of MPI to explore how sales leaders and business owners can move beyond experimentation and begin using AI as a strategic growth tool. 𝗬𝗼𝘂 𝘄𝗶𝗹𝗹 𝗹𝗲𝗮𝗿𝗻: ✔️Practical AI applications that can have an immediate impact on revenue ✔️Where to start and how to prioritize implementation ✔️The executive’s role in driving AI adoption across the sales organization ✔️How leading companies are using AI to improve qualification and deal health If you are a business owner, CEO, VP of Sales, or sales leader looking to integrate AI into your sales process in a practical and measurable way, this session will provide clarity and direction. 𝗜𝗳 𝘆𝗼𝘂’𝗿𝗲 𝗳𝗼𝗰𝘂𝘀𝗲𝗱 𝗼𝗻 𝗴𝗿𝗼𝘄𝘁𝗵, 𝗹𝗲𝗮𝗱𝗲𝗿𝘀𝗵𝗶𝗽, 𝗼𝗿 𝘀𝗵𝗮𝗿𝗽𝗲𝗻𝗶𝗻𝗴 𝘆𝗼𝘂𝗿 𝘀𝗮𝗹𝗲𝘀 𝘀𝘁𝗿𝗮𝘁𝗲𝗴𝘆, 𝘁𝗵𝗶𝘀 𝗶𝘀 𝗼𝗻𝗲 𝘄𝗼𝗿𝘁𝗵 𝗮𝘁𝘁𝗲𝗻𝗱𝗶𝗻𝗴. 🔗 𝗥𝗲𝗴𝗶𝘀𝘁𝗲𝗿 𝗵𝗲𝗿𝗲: https://lnkd.in/gXbGeubq #SalesLeadership #AIGrowth #SalesStrategy #BusinessDevelopment #CompetitiveAdvantage