How Digital Transformation Impacts Sales

Since our relaunch 3 weeks ago, I've talked to 40+ sales leaders who are evaluating AI tools to accelerate revenue. Their companies roughly fall into three categories: 1) ~40% - Not using AI yet because it's early 2) ~40% - Using AI to get more first meetings 3) ~20% - Using AI to improve win rates Simplistic, I know, but let me explain what I mean... 1) Not using AI yet because it's early I've been surprised by how many buyers remain in "wait and see" mode. They've heard about broken promises from AI vendors, implementation nightmares, and lack of funnel impact. I posted about this a few weeks back—there's growing skepticism in the market. The problem with waiting, though, is that competitors are trying everything and gaining an early edge. They are investing the weeks and months needed to learn how to customize and deploy these tools, retrain their employees, etc., to drive up sales productivity. They will be well positioned to move fast as the next generation of high-impact AI tools come to market. 2) Using AI to get more first meetings This is where most AI is used today. After all, pipeline generation is the #1 priority for most sales leaders. Companies are evaluating AI SDRs and digital workers to send emails, make calls, and book meetings at scale. While initial conversion results look promising and the business case is clear, conversion rates typically plummet over time. There's also a significant risk of burning through your TAM and damaging your brand if not executed thoughtfully. (One CRO I talked to said an AI SDR ruined their domain reputation, and it would take many months to crawl out of that hole.) This approach can work for SMB sales motions with large TAMs but struggles in enterprise sales. 3) Using AI to improve win rates Many sales leaders would choose more meetings over a higher post-first-meeting conversion rate, but that's a huge missed opportunity. If meetings are so hard to get, why waste the hard-earned ones you have? This is especially crucial in enterprise sales, where it can take 30 meetings to close a deal, and every interaction is a chance to win or lose. As one of our customers likes to say, "Every meeting is like the Super Bowl—it's win or lose. If you only spent 15 minutes preparing for the Super Bowl, how likely are you to win?" My prediction is that 2025 will see a massive shift here. Expectations will be reset on the ROI of simply scaling up cold outreach volume. Buyers focused on win rates who have invested in transforming their sales force to be AI-native will leave their competitors behind. Choose wisely 🙂

My version of 2025 B2B sales prediction post. Since I've been sharing about AI, this one is centered around that. Here are the key trends I'm watching: 🤖 AI will handle the grunt work, but human connection becomes MORE valuable. While AI excels at research and tailoring initial outreach, meaningful business relationships still require authentic human interaction. Ideally, you are using AI in such a way that you have more time to focus on relationship building. When you have the chance to meet in person, or show your face another way, do it! AI can't go to conferences and shake hands but you can. 🎯 Personalization will reach new levels. AI helps us understand prospect patterns and preferences, but the winners will be those who use these insights to have more relevant, human conversations. It's not about having AI write your emails - it's about using AI to better understand your prospects' needs. Ask AI to take the role of the person you are pitching and ask the LLM for feedback. Experiment with turning on the voice feature and have a conversation with it. 💡 Subject matter expertise becomes critical. As basic information becomes readily available through AI, buyers will increasingly value deep expertise and unique insights. The ability to apply knowledge in context will matter more than ever. This is especially true for professional services where your domain knowledge is central to solving your clients' problems. 🤝 The "tech-enabled human touch" will define success. The most effective sellers won't be those who use the most AI tools, but those who best blend AI capabilities with human skills like empathy, judgment, and relationship building. What I'm telling my clients: Don't focus on replacing your sales activities with AI. Instead, use AI to enhance your human capabilities and create more time for meaningful client interactions. How has AI changed how you're approaching work this year? #b2bsales #artificialintelligence #sales2025 #businessdevelopment"

Every prediction post about sales says, “AI will disrupt sales.” And I think it will... But not in the way most people are predicting. The hype is all about sales efficiency: - More emails. - More calls. - More contacts in the pipeline. But the real value of AI isn’t just creating sales efficiency by doing more things faster. The untapped promise of AI for sales is this: sales effectiveness. Not executing more or faster, but executing at a higher quality. AI has the potential to make us more effective—not just efficient. It’s not about AI SDRs decreasing your costs and increasing the scale of outreach. (Even if AI SDRs were ready for prime time, which they’re not). It’s about what developing talent has always been about: helping us be the best, most effective version of ourselves. AI can analyze our own behavior and data patterns in ways we can’t. It can surface insights that help commercial teams focus on what really matters: - Building trust. - Solving problems. - Delivering value. Because sales at its core isn’t about volume—it’s about connection. And the best salespeople don’t win because they’re faster. They win because they’re better listeners, smarter strategists, and more empathetic partners. AI can’t replace human connection. But it can amplify our ability to connect. As we look to the future, the sales teams who thrive won’t be the ones who simply do more. They’ll be the ones who leverage AI to do better.

Most AI tools in GTM are solving the wrong problem. They focus on maximizing outreach volume when the real challenge is something far more fundamental: maintaining meaningful context across hundreds of relationships. Think about your most successful sales relationships. It's never about sending more messages, it's about showing up at exactly the right moments with precisely relevant context. This matches what we've learned building AI systems for relationship intelligence. The magic isn't in automated outreach. It's in three core capabilities: 1️⃣ Tracking subtle signals about changing priorities 2️⃣ Spotting connection patterns across vast networks 3️⃣ Surfacing relevant context exactly when it matters Here's what's transformative: When AI handles these fundamentals, salespeople don't become less authentic. They become more present in the conversations that actually drive value. This is reshaping how we think about AI in sales relationships. The goal isn't to automate connection. It's to create space for real ones to happen systematically. Being authentic necessarily means timing and context matter more than volume. #startups #founders #growth

The AI Revolution Isn't Coming. It's Here. In 2025, we're witnessing AI reshape sales, revenue, and business strategy at an unprecedented speed. Deloitte's Tech Trends 2025 report just dropped, and it's a wake-up call for anyone leading a revenue function. BACKGROUND: For years, we've been talking about AI as the "next big thing." But here's the truth: It's no longer coming. It's here, and it's already transforming how we do business. ACT 1: AI IS BECOMING INVISIBLE Remember when having a website was a competitive advantage? Now, it's table stakes. AI is following the same path. In a few years, it won't be a tool - it'll be the foundation of everything. It will: - Personalize customer interactions in real time - Predict buying behavior before your team does - Automate 80% of what your reps are doing manually today The best sales orgs aren't waiting. They're embedding AI now. ACT 2: NO MORE SILOS Sales and marketing alignment has always been a challenge. But now? It's a survival requirement. AI-powered revenue intelligence is bridging the gap, ensuring that marketing fuels sales and sales informs marketing. High-performing teams are leveraging unified data across both functions to improve conversion rates and shorten sales cycles. If your sales and marketing teams aren't operating as one, you're already behind. ACT 3: AI FOR EXECUTION Forget just analyzing data - AI is now an active player in sales execution. AI-powered assistants are crafting sales emails, responding to prospects, and even booking meetings. Large AI models are shifting to smaller, more specialized AI agents that execute sales tasks autonomously. The next phase? AI agents that handle entire deal cycles - without a human rep. If you're still debating AI adoption, you're playing catch-up. TAKEAWAY: For sales leaders and founders, the message is clear: 1. Embrace AI or lose to those who do 2. Break down revenue silos - AI thrives on alignment 3. Shift from AI for insights to AI for execution The future of sales isn't about working harder. It's about working smarter - with AI as your unfair advantage. Where is your sales org in this AI evolution?

AI & ML are driving big transformations in sales. It's not slowing down in 2025. Keep reading for my top 3 AI predictions. What excites me most is how these tools are helping sales teams streamline their work so they can spend more time actually selling. It’s no longer about adding more tools for the sake of it—it’s about using AI to focus on what matters most. ➡️ Here are 3 ways you can use AI to make a positive impact on your team: 1. Prioritizing the Right Prospects: AI tools can analyze huge data sets to highlight the leads most likely to convert. This isn’t guesswork; it’s using patterns and insights to help sellers focus on opportunities with the highest payoff. This is especially important as we continue to see a trend back to full-cycle AEs. 2. Improving Personalization at Scale: With AI-driven recommendations, email copy and call prep can reflect what’s most relevant to the prospect without the time-consuming manual work. AI can both identify the right timing and best platform to optimize your chance that you capture attention. I'm also super excited to see how teams use AI to do more signal-based selling in 2025. BEWARE: Signals alone are meaningless. It's up to you to connect the dots so our signal-based outreach is RELEVANT TO THEM. Let's leave "Congrats on your Series A" & "I see you're the VP at ABC Company." in 2024. Deal? 3. Driving Smarter Forecasting: By spotting pipeline trends and risks earlier, AI allows leaders to adjust their strategy in real time, instead of scrambling at the end of the quarter. I'm also seeing some cool applications of predictive, AI-led coaching tools (see: Luster, Pod) ➡️ Here is what I am absolutely certain will NOT happen in 2025 - Robots will not (effectively) steal your job. AI isn’t about replacing sellers—it’s about removing the noise so sellers can focus on the conversations that actually drive deals. As I have said from Day 1, when I was working with Regie.ai and they were using ChatGPT before people even knew what it was - AI is best used when it is assistive, not replacive. 📌 How are you using AI to make your sales team more productive in 2025?

Will you make AI your ride or die?  AI won’t replace all salespeople, but sales professionals who partner up with AI tools and tech will leave the rest behind. Yesterday I got to hang out with my friend, the brilliant Alexine Mudawar at the Salesforce World Tour Chicago. It's incredible how tools like Agentforce are reshaping B2B sales and other GTM functions. We heard repeatedly that AI autonomous agents like Agentforce aren't competitors for sellers or service representatives etc., they're collaborators.  We knew AI can take on tasks like scheduling or resolving service issues. Now we're seeing it happen without degrading experience.  One thing I never seem to hear enough about is how companies must invest in upskilling their teams.  Sadly, there are plenty of salespeople who engage at a more transactional level rather than consultative or serving as buyer advocates. These folks must level up in areas like creating a deeper connection, listening, and creating a sense of safety in sales conversations. That's how we differentiate. Business technology’s real power lies in the positive outcomes it creates for the businesses. But businesses must strategically establish those desired outcomes. While tools like Agentforce can play a valuable and even transformative role in the sales process—managing tasks, uncovering insights, and driving efficiencies—they can’t replace the uniquely human elements that differentiate one seller from another. At least not yet. The possibilities are mind blowing. BUT the key lies in striking the right balance between people and technology.  So, what do you need to DO as a sales leader going into 2025, a landscape where AI & Human collaboration will be a competitive edge? Here's the advice I'm giving to my sales leaders: 1. Get Back to the Basics  When was the last time you took a close look at your buyer's journey alongside the sales process? Walk through each touchpoint—where are opportunities for sellers to create differentiating value? Where are the tasks that AI can run effectively?  Y'all can’t assume this stuff-map it out. 2. Invest in Developing "Peopley" Skills  AI can’t replace the human qualities that truly differentiate in sales: empathy, active listening, curiosity, etc. The few sales leaders that I know who have worked through step 1 are now working with me now to build custom sales training on the uniquely human skills sellers need at touch points where differentiation can happen. 3. Set Clear Expectations for AI Be clear about what AI is for and what it’s NOT for. Salespeople are RESOURCEFUL and will look for every possible way to use AI to help in their plight. Define what AI will do well and what requires a human touch.  This will ensure your team uses AI to enhance their performance—not as a crutch. That's a wrap on events for 2024 - and a perfect one to end on. Thank you Salesforce Sales Cloud for introducing us to our new friend Benjamin Fox who was the best host ever. #agentforce

In February 1999, Marc Benioff started Salesforce with a vision to build “A World-Class Internet Company for Sales Force Automation.” 25 years later, there are hundreds of AI companies trying to build Salesforce automations. Zeya Yang, Angela Strange and I present Andreessen Horowitz's thesis on Sales Tech of the Future: We at a16z believe AI will so fundamentally reimagine the system of record and existing sales workflows that no incumbent is safe. Instead of a text-based database, the next sales platform will be multi-modal (text, image, voice, video), containing every customer insight from across the company. As a result, the way sellers and buyers interact will be fundamentally different. Emerging AI-native sales solutions are not simply AI-powered versions of existing categories. Instead, they are enabling new proactive sales motions and evolving to serve multiple use cases. As a result, point solutions in adjacent spaces are overlapping with each other more than ever. With this in mind, we've redefined the best way to bucket sales technology companies. Gone are the days of GTM market maps with 12 sub-categories. Everything rolls into one of: Intelligent Pipeline, Digital Workers, Sales Enablement + Insights, or CRM + Automations. So what does this all mean for the market? Ultimately, we see three important sea changes already taking place: 1/ Sales, marketing and customer success will all blend together. With more comprehensive shared context and insights, GTM teams will be more in sync and better able to collaborate with each other. This will impact both org and compensation structures (e.g. team- or account-based quotas). 2/ GTM strategies will become more fluid. Today, companies typically decide where to focus resources based on target segments and ACV ranges. Tomorrow, companies will be able to reorient their resource allocation around what’s best for the customer — to close this account, what’s the best go-to-market approach? 3/ Per seat pricing --> outcome-based pricing. This has been widely discussed throughout tech and venture, but read our piece for a detailed example with Zendesk. The key question will be which metrics or outcomes are the right ones to serve as the atomic unit for billing. In summary: AI’s potential will not be limited to streamlining the sales activities we have today; instead AI will compel us to reimagine sales processes and workflows completely. The relationship between sellers and buyers will evolve, as will GTM strategies. Read the entire piece below. If you’re building toward this future, we’d love to talk to you. Reach out to zyang at a16z dot com, mandrusko at a16z dot com, and angela at a16z dot com.

𝗜𝗻 𝘁𝗵𝗲 𝗔𝗜 𝗲𝗿𝗮, 𝗱𝗮𝘁𝗮 𝗶𝘀 𝘆𝗼𝘂𝗿 𝗰𝗼𝗺𝗽𝗮𝗻𝘆'𝘀 𝗺𝗼𝘀𝘁 𝗶𝗺𝗽𝗼𝗿𝘁𝗮𝗻𝘁 (𝗮𝗻𝗱 𝗺𝗼𝘀𝘁 𝗲𝘅𝗽𝗲𝗻𝘀𝗶𝘃𝗲) 𝗮𝘀𝘀𝗲𝘁. 𝗧𝗿𝗲𝗮𝘁 𝗶𝘁 𝗮𝘀 𝘀𝘂𝗰𝗵. Data issues prevent revenue teams from adopting AI, which improves pipeline efficiency. The convergence of data from marketing, sales, and customer experience allows AI to streamline information and fast-process everyday tasks, empowering sales teams to focus on customer relations. AI revenue enablement initiatives must be implemented within the framework to show results and quick wins. Thus, leadership must prepare revenue teams for #AI. 𝐂𝐫𝐞𝐚𝐭𝐞 𝐚𝐧 𝐢𝐧𝐭𝐞𝐫𝐢𝐦-𝐥𝐞𝐝 𝐝𝐚𝐭𝐚-𝐫𝐞𝐯𝐞𝐧𝐮𝐞 𝐀𝐈 𝐭𝐚𝐬𝐤𝐟𝐨𝐫𝐜𝐞. Form a marketing, sales, and customer experience team to collaboratively document all siloed and cross-functional data and processes. Ledro et al. (2023) advocated this inclusive strategy as crucial to assisting employees in adjusting to AI systems and data integration. The team will help identify AI-enabled practices, data governance, and future-ready opportunities. For example, start with marketing lead generation, top 75% funnel effectiveness, and customer onboarding. Track results and improve for future use. 𝐂𝐫𝐞𝐚𝐭𝐞 𝐀𝐈 𝐩𝐢𝐥𝐨𝐭𝐬 𝐟𝐨𝐫 𝐩𝐫𝐢𝐦𝐚𝐫𝐲 𝐜𝐨𝐦𝐦𝐞𝐫𝐜𝐢𝐚𝐥 𝐝𝐚𝐭𝐚 𝐩𝐫𝐨𝐝𝐮𝐜𝐭𝐬 𝐚𝐧𝐝 𝐈𝐂𝐏 𝐝𝐢𝐠𝐢𝐭𝐚𝐥 𝐭𝐰𝐢𝐧𝐬. Standardizing data products for crucial business entities is the task. Each data product provides a 360-degree view of the entity based on customer patterns, creating security, governance, and metadata standards for reliable data. Information management should focus on data collection, governance, and using processes and systems (Janssen et al., 2020). For more accurate forecasts and informed business decisions, team specialists can curate and select training set data points. 𝐅𝐢𝐧𝐝 𝐰𝐚𝐲𝐬 𝐀𝐈 𝐜𝐨𝐮𝐥𝐝 𝐬𝐢𝐠𝐧𝐢𝐟𝐢𝐜𝐚𝐧𝐭𝐥𝐲 𝐢𝐦𝐩𝐫𝐨𝐯𝐞 𝐛𝐮𝐬𝐢𝐧𝐞𝐬𝐬 𝐨𝐩𝐞𝐫𝐚𝐭𝐢𝐨𝐧𝐬. Data management and integration should have a shared strategy for AI implementation that supports business goals. Ledro et al. (2023) suggest involving end-users like marketing professionals to create agile, user-friendly, and business-adaptable systems. AI-generated hyper-personalized content can significantly improve outreach and lead generation in high-impact, low-cost, low-risk use cases to support customers and reduce risk. 𝐈𝐧𝐭𝐞𝐫𝐬𝐞𝐜𝐭 𝐀𝐈 𝐰𝐢𝐭𝐡 𝐩𝐫𝐞𝐝𝐢𝐜𝐭𝐢𝐯𝐞 𝐚𝐧𝐚𝐥𝐲𝐭𝐢𝐜𝐬. It can improve sales projections, lead generation, and customer interactions. To improve sales efficiency and productivity, integrate and curate customer-facing data and treat it as your most valuable product to align AI-powered PE with sales and Cx. With the right tools, data, and inputs, AI can crunch numbers instantly and provide valuable sales cycle insight. It can find patterns in this data and identify sales process gaps. The more integrated your sales team is, the better they can target high-value leads.

AI in sales: The key to scaling or a step toward losing connection? AI is transforming the sales landscape, offering new opportunities to enhance efficiency, personalization, and decision-making. But like any powerful tool, it comes with its challenges. Let’s break it down: 𝙏𝙝𝙚 𝙋𝙧𝙤𝙨 𝙤𝙛 𝘼𝙄 𝙞𝙣 𝙎𝙖𝙡𝙚𝙨 𝗘𝗻𝗵𝗮𝗻𝗰𝗲𝗱 𝗘𝗳𝗳𝗶𝗰𝗶𝗲𝗻𝗰𝘆 AI automates repetitive tasks like data entry, follow-ups, and lead scoring, giving sales reps more time to focus on closing deals and building relationships 𝗗𝗮𝘁𝗮-𝗗𝗿𝗶𝘃𝗲𝗻 𝗜𝗻𝘀𝗶𝗴𝗵𝘁𝘀 AI analyzes massive amounts of data to predict buyer behavior, identify trends, and highlight opportunities, enabling smarter, faster decision-making. 𝗣𝗲𝗿𝘀𝗼𝗻𝗮𝗹𝗶𝘇𝗲𝗱 𝗢𝘂𝘁𝗿𝗲𝗮𝗰𝗵 𝗮𝘁 𝗦𝗰𝗮𝗹𝗲 AI tools craft hyper-personalized messages, creating tailored experiences for prospects while saving time. It’s the perfect blend of personalization and productivity. 𝗜𝗺𝗽𝗿𝗼𝘃𝗲𝗱 𝗟𝗲𝗮𝗱 𝗤𝘂𝗮𝗹𝗶𝘁𝘆 AI-powered algorithms help identify high-potential leads, reducing wasted time on unqualified prospects and increasing conversion rates. 𝗥𝗲𝗮𝗹-𝗧𝗶𝗺𝗲 𝗖𝗼𝗮𝗰𝗵𝗶𝗻𝗴 AI tools can provide instant feedback during sales calls, offering tips on tone, timing, and responses to objections—improving performance on the spot. 𝙏𝙝𝙚 𝘾𝙤𝙣𝙨 𝙤𝙛 𝘼𝙄 𝙞𝙣 𝙎𝙖𝙡𝙚𝙨 𝗟𝗮𝗰𝗸 𝗼𝗳 𝗛𝘂𝗺𝗮𝗻 𝗘𝗺𝗼𝘁𝗶𝗼𝗻 AI can’t replicate the empathy, intuition, or creativity of human interactions, which are often the key to building trust and closing complex deals. 𝗢𝘃𝗲𝗿-𝗥𝗲𝗹𝗶𝗮𝗻𝗰𝗲 𝗼𝗻 𝗧𝗲𝗰𝗵𝗻𝗼𝗹𝗼𝗴𝘆 Relying too heavily on AI can lead to a lack of critical thinking and human judgment, especially when dealing with nuanced or unpredictable buyer behavior. 𝗗𝗮𝘁𝗮 𝗣𝗿𝗶𝘃𝗮𝗰𝘆 𝗖𝗼𝗻𝗰𝗲𝗿𝗻𝘀 Using AI for sales often involves handling vast amounts of customer data, which can raise concerns about security, compliance, and trust. 𝗖𝗼𝘀𝘁 𝗮𝗻𝗱 𝗖𝗼𝗺𝗽𝗹𝗲𝘅𝗶𝘁𝘆 Implementing AI tools can be expensive and requires time to integrate, train teams, and adapt processes, which may be challenging for smaller businesses. 𝗥𝗶𝘀𝗸 𝗼𝗳 𝗟𝗼𝘀𝗶𝗻𝗴 𝘁𝗵𝗲 𝗛𝘂𝗺𝗮𝗻 𝗧𝗼𝘂𝗰𝗵 If not used carefully, over-automation can make interactions feel impersonal, potentially alienating prospects who value a human connection. AI in sales is a powerful tool that can revolutionize processes, drive efficiency, and deliver insights. But it’s not a magic wand. The key is balance. Use AI to empower your team, not replace them, and always keep the human element at the heart of your sales strategy. --- Follow Michael Cleary 🏳️🌈 for more tips like this. ♻️ Share with someone who would like to learn more about AI in sales #sales #ai #marketing