Artificial Intelligence in Sales

I wasted $47k testing 200+ AI sales tools so you don't have to. Here's the exact stack that took us to $6M ARR: 1,300+ AI sales tools exist in 2025. Most are unnecessary. Here's what you actually need: 1/ Accurate B2B data Data quality determines campaign performance. Everything downstream depends on this foundation. Your sourcing options: - Standard databases: LinkedIn Sales Navigator, Ocean.io, Apollo - Niche targeting: Openmart for local business focus - Custom scraping: Apify, Instant Data Scraper for specific requirements - Intent signals: Clay, Common Room - prospects showing buying behavior - AI agents: Claygent, Relevance AI, Exa, Linkup - automated prospect discovery 2/ Reliable data enrichment Valid contact information is non-negotiable. You need verified emails and phone numbers. Two approaches: - Point solutions: Prospeo.io, Wiza, LeadMagic - specialized tools - Waterfall platforms: FullEnrich, Clay - multiple data sources in sequence 3/ Engagement platforms - Email solutions: Instantly.ai - LinkedIn outreach: Expandi.io, Valley - Multi-channel: lemlist - email + LinkedIn 4/ Deal execution When prospecting generates consistent pipeline, you need a system to close those deals: - CRM: Attio, Breakcold for deal tracking - Intelligence: Attention, Momentum.io - call recording, CRM enrichment, next-step recommendations The strategic advantage comes from integration, not tool quantity. What's your latest stack addition? Want weekly breakdowns of the tools that actually work? Join 10,000+ reading getting our AI sales newsletter.

AI is transforming productivity across industries but sales is still a frontier waiting to be unlocked. Bain & Company’s research shows that while generative and agentic AI are already freeing up hours of work in marketing and operations, adoption in sales is lagging behind. That’s surprising, because sales is one of the most time-intensive, high-impact functions and even small conversion gains can deliver outsized business results. For CMOs, CROs, and GTM leaders, the opportunity is clear: use AI to give sellers back time, improve decision-making, and boost win rates. And here’s what often gets overlooked: buyer-group expansion and engagement are two of the most powerful drivers of those win rates. The more effectively teams can identify, engage, and influence the full buying committee- the CIO, the CFO, the head of engineering, security, procurement- the greater the likelihood of advancing and winning deals. AI can now do this at a scale and speed that simply wasn’t possible before. AI in sales isn’t about replacing people, it’s about equipping them with better tools. The organisations that act early will be the ones to capture the biggest gains. At Thoughtworks, we’ve been actively working toward this vision. Our award-winning PerformanceAI agent removes the need for sales and marketing teams to click through endless dashboards and instead delivers insights in plain English, on demand. Less time on analysis and more time on insight and action. We’re also reducing manual work through automation, from data entry to intelligence orchestration. We’ve invested in tooling that mines sellers’ conversations across voice, email, and calendar to extract key signals, map the buying group, and match insights to the right accounts and opportunities. And in the AI era, adoption in sales has become much simpler. The technology runs quietly in the background rather than becoming another system sellers need to feed. When human input is needed, we’re moving toward a voice-first experience so no navigating complex CRM interfaces, and sellers can make updates on the go right after a client meeting. How is your team approaching AI in sales today? Let me know in the comments.

AI in Sales—Augment, Don’t Replace! 🚀 AI won’t replace salespeople. But salespeople who use AI strategically will outperform those who don’t. I’ve been in sales since Girl Scout cookies were 50 cents a box, and I’ve seen the game change. But nothing has been more transformative than AI. According to LinkedIn for Sales Connect monthly newsletter, AI can reclaim 29% of a rep’s time by automating admin tasks, data collection, and customer insights. The key? Using AI to amplify human strengths, not replace them. Yet, there’s a challenge: 60% of sales teams report being overwhelmed by the sheer volume of administrative work.AI can help offload up to 10 hours of non-selling tasks per week, effectively doubling selling time from 10 to 20 hours. That’s the kind of efficiency shift that drives real revenue. Here’s how to strategically automate without losing the personal touch: ✅ AI-Powered CRM: Let AI handle lead scoring, email follow-ups, and data entry so reps can focus on relationship-building. ✅ Smart Workflows: Use AI tools to automate routine tasks, freeing up time for strategic selling. ✅ AI as a Guide: Train your team to use AI-generated insights as a tool, not a crutch. Judgment and creativity still win deals! 📌 Actionable Step: Identify 3 repetitive tasks in your sales process (CRM updates, lead research, follow-ups) and integrate AI-powered automation. Measure the time saved and reallocate it to higher-value selling activities. AI isn’t the future of sales—it’s happening NOW. How is your team leveraging it? Let’s talk in the comments! #AIinSales #SalesLeadership   #WomenInSales #EnterpriseSales #1MillionWomenby2030 

Most sales teams fail with AI. They pick the wrong tool for the job. AI mastery is about matching the model to the moment. Let’s break it down. 1. Research AI and Reasoning AI are not the same. Top sales teams know the difference. They use each for what it does best. → Research AI is for facts. It finds the data you need, fast. Funding rounds. Hiring spikes. Leadership changes. New partnerships. Competitor moves. It delivers verified information. No guesswork. No wasted time. → Reasoning AI is for depth. It helps you understand context. Builds your ICP. Crafts personalized messages. Handles objections. Shapes your narrative and strategy. This is where insight and creativity win. 2. Mixing both is how you win more deals. Here’s the real playbook: • Use research-focused AI to gather signals. • Use reasoning-focused AI to turn those signals into messages that land. • Combine both to create relevance at scale, without sounding robotic. Examples: • Research AI finds a company’s new funding round. • Reasoning AI helps you write a message that connects that news to your prospect’s pain. • Research AI tracks competitor moves. • Reasoning AI helps you position your offer as the better choice. 3. The best teams orchestrate, not just automate. They map every step of their outbound. They pick the right AI for each task. They move faster, stay accurate, and book more meetings. Average teams stick to one model and stall out. Winning teams build a stack that fits every step. Mastering AI for sales is not about picking sides. It’s about building the perfect workflow for every job.

AI didn’t change the game. It just made weak sales systems visible. Top performers didn’t add more activity. They built systems that think with them. I run my advisory and sales work with 𝗳𝗶𝘃𝗲 𝗔𝗜 𝘁𝗼𝗼𝗹𝘀 that let me operate like a senior deal team, without hiring one. Here’s the stack I actually trust 👇 🔎 𝗣𝗲𝗿𝗽𝗹𝗲𝘅𝗶𝘁𝘆 (https://www.perplexity.ai/) ↳ My pre-call weapon ↳ Rapid market, company, and competitor intelligence ↳ Gives me context before the first “nice to meet you” If you walk into calls uninformed, you’re already behind. 🧠 𝗦𝘂𝗯𝘀𝘁𝗿𝗮𝘁𝗮 (https://www.substrata.me) ↳ Reads power dynamics in meetings, emails and in-between ↳ Flags hesitation, dominance shifts, and hidden resistance ↳ Helps me respond effectively and close deals faster Deals aren’t lost on price. They’re lost on misread nuances. 📊 𝗖𝗼𝗱𝗮 (https://coda.io/) ↳ My sales and advisory command center ↳ Pipelines, follow-ups, client notes, next moves ↳ Everything structured, nothing forgotten If your system lives in your head, it’s already broken. ✍️ 𝗖𝗵𝗮𝘁𝗚𝗣𝗧 (www.chatgpt.com) ↳ Pressure-tests my emails and proposals ↳ Reframes objections before I hit send ↳ Turns weak wording into confident positioning Polite doesn’t close. Clarity does. 🤖 𝗔𝗽𝗽𝘆.𝗮𝗶 (https://appy.ai/) ↳ Turns my frameworks into AI agents ↳ Lets prospects self-qualify before we talk ↳ Monetizes judgment, not hours If you still sell only time, you’re capping your upside. These tools don’t make you average faster. They 𝗮𝗺𝗽𝗹𝗶𝗳𝘆 𝘄𝗵𝗼𝗲𝘃𝗲𝗿 𝘆𝗼𝘂 𝗮𝗹𝗿𝗲𝗮𝗱𝘆 𝗮𝗿𝗲. In sales, that means one thing: The prepared win more. The strategic win bigger. AI won’t replace sales reps. But sales reps who use AI will replace the rest. Which part of your sales process still relies too much on you personally?

AI is quietly rewiring sales enablement from the inside out. Not replacing it, but elevating it. As automation takes care of the repetitive, enablers have an opportunity to focus more on what actually moves the needle: • strategy, • measurament, • stakeholder mgmt, • precise diagnosing, • cross-functional alignment • scalable programme design. Over the past year, I’ve tested hundreds of AI tools – experimenting boldly within organisational contexts – and spoken with many enablement leaders and experts doing the same. That experience taught me to separate the shiny objects from the use cases that truly move performance in a sales organisation. When applied thoughtfully, AI doesn’t just add efficiency. It becomes the infrastructure that powers enablement to drive massive impact – reshaping how we design, deliver, and scale our work. --- I’ve previously shared in-depth guides on areas like AI sales roleplay, AI co-pilots, and AI-powered digital sales rooms. But this time, it wanted to zoom out. In partnership with GTM Buddy – a company pioneering the path toward autonomous revenue enablement – I’ve created my latest guide mapping 26 real AI use cases across five categories: ⚙️ Training & onboarding 🧭 Coaching & readiness 📚 Content, knowledge, & buyer enablement 📊 Insights & decision intelligence 🧩 Operational efficiency Each one shows how AI helps tackle core challenges across sales execution, sales operations, and enablement operations. --- 💬 What’s one AI use case that has already made a tangible impact in your GTM organisation? If you’d like the high-res one-pager and full guide, drop “AI in enablement” below and I’ll share it with you. ✌️ #business #sales #salesenablement #ai

AI in Sales: Superpower or Crutch? A recent study hit me like a revelation: AI tools are making A-players better, having zero impact on B-players, and actually making C-players worse. This perfectly explains what I'm seeing across GTM teams and in my inbox. We all want every rep to perform like our top performers, but AI is creating the opposite effect—our B and C players are becoming more robotic, not more human. The scary part? Leadership can't see it, but customers absolutely can. We've rushed to arm reps with AI tools without focusing on the real leverage point: their managers. The reality for sales leaders today: Expected to staff, lead, train, and motivate at unprecedented scales No time to prepare for meaningful one-on-ones Struggling to provide real-time, actionable feedback What if we flipped the script? Instead of trying to make reps superhuman, what if we made managers superhuman? Imagine giving leaders real-time dashboards that surface each rep's best calls, key insights, and improvement opportunities—automatically. The teams piloting this approach with us are seeing dramatic results. Managers are finally able to deliver personalized, timely coaching that actually sticks. Reps are improving because they're getting human guidance enhanced by AI insights, not replaced by them. The paradigm shift isn't about better tools for reps. It's about empowering the humans who develop them. #SalesLeadership #AIinSales #SalesCoaching #GTM

This has been called the best show people have attended on AI in sales. How is AI rewriting the rules of modern selling? It’s not some far-off future. It’s here. It’s now. And it’s not just about automating tasks. It’s about amplifying YOU—your message, your reach, your effectiveness, and your ability to connect deeply with the right people at the right time. Tom Burton and I mix it up on the latest Mastering Modern Selling and talk about how to master modern selling in an AI world—while staying radically human. Every seller has a sticking point. Maybe it’s prospecting. Maybe it’s follow-up. Maybe your forecasts are based on wishful thinking instead of actual science. For me, AI has become my go-to partner in dissecting every stage of the sales cycle and finding new ways to improve probability of success. Because at the end of the day, that’s what sales is—a game of odds. Whether it’s the start or end of your fiscal year, AI helps you analyze your book of business. What’s your addressable market? Where are the gaps? What patterns does your data reveal? What should you focus on next? I’ve literally prompted AI to review my Power BI dashboards and generate a strategic plan for each workload. I love prospecting. I’m one of those sickos. But now, with AI, I can write tailored outreach to 600 leads in minutes. I can scan LinkedIn profiles, customer websites, and news alerts to craft 3-bullet-point value messages that speak directly to someone’s mission—and AI helps me do it 10X faster and smarter. Ever get ghosted after a great demo? Me too. Now I ask AI: “Write me a short message in my tone that derisks their fears and reopens the door.” It gives me empathetic, insight-driven language that gets responses and restarts the conversation. In real-time, I use AI to generate talking points while I’m in the room with a CEO. My brain might come up with 3–5 value props. AI gives me 6–10. And sometimes, bullet #7 is the one that gets the head nod. AI can draft the message, but it can't deliver it with your heart. AI can highlight insights, but it can't form relationships. AI can help you scale, but it can't replace trust. Every message, every call, every touchpoint still needs your humanity—your voice, your authenticity, your understanding of the person on the other end. Because you don’t sell to accounts. You sell to people. Last year, I asked my team to give me their toughest accounts. 150 of them. Using AI, I crafted brief, bullet-point-heavy, custom outreach to 50+ contacts per account. We opened over 100 accounts. Deals that had gone untouched for years. Why? Because AI helped me be fast, focused, and bold. But it was me—a real human—who built the trust once the conversation started. How are you using AI to improve your sales process? #AIforSales #ModernSelling #SalesLeadership #SocialSelling #FutureOfWork #SalesStrategy #Copilot #SalesEnablement #DigitalTransformation

𝐀𝐈 𝐈𝐬 𝐑𝐞𝐝𝐞𝐟𝐢𝐧𝐢𝐧𝐠 𝐖𝐡𝐚𝐭 ‘𝐏𝐫𝐞𝐩𝐚𝐫𝐚𝐭𝐢𝐨𝐧’ 𝐌𝐞𝐚𝐧𝐬 𝐢𝐧 𝐒𝐚𝐥𝐞𝐬. 𝐀𝐫𝐞 𝐘𝐨𝐮 𝐑𝐞𝐚𝐝𝐲? When I first rolled into sales research looked like this: company website, annual reports, 10-K filings, AM Best data and it took hours of digging just to understand a potential buyer. Then you’d build an account plan: define the ICP, pinpoint their problems, tailor outreach. All so your message wasn't generic, 𝘪𝘵 𝘴𝘱𝘰𝘬𝘦 𝘵𝘰 𝘵𝘩𝘦𝘮. But that prep time pulled sales teams away from what they should’ve been doing: 𝐬𝐞𝐥𝐥𝐢𝐧𝐠. A client once said, “𝐊𝐞𝐫𝐫𝐲, 𝐰𝐞 𝐣𝐮𝐬𝐭 𝐧𝐞𝐞𝐝 𝐦𝐨𝐫𝐞 𝐦𝐞𝐞𝐭𝐢𝐧𝐠𝐬.” My reply: “𝐍𝐨, 𝐲𝐨𝐮 𝐧𝐞𝐞𝐝 𝐦𝐨𝐫𝐞 𝐨𝐟 𝐭𝐡𝐞 𝐫𝐢𝐠𝐡𝐭 𝐦𝐞𝐞𝐭𝐢𝐧𝐠𝐬.” After decades in B2B solution selling (especially in insurance/insurtech), I've learned quantity is meaningless without relevance. A C-level buyer told me: “𝐓𝐡𝐞𝐲 𝐮𝐬𝐞 𝐭𝐡𝐞 𝐬𝐜𝐫𝐢𝐩𝐭. 𝐀𝐬𝐤 𝐦𝐞 𝐰𝐡𝐚𝐭 𝐦𝐲 𝐩𝐫𝐨𝐛𝐥𝐞𝐦𝐬 𝐚𝐫𝐞, 𝐭𝐡𝐞𝐧 𝐬𝐞𝐥𝐥 𝐭𝐡𝐞 𝐭𝐞𝐜𝐡𝐧𝐨𝐥𝐨𝐠𝐲, 𝐬𝐞𝐫𝐯𝐢𝐜𝐞 (‘𝐰𝐞 𝐡𝐚𝐯𝐞 𝐢𝐧𝐝𝐮𝐬𝐭𝐫𝐲 𝐞𝐱𝐩𝐞𝐫𝐭𝐬’), 𝐚𝐧𝐝 𝐟𝐞𝐚𝐭𝐮𝐫𝐞𝐬 𝐭𝐡𝐚𝐭 𝐩𝐮𝐫𝐩𝐨𝐫𝐭 𝐭𝐨 𝐚𝐧𝐬𝐰𝐞𝐫 𝐚𝐥𝐥 𝐦𝐲 𝐩𝐫𝐨𝐛𝐥𝐞𝐦𝐬. 𝐓𝐡𝐢𝐬 𝐢𝐬 𝐜𝐚𝐧𝐧𝐞𝐝 𝐚𝐧𝐝 𝐢𝐭’𝐬 𝐛𝐮𝐥𝐥𝐬𝐡𝐢𝐭.” Ouch! But true. Show up with the same playbook, you’ll get ignored. That’s where #AI enters the picture. According to Gartner, the role of AI in sales is rapidly shifting: 🔵 By 2027, 95% 𝐨𝐟 𝐬𝐞𝐥𝐥𝐞𝐫 𝐫𝐞𝐬𝐞𝐚𝐫𝐜𝐡 𝐰𝐨𝐫𝐤𝐟𝐥𝐨𝐰𝐬 𝐰𝐢𝐥𝐥 𝐛𝐞𝐠𝐢𝐧 𝐰𝐢𝐭𝐡 𝐀𝐈, up from less than 20% in 2024. 🔵 Gartner reports that AI enables the creation of “atomic insights” — distilled, actionable buyer-centric intelligence that sellers can convert into hyper-targeted value messaging. 𝐈𝐧 𝐬𝐡𝐨𝐫𝐭: The sales research and outreach you used to do in hours or days, can now be done in minutes. You can arrive at the conversation already informed, relevant, and impactful. But only if you embrace 𝘈𝘐 𝘢𝘯𝘥 𝘳𝘦𝘵𝘢𝘪𝘯 𝘵𝘩𝘦 𝘩𝘶𝘮𝘢𝘯 𝘪𝘯𝘴𝘪𝘨𝘩𝘵. So if you’re a B2B solution provider, here’s the call to action: 𝐒𝐭𝐨𝐩 𝐚𝐬𝐤𝐢𝐧𝐠 𝐟𝐨𝐫 𝐦𝐨𝐫𝐞 𝐦𝐞𝐞𝐭𝐢𝐧𝐠𝐬. 𝐒𝐭𝐚𝐫𝐭 𝐠𝐨𝐢𝐧𝐠 𝐚𝐟𝐭𝐞𝐫 𝐭𝐡𝐞 𝐫𝐢𝐠𝐡𝐭 𝐦𝐞𝐞𝐭𝐢𝐧𝐠𝐬. 𝐒𝐭𝐨𝐩 𝐬𝐞𝐧𝐝𝐢𝐧𝐠 𝐭𝐡𝐞 𝐬𝐚𝐦𝐞 𝐬𝐜𝐫𝐢𝐩𝐭𝐞𝐝 𝐩𝐢𝐭𝐜𝐡. 𝐒𝐭𝐚𝐫𝐭 𝐝𝐞𝐥𝐢𝐯𝐞𝐫𝐢𝐧𝐠 𝐩𝐞𝐫𝐬𝐨𝐧𝐚𝐥𝐢𝐳𝐞𝐝 𝐢𝐧𝐬𝐢𝐠𝐡𝐭. And if your sales process isn’t using AI today to support your team’s preparation, your personalization and your thought-leadership outreach, you will be overlooked. Because your buyer doesn’t want your pitch. They want your relevance. They want your insight. They want you to show up like you understand their business, their pressures, their world — before you ask for the meeting. 🔜 Next week I’ll dive into how AI is reshaping that prep work and why it’s no longer optional if you want to win in today’s buyer-driven world. #SalesLeadership #B2BSales #SalesStrategy #AIinSales #GoToMarket #SalesEnablement #ThoughtLeadership #InsurTech