Strategies for Selling to Enterprises

After talking with many high-growth B2B companies, here is the modern B2B marketing playbook. Paid Advertising > target intent, creative tests at scale, data models for attribution (indirect/direct ROAS) + elasticity. SEO/AEO > target transactional keywords for Google’s traditional search engine, a broad set of prompts for AI engines, and a big focus on citations. Affiliate is increasingly being folded in here to help broaden citations to improve visibility in AI engines. Social > primary focus is growth through the founder’s social + select employees. Employees with an existing following are a bonus. Social strategy for branded channels is more personality-driven; short-form video is critical. Creators > is a key part of a modern distribution strategy. Mostly done via existing platforms like Passionfroot. Some companies create bespoke programs, mixing incentives through tiers based on audience size. Lifecycle > very AI-led. Data quality is a must. Data enrichment is a big part of the role. Establish fit/intent models. AI-SDR for website demand capture. AI prospecting for incoming demand and expansion. AI-outbound for net new ARR (quite saturated). Product marketing > positioning has never been more important. Needs to be memorable and consistent across channels. Incredibly close partnership with product. Turn launches into a distribution engine. Be great at content; ensure product story is visible across every channel. Creative > visual identity that rises above the AI slopification of everything. Creative engine that allows the team to focus on tier 1 work and others to self-serve everything else. Brand > build and capture attention. Inspired by modern B2C playbooks vs. traditional B2B playbooks. Bring product to life in creative ways. Find ways to create in-person moments of magic via communities, in-person events, meetups, etc. Obsess over talent; have super-ICs who can do more with AI, and a rigorous operating model that runs in sprints and is outcome-focused.

AI Agent Studio Inspiration Series Next up: transforming B2B commerce with an end-to-end SmartQuote Navigator agent, built using Oracle Fusion AI Agent Studio. Always Built in, Not Bolted on! Today’s B2B buyers expect a fast, intuitive, self-service experience yet complex product configurations, pricing rules, and manual approvals often slow the process to a crawl. This agent changes that. What it does: - Smart Config Validation Buyers submit custom product needs, and the agent instantly validates configuration feasibility. - Real-Time Pricing + Margin Checks Instantly retrieves pricing via CPQ and validates margin thresholds. - Automated Quote Generation Delivers a CPQ-backed quote within seconds with no human intervention required. - AI-Driven Approvals Compliant quotes auto-approve; edge cases are escalated to managers as needed. - Order Conversion + Sync Seamlessly converts approved quotes into sales orders in Fusion, with real-time updates sent to the buyer’s dashboard. This is a real AI Agent working across Oracle Commerce, CPQ, and Fusion Sales delivering a fully autonomous quote-to-order experience. Built by these Hackathon Champions!: Ramesh Vangala Yashwanth Reddy Vikas Jain This is how AI can elevate customer experience while removing manual bottlenecks from the sales cycle. #OracleAI #FusionAI #CX #AIStudio #AIAgentStudio #SmartQuote #CPQ #QuoteToOrder #GenAI #AIInspiration #CustomerExperience

Something interesting is happening that some leaders are not talking about publicly. While companies make headlines about downsizing in their home countries many of these same organizations are quietly establishing significant operations in Manila. JPMorgan takes over 2nd Uptown BGC tower which doubled Manila workforce to 20,000. Amazon also inaugurated its first operations services office in Cebu City which created hundreds of employment opportunities. According to Business World Online, office sector net absorption of 281,000 sq.m. in H1 2024 is driven by return-to-office mandates and office expansion. The numbers actually do not lie. Indeed, major tech companies, financial services firms, and consulting organizations are building substantial teams in the Philippines while maintaining different narratives in their public communications. This goes beyond cost-cutting anymore. It speaks about competitive advantage. The real reasons behind this quiet expansion reveal strategic thinking. The Philippines offers something unique. There is a mature business ecosystem with Western-compatible work culture, timezone flexibility for global operations, and a talent pool that scales with quality. Companies are not just finding cheaper resources. They are finding better operational models. The Philippines has become the preferred destination for serious business growth because it solves multiple problems simultaneously. English proficiency eliminates communication friction. Cultural compatibility reduces management overhead. Government support creates favorable business conditions. And the talent infrastructure can absorb rapid scaling without quality degradation. But what people often most miss is that companies are keeping this expansion quiet because it represents a competitive approach. While competitors struggle with domestic hiring challenges and inflated salary expectations, these organizations are building efficient and high-performing teams that operate seamlessly across global markets. Companies that figured this out early are scaling faster, operating more efficiently, and building sustainable competitive advantages while others debate the future of work. The Philippines is not just another offshore destination. It has become the operational backbone for companies that understand global talent strategy.

The CFO never looked up from his phone. Until I changed two words in my pitch. Budget approved in 120 seconds. My mentor didn't even open my deck. Three months of customer insights. All he wanted was one number. "But our satisfaction scores are incredible-" "Justin, let me tell you a story." He pulled up an old presentation: "See this chart? Best customer feedback in company history. Team got cut the next quarter." I sat there stunned. "Now watch this." He opened another deck. Just three slides: - $2.1M in prevented churn - $800K in accelerated deals - $1.2M in expansion revenue "Same exact work. Different story." Then he taught me the million-dollar translation: Instead of: "Customers love our new feature!" Say: "Usage drove $300K in upgrades." Instead of: "Satisfaction is at an all-time high!" Say: "We prevented $1.2M in churn." Instead of: "Customers are referring more!" Say: "Referrals accelerated $500K in pipeline." The work didn't change. The words did. When I pitched Q3 results. The CFO stopped checking his phone. The CEO leaned forward. Budget discussions lasted 2 minutes. Because I wasn't selling happiness. I was showing money. Your metrics tell a story. Make sure it's one worth funding.

Enterprise Sales is a different beast. You’re thinking about it all wrong. The difference between a $50K and a $500K deal is NOT fancy Negotiation skills or Disco tactics. You need to learn BUSINESS ACUMEN like a VP. I’ve worked 100s of $6-7 fig deals. Here are the 5 hardest lessons I wish I knew before going upmarket: 1. AEs Don’t Close Deals—They Rally The Troops Lone wolves don't close 7-fig deals. Enterprise AEs are like film directors—connecting champions, execs, and influencers across both companies, so the deal feels inevitable. It’s never about one hero; it's about orchestrating every player: CEO who shares the vision, VP Product who tackles tough questions, Exec Sponsor who secures buy-in. High-stakes deals demand the best your company can offer. Great AEs know how to get it. 2. Complex Sales = World Class Project Management In enterprise deals, you’re more PM than a seller. Big deals die in the details: missed tasks, unaligned stakeholders, and endless email threads. New people jump in mid-cycle, each needing context. Your job: bring order to chaos. Protect momentum, keep everyone aligned, and ensure nothing slips. Top AEs co-create timelines, organize materials in Deal Rooms and tailor every detail. 3. AEs Master Buying (not Selling) My biggest breakthroughs came not from sales training but from buying software and interviewing CXOs. That’s when I realized: If you understand how budgets, approvals, and internal priorities work, you don't need sales tactics. Empathy becomes your superpower because you know what each stakeholder needs (financially and politically) to say YES. Want to excel at enterprise? Study how companies justify ROI, CFOs think, and champions navigate approvals. 4. There’s No Sales Process—Only a Buying Process Your buyer doesn’t care if you’ve hit Stage 3 in your CRM. They care about their own maze of priorities, budgets, and internal politics. Top AEs ‘dance’ around the sales stages. They choreograph moves based on what the deal needs next—like looping in a board member to champion them behind the scenes or going after end-users to outshine a competitor who started at the top. 5. AEs Think Transformation, Not Pain Points Execs won’t write $1M checks to fix a clunky spreadsheet workflow. They need to see a solution driving company-wide impact—like a strategic pivot or entering a new market. If you’re only uncovering small headaches, expect a small deal. But connect those symptoms to a transformation—and the CFO listens. —— Enterprise sellers think and act like business leaders. Not salespeople who want to close deals. Yes, they know the fancy sales tactics. But that's not the point… When buyers see you think like them. When you work a deal like it’s their internal project. You unlock trust that deserves 6-7fig budgets. P.S. We built Aligned to help manage the complexity of Enterprise Sales. A 100% FREE Deal Room used by 40K sellers. Try it https://lnkd.in/dwX_Zizk

My team and I once tried to hand-wave our way past Jeff Bezos with a large headcount request. He asked one question, was disappointed by the answer, and dug deeper. After a weak answer to question two, it was game over. Jeff declared that he trusted NONE of our proposal and sent us back, telling us, "Break down your requests to no more than 2 or 3 heads, tops, per line item. Then explain exactly what these small buckets will do." Once we did this, he went through the request line by line, telling us what we could and could not have. Overall, it was probably the most brutal experience I had with him in my 15 years at Amazon. While some people will read this and feel it was micromanagement, he was entirely right. We thought we had a blank check, so we made a big, broad funding request. We learned very quickly that while Jeff supported our mission, he expected us to spend "his" money carefully. Most people think executive influence happens in the room, by talking slick or having the right alliances. While communication and connections are hugely important, most of your influence is built before the meeting starts. Getting executive buy-in comes from understanding your executives, anticipating their concerns, and structuring your message around what they value. Here are two quick specifics: 1. Preparation If you walk into a key stakeholder meeting without preparing, like I did, you’ve already lost. The first step in preparation is clarity: What are you trying to achieve, by when, and why now? Then, define exactly what you’re asking for: a decision, resources, or permission to move forward. Finally, decode the humans. What does each stakeholder care about? What do they fear? How do they make decisions? Build your case in their language and plan your approach with intention. 2. Focus on Facts Executives are moved by accurate, outcome-driven facts. Shortly after this disastrous headcount audit, I was asked to lead the global expansion of the Kindle Appstore. This required taking 55 engineers away from other executive leaders to staff our rush effort. Our team won support by anchoring on three facts: (1) Kindle’s success in the U.S. was undeniable (2) The holiday deadline couldn’t move (3) Leadership had already approved a one-year draft to make it happen. Those facts aligned perfectly with what executives valued most: growth, timing, and company priority. If you master these skills, you’ll earn trust and support from senior leaders. In large organizations, this translates to success in your projects and success in your career. I've written a much more in depth Newsletter that covers these skills and more: https://lnkd.in/geEBPazP When have you either fallen into hand-waving or had to call your team on it?

Empowering Artisans Through Sustainable Raw Materials: A Revolutionary Initiative by Craft Village Transforming Natural Waste into Livelihood Opportunities Imagine a world where raw materials for traditional crafts are available at no cost—how significantly would this impact artisans? Craft Village, in its commitment to fostering self-reliance under the Aatmanirbhar Bharat initiative, has pioneered an innovative approach to sustainable craft production. By utilizing natural grasses such as lotus and water hyacinth, this initiative not only empowers artisans but also addresses critical environmental challenges. Harnessing Abundant Natural Resources for Sustainable Craftsmanship India’s lakes and water bodies are increasingly clogged with invasive vegetation like water hyacinth, disrupting ecosystems and affecting freshwater sources. Governments spend crores annually on mechanical cleaning methods, which leave a considerable carbon footprint and generate excessive bio-waste. Recognizing this challenge, Craft Village introduced a sustainable model that repurposes these abundant natural resources into valuable craft materials, thereby reducing environmental damage while revitalizing lost artisanal knowledge. Reviving Traditional Knowledge and Strengthening Artisan Economies Historically, India’s agrarian communities thrived on a circular economy where farm residues were transformed into craft products. This sustainable approach ensured economic stability, facilitated trade through barter systems, and nurtured craftsmanship as a vital part of family enterprises. Craft Village’s intervention is rekindling this tradition by equipping artisans with the knowledge to convert wild grasses and agricultural residues into high-value craft products. Economic and Environmental Impact Raw material costs typically account for 50-60% of an artisan’s total production expenses. By providing access to free natural resources, Craft Village significantly enhances artisans’ earning potential, reduces production costs, and promotes environmentally sustainable practices. This initiative also presents a viable alternative to plastic-based materials, fostering a cleaner and more sustainable future. A Call for Sustainable Policy and Industry Adoption This initiative serves as a model for policymakers, industry leaders, and sustainability advocates to explore innovative solutions that integrate environmental responsibility with economic empowerment. Supporting such initiatives can help scale traditional crafts, preserve heritage skills, and reduce dependency on industrially manufactured materials that contribute to pollution. Craft Village’s interventions underscore the need to rethink raw material accessibility, ensuring that artisans not only sustain their livelihoods but also contribute to a greener planet. By leveraging nature’s abundance, we can create an ecosystem where sustainability and economic growth go hand in hand.

𝐒𝐭𝐨𝐩 𝐛𝐮𝐢𝐥𝐝𝐢𝐧𝐠 𝐦𝐨𝐫𝐞 𝐀𝐠𝐞𝐧𝐭𝐬. 𝐁𝐮𝐢𝐥𝐝 “𝐇𝐞𝐫𝐨𝐞𝐬.” In my work helping organizations navigate the shift to Agentic AI, I see the reality on the ground: most enterprises are drowning in a sea of disconnected agentic experiments. They are launching dozens of initiatives that look good in a sandbox, but never actually scale to produce value. The mistake? They are building agents the way they build apps—prioritizing quantity and features over deep business impact. That’s why I found Box’s strategy so refreshing. They take a different approach. They filter everything down to find the “Hero Agents”—the elite few that can actually move a whole function. As you can see in the graphic, the path to becoming a "Hero" isn't a straight line. It's a funnel. They start broad, and then they get ruthless: 1️⃣. Ideation (Go Broad): Lots of experiments. Hackathons. Demo sandboxes. But the goal isn’t volume. The goal is to identify the few high-impact bets worth making. 2️⃣. Pilot (The Stress Test): They build an MVP, ship to a small group, and measure. One example hit hard: Their prospecting agent dropped message creation time from 60 minutes to ~5. That’s not just “productivity.” That’s a different operating model. 3️⃣. Rollout & Scale (The Trust Shift): This is where most fail. It’s the shift from “it works” to “we trust it.” Permissions, integrations, and governance. But the biggest lesson here is a line that every leader should memorize: Access is not impact. Adoption is a management job. You have to redesign the workflow so the agent becomes the default, not just an option. It’s a fascinating look at the rigors of execution. You can read the full breakdown of their phases here: https://lnkd.in/ejrE-ZhU 👉 A question for you: If you had to kill 80% of your current AI projects tomorrow to focus on the "Heroes," which 20% would you keep? #BoxAmbassador #AgenticAI #AIAgents #ArtificialIntelligence #FutureOfWork #DigitalTransformation #EnterpriseAI

For my first 16 years in tech sales, I averaged 240K/year W2 income. In my last 4 years, I averaged 720K/year. In order to triple my income, I had to change my sales approach entirely. Here's what I changed: I started using a new approach that I now call Yo-yo selling: 🪀 Yo-yo selling emphasizes starting at the executive level, conducting thorough discovery within the organization, and then returning to the executive with a tailored business case. Like holding a yo-yo, you are constantly in communication with the Executive Sponsor and updating them as you collect information and conduct deep discovery lower down in their organization. You are literally going up and down the organization, but always taking everything back to the Executive Sponsor to surface your findings along the way. Here's a breakdown of the framework: 🎯 𝐈𝐚𝐧 𝐊𝐨𝐧𝐢𝐚𝐤’𝐬 “𝐘𝐨-𝐘𝐨 𝐒𝐞𝐥𝐥𝐢𝐧𝐠” 𝐅𝐫𝐚𝐦𝐞𝐰𝐨𝐫𝐤 This strategy involves a three-step process: 1. Start at the Top (Executive Engagement) Initiate contact with a senior executive to understand their most pressing challenges, the reasons behind the need for change, and the consequences of inaction. If your solution aligns with their needs, secure their sponsorship for further discovery within their organization. To secure the Executive Meetings, it's essential to create a tailored POV (point of view) on where you think you may be able to help them based on your initial research of their highest level goals and priorities. Chat GPT has made this research a LOT faster now. 2. Conduct In-Depth Discovery (Middle Management) Engage with department heads and key stakeholders to uncover the day-to-day challenges they face. Focus on understanding their processes, pain points, and the implications of current inefficiencies. Gather direct quotes and insights to build a comprehensive view of the organization's needs. 3. Return to the Executive (Present Findings) Compile the insights gathered into an executive summary and business case. Present this to the executive sponsor, highlighting how your solution addresses the identified challenges. Tailor your demonstration to focus solely on relevant aspects that solve their specific problems. 🚀 Why It Works 1. Accelerates Sales Cycles: Engaging executives early ensures alignment and expedites decision-making. 2. Builds Credibility: Demonstrates a deep understanding of the organization's challenges and showcases a tailored solution. 3. Facilitates Internal Buy-In: By involving various stakeholders, you ensure that the solution meets the needs of all parties, increasing the likelihood of adoption. I'm pleased to share that that Yo-yo selling was recently awarded as a Top 15 Sales Tactic of All Time by 30 Minutes to President's Club, and I received a cool plaque for entering the 30MPC Hall of Fame. Since I have no chance of entering the Hall of Fame for my baseball or golf game, this is a nice consolation prize 😁

Selling to the C-Suite? Here’s what they actually care about. Most reps blow the meeting before it even starts. Not because their product sucks... but because they show up sounding like a feature brochure with a pulse. When you’re in front of a C-level exec, you’ve got 30 seconds to prove: ✅ You understand their world ✅ You’re not here to waste time ✅ You can move the needle on what matters to them What that looks like, by title: 🧠 CEO – Growth + Risk ✖ Don’t pitch features. ✔ Show how you help them scale faster, cut risk, or hit strategic goals. 💬 “This helps teams like yours enter [X market] 3x faster - with fewer moving parts.” 💰 CFO – Cost + ROI ✖ “This will improve productivity” = fluff. ✔ Quantify ROI. Speak in margins, efficiency, risk reduction. 💬 “We reduced vendor cost 18% and freed 22 hours/month for [role].” 🛠 COO – Efficiency + Execution ✖ Don’t say “streamline.” Prove it. ✔ Show how you simplify ops, reduce friction, and speed up delivery. 💬 “We eliminate 4 handoffs in your process, cutting fulfillment time in half.” 📈 CRO – Pipeline + Predictability ✖ Don’t pitch dashboards. ✔ Show how you help them hit number faster - with fewer surprises. 💬 “We help reps close 12% more deals without changing your CRM.” 📣 CMO – Leads + Attribution ✖ Don’t promise “awareness.” ✔ Show how you help convert demand into real pipeline. 💬 “We cut cost per qualified lead by 38%... and proved it with revenue impact.” 👥 CHRO – Retention + Culture ✖ Don’t pitch “engagement.” ✔ Tie your solution to retention, onboarding, or team performance. 💬 “Your reps ramp 30% faster...and stay longer because the system supports them.” CIO/CTO – Security + Scalability ✖ Don’t ignore technical friction. ✔ Preempt risk and show how your tool fits their stack. 💬 “No extra infrastructure, fully SOC 2 compliant, and deployed in 48 hours.” CPO – Velocity + Adoption ✖ Don’t talk features to a feature owner. ✔ Show how you drive product adoption and roadmap execution. 💬 “Adoption jumped 44% in 3 months - because we removed friction at the edge.” You’re not selling your product. You’re selling outcomes to people with power, pressure, and no patience. 👇 Which C-level convo are you prepping for next? — 📬 Want access to practical sales resources and advice from top sellers every day? Subscribe here: SalesDaily.co