How to Prepare for Enterprise Software Sales

Every January, your sales team has a kickoff. New methodology training. Updated battle cards. Refreshed pricing. Three days in Vegas pretending to learn while nursing hangovers. Know what your buyers don't have? A "How to Buy Your Software" kickoff. As Todd Caponi reminded everyone during Sales Assembly’s Revenue Manager Lab the other week, these folks have never bought your category before. Maybe once in their entire career. While you've sold it 147 times just this year. Yet what do most reps do? - "So what's your evaluation process?" - "What are your next steps?" - "How do you typically make these decisions?" That's like a sherpa asking you which route you want to take up Everest. I don't know, man. YOU'RE the sherpa. I'm just trying not to die. Your buyers are lost. They're scared. They have no idea what happens next. Their last software purchase was a disaster that almost got them fired. And you're asking THEM to lead? Per Senator Caponi, here's what to do: - Stop asking: "What's your process?" - Start saying: "Here's what we typically see work for companies like yours." - Stop asking: "Who needs to be involved?" - Start saying: "Usually, procurement wants X, IT needs Y, and finance requires Z. Should we loop them in now or wait until after the pilot?" - Stop asking: "When do you want to make a decision?" - Start saying: "Based on your Q4 deadline, we need signatures by September 15th to have you live by October 1st. Here's the timeline that gets us there." Create the Mutual Action Plan, but not as some seller-centric checklist you force on them. Position it as your gift of experience: "Listen, we've done this 200 times with companies exactly like yours. Here are the seven things that always come up, the three that usually kill deals, and how we avoid them. Want me to map out what the next 90 days looks like?" Their relief will be palpable. Always, always, always remember that your buyers are drowning in uncertainty: - Will this work? - Will I look stupid? - What if we pick wrong? - How do we even evaluate this? - What questions should I be asking? Every time you ask them to lead their own buying process, you're adding to that uncertainty. Your job isn't to sell. It's to sherpa. You've been up this mountain before. They haven't. Act like it! Stop asking for their map. Start drawing them one. Because the difference between a vendor and a trusted advisor isn't expertise in your product. It's expertise in THEIR journey.

IT SALES HAS CHANGED. Your sales strategy should too. In 2026, sending a generic pitch like: “Hi, we provide web and mobile development services. Can we schedule a call?” …isn't a sales strategy. It’s an invitation to be ignored. The IT buyers you’re trying to reach are more informed than ever. They can compare agencies, pricing, technologies, portfolios and even AI-generated solutions before they ever talk to you. So what actually works? Stop selling development. Start selling business outcomes. Instead of: ❌ “We build custom software.” Say: ✅ “We help businesses reduce manual operations by turning repetitive workflows into automated systems.” Instead of: ❌ “We provide dedicated developers.” Say: ✅ “We help you scale your product team without the cost and delay of hiring internally.” And here's the strategy I'd use in 2026: 1. Research before outreach Know the company's business, recent growth, product, hiring activity and likely challenges. 2. Personalize the problem, not just the name “Hi John” isn't personalization. Showing that you understand their business problem is. 3. Lead with insight Give prospects a useful observation before asking for a meeting. 4. Use AI for research—not relationships Automate prospect research, account scoring and follow-ups. But keep the actual conversation human. 5. Build authority before asking for the sale Share case studies, lessons, mistakes, opinions and industry insights consistently. 6. Follow up with value Don't send: “Just following up.” Send something that gives them a reason to reply. 7. Sell the outcome, not the hours Clients don't really want 3 developers for 6 months. They want a business problem solved. That’s the biggest IT sales shift in 2026: The best salespeople aren't the ones who pitch the fastest. They're the ones who understand the client's business better than the client expected. What’s working for you in IT sales right now?

You are probably not ready for Enterprise Sales. I’ve led teams closing $1M deals but also seen CEOs fire half their teams after their enterprise push failed. While your board might be right about ACV, trying to go upmarket can kill you. Here are the 5 biggest lies companies tell themselves about enterprise sales (and how to really grow ACV): 1. “We’ll Just Use the Same Product Up Market” Enterprise introduces new buyer personas, new competition, and new business needs—all of which force you to change your roadmap. InfoSec teams will make you implement SSO, ISO, SOC2… Meanwhile, higher product usage will break your architecture or create chaos in implementation. Your product won’t scale. 2. “Our Current Sales Team Can Close Bigger Deals if We Just Book Apple” Enterprise AEs are a different breed. They’re strategic, detail-oriented project managers who are experts in buying (not just selling). Even if your current reps can learn, there’s no way they’ll successfully juggle between fast (1-3 month) and long (12+ month) cycles effectively. It’s just a completely different world. 3. “If We Hire Rockstar Enterprise AEs from Oracle We Will Crush 2025 Targets” Hm… Goodbye 2025 targets. Most likely you’ll hire them in March, they’ll ramp until September, shift 30% of your roadmap, take 20% of your team’s time for RFIs/RFPs, and require management’s involvement at every step. You might see progress with big logos but end up closing only 1–3 low-ACV pilots. 4. “We Just Need Meetings with Bigger Logos” Easier said than done. A brand and demand-gen motion that attracts enterprise executives is not the same as the one that attracts SMB buyers. Your SDRs will also get mostly low-level meetings that waste everyone’s time. You’ll probably need partnerships for executive referrals, ABM strategies, and relevant events to reach the right people. 5. “We Just Have to ‘Level Up’ Sales” Wrong. Good luck transferring a $1M account to a CSM who’s used to juggling 70 small accounts and holding casual syncs. Your CSM must be AS SKILLED as your enterprise AE, or you risk losing a major logo. Imagine that board meeting. —— 2025 ACV plan: Instead of trying to punch above your weight. Create a strategic plan of incremental changes that drive ACV up: - Level up complex selling skills - Update your pricing tiers or model - Split AEs to SMB and MM/Small Ent - Prioritize enterprise deal-making features - Build a playbook on involving your management - Invest in Buyer Enablement tools (e.g. Deal Rooms) —— Enterprise isn’t just bigger deals. It’s a whole new GTM motion. New company. New set of risks. Growing ACV over time is critical. But try it too fast, and you will get burned. Learn what this GTM means–first. Communicate back to your board. Then move. No shortcuts. P.S. We built Aligned to help manage the deal complexity of Enterprise Sales. A 100% FREE Deal Room used by 30,000 sellers. You can try it here:  https://lnkd.in/dwX_Zizk

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 😁

I’ve now been involved in buying software at 4 companies. I never realized how many mistakes I was making as an AE until I was on the other side. Why is “How we buy” not a part of every AEs onboarding? AEs listen up. Here is where I got it wrong and what I think is important to understand: 1️⃣ Your buyer has a full-time job. Evaluating software is an additional task that is time consuming, requires some internal political pull and can likely mean they are putting themselves (or their jobs) on the line. Understand this and don’t take it lightly. It’s important you understand whether this person has bought software before and HOW RECENTLY. Why? If I happened to just buy a software last month, I likely used up some of my “internal pull” and energy on it. This matters more than you think. 2️⃣ Buying cycles are slightly different based on whether somebody came inbound or outbound. If I request a demo, it may be out of curiosity, but usually this is an initiative that has already been talked about internally with various stakeholders, potentially a budgeted line item and half the decision has already been made. This person is likely a champion, needs less convincing of the problem/solution and is probably talking with other vendors. Focus on differentiation early here. For outbound, this potentially means a much larger uphill battle for your buyer. You must identify key stakeholders early and start multi-threading and helping that champion sell. One of my favorite things to do here is spin up a digital sales room like Aligned and uncover who is actually looking at the material I’ve sent over. 3️⃣ Buying software is not rooted in rationality. Humans are not rational actors. Your ROI numbers are likely irrelevant… especially if we didn’t specifically sit down and confirm them. Example: Let’s say your solution ultimately helps me get more qualified pipeline. There are HUNDREDS of ways that I can go about doing this. Better contact data, better signals, better research on accounts, better emails, better training etc. You need to help me prove that you are the BEST way to do that. 4️⃣ Make it extremely easy for me to sell internally. No exec watches demo recordings, reads case studies or has time for 20 slides in a deck. Gal Aga said it best in a post the other day: 1. Equip them with a CXO-ready business case 2. Co-build all internal assets (ROI, TCO, FAQs) 3. Pre-plan rollout (beyond just closing) 4. Pressure-test expected internal objections 5. Prep champions for CFO skepticism 6. Map risks openly—no deal is risk-free 7. Constantly challenge: "What could kill this project?" Please don’t just send over a bunch of links or PDFs. Get yourself Aligned and make it easy for buyers to have a hub with all documentation in one place. Try it for free here: https://lnkd.in/eqcE6G9r

Nobody tells you this about enterprise sales The biggest deals are lost in the first 5 minutes. Not because of your pitch. Not because of your price. Not because of your product. But because of the language you use. Here's what I discovered after analyzing 1000+ sales calls: The higher the deal value, the simpler the language needed to win. Example: $5K deal (Lost) Rep: "Our value proposition addresses critical pain points in your tech stack integration, offering seamless scalability..." $50K deal (Won) Rep: "We help companies stop losing customers due to slow website loading times." See the difference? I tested this with a struggling SaaS team: Before: Complex sales language - 22% close rate - 108-day sales cycle - $127K average deal After: Plain English only - 41% close rate - 71-day sales cycle - $198K average deal Simple change. Massive impact. The truth is, every exec can smell rehearsed "sales talk" from miles away. Want to close bigger deals? Drop these phrases: - "Value proposition" → Say how you help - "Pain points" → Say what problems you solve - "ROI analysis" → Say how much money they'll make - "Scalable solution" → Say how you grow with them - "Best-in-class" → Say why you're better Top performers don't sound like salespeople. They sound like trusted advisors who happen to sell. Start talking like a human. Watch your deals grow. What's the worst sales jargon you've heard lately? P.S. If you need help with your sales, send me a message Let's talk about finding your breakthrough strategy

In 6 years, I was promoted 3 times to become the youngest L7 Sales Leader at AWS, leading a team that hit 119% attainment on >$150M yearly quota. Here are 5 hard lessons I learned about enterprise sales: 1. Enterprise Sales = Team sport Winning big deals means selling internally as much as externally. I spent almost as much time getting internal resources, securing executive buy-in, and aligning product teams as I did in front of the customer. 2. Trust Beats Price Every Time I’ve seen won deals where we weren't the cheapest option. Why? Trust. Building relationships where the client believes in your long-term partnership is the single biggest lever you can pull in enterprise sales. 3. FOFU > FOMO The buyer doesn’t care about FOMO as much as they care about FOFU: fear of fucking up.The biggest question they’re asking themselves is, “Will this decision get me fired?” Your job is to make the deal as risk-free as possible. 4. Always Build a Business Case Enterprise buyers need justification for spending big. If you’re not building a clear, data-backed business case, you’re asking your champion to sell for you—and they won’t. The stronger the ROI/COI (cost of inaction) argument, the easier the sale. 5. You’re Not the Hero, You’re the Guide Perhaps the most important thing to internalize. Your role shifts from salesperson to strategist. EMPOWER. Don't OVERPOWER. Guide your champion on how to sell internally. Set a clear, step-by-step strategy with them. Orchestrate the entire process—internally and externally—and ensure all the pieces are aligned and moving in the same direction. TAKEAWAY: In enterprise sales, you’re the quarterback. not the one carrying the ball to the endzone. Your job is to: orchestrate the play, guide your champions, and set your team up for success. It's not about doing it all yourself; But leading the right people in the right direction at the right time.

Here's what it takes to successfully sell to enterprises in 2025. Enterprise sales is way harder today than it was even five years back! There are many reasons for it: 1. More noise 2. More decision makers 3. Lower attention spans 4. Success margins are thin Using traditional tactics is a recipe for failure. These five key approaches will help your team break through the complexity. 1. Multi-stakeholder mastery Generic pitches stall! Map every buyer persona (finance, IT, security, legal, ops, end-users) and arm reps with domain-level fluency so they can speak each team’s language. 2. Dynamic, contextual collateral on tap Build a modular content library tagged by role, pain point & stage. You should be able to deliver just-in-time one-pagers, ROI models, security briefs, etc. No one has time for “let me get back to you” cycles! 3. One intelligence layer Aggregate CRM data, intent signals, and AI insights into a single workspace. Don't serve dashboards to your reps but clear, easy to consume point-of-view packs. 4. Focus on helping buyers buy Co-create a decision roadmap with the champion (milestones, approvers, proof points). Imagine you are a consultant working with them to help them buy. Measure decisions advanced, not sales activities you've logged. 5. Precision, Bespoke Whatever you want to call it. Make stakeholder briefings data-backed and precise. Drop the generic and go deep and customized (its possible now with the tools and while slow initially accelerates the selling process eventually) Enterprise sales today isn’t pure volume play. Equip teams with clear, precise information to spearfish! #GTMStrategy #EnterpriseSales #SalesLeadership

Selling to leadership is tough. Learn to speak finance, and everything changes. (This works for both B2B sales and internal pitches.) Speak the language of financial metrics and business impact, and you’ll earn buy-in. Whether you’re pitching a product, service, or internal idea, this skill makes you a trusted partner to decision-makers. Want to dive deeper? Download my free guide “10 Levels of Profitability” here: https://bit.ly/40pY3CQ Here’s why: Executives don’t want fluff. They need to know *how* your solution or proposal will impact their business financially. Here’s how to make your pitch resonate: 1️⃣ Talk Margins, Not Just Savings ↳ Show how your solution improves gross, operating, or net profit margins. Make it clear how it improves topline or streamlines processes to ultimately add value to the bottom line. 2️⃣ Connect to Cash Flow ↳ Highlight how your solution will boost cash flow, not just the bottom-line. Smart executives prioritize cash flow over simple revenue increases or cost savings because it keeps the business stable and flexible. 3️⃣ Show ROI and Payback Period ↳ Present clear numbers on return on investment (ROI) and how quickly they’ll see a payback. Executives need to know when their investment will yield results. 4️⃣ Impact Key Financial Ratios ↳ Explain how your proposal enhances key metrics like ROE (Return on Equity), ROA (Return on Assets), or EBITDA. This demonstrates that you understand their financial framework and how your solution strengthens it. 5️⃣ Talk Risk Management ↳ Show that you’ve considered potential downsides. Demonstrate how your proposal mitigates financial risk and supports long-term stability—not just quick gains. Why this matters: 1️⃣ You Stand Out ↳ Most sales pitches and internal proposals focus on benefits. When you speak in terms of financial strategy and impact, you differentiate yourself. 2️⃣ You Build Trust ↳ Speaking their language shows you understand their challenges, priorities, and goals. 3️⃣ You Become Indispensable ↳ When you can prove your solution impacts key business metrics, you shift from being just another vendor or team member to a trusted advisor. If you want to learn finance strategy to elevate your pitch and proposals, join 3,000 learning with me here: https://bit.ly/famcol Remember: Learn to speak finance, and you’ll open doors that most can’t. ♻️ 𝐋𝐢𝐤𝐞, 𝐂𝐨𝐦𝐦𝐞𝐧𝐭, 𝐑𝐞𝐩𝐨𝐬𝐭 to help someone else. And follow Oana Labes, MBA, CPA for more  

Mastering Consultative Sales: Strategies to Win Enterprise Clients To win large enterprise clients, you must shift from a traditional sales approach to a consultative one. Enterprise clients don’t just want to hear about your product; they want insights they don’t already have. Here’s how to position yourself as the most consultative partner they’ve ever worked with: 1. Adopt a “One-Up” mindset: Know more about your client’s problems and critical decisions than they do. You’ve had more conversations like this, and that knowledge is your advantage. 2. Lead the buyer’s journey: Don’t wait for the client to steer the conversation. By leading them, you show you can help them succeed. 3. Give recommendations based on experience: Share specific advice on who to involve and which steps to prioritize. Tailor it to their needs, not just your solution. 4. Leverage information asymmetry: You know what they don’t. Use that knowledge to provide value and guide them to better decisions. 5. Offer advice with confidence: Don’t shy away from telling the client what they need to hear. Your expertise builds trust and sets you apart. By embracing a consultative approach, you’ll gain a sustainable advantage and secure larger, more meaningful deals. #ConsultativeSales #EnterpriseClients #SalesLeadership #SalesStrategy #SalesExecution