Managing the Full Sales Cycle in IT Consulting

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 😁

Hey Salespeople: Do you truly understand the Challenger sales methodology (teach, tailor, take control)? It does not mean being aggressive. TEACH – Provide insights that challenge the prospect’s current thinking and help them see an unrecognized problem or opportunity. This approach positions the salesperson as a trusted advisor rather than just a vendor. Example: Instead of just pitching accounting software, show a CFO data revealing they're spending 40% more time on compliance than industry peers, costing them $200K annually in labor inefficiency. TAILOR – Customize the conversation to align with the prospect’s industry, company priorities, and individual stakeholder concerns. Example: When speaking with the IT Director, focus on integration and security features; with the CFO, emphasize ROI and cost reduction; with end-users, highlight ease of use and time savings. TAKE CONTROL – Taking control involves guiding the sales conversation confidently, addressing objections proactively, and steering the prospect towards a decision. This doesn't mean being aggressive, but rather being assertive and value-focused Example: After demonstrating value, saying "Based on what we've discussed, I recommend starting with our enterprise package at $85K annually. To hit your Q3 goals, we should begin implementation within three weeks. Does your team have the authority to move forward, or should we include someone else in our next conversation?"

I'm watching salespeople leave money on the table every day. The data doesn't lie. B2B deals require 6.8 stakeholders to reach consensus. Yet most reps focus on ONE relationship. This single threading approach is why deals: = Go dark without warning = Disappear when priorities shift = Get cut first when budgets tighten = Take 2X longer to close than necessary After coaching 500+ AEs who've collectively closed $750M+ in revenue, I've found the solution hiding in plain sight. It's Account Mapping in LinkedIn Sales Navigator. But not just basic mapping. Strategic multi-threading. Here’s the play: 1. Pull up your target account in Sales Navigator 2. Click "View Account Map" (shockingly, most reps don't know this exists) 3. Identify key players in the buying committee 4. Assign roles: Decision-Maker, Champion, Influencer, User, etc. 5. Develop personalized outreach for EACH stakeholder When you deploy this strategy, something magical happens: One stakeholder goes dark? You have 5 other active relationships Technical objection arises? Your champion in Engineering addresses it internally Budget concerns surface? Your Finance contact provides insider perspective Decision-maker changes? You're already connected to their peer group Here’s a real world example: Last month, my client was working a $500K deal that seemed solid. Their single point of contact suddenly stopped responding for 3 weeks. Dead deal? Not quite. We implemented the multi-threading approach, mapped the account, and connected with 4 additional stakeholders. Turns out, their champion was on medical leave but the team was still evaluating solutions. Deal closed 40% faster than their average cycle. By the way… my favorite question to get me multi-threading from the get go? During discovery calls, I teach reps to ask: "Besides yourself, who else will be involved in evaluating this solution?" Then follow up with: "And who else might influence this decision, even indirectly?" “Who else?” Map these names immediately in Sales Navigator. Look for connections between them. Identify potential champions at EACH level of the organization. While your competition waits for ghosted emails, you're having productive conversations with multiple stakeholders. All moving toward consensus. The biggest deals CANNOT be won through a single relationship. Stop leaving commissions on the table. Start multi-threading today. Check out my Sales Navigator deep dive video (and how to use AI with it). : https://lnkd.in/gtE-FWax

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.

Something remarkable happened when we started bringing Customer Success leaders into our sales conversations. The traditional sales process transformed into a strategic partnership discussion that benefited everyone involved. After implementing this approach across hundreds of deals, we discovered benefits that went far beyond our initial expectations. Sales teams gained a deeper understanding of post-implementation challenges, which helped them qualify opportunities more effectively. Instead of focusing solely on closing deals, they began asking questions about operational readiness, internal champions, and resource allocation. Prospects received authentic insights into what successful implementation truly requires. Our CS leaders shared real examples of customers who thrived and openly discussed common obstacles they might face. This transparency built trust and helped prospects make informed decisions. Better aligned customer expectations from day one. When CS leaders joined these conversations, they highlighted potential roadblocks and success metrics based on similar customer profiles. This practical guidance helped prospects understand the work required to achieve their desired outcomes. This early involvement proved invaluable for our CS team. They gained visibility into the customer's vision before contracts were signed, allowing them to proactively plan resources and create tailored onboarding strategies. A surprising result was the reduction in "rescue" situations during implementation. We eliminated many issues that typically surfaced months into the relationship by addressing potential challenges during sales discussions. The data supported our approach. Deals that included CS leaders showed 40% higher implementation success rates and 25% faster time-to-value. More importantly, these customers renewed at significantly higher rates. For those considering this approach, start small. Choose strategic opportunities where CS insights could substantially impact the prospect's decision-making process. Document the outcomes and refine your strategy based on that feedback. Great customer relationships begin with the very first conversation.

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?

Last week, we closed a deal with a $10 billion (revenue) company. No click bait. Just a story that marks a new era. Here's what their SVP told me: “A few years ago, our sellers didn’t need real skills. Tailwinds and great product-market fit carried us. We had nothing more than order-taking skills.” He went on: “But today? Sales cycles are complex. Buying committees are more educated & skeptical. The ZIRP era won’t come back for another generation. We need to maximize revenue per rep. That starts with skill capacity.” We’re no longer in the ZIRP era. We’re in the Skill Capacity Era. I asked him what skills matter most now. Here’s what he said: 1. Disruptive Insight Selling. Great sellers don’t pitch. They reframe the problem. They introduce a unique insight that shifts the buyer’s thinking. In a way that favors a purchase. Most AEs can’t do this. They offer thinly veiled product pitches. No insight. No acumen. Top sellers reframe the buyer’s mind. They communicate, without saying it: “I know your business — and I understand this problem better than anyone else.” 2. Developing and Quantifying Value. Open your CRM. Look at the notes in the ‘pain’ field.' Now ask yourself: Are these the problems C-level execs care about? Or mid-level frustrations? Most AEs stop at surface pain. The best go deeper — and quantify what they find. They uncover the need behind the need. That’s where the deal lives. 3. Frictionless Multi-Threading. Buying committees are larger. Buying committees are more risk averse. Buying committees are prone to “do nothing.” Yet sellers have the same multi-threading habits they did two years ago: Work with one, MAYBE two people. Stick with the most comfortable contact. Avoid the skeptics. The best salespeople don't just multi-thread. They drive consensus. 4. CFO-Level Business Cases You don’t need to be a spreadsheet wizard. But you do need to speak CFO. If your ROI pitch sounds like a sales deck? At best, they’ll roll their eyes. If it sounds like a financial case with scenarios? You’ll get to “yes” faster. 5. Taking Control. The Challenger Sale gave sellers a game-changing framework: Teach. Tailor. Take Control. Most AEs don’t know how to do that without sounding tone-deaf to buying dynamics. They defer. They wait. They follow the buyer’s process and hope for the best. But in this market? Hope is not a strategy. AI can’t lead a room. It can’t challenge a buyer’s process. It can’t manage power dynamics. That’s your job. The best AEs define the pace and tone of every deal they touch. ZIRP is gone. The order-taker economy is dead. Welcome to the Skill Capacity Era. The CRO flex isn’t bloated headcount anymore. It’s skill density × revenue per rep. P.S. Start transforming your revenue team with these 24 skill transformation tips: https://lnkd.in/g_JF-ytC

Most companies are flying blind when it comes to revenue 📊 "Some months we're closing deals left and right, other months it's crickets. I never know what's coming next month." Every month I meet with business owners who tell me exactly this. Revenue unpredictability kills everything. You can't plan hiring, you can't forecast growth, and you definitely can't sleep well at night wondering where next month's revenue is coming from. Well here's the thing...it doesn't have to be this way. ➡️ THE SOLUTION: PIPELINE DRIVEN FORECASTING Stop guessing at your revenue and start building forecasts based on actual pipeline data. Think about that difference. Instead of hoping deals close, you're working with real data from real prospects. STEP 1️⃣ → STRUCTURE YOUR CRM Track each deal by stage, amount, and expected close date in your CRM system. See every deal needs to move through defined stages that actually reflect how your sales process works. You can't just throw deals in there and hope for the best. STEP 2️⃣ → EXPORT PIPELINE DATA Export your CRM data to Excel for revenue forecasting and analysis. You know what's amazing about this? You get complete control over how you manipulate and model your data. Plus Excel gives you that flexibility that most CRM reporting just can't match. STEP 3️⃣ → FORECAST REVENUE Use weighted pipeline data to predict future revenue with confidence. Apply probability percentages to each stage and calculate realistic monthly projections. That's pretty powerful when you think about it. ➡️ RECOMMENDED CRM TOOLS 🔵 Salesforce → Enterprise grade pipeline management for larger companies 🔴 HubSpot → All in one sales & marketing platform ⚫ Pipedrive → Simple, visual pipeline management for smaller teams Now you may be thinking which one should I choose? Well that depends on your company size and complexity, but any of these will work better than spreadsheets alone. ➡️ BEST PRACTICES FOR PIPELINE MANAGEMENT 📅 Keep data updated weekly 📊 Track conversion rates by stage 📋 Define clear stage criteria 📝 Review forecasts monthly ⚙️ Set up CRM automations 🗓️ Set realistic close dates The key is to export pipeline data monthly to maintain accurate revenue forecasts. This monthly ritual will completely change how you plan and operate your business. === I've seen this transform companies from reactive revenue planning to predictable growth patterns. Instead of crossing your fingers each month, you'll know exactly what's coming and can make strategic decisions accordingly. What's your experience been with pipeline management? Are you still flying blind or do you have a system that works?

Selling into a Fortune 50 company isn’t a straight shot—it’s a multi-threaded, high-stakes game where you have to win over three completely different audiences at the same time. 👑 C-Suite (aka "The Big Picture People") – They care about risk, revenue, and competitive advantage. If your pitch doesn’t tie back to a business outcome, it’s dead on arrival. Keep it short, strategic, and dollar-driven—they have about 30 seconds before they mentally check out. 🧠 Technologists & Strategists (aka "The Architects of the Future") – These folks are your deal-makers or deal-breakers. They want to know if your solution fits their long-term IT roadmap, scales, and won’t become next year’s tech debt. If you can’t show how your product integrates seamlessly with what they already have, you’re in for a long road. ⚙️ Practitioners (aka "The Ones Who Actually Use the Thing") – These are the engineers, security teams, and network admins who will either champion your solution internally… or fight it tooth and nail. If your product makes their lives easier (less manual work, better automation, no fire drills at 2 AM), they’ll become your secret weapon in getting the deal done. 🎯 The Trick? Selling to All Three in Parallel. C-suite? Tie it to revenue and risk. Technologists? Prove it’s a strategic fit. Practitioners? Make their job easier. The best enterprise salespeople aren’t just selling—they’re orchestrating. Every great deal is won at multiple levels. How do you navigate selling to different stakeholders? Drop your best tips below! ⬇️ #EnterpriseSales #TechSales #StrategicSelling

"I’m asking my boss for budget tomorrow” is the BIGGEST 'miss moment' in sales. Most AEs train like marathon runners for months, only to sabotage themselves with pizza and a late-night party the day before the race—casually responding “ok talk soon". Here’s our 5-Step Champion-Exec Selling Playbook to stop losing budget meetings at the finish line: BACKGROUND: What most AEs do: - Hear: “I’ll ask my boss for budget” - Celebrate and bump the forecast to 50% - Assume the champion knows how to pitch it internally - Provide 25-page deck and pulls random files from email - Champion says: “Hey, there’s this cool tech I want…” Why it fails: - 62–75% of buyers are inexperienced (Gartner) - Your champion has never bought in this space (if at all) - They’ll face ROI and priority pushbacks for the first time - Execs want bottom-line clarity, not an info dump - Boss: “No budget right now sorry—maybe next quarter" Deal runs for 1,000s of minutes and dies in 5. (and you’re not there to counter). Here’s what to do instead… —— 1. Get Champion Buy-In Respond with questions: “What in your mind are the most compelling points your boss needs to hear?”, “What if they push back on ROI?”. When their answers have holes, and they always do—share your perspective and get buy-in to prep them for this meeting. Show why they should listen; and they will. 2. Neutralize Objections Early Prevent surprises: “Which questions do you expect your boss might ask?”. Brainstorm answers—especially around budget, competing priorities, and risk. 3. Facilitate the Conversation Provide killer talking points: (1) problem, (2) cost of inaction, (3) your solution, (4) proof. Turn it into a 1-Page Business Case—which you started drafting early. 4. Share Champion Assets (Digital Sales Room) House everything in one place—If your champion ends up pulling 25-slide decks, or digging in emails for info, you’re toast. Include the 1-Page Business Case, Scope, Onboarding, Proposal, Eval Recap, Why Us, and Client Stories. Make it easy to edit with champions, forward, skim, and to say “Yes, let’s do it”. 5. Confirm the Follow-Up Book a 15-minute check-in right after their convo. If the champion wants to “wait until next week,” push for a same-day or next-day sync. Urgency signals you’re serious—and it keeps momentum alive. —— End of quarter is around the corner. Don’t wing it with champions. Hopium isn’t a strategy. Want our exact Champion Assets Template? (Business Case, Project Scope, Onboarding, Proposal, Eval Recap, etc.) - Like this post - Comment “Champion” 👇 - We’ll send it to you in a week - Then share it with everyone else Happy EOQ!