End-to-End Sales Operations Strategy

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 was ready to quit.  My startup was flatlining.  Sales were a rollercoaster—one month we were celebrating, the next we were scrambling to make payroll.  Then, everything changed.  We discovered a systematic sales approach that transformed our struggling venture into a thriving powerhouse.  𝗛𝗲𝗿𝗲’𝘀 𝘁𝗵𝗲 𝘁𝗵𝗶𝗻𝗴:   ↳ It wasn’t flashy.   ↳ It wasn’t revolutionary.   ↳ It was just consistent, measurable, and repeatable.  𝗛𝗲𝗿𝗲’𝘀 𝗵𝗼𝘄 𝘄𝗲 𝗱𝗶𝗱 𝗶𝘁:  1️⃣ 𝗟𝗲𝗮𝗱 𝗚𝗲𝗻𝗲𝗿𝗮𝘁𝗶𝗼𝗻 We defined our ideal customer profile and launched targeted campaigns.  2️⃣ 𝗤𝘂𝗮𝗹𝗶𝗳𝗶𝗰𝗮𝘁𝗶𝗼𝗻 We built a scoring system to prioritize high-value leads.  3️⃣ 𝗢𝘂𝘁𝗿𝗲𝗮𝗰𝗵 We created templates for every touchpoint—cold emails, follow-ups, you name it.  4️⃣ 𝗗𝗶𝘀𝗰𝗼𝘃𝗲𝗿𝘆 We developed a framework to uncover customer pain points.  5️⃣ 𝗣𝗿𝗲𝘀𝗲𝗻𝘁𝗮𝘁𝗶𝗼𝗻 We standardized our pitch decks and demo scripts.  6️⃣ 𝗡𝗲𝗴𝗼𝘁𝗶𝗮𝘁𝗶𝗼𝗻 We set clear guidelines for discounts and terms.  7️⃣ 𝗖𝗹𝗼𝘀𝗶𝗻𝗴 We implemented a smooth handoff process to customer success.  𝗧𝗵𝗲 𝗿𝗲𝘀𝘂𝗹𝘁𝘀? ↳ 37% shorter sales cycles   ↳ 52% higher conversion rates   ↳ 215% revenue growth YoY   ↳ 28% lower customer acquisition costs But the real win?  Predictability.  We could forecast with accuracy, scale efficiently, and sleep at night knowing we had a repeatable path to success.  𝗛𝗲𝗿𝗲’𝘀 𝘄𝗵𝗮𝘁 𝗜 𝗹𝗲𝗮𝗿𝗻𝗲𝗱: Consistency > Charisma   Data > Gut Feelings   Process > Luck This systematic approach didn’t just save our startup—it became our competitive advantage.  👉 Want to transform your sales?  Stay tuned for the launch of “The B2B Sales Playbook”—a step-by-step guide to building a scalable, predictable revenue engine.  P.S. What’s your biggest sales challenge? Drop it in the comments, and let’s brainstorm how a systematic approach could help.  #SalesTransformation #StartupGrowth #B2BSales

We made a big bet on Enterprise Sales - and nearly pulled the plug. Then Dylan Steele hit 204% in Q2. Crushed it. ACV 2x’d. A $480K deal closed. That’s when we finally felt it: the system was clicking. But getting there? Not fun. Here’s what I wish we’d known sooner (and what actually worked): 1. Specialize Early We thought our senior AEs could handle all deal sizes. “We’re a small team, no time to specialize.” Wrong. Win rate dropped to 20%. Why? Because our AEs were stuck chasing 10 $10K deals or one $100K deal, and missed both. The context switch is brutal. Different buyers. Different tempo. Different stakes. Enterprise needs depth, not speed. Specialize early. Do it. Result: Win Rate >30%, ACV 2x’d in Q2, 100% of Enterprise AEs overachieved. 2. Inbound Misses Execs We’re 100% inbound. 1,000s of users sign up for our free plan or request demos every month. Our SDRs follow product signals and work their way up. It’s great for volume. But execs don’t fill out forms. We’d find champions. But without exec buy-in, deals died at the top. Now we blend outbound from day one and run exec-to-exec outreach. CROs on first calls. Result: In Q2, a big logo closed in 64 days with CRO & VPs engaged on day 1. 3. Upmarket Is a NEW Market Enterprise wasn’t just bigger deals. It was a different game: New personas, requirements, and entirely new competition. We weren’t just selling Digital Sales Rooms anymore; we were up against Sales Enablement giants buyers had used for 10+ years. Don’t assume what worked downmarket still applies. The playbook MUST be rewritten. Result: In Q3, we displaced 3 legacy vendors. 4. Weekly War Rooms Every week, we deep-dive into all strategic deals. I join these calls to help. These kinds of deals must be orchestrated, not sold to. We get requirement docs, uncover existing executive connections, tackle issues that require unique troubleshooting. Every AE has the entire team at their service. Result: Today, every big deal has an Exec Sponsor. 5. Protect Seller Focus Big deals don’t need more hours. They need better ones. More research. Better business case. Sharper strategy. Most companies buy tech to help. We’re building ours in-house, customized and soon productized. Agents that help reps prep, update CRM, raise flags, and move faster. Result: Every deal now has a Business Case using Aligned's AI. 6. Brand Brand Brand The more we invest in what we can’t measure, the faster we scale. When buyers already trust you, deals move faster. They loop in execs. They have fewer objections. They know your name. You can’t calculate the ROI, but good luck closing 6-fig deals when your AE is the only engine building trust. Result: We show up 10x per day in our ICPs feed. 700+ join our webinars. —— Stop hiring enterprise reps hoping they’ll fix your GTM. If the system’s not built, they can’t win. It’s not on them. It’s on you. Don’t blame the people doing the hardest job. What’s worked for you going upmarket?

A perfect sales process on paper often fails in reality because it ignores one variable: The human behavior of the seller. 🙈 We spend millions designing "Systems of Record" for the business. We rarely spend enough time designing "Systems of Action" for the rep. As a leader who has led global enablement teams, I bring a complementary lens to the Operations partnership: 💻 The Seller's Reality. You can build the most sophisticated CRM architecture in the world. But if it forces a seller to toggle between six tabs to find a price, adoption will be zero. And your data will be garbage. When I partner with RevOps to design a new workflow, I don't start with the schema. I start with the user story. 1. The "Click Tax": I audit the workflow from the seller’s perspective. How many clicks to log a meeting? How many fields are mandatory but irrelevant? If the administrative tax is too high, the high-performing seller will bypass it. Every time. 2. The Invisible Friction: Most friction isn't technical. It's cognitive. Are we asking them to switch context just to tag a competitor? Here's how we leverage AI to bring the process to the seller: ☝We use context-aware triggers to surface battlecards inside the Opportunity record, so they don't have to search. 🤘We use Conversation Intelligence to auto-capture data, populating the CRM without forcing the rep to touch a keyboard. 3. The Outcome: When you solve for Seller Experience, you solve for the business. ✔️ Reduced friction = Higher Adoption. ✔️ Higher Adoption = Clean Data. ✔️ Clean Data = Accurate Forecasting. True Sales Innovation isn't just about adding tools to the stack. It's about having the empathy to design a workflow that humans actually want to use. #RevenueOperations #SellerExperience #SalesEnablement #ProcessDesign #AI

In this edition, I dive into the Sales Cloud End-to-End Sales Flow—breaking down the key Salesforce objects and how they interact across the entire customer lifecycle. From Lead → Account/Contact → Opportunity, this is more than just a process walkthrough. It’s about understanding how data model decisions (especially account models) directly impact scalability, governance, reporting, and integrations in enterprise implementations. 🔍 What’s covered: • How core objects power each stage of the sales lifecycle • The role of Campaigns & Campaign Members in attribution • Where automation, AI, and forecasting fit in • Why account model choices matter more than you think 💡 Whether you're a Salesforce Admin, Architect, or Sales Ops leader, this is a quick 4-minute read packed with practical insights. 👉 Read the full post: https://wix.to/JBCFeN0 #Salesforce #CRM #SalesCloud #SalesOperations #EnterpriseArchitecture #SFDC #TechLeadership

This is what happens when sales talks first and engineering talks later. If you want fewer broken promises and more closed deals that actually stick follow this exact flow: 📌 Step 1: Turn every customer request into a clear use-case Instead of asking engineering: “Can we build this feature?” Ask: “The customer wants to automate X to save Y hours - what’s realistically possible today?” Engineers think in systems, not sales language. 📌 Step 2: Get a fast feasibility check (15–30 minutes max) Before any pitch: Share with engineering: * Customer goal * Expected outcome * Deadline Ask for: ✅ Can do now ⚠️ Can do with work ❌ Not possible Document it. 📌 Step 3: Pitch only what got a green or yellow light Green → sell confidently Yellow → sell with conditions Red → don’t sell If it’s yellow, say: “We can reach this result in phases, not instantly.” This keeps excitement without lying. 📌 Step 4: Lock scope in writing after the call Send a quick recap: “Here’s what we agreed is possible in phase one…” This protects: * Sales credibility * Engineering bandwidth * Customer trust 📌 Step 5: Create a weekly sales-engineering sync (30 mins) Agenda: * New deals in pipeline * Risky promises * Technical blockers This one meeting prevents 80% of post-sale chaos. 📌 Step 6: Track one metric 👉 % of deals delivered without scope change If it’s low → sales is overselling If it’s high → alignment is working That's it!

The best sales teams stopped hiring salespeople. They hired engineers instead. The old go-to-market playbook had three moves: 1. Hire more reps. 2. Buy the category-leading tools. 3. Let sales and marketing work in separate silos. That playbook treated pipeline as a headcount problem. The top teams now treat it as an engineering problem. A small RevOps + GTM Engineer team runs the whole machine. Nine steps, in order: 1. Ideal customer profile. Export Closed Won and Closed Lost from the CRM. Feed both into Claude Code to find the patterns. Build the profile on three layers: firmographics, account signals, technographics. 2. Market map. Every company that fits the profile: Apollo.io 's company database, Ocean.io for lookalikes, AI Ark for keyword search, Clay 's database for the rest. 3. Account research. Enrich every account at scale: Apollo.io for firmographics, Claygent + Claude for fit signals, Exa for deep web research, Sumble for technographics, Findymail for social signals. 4. Tier and score. Split accounts into Tier 1, 2, 3. Score each one by awareness stage: identified, aware, interested, considering, selecting. 5. Contact sourcing. Clay + AI Ark to find the buying committee. Findymail to find and verify emails. BetterContact for phone numbers. 6. Demand generation. Only now do the channels turn on. Content (LinkedIn, X, website), outbound (LinkedIn, email, calls), and ads (LinkedIn, Meta, Google) run together on the same foundation. 7. Meeting booked. Clay routes the lead to HubSpot. Cal.com books the call. 8. Sales process. Ergo for account intel before every call. Nooks for dialing. Apollo.io + HubSpot to run the pipeline. Qwilr for proposals. Claude as the copilot through all of it. 9. Closed won. Every closed deal feeds back into step 1 and sharpens the next search for lookalikes. Count the steps before anyone writes a single email: five. The old playbook started at step 6. That's why it's broken.

Top 10 Facts To Know About Sales Operations Commercial Sales Operations is the competitive advantage most early-stage MedTech companies never build soon enough. Early teams obsess over hiring reps. The smart companies obsess over building the systems that make those reps dangerous. Compensation planning, territory design, pricing discipline, forecasting rigor, and clean CRM guardrails. All the infrastructure that transforms individual talent into repeatable revenue. • TAM analysis creates rational territories, balanced quotas, and a clear understanding of upside potential. Without it you create random success, rep frustration, and executive churn. • Proper compensation design motivates the exact behavior you want. Team rankings, quarterly accelerators, behavioral bonuses. A plan that is simple to understand and hard to game. A plan that rewards loyalty and long-term thinking. • Compensation guardrails protect your margin. Forecast accuracy protects your board credibility. Operational cadence protects your culture. • Salesforce mapping, quoting workflows, contract templates, discount tiers, site readiness, and quote-to-install orchestration build predictability that investors trust and commercial teams rely on. • More data is not the goal. Clean data is the goal. Input discipline today becomes pipeline intelligence, price-sensitivity analysis, and investor-facing metrics tomorrow. • Mature Commercial Operations leaders do not just manage process. They operationalize truth. Where deals die. Where reps stall. Where ROI narratives collapse. Where pricing erodes. Where training gaps are hiding. • Compensation planning is the single most powerful lever. A great plan creates retention, pride, and urgency. A weak plan creates politics, excuses, and turnover. • Early-stage MedTech companies should finalize comp plans by March at latest (every year), keep the planning team small (Commercial Operations, Legal, HR), and model scenarios obsessively. • The first 15% of your process maturity is what prepares you for early adopters. The next iteration is what prepares you for the majority. • Commercial Operations is not overhead. It is the spine that holds your revenue engine upright. If you build Commercial Operations early, you will not only grow faster... You will keep the people who helped you grow.

“I want to be CRO…but I don’t want Marketing or CS reporting into me.” - the subconscious mind of a CRO at a SaaS 🤷🏽♀️ I'm big on breaking things down. It's the ENTJ in me. if your title is Chief Revenue Officer, let’s unpack what that really means. ➝ Chief = 1 of the most senior leaders in the organisation ➝ Revenue = The total value the business earns from what it sells ➝ Officer = A person with formal authority to execute decisions and lead 𝗦𝗼 𝘁𝗵𝗲 𝗖𝗥𝗢 𝗶𝘀 𝘁𝗵𝗲 𝗺𝗼𝘀𝘁 𝘀𝗲𝗻𝗶𝗼𝗿 𝗽𝗲𝗿𝘀𝗼𝗻 𝘄𝗶𝘁𝗵 𝗮𝘂𝘁𝗵𝗼𝗿𝗶𝘁𝘆 𝗼𝘃𝗲𝗿 𝗵𝗼𝘄 𝗿𝗲𝘃𝗲𝗻𝘂𝗲 𝗶𝘀 𝗴𝗲𝗻𝗲𝗿𝗮𝘁𝗲𝗱, 𝘀𝘂𝘀𝘁𝗮𝗶𝗻𝗲𝗱, 𝗮𝗻𝗱 𝗴𝗿𝗼𝘄𝗻. Not just how much we make — but how we go to market to make it. If my CFO gave me $100K today and said, “Turn this into $1 million,” I wouldn’t start with outbound, or new hires, or tech. I’d start by operationalising revenue — by treating it like a system, not a scoreboard. That means looking at: ! Are we forcing buyers to repeat themselves? ! Are we making promises we don’t deliver on? ! Are we measuring utility, or just activity? ! Are handoffs creating clarity, or confusion? ! Are we capturing real signals — and acting on them? Too many GTM teams are flying blind. Or they are walking past dollars to pick up cents. One of my fave lines from Ryan Person It’s a strategy problem. Because at the core of all of this is one thing: having a clear, coherent plan for how you bring your products and services to market. That’s what operationalising revenue actually is. It’s the connective tissue between your GTM strategy and the buyer’s real-world experience. It’s the difference between hope and precision. Between chasing revenue — and building a system to generate it. CRO....it's a systems job. And no I dont mean technical systems. If you’re not operationalising revenue, you’re just reacting to it. 𝗧𝗵𝗿𝗲𝗲 𝘁𝗮𝗰𝘁𝗶𝗰𝗮𝗹 𝘁𝗮𝗸𝗲𝗮𝘄𝗮𝘆𝘀 𝗶𝗳 𝘆𝗼𝘂 𝘄𝗮𝗻𝘁 𝘁𝗼 𝗱𝗼 𝘁𝗵𝗶𝘀 𝘄𝗲𝗹𝗹: 1. Map your buyer journey and overlay your internal handoffs. Where is the friction, frustration & fuck-ups? That’s where revenue is leaking. 2. Align Sales, Marketing, and CS on shared definitions of qualification, readiness, and success. No shared language = no shared outcomes. 3. Build feedback loops into your GTM engine — not just dashboards. Revenue is a system. And systems need signals. #GTMStrategy #SymbioticSale #ChiefRevenueOfficer ___ Thanks for reading. I share insights from 17 years working with 40+ B2B SaaS GTM teams. I use LinkedIn to start conversations — so if this resonated, follow me to see more. And if you think I can help you — you know what to do.

Many salespeople get this dead wrong. They start with cold outreach - sequences, DMs, emails, cold calls… But if you haven't nailed the other 3 layers below that, you’re not doing sales... you’re playing the lottery. Here’s the real order of operations if you want predictable pipeline: 🎯 01 Focus Who are we selling to? ✔ ICP definition ✔ Key roles in the buying process ✔ Buying triggers & decision criteria ✔ Industry-specific motion If you're not crystal clear on this, everything above it falls apart. 🧭 02 Positioning Why would they choose us? ✔ Pain points that matter ✔ Clear ROI metrics & value props ✔ Proof you’ve solved this before ✔ Impact of doing nothing This is where most deals are won or lost - before a single call even happens. 📂 03 Pitch What do we say to earn trust? ✔ Talk tracks that resonate ✔ Smart discovery ✔ Objection handling baked in ✔ Stories & customer proof It’s not about your product. It’s about showing you understand their world. 📬 04 Outreach How do we reach them? ✔ Warm intros ✔ Exec alignment ✔ Multithreading ✔ Cold outbound (done right) Don’t start here. Start at the bottom. Build a system that works in any market, not just when leads are hot. If you liked this, you’ll love SalesDaily, where I curate what’s actually working for top reps, managers, and teams. ✔ Battle-tested tactics ✔ Cold email & call frameworks ✔ Daily insights from real sellers Sign up here: https://lnkd.in/gDwCegjS