Corporate Sales Structures

Notes from the field ✍ Agents are taking two very different paths into the enterprise: ▪️ Horizontal Agent Platforms: Sell the “What” These companies position as: “Build a fleet of agents” or “Your enterprise AI layer.” It’s a noun-first pitch. You are buying “agents” - powerful, general and, in the abstract, quite compelling. The problem? The buyer now has homework: define the use case, find budget, justify ROI. In other words, the hardest part of the sale gets outsourced to the customer. The usual response: - “Cool… what should we use it for?” - “Who owns this?” - “Which budget does this come from?” - “Can you help us design a use case?” Sales turn into co-creation and roadmaps resemble consulting. Most didn't set out to become systems integrators, but that is where gravity pulls them when the use case must be invented alongside the sale. These platforms are technically powerful but commercially blunt because they lead with capability (agents) instead of pain (a specific broken workflow). ▪️ Vertical Agents: Sell the “Why” They start with: “Reduce support cost per ticket” or “Resolve 60% of IT tickets autonomously.” Now the nouns are irrelevant. Call it an agent, a bot, or magic. What matters is that it attaches to an existing metric and budget. There is an incumbent to displace - no category creation required. Think Decagon in B2C support, Pylon in B2B support, Serval in ITSM. They’re selling outcomes, not AI. The vertical starting point may looks narrower. Increasingly, operators and CTOs are telling a different story: the fastest way to go broad is to start specific and earn your way out. Traditional vertical SaaS gets boxed in by its workflow. AI-native agents don’t, because the core asset is not the workflow but the layer that observes, orchestrates, and accumulates context across systems. Imagine: - A company launches a customer support agent - automating refunds, order changes, subscription issues. Soon they realize most issues are symptoms of pricing and billing friction. Embedded across CRM and billing, it starts triggering fixes, not just answering complaints. Support automation → control layer for customer experience and revenue leakage. - Another launches in IT - password resets, access requests, provisioning. Soon they realize most tickets stem from identity drift. Sitting across HR and IAM, it expands into security (privilege risk, audit) and finance (license optimization). IT automation → control layer for access entropy. Most enterprise workflows are artifacts of how software was purchased, not how work actually happens. You can have different tools across IT, Support, and Security all compensating for the same upstream limitation. Fix the root constraint and you’re not improving a workflow, you’re collapsing artificial boundaries between them. That’s the opportunity. Start vertical to get distribution, trust, and data. Expand horizontally by following the problem, not by declaring a platform.

One pattern keeps repeating in Enterprise Sales right now. I hear it from every Sales leader, CRO and Sales Rep I speak to. Some are calling it 'Deal Slippage' Others "Elongated Sales Cycles' or simple 'Do Nothing' outcomes. But the premise is the same, deals getting stuck mid-pipe. These deals are a killer for morale, for forecast accuracy and of course for quota attainment. You know the deals I'm talking about...The client is strongly engaged in the early stages, there's a genuine problem to be solved, good traction with their team and then something happens. The momentum disappears, the can quietly gets kicked a bit further down the road. These Zombie deals never quiet die do they?...Instead they just lurch from quarter to quarter, with just enough life to keep them in CRM. If you're dealing with this issue, either personally or across your sales teams, here are 10 Client Red Flags we're consistently seeing in our Client Loss Reviews at the moment. Avoid these 🚩 and you just might put the breaks on your deal slippage problem... 🚩No Genuine Exec Sponsor: If no-one internally has stepped up to defend your deal in the boardroom, or better yet sell the value on your behalf, that's a big red flag. 🚩Lack of Resourcing Depth – Delivery Risk is a huge concern to clients at the moment. If your team feels light or lacking in real-world experience, its a big red flag. 🚩Transition Cost Ambiguity – Hidden, deferred or unclear costs over the life of a project are huge red flags for procurement, who will usually assume the worst and penalise you accordingly. 🚩Top Heavy Team – When sales reps or senior leaders do all the talking, but the delivery team stays quiet, buyers immediately lose faith. 🚩Generic Industry Stories – If client case studies and references don’t sound exactly like their lived experiences, it's a big red flag that you haven't done this before. 🚩Q&A Avoidance – Dodging the hard questions or glossing over the risks, makes buyers assume you can’t answer their critical questions or worse, you don't want to. 🚩Rigid Pricing Models – One number, no options, no flexibility, means buyers feel boxed in and misunderstood, suggesting heighted risk, not certainty. 🚩Governance Gaps – “We’ll work it out post-award” is code for chaos, poor governance and delivery risk. Avoid at all costs! 🚩Slow Responsiveness – Slow response times, suggest slow delivery times, a lack of urgency and poor internal process. Clients think "If this is what you're like before we sign, how slow will you be after we buy" A huge red flag for enterprise clients. 🚩Risk Blind Spots – If you can’t name, explain, manage and mitigate their risks, clients will assume you haven’t seen them or worse, have intentionally ignored them. I could easily share another 20 client 🚩 we often uncover on a daily basis. Instead I'd love to hear one red flag you always look out for, as a sign a deal maybe straying off course?

How I run sales meetings that lead to next steps 90% of the time. Running a successful sales meeting involves clear communication before, during, and after. Often, attendees aren't sure what to expect, so we have to make sure to set the tone before the call even happens. So I send an agenda 24 hours prior to the call and include the following. • What topics will be discussed • Questions to answer beforehand • Use cases if applicable Also, make sure to do some research about the company so you have context. No one likes an unprepared sales rep. During the call immediately set expectations. • Ask if they have a hard-stop • Refer back to the email to set the agenda for the call • Mention that you did some research and tell them what you found Be an active listener and ask deep discovery questions to uncover pain. As the call wraps up, make sure to leave 7-9 minutes to guide them through the next steps. Here is an example: "Typically, when we see a problem like this, we would most likely include (x person) and (y person) on the next call to discuss how we help in that area. Would Thursday at 10am EST work for you?" I book these meetings directly from Calendly's browser extension while still on the call because it's quick, smooth, and instant. Calendar invites are sent before we end the call so you remove the possibility of being ghosted after. We still have work to do after you nail down the next steps. We ain't done yet. Send a summary email, not to do more selling but to recap for accountability. • What their main goals/priorities are • Timeline • Next steps When you have a system to run better meetings, it leads to great results. P.S. Do you agree with this framework? #BetterMeetings

One salesperson had brought in 20 of the company’s 23 customers. That wasn’t only a success story. It was a warning. The person was clearly talented. They had strong relationships. They understood the market. They knew how to create trust and move conversations forward. But the number exposed something else. The company had not built a sales capability. It had built a dependency. There is nothing wrong with having exceptional performers. Every company wants them. The risk begins when customer trust, account knowledge, sales judgment, and revenue creation remain concentrated in one or two people. That creates vulnerabilities many CEOs do not see until something changes. The top seller leaves. They burn out. They reach their capacity. A key contact moves to another company. Their existing network stops producing at the same rate. Then leadership realizes the rest of the team was never truly developed. A strong sales organization is not defined only by how much its best person can produce. It is also defined by how well the company transfers what works. Can managers develop sound judgment in other sellers? Can multiple people build executive relationships? Can customer knowledge survive a transition? Can the team create pipeline without relying on one person’s reputation? Can the company continue growing when the hero is no longer available to carry it? Your top performers should be an advantage. They should not be the infrastructure. How much of your revenue confidence still lives with the same one or two people?

This is the most underrated problem I've seen when trying to build or expand partnership GTM: Leadership is initially fully behind a new partnership, excited about its potential, but that enthusiasm never makes its way down to the sales teams who are expected to execute. Without alignment, even the best partnership can stall before it has a chance to succeed. Why does this happen? Sales teams are often focused on their core products, and if a partnership doesn’t clearly benefit them or fit into their day-to-day operations, it becomes an afterthought. To turn things around, you need to make sure your partnership incentives, compensation, and training are in lockstep with the teams that will be selling your product. Here’s how to align incentives and drive results: 1. Ensure your incentives are compelling enough for frontline teams. It’s not enough to excite leadership—sales teams need a clear, tangible reason to sell your product. - Introduce a financial incentive or bonus structure that’s competitive with what reps earn on their core products. This could be a one-time bonus for the first sale, or an ongoing commission that rewards consistent effort. -Tie the incentive to their existing sales goals. If your product helps them hit their targets more easily, they’ll naturally prioritize it. 2. Structure partner compensation to motivate co-selling. If your partner compensation doesn’t align with their core goals, they won’t push your product. - Design a compensation plan that aligns with both the partner’s and your business objectives. For instance, if your partner’s core offering is hardware, incentivize bundling your software as part of the sale to create a win-win situation. - Offer performance-based incentives that reward partners for hitting key milestones—whether that’s a certain number of units sold, a specific revenue target, or even customer engagement metrics. Keep it simple and measurable. 3. Provide consistent training and engagement so your product isn’t just another checkbox. Sales teams won’t advocate for your product if they don’t fully understand its value or how to sell it. - Develop ongoing, bite-sized training sessions that fit into their schedules. Instead of overwhelming them with lengthy sessions, focus on 15-minute, high-impact trainings that teach them how to identify the right opportunities. -Pair training with real-time support. Join sales calls, offer one-pagers, and provide direct assistance during key customer engagements. When they feel supported, they’re more likely to feel confident pushing your product. This kind of alignment can make the difference between a stalled partnership and a thriving one. When sales teams are motivated, equipped, and incentivized to sell your product, the partnership stops being just another checkbox—it becomes a key driver of growth.

𝗪𝗵𝗲𝗻 𝗘𝘃𝗲𝗿𝘆𝗼𝗻𝗲 𝗢𝘄𝗻𝘀 𝗔𝗹𝗶𝗴𝗻𝗺𝗲𝗻𝘁 - 𝗡𝗼 𝗢𝗻𝗲 𝗗𝗼𝗲𝘀 Every team claims they’re “aligned.” Until you ask them to show 𝘵𝘩𝘦 𝘴𝘢𝘮𝘦 𝘯𝘶𝘮𝘣𝘦𝘳𝘴. Marketing shows sourced pipeline. Sales shows committed pipeline. Finance shows recognized revenue. Ops shows dashboards that don’t match any of the above. That’s not alignment. That’s four versions of truth fighting for airtime. Alignment dies when it’s everyone’s responsibility and no one’s scoreboard. Real alignment isn’t a slogan. It’s operational. It looks like this: 1️⃣ 𝗦𝗵𝗮𝗿𝗲𝗱 𝗗𝗲𝗳𝗶𝗻𝗶𝘁𝗶𝗼𝗻𝘀. “Pipeline” means the same thing in every system. No shadow spreadsheets. 2️⃣ 𝗦𝗵𝗮𝗿𝗲𝗱 𝗧𝗶𝗺𝗲𝗳𝗿𝗮𝗺𝗲𝘀. Everyone reports on the same window - not one team on months, another on quarters. 3️⃣ 𝗦𝗵𝗮𝗿𝗲𝗱 𝗖𝗼𝗻𝘀𝗲𝗾𝘂𝗲𝗻𝗰𝗲𝘀. If a number misses, all owners feel it - not just one function. Because alignment isn’t a meeting or a mindset. It’s a contract between teams. And like any contract - it’s meaningless without enforcement. 𝗤𝘂𝗲𝘀𝘁𝗶𝗼𝗻: When your teams say they’re aligned, what’s the proof? #RevenueActivation #Leadership #GTM #SalesAlignment #Execution

My client called me in a panic "Our sales have flatlined for 3 quarters straight. We've tried everything." I asked to see their pipeline metrics Within 60 minutes, I spotted the problem Their sales weren't dying at the closing stage → They were dying in the handoff between SDR and AE Here's what the data revealed: - SDRs were generating 40% more meetings than last year - But 60% of those meetings never progressed past call #1 - The prospect was interested, then... nothing I shadowed 5 of these handoff calls The issue became painfully obvious: - The SDRs were selling a dream - The AEs were selling reality Different messages Different promises Different expectations The prospects felt deceived, so they disappeared Over 10 years helping companies accelerate sales growth, I've seen this pattern repeatedly Sales teams think they have a closing problem What they actually have is an alignment problem We implemented a 3-Stage Pipeline Alignment Framework: - Created a unified talk track across all buyer touchpoints - Developed a structured handoff protocol with specific language - Built a feedback loop between SDRs and AEs Results after 60 days: Meetings-to-opportunity conversion: Up 70% Sales cycle: Reduced by 22 days Win rate: Increased 30% Q4 revenue: Beat target by 28% This wasn't about new leads or better closing techniques It was about fixing the invisible leak that was draining their pipeline Your sales team doesn't need more prospects It needs a seamless revenue motion What's your biggest sales pipeline concern right now? P.S. If you need help with your sales, send me a message

Last year, I worked with a SaaS team where Sales blamed Marketing for “bad leads,” and Marketing blamed Sales for “not closing enough.” Sound familiar? Fast forward 6 months: They closed 4 enterprise deals worth $2M ARR. The change? They didn’t “work harder”—they worked together. If you’re running ABM and your Sales and Marketing teams are siloed, you’re leaving $$$ on the table. Here’s why: 💡 ABM isn’t a “marketing strategy.” It’s a team sport. Want Sales and Marketing to stop clashing and start cashing in? Here are 4 battle-tested moves for killer collaboration: 1️⃣ Build ONE Playbook. Share insights into target accounts. Map engagement history (no “who emailed them first” drama). Align on pipeline progress in real time. 2️⃣ Sync on Tech. Use the same CRM and automation tools. Real-time data = no excuses. Example: When an account downloads a whitepaper, Marketing preps the nurture sequence while Sales plans the next call. 3️⃣ Tailor Content Like Pros, Not Amateurs. Marketing: Create hyper-relevant content for specific accounts. Sales: Feed Marketing intel on what prospects are actually asking. Together: Deliver messaging that solves real problems, not just “thought leadership.” 4️⃣ Meet, Measure, Repeat. Weekly strategy sessions = no surprises. Shared KPIs (engagement, pipeline velocity, deal size) = accountability. Celebrate the wins together (or fight over who gets the credit later). 😉 Here’s the punchline: When Sales and Marketing stay misaligned, ABM becomes “Account Blaming Marketing.” But when they sync up, magic happens: 🔹 Better engagement. 🔹 Shorter sales cycles. 🔹 Higher ROI. The question is: Will your teams collaborate or compete in 2025? Let’s hear it—what’s your #1 tip for aligning Sales and Marketing for ABM? Or what’s your biggest challenge? 👇 #ABM #Sales #Marketing #Collab #B2B #SAAS

Strategy isn’t a slide. It’s a fight worth having. I’ve been quiet here for a day because I just came out of two intense, energizing sessions with our extended strategy team. And I’m still fired up. 💥 We pushed each other hard. We challenged assumptions. We laughed a lot. And we left with crystal-clear alignment and a shared determination to think bigger, move faster, and win as one team. Our focus: ✅ Think Big, Go Fast Not in months and quarters. In days and weeks. ✅ Win Every Key Moment in the Customer Journey Especially the ones that define value and long-term loyalty. ✅ Win as One Team Not your team, not my team. Our team. Rooted in shared goals, not personal preferences. For some reason, I usually get to help moderate these sessions. That’s no small task with 25 to 30 strong leaders in the room from every department. But it gives me a front-row seat into how we build alignment that lasts. Here’s what works for us and might work for you: 1️⃣ Be clear up front Why are we meeting? What are the most important objectives? And how exactly are we going to win together? Set the tone early. Remove ambiguity. Drive purpose. 2️⃣ Bring the voice of the customer into the room 🎤 The most substantial alignment starts with empathy and clarity around what matters most to our customers. When we anchor the conversation in value needed and delivered, priorities become clearer and conflict becomes productive. Customer insights create unity. 3️⃣ Make cross-functional ownership real 🤝 Everyone says “we’re one team.” But real alignment means we walk out with shared KPIs, not siloed tasks. Product, Sales, CS, Ops, we all succeed only when we move together. 💬 So here's my call to action for you today: If you’re leading in CS, CX, Product, or Revenue, and you’re halfway through Q3, ask yourself: Are you chasing alignment? Or are you building it through purpose, participation, and shared accountability? The next level doesn’t arrive by accident. We create it. Together. #CreateTheFuture #LeadershipInAction #CustomerSuccess #StrategyExecution #CrossFunctionalAlignment #OneTeamOneMission #Q3Momentum

The fatal flaw killing most go-to-market strategies (and no, it’s not pricing)... Being a CRO was the best thing I could’ve done for my career, not just for understanding sales, but for seeing how broken the relationship between sales and marketing can be. Most companies still treat them as separate functions, sometimes even rival camps. But if you’ve ever actually carried a revenue number, you know: Sales needs to embed within marketing. Not “collaborate with.” Not “align with.” Embed. 👉 Companies with strong sales and marketing alignment achieve 208% higher marketing revenue than those without it. 👉 And yet, 90% of B2B buyers say their purchase journey is disjointed... the result of siloed messaging and poor handoffs. Why? Because in too many orgs, sales is flying blind on what marketing is producing, while marketing doesn’t hear what’s happening in the field. But the best sales orgs are shaping demand, reading the market in real time, and feeding that signal back into messaging, creative, targeting, and even product. They're not sitting around waiting for leads. The loop between sales and marketing should be tight. Sales should know what campaigns are going out next week, and marketing should know what objections are coming up on calls today. When I was CRO, I sat inside the marketing team. Listened to campaign planning. Reviewed creative briefs. Gave direct feedback on what the sales floor was actually hearing. It made a difference. That experience forever changed how I think about building go-to-market teams. It’s not about “alignment.” It’s about complete integration.