How to Engage Stakeholders as an Enterprise Seller

Most sellers only uncover ONE level of impact in discovery. That’s why their deals stall, why their ROI slides don’t land, and why their champions can’t sell internally. The truth? There are 4 levels of impact—and if you miss even one, you’re selling half-blind. Selling is helping. But helping means going deeper than “company KPIs.” Here’s the framework I coach every AE on when they’re trying to win enterprise SaaS deals: 1. Company Impact This is where 90% of reps stop. “What’s the cost savings? What’s the revenue upside?” That’s table stakes. If you don’t tie your software to actual numbers—lost revenue, margin impact, labor cost—your ROI story collapses in front of a CFO. Example: A Service Cloud rep I coached quantified millions lost in unbooked hospital referrals because of missed scheduling calls. That turned a “$500K tool is too expensive” into “8X ROI, no-brainer.” 2. Buyer Impact Your champion has skin in the game. They left a stable job. Their reputation, career trajectory, even their family’s well-being are tied to this project. If you can show them how your solution makes them the hero internally, you create unstoppable personal buy-in. 3. User Impact These are the people who log in every day. If they hate the tool, adoption dies. If they love it, productivity soars, morale improves, turnover drops. Shadow them. Ask what frustrates them. Show them a better day in the life. 4. Customer Impact The most overlooked layer. How does your product improve the end customer experience? Faster service, better outcomes, less stress? For a hospital, it’s not about “efficiency.” It’s about a patient getting a life-saving scan booked in hours instead of days. Stop selling features. Stop selling “savings.” Start selling IMPACT. - Company. - Buyer. - User. - Customer. Miss one—and you’ll miss the deal. Hit all four—and you’ll never sell the same way again. Selling is helping. Always.

The #1 reason your enterprise deals are stalling (and it's not what you think) I watched a sales team lose a $700K deal last month because they were relying on ONE champion to push it through. The champion loved the product. The champion had authority. The champion was "fully committed." Yet the deal still died. Why? Because in 2025, the "single-threaded" sales approach is completely broken. Modern B2B deals involve 11+ stakeholders, and if you're not building relationships with ALL of them, you're setting yourself up for failure. Here's what actually works: 1) Build a complete relationship web After EVERY meeting, send the group recap AND individual personalized emails to each attendee. This creates multiple champions instead of one. 2) Move contacts strategically through stages Contact → Trust Building → Advocate For each stakeholder, send targeted content that addresses THEIR specific priorities, not generic materials. 3) Be the orchestration catalyst 84% of companies report poor internal collaboration. Your prospects don't know how to buy effectively. Pre-plan the additional meetings needed ("We'll need a technical deep dive with your IT team next week, then a separate ROI discussion with finance") 4) Use digital tools to scale yourself Create 3-4 minute targeted demo videos for different stakeholders (one for Marketing, another for Finance, etc.) Use LinkedIn Sales Navigator's relationship map to visualize and track your relationship web. The deals I'm seeing die aren't lost to competitors, they're lost to indecision and lack of consensus. Master buying team orchestration, and you'll close deals your competitors can't even keep alive.

Last week I spoke with an enterprise AE at F100 company who closed over $5M in 2023 (3x his quota). The surprising part? He generated 90% from Linkedin. Here’s what the enterprise social selling playbook looks like: 1. Community: Successful sales reps are constantly enhancing their community on Linkedin. They invite key prospects, customers and other stakeholders to their network. As an AE or Exec, it helps to stay in the same domain over time so you can engage with the same community but across different employers. The compounding effect of your network is exponential. 2. Content: Engage frequently with your community. Stay ahead of the curve and ensure your content reflects that. Not all content has to be original and unique. Most Linkedin users are looking to consume content that will help them be better at their job today. Share best practices, success stories and recommendations. If you stay in the same domain, the quality of your content will grow as you build trust within your community. 3. Signals: Get a good understanding of the triggers and signals that impact demand in your target segment. Use these signals to focus your attention on select individuals as they become active. 4. Offer Help: Be mindful of any request for assistance within your community. If you are going to stay in the same domain for long, expect your community to do the same. Offer to assist even if it does not directly help your business. Chances are these interactions will lead to deep relationships in the long run. 5. LinkedinOps: This is often an ignored part of social selling. For the same reason that Inbound leads perform so well (because they are warm), somebody that visited your profile also has a relatively high probability to respond in the first 24hr. It’s the job of LinkedinOps to run all active engagers through an ICP filter and then follow up on good fit candidates. 6. Outreach: I have seen some successful reps use personalization tools to find the right messaging or conversation opener for Linkedin outreach. It makes sense to do an outreach with the good-fit engaged audience within 24-48 hrs of the engagement. Don’t hesitate to ask for referrals. 7. Tracking: Track engagements and metrics. Score and rank your audience every week for good fit top engagers. Your top engagers are the ones who will likely take your call. Your LinkedinOps can help you with analytics. 8. Convert: Know when and how to move your conversation outside Linkedin. Linkedin is great for capturing demand signals or for generating trust. Look for the right moment to share a calendar link or an email to move the conversation to a different platform. TAKEAWAY: Your buyers are already on Linkedin. With a little discipline and LinkedinOps, you can close revenues while enhancing your brand and handling objections at scale. I've been helping GTM teams for 15+ years. Never before have they had access to such a powerful platform. Take advantage.

I’ve now closed $7M in enterprise deals. Here’s how I personalize the pitch for each stakeholder: 1/ Talk to THEIR customers Before the first pitch, I talk to people who already use their product. Instead of selling features, I use their users’ words to diagnose their problem: “I talked to a few of your customers, and they mentioned that X was a pain. What if there was a way to have [solution]?” ----- 2/ Reframe using analyst positioning I read reports from Gartner, Forrester, or G2 to see who the buyer is being lumped in with. Because every enterprise buyer has a comparison they hate. I’ll often anchor the conversation with: “This gives you a concrete way to separate from X, Y, and Z when those comparisons come up.” This gets us talking about positioning, risk, and narrative, which helps me uncover what the execs actually care about. ----- 3/ 10-K reports are your friend A 10-K is the company telling you what matters this year. In one deal, I kept getting polite interest, but no urgency. So before the next meeting, I read their most recent 10-K. One thing jumped out: they had explicitly committed to improving reliability as a top company priority. In the next call, I honed in on how we can help with that. That was the first time the conversation clicked. Suddenly, we were tied to something leadership had already promised the market. ----- The goal of all this is nuance. You’re trying to speak their language.

The best AEs break the buyer / seller dynamic early and continually throughout a sales cycle. They provide value, serve as a trusted advisor, and foster constructive tension to drive action. The rubber band analogy always stuck with me, the best reps stretch the rubber band and create that healthy tension, just before the point where it snaps. It’s in that healthy tension where value is created and action is taken. You will be uncomfortable, and that’s a good thing. A few of my favorite ways to do this- 📊 Bring Insights: Share something they don’t know about their own business, reframing their problem in a way that makes them think differently. This positions you as an expert and shifts the dynamic from seller to advisor. You need to be able to add actual value to their business, beyond product promises. —“Most companies in your space think their biggest challenge is [X], but what they’re missing is how [hidden challenge / insight] is actually driving those inefficiencies. Here’s what top performers are doing differently to stay ahead…”— 💵 Reframe Value: Stop talking price - focus on the business impact. Show them the cost of doing nothing and tie your solution directly to the outcomes they care about. Make it impossible for them to ignore the value. —“Right now, you’re spending [X amount of time/resources] to address this, but it’s costing you [specific business impact]. If we can fix this, you’re looking at [clear business outcome]. What would that kind of impact mean for you this quarter?”— 🤝 Create Constructive Tension: Push them out of their comfort zone. Use data and smart questions to show why sticking with the status quo is risky. The goal is to make staying the same feel more uncomfortable than making a change. —“If nothing changes, how long can you sustain [current situation] before it starts affecting [key business priority]? Based on what I’ve learned, and other companies I’ve spoken to in your situation, it sounds like this isn’t something sustainable, would you agree?”— 🎯 Tailor to the Buyer: Know your audience. Speak to what matters most to each stakeholder - ROI for the economic buyer, seamless integration for the technical team, and real results for the end users. The more personal, the more effective. —“For you as the [economic buyer/technical lead/end user], I know [specific priority] is critical. Here’s how we’ve helped companies in similar roles solve [specific pain point] and achieve [measurable outcome]—does that align with what you’re trying to accomplish?”— Shed the bad habits from the ZIRP era, and start selling!

Your "enterprise deal" is actually six small deals, each standing on each other's shoulders, wearing one of those creepy trench coats. Justin broke things down this way during a Sales Assembly session, and IMO it provides some clarity on how you think about moving upmarket. Every stakeholder in your deal is their own sales cycle. Your champion is one deal. The CFO is a different deal. The IT lead is a different deal. You're running five or six simpler sales in parallel, and the ones you forget to run are the ones that kill you. Colin on the buying committee might be upside down on his mortgage, thinking in 90-day survival windows. Lisa might be planning her career in 36-month horizons. Same deal. Completely different buying psychology. If you pitch them the same story, you'll lose one of them. Probably both. So the move is treating each stakeholder like their own opportunity with their own stage, their own fears, and their own definition of winning. Build a stakeholder deal board. Each person gets their own row: - What they care about personally. - What scares them about this decision. - What winning looks like for them. - Where they are in their own mini-cycle. Your champion might be at "ready to fight for this internally." Your CFO might still be at "hasn't connected this to a problem I care about." Those are two completely different stages inside the same opportunity, and your CRM record says "Stage 3" for both of them. Then ask different questions to different people: - Your champion gets "what do you need from me to sell this internally?" - Your CFO gets "what would have to be true for this to make your priority list this quarter?" - Your IT lead gets "what's failed before and what made it fail?" Running the same discovery script across a buying committee is like prescribing the same medication to six patients with six different conditions. Finally, here's a nugget that should change how you map deals: find out how each stakeholder is actually evaluated by their boss. If Lisa gets bonused on headcount efficiency and you're pitching a solution that "reduces manual workload," she might be hearing "this tool eliminates my team's justification for existing." Same feature. Opposite reaction depending on whose career it touches. Tie your value to their personal win condition, not just the company's business case. The deals that die in ENT do so in the gap between the stakeholder you sold and the stakeholder you forgot existed. Run a weekly check: who haven't you talked to in two weeks? Who has never told you why they personally want this? That silence is where deals go to quietly suffocate a slow, uncomfortable death. ENT deals should NOT be treated as one big complicated thing. Treat them as six small clear things that all need to close on the same timeline. Don't let the complexity paralyze you. Just break it into humans and sell to each one.

If I could give one piece of advice to a seller trying to engage me, a VP of Talent Acquisition, it would be this: Stop leading with your technology features…and start by showing a deep, nuanced understanding of my single biggest challenge: attracting and retaining top-tier talent at scale. Here’s the common misconception: Sellers often assume I’m driven by cutting costs or chasing the latest shiny tech. In reality, my 20+ years leading and scaling global HR functions have taught me that my ultimate responsibility is to secure the talent that fuels company growth…whether that means building a small, high-performing team or hiring 3,000+ people in a single year. What makes me tune out: Boilerplate emails about “improving efficiency” or “streamlining processes” with no connection to real talent outcomes. I’ve built and launched global TA functions. I’ve implemented countless TA platforms and tools. A generic pitch tells me you haven’t researched my business priorities. What makes me lean in: A seller who connects their solution directly to my strategic goals: > How will your solution help us manage massive volume and maintain quality, matching the success of my former team, which hired over 3,000 people in a single year, all without lowering the quality bar? > Targeted Engagement: How does your technology dramatically improve our ability to strategically identify and engage passive, high-demand talent and convert them into active candidates? > Driving Diversity & Quality: At a prior employer, I achieved a 63% diversity hire rate. Can you show me how your product will enhance that kind of D&I strategy? > Data integrity & Analytics: Reliiability of data is paramount. The ability to then analyze that data is mission critical. Does your solution solve this historical shortcoming of the TA tech stack? > Elevating Experience: How does your technology materially improve the hiring manager and candidate experience, turning a high-volume process into a high-touch strategic engagement? Frankly, in a high-growth environment, I’m already leveraging AI tools for competitive advantage. The best sellers use those same tools (like Salesloft’s Buyer Identification Agents and Person Research Agents) to understand my background before they ever reach out. My advice is simple: Great selling means understanding that my strategic goals aren't about the tool. They’re about talent. Show me how you help me win the talent war, and you’ll have my full attention. #talentacquisition #leadership #sales #AI #salesloft

𝘐 𝘸𝘢𝘴 𝘣𝘭𝘰𝘸𝘯 𝘢𝘸𝘢𝘺 𝘺𝘦𝘴𝘵𝘦𝘳𝘥𝘢𝘺 𝘴𝘱𝘦𝘢𝘬𝘪𝘯𝘨 𝘵𝘰 𝘢 𝘚𝘢𝘭𝘦𝘴 𝘋𝘪𝘳𝘦𝘤𝘵𝘰𝘳 𝘢𝘵 𝘢 𝘍𝘰𝘳𝘵𝘶𝘯𝘦 10 𝘤𝘰𝘮𝘱𝘢𝘯𝘺. He asked: “𝗔𝗿𝗲 𝗯𝘂𝘀𝗶𝗻𝗲𝘀𝘀 𝘀𝗽𝗼𝗻𝘀𝗼𝗿𝘀 𝗿𝗲𝗮𝗹𝗹𝘆 𝘁𝗵𝗮𝘁 𝗶𝗻𝗳𝗹𝘂𝗲𝗻𝘁𝗶𝗮𝗹 𝗶𝗻 𝗯𝘂𝘆𝗶𝗻𝗴 𝗜𝗧?” 🤯 It stopped me in my tracks – because while I know the answer, there is a group who do not. Spoiler: the answer is an emphatic 𝗬𝗘𝗦! In fact, in today’s enterprise sales, 𝗯𝘂𝘀𝗶𝗻𝗲𝘀𝘀 𝘀𝘁𝗮𝗸𝗲𝗵𝗼𝗹𝗱𝗲𝗿𝘀 𝗼𝗳𝘁𝗲𝗻 𝗵𝗼𝗹𝗱 𝘁𝗵𝗲 𝗸𝗲𝘆𝘀 to the biggest, fastest technology deals. Here’s what the data and experience are telling us: 🔑 𝗕𝘂𝘀𝗶𝗻𝗲𝘀𝘀-𝗹𝗲𝗱 𝗯𝘂𝘆𝗶𝗻𝗴 𝗶𝘀 𝗵𝘂𝗴𝗲: Non-IT executives now control 𝘵𝘩𝘦 𝘮𝘢𝘫𝘰𝘳𝘪𝘵𝘺 of tech spending. Departments like marketing, finance, and operations are routinely sourcing their own software solutions. If we’re only selling to the CIO or IT manager, we’re missing where 60–70% of the budget lives. 𝗧𝗵𝗲 𝗲𝗿𝗮 𝗼𝗳 “𝘀𝗵𝗮𝗱𝗼𝘄 𝗜𝗧” 𝗶𝘀 𝗼𝘃𝗲𝗿 – 𝗯𝘂𝘀𝗶𝗻𝗲𝘀𝘀 𝗹𝗲𝗮𝗱𝗲𝗿𝘀 𝗮𝗿𝗲 𝗳𝗿𝗼𝗻𝘁 𝗮𝗻𝗱 𝗰𝗲𝗻𝘁𝗲𝗿 𝗶𝗻 𝘁𝗲𝗰𝗵 𝗱𝗲𝗰𝗶𝘀𝗶𝗼𝗻𝘀. 🚀 𝗕𝗶𝗴𝗴𝗲𝗿 𝗱𝗲𝗮𝗹𝘀 & 𝗳𝗮𝘀𝘁𝗲𝗿 𝗰𝘆𝗰𝗹𝗲𝘀 𝘄𝗶𝘁𝗵 𝗯𝗼𝘁𝗵 𝗼𝗻 𝗯𝗼𝗮𝗿𝗱: When you 𝗮𝗹𝗶𝗴𝗻 𝗮 𝗯𝘂𝘀𝗶𝗻𝗲𝘀𝘀 𝘀𝗽𝗼𝗻𝘀𝗼𝗿 𝗮𝗻𝗱 𝗜𝗧 𝘀𝗽𝗼𝗻𝘀𝗼𝗿, magic happens. The deal scope gets larger (because the business side sees more use-cases and is willing to invest more), and the process speeds up (because a senior executive can fast-track approvals and budgets). On the flip side, only pitching to IT often results in smaller, tactical deals – or slow, endless evaluations. 📈 𝗣𝗿𝗼𝗼𝗳? 𝗛𝗶𝗴𝗵𝗲𝗿 𝘄𝗶𝗻 𝗿𝗮𝘁𝗲𝘀: There’s research to back this up. Forrester finds that deals with an executive sponsor are far more likely to close than those without one – as high as ~80% better conversion. When you have the CFO, Head of Sales, or another business leader pushing alongside IT, you dramatically increase your chances of success. 𝗧𝗵𝗲 𝗯𝗼𝘁𝘁𝗼𝗺 𝗹𝗶𝗻𝗲: If you're in sales and are mostly contacting IT Directors, look at ways to expand your scope to other personas and engage them on the business problems that your technology solves. 𝗦𝗲𝗹𝗹 𝗮 𝘃𝗶𝘀𝗶𝗼𝗻 𝗼𝗳 𝗯𝘂𝘀𝗶𝗻𝗲𝘀𝘀 𝘃𝗮𝗹𝘂𝗲 (𝗴𝗿𝗼𝘄𝘁𝗵, 𝗲𝗳𝗳𝗶𝗰𝗶𝗲𝗻𝗰𝘆, 𝗿𝗲𝘃𝗲𝗻𝘂𝗲, 𝗰𝗼𝗺𝗽𝗲𝘁𝗶𝘁𝗶𝘃𝗲 𝗲𝗱𝗴𝗲, 𝗿𝗶𝘀𝗸 𝗿𝗲𝗱𝘂𝗰𝘁𝗶𝗼𝗻) to business stakeholders 𝘢𝘯𝘥 addressing the 𝘁𝗲𝗰𝗵𝗻𝗶𝗰𝗮𝗹 𝗻𝗲𝗲𝗱𝘀 (𝘀𝗲𝗰𝘂𝗿𝗶𝘁𝘆, 𝗶𝗻𝘁𝗲𝗴𝗿𝗮𝘁𝗶𝗼𝗻, 𝗿𝗲𝗹𝗶𝗮𝗯𝗶𝗹𝗶𝘁𝘆) with IT. This creates synergy that leads to 𝗯𝗶𝗴𝗴𝗲𝗿, 𝗳𝗮𝘀𝘁𝗲𝗿 𝗱𝗲𝗮𝗹𝘀. 💰⏱️ Miller Heiman devised this approach over 35 years ago and it still works... 𝗬𝗼𝘂𝗿 𝘁𝘂𝗿𝗻: Have you seen this in your world? 🤔 What other articles, blogs, or books have influenced the way you sell to multiple stakeholders in an account? I’d love to hear about any research or personal examples on engaging business vs. IT buyers. Drop your recommendations in the Comments below! 🙌📚

Enterprise deals die in internal meeting you’re not invited to. It's when your champion presents your solution to the CEO, CFO, or executive committee…and completely butchers the pitch. Not because they don’t believe in you. But because you didn’t equip them to win the room. In enterprise sales, your job isn’t to close the champion. Your job is to make sure the champion closes the real buyer. That means: Building the story they’ll tell the Decision Maker. And anticipating the landmines before they step on one. Here's what Untap Your Sales Potential taught me 1. First, map the buying group. Who else needs to say yes? Who has veto power? 2. Then, co-author the STORY. Use their language. Insert your solution into their goals. 3. Put it all into their template. Make it look like it came from them. 4. And walk them through every likely objection so they show up confident and ready. Here’s a simple story format I’ve used with Champions to win 7/8-figure deals: - What’s the problem? - Why does it matter now? - What’s the cost of doing nothing? - What’s the solution? - What will it take to win? (Cost, timeline, resourcing) - Who else has done it—and what did they get out of it? - What are the next steps? Nail this... And you’ll stop losing deals when you're not in the room. Because the best sellers don’t just find champions. They build internal sellers. Train your champion!!

One of the biggest mistakes I see sellers making is disappearing between meetings. A buyer agrees to a first meeting. Then a second. Then a third. And in between? Silence. No value. No insight. No momentum. Just a calendar invite for the next call. The best sellers that I have ever worked with understand that deals are won and lost between the official meetings. While your buyer is navigating internal politics, evaluating alternatives, and building consensus, you should be helping them move forward. Some simple actions that create momentum: 👉 Share a relevant article that supports a challenge they mentioned. 👉 Introduce them to a customer with a similar business problem. 👉 Send a short video summarizing key takeaways and agreed actions. It could be shared with the broader consensus team. 👉 Connect with additional stakeholders involved in the decision. 👉 Share proof points that reinforce confidence in your approach. 👉 Engage with their content on LinkedIn to stay visible and relevant. 👉 Provide industry trends or competitive insights they can use internally. 👉 Send a concise recap email that helps them socialize the opportunity with colleagues. None of these activities feel like selling. That’s the point. Modern buyers need help making a decision. The sellers who create value between meetings build trust, maintain momentum, and make it easier for buyers to achieve consensus. Curious. Do you do any of these or anything else between meetings that consistently helps move opportunities forward? #B2BSales #BuyerExperience #SalesLeadership #RevenueGrowth #EnterpriseSales #Sales