Building Trust with Enterprise Clients as a Small Vendor

68% of enterprise buyers trust founders more when they share specific failures instead of polished success stories. 1. Founders who shared detailed breakdowns of specific failures saw more sales conversations. 2. Posts about "product pivot failures" outperformed "success story" content. 3. Enterprise buyers spent much longer time engaging with failure analysis content. 4. Follow-up response rates jumped 287% when outreach referenced specific founder learnings. 5. Deal velocity increased to nearly double when failures were openly discussed during sales process. IT'S CRYSTAL CLEAR. But most founders are still stuck in the "we must look perfect" trap, unknowingly destroying trust with their ideal customers. Here's the reality nobody talks about: Enterprise buyers don't trust polished success stories anymore. They've been burned too many times by vendors who oversold and under-delivered. What they desperately want is proof that you understand the real challenges because you've lived them yourself. But there's a specific framework for turning failures into trust-building content that actually drives pipeline: 1. Focus on one specific failure (not general "lessons learned"). 2. Share exact numbers and metrics. 3. Break down the false assumptions that led to the failure. 4. Detail the specific changes made afterward. 5. Show clear before/after results. The founders who master this framework consistently outperform their competitors in: - Pipeline generation - Sales conversation quality - Deal close rates - Customer retention Because they're building real authority through authenticity, not manufactured "thought leadership."

Your clients think you’re replaceable.... Here’s why: Most MSPs only show up → When something breaks. → When there’s a ticket. → When it’s already too late. So your client sees you as: ✅ A cost ❌ Not an investment ❌ Not a partner ❌ Not a strategic advantage And that’s the problem. Because the moment someone cheaper shows up… They’ll leave. You’ve made yourself optional. You’re not building trust. You’re fixing issues. You’re not guiding direction. You’re reacting. And firefighting may feel productive. But it’s not progress. It’s just survival. If you want to stay top of mind, If you want to be irreplaceable, You need to stop showing up only when it’s urgent. Start showing up when it’s strategic. One of the best ways to do that is by having regular check-ins with your clients. Most call it QBRs, but it doesn’t matter what you call it. What matters is how you run them. Here’s how to run a QBR that makes you a partner 👇 1️⃣ Set the tone early Let your client know this isn’t about ticket reviews. It’s about where their business is going and how tech can help them get there. That shift alone positions you as a partner, not support. 2️⃣ Ask smarter questions You’re not there to report. You’re there to uncover opportunities. Ask things like: • What’s slowing your team down right now? • What’s your top growth goal this quarter? • Where are you wasting time or money? • If tech could fix one thing, what would it be? This turns a basic review into a strategic conversation. 3️⃣ Bring relevant, high-impact recommendations Skip the PDF reports. Show up with 2–3 clear, strategic suggestions. Examples: • Automate onboarding for new employees • Improve remote work experience • Prep systems to handle hiring growth Every idea should tie back to a business goal. Not just a technical fix. 4️⃣ Share one proactive insight Bring something they didn’t ask for but need. This builds trust fast. Spot a risk? Highlight it. See an opportunity? Lead with it. That’s how you show leadership, not just service delivery. 5️⃣ End with a clear next step Always leave the QBR with forward motion. Agree on a decision or action: • Approve a proposal • Run a tool trial • Book a deep-dive audit • Create a 30-day improvement plan No vague “follow-ups.” Give them clarity before you close the call. 6️⃣ Schedule the next QBR before you leave Don’t wait for the relationship to go quiet. Book the next session on the spot. That consistency builds trust over time. It keeps you top of mind. It makes you harder to replace. It creates long-term growth. If you're focused on doing more of that— I'm launching my FREE MSP community today. It's for owners who want to scale with real systems, free resources, and support that actually helps. DM me, and I’ll send you the link when it goes live. Would love to have you in there!

“You’re the one who closed it. You’re the one who owns it.” That’s what I was told after closing my first seven-figure enterprise deal—into a market our company had never sold into before. I assumed there’d be a handoff. Instead, I became the face of the partnership. Onboarding. Product delivery. Executive alignment. Renewal strategy. All of it. We had committed to roadmap work and new workflows. Expectations were sky-high, and we were building as we went. There was no process for handling escalations. So I wrote one. There was no precedent for how to communicate when we missed. So I set the tone. I remember one of our first post-sale calls. The customer asked me to send a recap. I had taken notes—but I hadn’t expected to be the one sharing them. That moment reshaped my thinking. In the post-sale phase, the expectations aren’t lower. They’re higher. The details matter more. And how you follow through becomes the measure of trust. Then came the moment I’ll never forget. At the customer’s annual conference, one of their daily users approached me during a happy hour with a list of concerns. I listened, acknowledged, and promised to follow up. She kept going—not because she didn’t believe me, but because she needed to believe someone would act. That’s when her CEO stepped in and said: “If Sarah says she’ll follow up, she will. I’ve seen it firsthand—she delivers.” That moment stayed with me. Because trust may begin in the sales cycle, but it’s earned through execution—especially when things don’t go according to plan. Years later, at another event, a different end user from that same customer came up to me and said: “Thank you. What we’re doing together is making a real difference in people’s lives.” I managed that relationship for over a decade. What started as a new market experiment became a flagship account and a defining chapter in my career. Here’s what I’ve learned: * Set the tone early. The way you show up during the sales process shapes how customers experience everything that follows. * Think long-term. It’s not just about the close. It’s about building value that compounds over years. * Own the outcome. When issues arise, don’t deflect—lead. Be the steady voice that drives solutions. * Build trust that lasts. Trust is earned through consistency. Deliver on what you say, especially when it’s hard. Because the best sellers don’t just hit quota. They lead. They deliver. They become the reason customers stay.

Here's the playbook we used to close our first couple of public company customers as an early-stage startup. First, selling to enterprises is very different than SMBs. It is less transactional and more about relationships. Here are some things we did that helped us - Start consultative - In all of the deals our initial calls were consultative. We would give a short introduction, 2-3 min of our background and product, and the rest was active listening. The goal was to understand what matters to them, where are they focused as an org that you can potentially help with. Deep Research - Before even the first call you should have a thesis on how your company can help them. Understand everything that is going on in the company. I review - earnings calls, LinkedIn profiles + posts from people we are meeting, news articles about the company, what is on the website, podcast appearances from leadership, and job openings. Do the work - The burden of proof is on you - not only would we do live demos, during the process we would go out of our way to show how we can deliver value. One example involved shipping a potential feature discussed in a 4 p.m. meeting by 9 a.m. the next day, so our champion could showcase it in an internal meeting. Another - we built a simple POC for them to prove our product could solve EXACTLY what they were looking for before signing any contracts. There is some risk here - but until you have a brand name, it is up to you to earn their trust. Get on the plane - All of the deals had multiple in-person touch points with different stakeholders. We found this to be important during the building trust phase. Multithreading is key - Doing things like sending emails to invitees in advance of calls was a helpful strategy to know what to address. Then, after each call or conversation with multiple participants, I would send personalized follow-ups addressing things we discussed that were relevant to them. I have been leaning into all of the above for our existing pipeline as well and seeing great results. If you are looking for additional sales advice for founder-led sales, I learned a lot from - Jason M. Lemkin, Jen Abel, Peter Kazanjy, and Sam Blond

When I started building Nerdio, my biggest decisions weren’t about technology stacks or feature roadmaps. They were about trust. Even before flexible work became a necessity, we made it a core value. We trusted our people to work wherever, whenever—as long as they were crystal clear on our mission and on what outcomes truly mattered. Instead of the typical top-down policies, we fostered real autonomy and ownership. Our culture started feeling less like a hierarchy and more like a partnership. But here’s the unexpected part: That trust didn’t stay inside the company. It overflowed into our relationships with customers. When our team feels empowered and heard, they show up for customers with more energy and urgency. And when customers know we’re not just listening—but acting on their feedback—the trust goes both ways. We gain even more insight into which problems are urgent and which solutions will really move the needle. This trust, internally and externally, drives a feedback loop you can see every day: in how we build, how we support, and how we automate the messy parts of Microsoft cloud management for IT teams who are stretched thin. For our customers—MSPs and enterprise IT leaders who juggle unpredictable environments—how we treat our team is directly reflected in the experience we deliver. If I could give my younger self one lesson, it would be that: Treat your team as trusted partners. The experience they have internally is the one your customers will feel externally.

Long-Cycle Sales Are Not Won with Pressure… They’re Closed with Precision. Most sales reps treat enterprise contracts like short-term quotes. Big mistake. You’re not just selling a service. You’re managing a complex decision-making process across multiple stakeholders, risk profiles, and compliance fears. Sound familiar? - Months-long buying cycles - Procurement reviews - Budget objections etc... You’re not in transactional sales anymore. You’re in enterprise sales. Here’s what the top closers are doing differently: 1. Build Trust Like a Consultant, Not a Closer 87% of B2B buyers say trust is the #1 factor in their decision. > Not price. > Not speed. > Not ROI. That means: - Leading with insight, not pressure - Admitting when you’re not the best fit - Knowing their industry as well as your own Your credibility is the contract. Lose it, and the deal’s dead... 2. Create Urgency Without Destroying Trust Artificial deadlines? Gimmicks? Buyers see right through it and they vanish. Instead: - Show the cost of inaction (lost revenue, failed audits, poor reviews) - Tie your timeline to their goals I.E. what's important to there business. - Offer exclusive benefits for early adopters Urgency works best when it feels like alignment, not pressure. 3. Guide the Buying Journey with a Mutual Action Plan (MAP) 77% of B2B buyers say their buying process is overwhelming. If you’re not leading the process, you’re losing it. The best reps co-create a roadmap that outlines: - Who’s involved - What needs to happen - What success looks like This removes friction. It keeps momentum. And it positions you as the pro who’s orchestrating success... 4. Engage Every Stakeholder… Especially the Skeptics Most pest control reps talk to their champion and hope for the best. Elite closers multi-thread across departments: - Ops - Legal - Procurement They ask: > “Who else needs to be involved so we can get this done right?” - They find the skeptic. - They win them over early. - They never leave the champion to fight alone. 5. Close with Proof, Not Pressure In the final mile, trust alone won’t close the deal. You need: - ROI calculators - Case studies - Visual proposals - Risk mitigation data Make the business case so strong… The only rational answer is “Let’s go.” What Sales Reps Must Remember: You’re not just selling a solution. You’re selling safety, reputation, and operational continuity... And if you're still relying on pressure tactics instead of enterprise precision? You’re going to lose. But if you’re ready to start closing like the pros? - Lead with trust - Anchor urgency in reality - Back it all with proof Then you’ll not only win the deal. You’ll own the process... "Lead Different. Sell Smarter. Win with Purpose." --- ♻️ Share this post with a sales leader who needs to hear it. 👉 Click here: Follow me on LinkedIn: https://lnkd.in/eA7csH2q Join our community of 39,000+ sales professionals today! P.S. Thanks for reading!

I Lost a client, Then I Learned This. 3 years ago, I was talking to a potential client who needed help with business development. They were struggling to generate leads and close deals, and I knew we could solve their problem. I did what most business developers do, I pitched. I told them about our proven strategies, our automated systems, how we’ve helped other companies grow. I thought I nailed it. But then… silence. They ghosted me. A few weeks later, I saw that they had signed with someone else. Curious, I reached out and asked what made them choose another company. Their answer? “They gave us so much value before we even signed. It just made sense to go with them.” That hit hard. But it was a game-changer. From that moment, I stopped selling first and started helping first. Now, before I ever pitch, I: ✅ Share insights on business growth strategies and industry trends. ✅ Audit their current lead generation and sales process (for free). ✅ Introduce them to someone valuable in my network. The result? I don’t chase clients anymore. They come to me. Lesson: People don’t buy because you have a great service. They buy because they trust you. And trust is built by giving first. What’s one way YOU provide value before selling? #BusinessDevelopment #Sales #Trust #Entrepreneurship