Common ERP Sales Cycle Challenges

After multiple conversations with multiple sales leaders lately, one thing is clear. Sales cycles are getting longer! It’s no longer just about delivering a great pitch or having the perfect product — decision-making is slowing down, and here’s why: ✅ Budget Scrutiny: With economic uncertainty, buyers are digging deeper into ROI before signing off. ✅ More Stakeholders: The average deal now involves multiple decision-makers, often with conflicting priorities. ✅ Risk Aversion: Companies are hesitant to take risks, preferring to stick to “safe” solutions or delay investments altogether. 🔑 What Can We Do? 1. Lead with Value: It’s critical to show measurable ROI upfront. Solve a pain point before talking features. 2. Focus on Education: Help your buyers justify the purchase internally with resources, data, and insights. 3. Strengthen Relationships: Deals might take longer, but consistent follow-ups and genuine connection-building will keep you top of mind. People but from people. 4. Maximise time: We ask "who else should we send the invite to?" for every introductory meeting. Get everyone that needs to be in the room there from as soon as possible. 5. Segmentation of products: One business said they are releasing different commercial options to allow them to bring in additional revenue (cheaper alternative for smaller businesses) while working on their traditional enterprise market. Longer cycles aren’t going anywhere, but the way we approach them can make all the difference. What’s working for you and your team to navigate this shift? 👇

I just watched an AE lose a $1.2M deal after running a "successful" product trial that the prospect LOVED. After 8 weeks of work, the CFO killed it with five words: "Let's try our current vendor." This happens because most reps treat trials as product demos instead of what they actually are: RISK ELIMINATION EXERCISES. After analyzing 200+ enterprise sales cycles at companies like Salesforce, HubSpot, Thomson Reuters, and Workday, I've identified the exact framework that separates 80%+ trial conversion rates from the industry average of 30%. Here's what most reps get wrong: They skip qualification and jump straight into the trial. Big mistake. Before any trial, ask these 3 questions: → "What happens if you don't solve this problem in the next 90 days?" → "How have you tried solving this before?" → "Who else is affected by this problem?" These eliminate 68% of unqualified trials before they start. Next, define success upfront: → Technical requirements that must work → Business metrics they expect to see → Timeline for implementation → User adoption patterns needed Get confirmation: "Just to confirm, if we demonstrate these criteria, you'd be ready to move forward with purchase by [date]. Correct?" Map every stakeholder: → Technical buyers (include every trial user) → Economic buyers (CFO/budget holder) → Political influencers (who can kill deals) → Current solution advocates (who benefits from status quo) For each person, document their personal win/loss scenarios. Have legal review agreements BEFORE starting trials. "We typically have legal review the agreement structure ahead of time so there are no surprises later. Would you be open to having them review a blank agreement while the trial is running?" Finally, handle the current vendor objection upfront: → "Have you discussed these challenges with your current vendor?" → "What was their response?" → "What specific capabilities do they lack?" Document these answers to build your business case. Results from this approach: ✅ Trial conversion: 32% to 83% in 60 days ✅ Deal size increased 40% ✅ Sales cycle shortened 37% ✅ Forecast accuracy improved 92% ✅ 43% less time on unsuccessful trials Stop running trials. Start running risk elimination exercises. — Sales Leaders! Your reps don’t need another training. They need a Revenue OS™. Check this out: https://lnkd.in/ghh8VCaf

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?

What’s Really Happening in Enterprise Sales (2024–2025) Enterprise sales didn't collapse, but they’ve quietly reshaped themselves while most teams keep selling like it’s still 2019. The rules have changed. If your team hasn’t adapted, you’re probably already feeling it: slower cycles, ghosting buyers, unpredictable quarters, and frustrated reps. Here’s what I’m seeing across every enterprise org I advise: 1. Sales Cycles Got Longer - The average cycle for large deals is now 6 to 12 months, often longer. - Budgets are tighter, and approvals are more layered. - Pilots and proof-of-concepts are now expected in most deals. 2. Stakeholders Multiplied - Deals now involve 5 to 10 or more decision-makers. - You’re not selling to a champion; you’re selling to finance, IT, legal, security, and operations. - Any one of them can stall, derail, or block a deal. 3. Buyers Are Overloaded and Guarded - Attention spans are shrinking while inboxes overflow. - Every “quick intro” feels like another task to manage. - Buyers now expect clear value upfront before they take a meeting. 4. Reps Must Become Strategic Advisors - No one wants a pitch; they want a navigation partner. - Enterprise sales now mean consulting on internal change, building business cases, and multi-threading effectively. - Top reps spend 60% - 70% of their time mapping influence and removing blockers, not demoing the product. 5. Internal Pressure Is Sky-High - Sales leaders must hit aggressive quotas with leaner teams. - One stalled deal can derail an entire quarter. - Forecast accuracy and pipeline quality now matter more than raw volume. - The spotlight is on deal progression, not activity dashboards. If you’re still running a 90-day playbook in a 9-month sales world, it’s not your reps. It’s the model. #EnterpriseSales #SalesLeadership #GTMStrategy

The biggest businesses can get major programmes horribly wrong. Here are 4 famous examples, the fundamental reasons for failure and how that might have been avoided. Hershey: Sought to replace its legacy IT systems with a more powerful ERP system. However, due to a rushed timeline and inadequate testing, the implementation encountered severe issues. Orders worth over $100 million were not fulfilled. Quarterly revenues fell by 19% and the share price by 8% Key Failures: ❌ Rushed implementation without sufficient testing ❌ Lack of clear goals for the transition ❌ Inadequate attention and resource allocation Hewlett Packard: Wanted to consolidate its IT systems into one ERP. They planned to migrate to SAP, expecting any issues to be resolved within 3 weeks. However, due to the lack of configuration between the new ERP and the old systems, 20% of customer orders were not fulfilled. Insufficient investment in change management and the absence of manual workarounds added to the problems. This entire project cost HP an estimated $160 million in lost revenue and delayed orders. Key Failures: ❌ Failure to address potential migration complications. ❌ Lack of interim solutions and supply chain management strategies. ❌ Inadequate change management planning. Miller Coors: Spent almost $100 million on an ERP implementation to streamline procurement, accounting, and supply chain operations. There were significant delays, leading to the termination of the implementation partner and subsequent legal action. Mistakes included insufficient research on ERP options, choosing an inexperienced implementation partner, and the absence of capable in-house advisers overseeing the project. Key Failures: ❌ Inadequate research and evaluation of ERP options. ❌ Selection of an inexperienced implementation partner. ❌ Lack of in-house expertise and oversight. Revlon: Another ERP implementation disaster. Inadequate planning and testing disrupted production and caused delays in fulfilling customer orders across 22 countries. The consequences included a loss of over $64 million in unshipped orders, a 6.9% drop in share price, and investor lawsuits for financial damages. Key Failures: ❌ Insufficient planning and testing of the ERP system. ❌ Lack of robust backup solutions. ❌ Absence of a comprehensive change management strategy. Lessons to be learned: ✅ Thoroughly test and evaluate new software before deployment. ✅ Establish robust backup solutions to address unforeseen challenges. ✅ Design and implement a comprehensive change management strategy during the transition to new tools and solutions. ✅ Ensure sufficient in-house expertise is available; consider capacity of those people as well as their expertise ✅ Plan as much as is practical and sensible ✅ Don’t try to do too much too quickly with too few people ✅ Don’t expect ERP implementation to be straightforward; it rarely is

99% of the ERP demos that I sat through, from SAP, Oracle, Dynamics, Odoo, etc. The slides vendors push hardest are always hiding the biggest risks. The moment a vendor says: “Let me show you our workflow automation” or “Here’s how our reporting dashboard works”... I start looking for what's not being shown. Here are 5 slides that should trigger red alerts for any finance or IT leader: (1) “Out-of-the-box Reporting” → Ask: “Can I trace any P&L line item to source transactions across modules?” Most ERPs break down here. You get totals, not traceability. (2) “Low-Code/No-Code Customization” → Ask: “Show me one UOM change across inventory, procurement, and production. Live.” Because most low-code tools can’t handle cross-module logic without dev hacks. (3) “Global Tax and Compliance Ready” → Ask: “How many updates have you shipped for GCC VAT or e-invoicing this year?” If it’s less than 3, you’re going to fall behind local compliance—fast. (4) “Mobile Approval Workflows” → Ask: “Can an auditor see the GRN, invoice, PO, and vendor ID on the same screen?” Most systems force 6 tabs and zero context. Audit risk skyrockets. (5) “Implementation Partners Across 50+ Countries” → Ask: “How many projects has your local partner delivered in my industry, in the last 12 months?” Global logos don’t fix regional mess. I’ve seen $30M+ ERP projects fail because nobody asked these 5 questions during the demo. Next time you see a polished demo slide... ask yourself: “What’s the one thing they’re hoping I don’t ask right now?” ♻️ 𝐑𝐄𝐏𝐎𝐒𝐓 so others can learn.

I’m coaching through two live multimillion-dollar deals right now ($3.8M + $5.2M). When I jumped in, mapped the org, and got real context, two issues were obvious: 1) Nobody could clearly answer: “When are they signing?” Not “this quarter” or “soon.” I mean: What is the compelling event? What happens if they don’t act? Who inside the account is driving the timeline? If the customer isn’t anchored to timing, you’re not running a sales cycle - you’re running a hope cycle ;) 2) We were still with the wrong people (even at VP level) VPs can be great allies. But here’s the hard truth: A lot of VPs don’t actually need/can't get your deal done. So if you’re mapping enterprise orgs, you need to identify two different sponsors: Business-side Executive Sponsor The person who will push this through internally. Financial-side Executive Sponsor The person who will approve, defend, and fund it. So for example, your business sponsor could be the VP of Enterprise Systems and your financial sponsor could be CFO or CRO. These used to be the same person back in the golden days but more and more, they’re decoupled (and that’s why deals are failing, at least what I am seeing) What to do this week (practical steps) If you’re selling enterprise, go revalidate these 4 things in every active deal: What is the exact compelling event date? (“What has to be true by X date?”) Who owns the business outcome? (Not who likes the product.) Who owns the budget + scrutiny? (CFO org, Finance VP, procurement influence, etc.) Do we have a plan to engage ALL of power (economic + business)? Not “we’ll try" or "the VP said they will present for us" A real plan: path, messaging, and reason for them to care. Bonus: The easiest way to build bigger deals in Q1 Look for early renewals and “big bet” accounts now. If an account has: user growth consumption growth product expansion ANY meaningful momentum… …and a renewal in the next 12–18 months, you should already be laying groundwork for an early renewal expansion. Some of the biggest deals I’ve ever closed were SSR / supersede / buyback-style early renewals. You don’t need to close them in Q1. But you DO need them on the board early so you can reverse engineer your year and stop “surprises” from happening in Q3/Q4. Let's talk if you are ready to get to work.

Founders keep asking me why their sales cycles are so long. Let me walk you through what's actually happening inside the enterprise while you're waiting for that "yes." Month 1-3: Your champion finally gets budget approval to explore solutions Month 4-6: Security team runs internal assessment and realizes they need to involve compliance Month 7-9: Compliance says legal needs to review because of data handling Month 10-12: Legal marks up your contract and it sits in their queue Month 13-15: Procurement gets involved and wants you to match their preferred vendor terms Month 16-18: CFO asks why they can't just use the tool they already have Then maybe you close. What most founders don't understand: Security budgets aren't sitting there waiting for your innovation. They're allocated annually, often locked into existing vendor relationships. A CISO doesn't just decide to buy your product. They have to justify it to: → Their CFO who wants to cut costs → Their legal team who sees risk in every new vendor → Their compliance team who needs documentation you haven't built yet The startups that close deals faster: They're not waiting until month 10 to find out legal will be involved. They're asking about the approval process in the first meeting. They're not surprised when procurement shows up. They've built relationships with those teams early. This is why product-market fit isn't enough. You need process-market fit too. Understanding how enterprises actually buy is as important as building what they need. Founders, what surprised you most about your first enterprise security deal?

𝗔𝗿𝗲 𝘆𝗼𝘂 𝗜𝗺𝗽𝗹𝗲𝗺𝗲𝗻𝘁𝗶𝗻𝗴 𝗮 𝗡𝗲𝘄 𝗘𝗥𝗣 𝗶𝗻 𝗮 𝗠𝗮𝗻𝘂𝗳𝗮𝗰𝘁𝘂𝗿𝗶𝗻𝗴 𝗖𝗼𝗺𝗽𝗮𝗻𝘆? If so, you're likely facing one of the most common challenges: staff resistance to change. Implementing a new ERP system in manufacturing can revolutionize operations, but it often comes with unexpected hurdles. In my experience, the biggest obstacle is often resistance from shop floor and factory staff. Whether it is a fully integrated ERP, best of breed solution or a composable option, many frontline workers feel overwhelmed by new data entry tasks. They perceive that logging into devices and recording data will slow them down rather than improve efficiency. Recognizing and acknowledging these concerns is the first step to addressing them. 𝗧𝗮𝗻𝗴𝗶𝗯𝗹𝗲 𝗕𝗲𝗻𝗲𝗳𝗶𝘁𝘀 It will be important to communicate the tangible benefits: 📢 Real-time visibility of inventory to reduce the frustration of unexpected stock-outs. 📢 Automated scheduling, minimizing overtime and balancing workloads. 📢 Improved quality control, reducing rework and increasing job satisfaction. Employees naturally prefer familiar processes and the “old ways” of doing things. They may also wrongly anticipate that their jobs will be threatened by the new technology. It is therefore imperative that you address their concerns, showcase the tangible benefits, confirm job security and enrichment and involve them in the process. This will help you to convert their resistance to enthusiasm. You will need their support for successful ERP adoption. What suggestions do you have for overcoming this resistance to change? #erp #wms #changemanagement #projectmanagement #erpselection #manufacturing #engineering #factory #shopfloor

Long sales cycles are great! Said no salesperson ever Long sales cycles are rarely celebrated in the fast-paced world of sales, but they are a reality Understanding the dynamics at play can help turn a lengthy process into a successful outcome. 1. More Decision Makers, More Complexity: As business economics evolve, the decision-making process often involves more layers of authority. This change requires a nuanced approach to connect with each key stakeholder involved in the deal. 2. Understanding 'Power' in Sales: In ValueSelling, we often discuss the concept of 'Power,' defined simply as anyone who can say 'yes' or 'no' to a proposal. Each decision-maker has specific motivations and concerns that influence their stance toward your solution. 3. Tailor Your Approach: Avoid the mistake of using a one-size-fits-all value proposition. What works for one stakeholder might not resonate with another, especially those who might not have the Power to approve but can easily veto your proposal. 4. Strategic Patience and Persistence: Navigating through a long sales cycle demands patience and a strategic mindset. It’s about more than just waiting; it’s about actively engaging and re-engaging with stakeholders, reinforcing the value your solution brings, and aligning it with their evolving needs. 5. Avoid Deal-Breakers: Recognize that while you might not always need every stakeholder to say 'yes,' you definitely can’t afford a key 'no.' Long sales cycles challenge you to deepen your understanding of your clients' businesses and tailor your approaches meticulously. By appreciating the complexity and strategically engaging with each decision-maker, you can turn these prolonged timelines into successful, mutually beneficial agreements. Is the real challenge in long sales cycles convincing stakeholders or just getting them to answer your emails?