Sales Rep Challenges

Last week, a customer said something that stopped me in my tracks: “Our data is what makes us unique. If we share it with an AI model, it may play against us.” This customer recognizes the transformative power of AI. They understand that their data holds the key to unlocking that potential. But they also see risks alongside the opportunities—and those risks can’t be ignored. The truth is, technology is advancing faster than many businesses feel ready to adopt it. Bridging that gap between innovation and trust will be critical for unlocking AI’s full potential. So, how do we do that? It comes down understanding, acknowledging and addressing the barriers to AI adoption facing SMBs today: 1. Inflated expectations Companies are promised that AI will revolutionize their business. But when they adopt new AI tools, the reality falls short. Many use cases feel novel, not necessary. And that leads to low repeat usage and high skepticism. For scaling companies with limited resources and big ambitions, AI needs to deliver real value – not just hype. 2. Complex setups Many AI solutions are too complex, requiring armies of consultants to build and train custom tools. That might be ok if you’re a large enterprise. But for everyone else it’s a barrier to getting started, let alone driving adoption. SMBs need AI that works out of the box and integrates seamlessly into the flow of work – from the start. 3. Data privacy concerns Remember the quote I shared earlier? SMBs worry their proprietary data could be exposed and even used against them by competitors. Sharing data with AI tools feels too risky (especially tools that rely on third-party platforms). And that’s a barrier to usage. AI adoption starts with trust, and SMBs need absolute confidence that their data is secure – no exceptions. If 2024 was the year when SMBs saw AI’s potential from afar, 2025 will be the year when they unlock that potential for themselves. That starts by tackling barriers to AI adoption with products that provide immediate value, not inflated hype. Products that offer simplicity, not complexity (or consultants!). Products with security that’s rigorous, not risky. That’s what we’re building at HubSpot, and I’m excited to see what scaling companies do with the full potential of AI at their fingertips this year!

After analyzing hundreds of the world's most iconic speeches and presentations, I discovered a presentation framework that changed my life... I remember it like it was yesterday. I was in my office mapping this presentation framework over famous speeches like Martin Luther King’s ‘I Have a Dream’ speech and Steve Jobs’s presentation of the first iPhone. Over and over, these iconic presentations DIRECTLY aligned with this framework. It was so startling that I actually cried (a little). This discovery changed everything for Duarte and led to the creation of a framework that’s at the core of our business. We call it the Presentation Sparkline™. Whether you’re launching a new product, you’re trying to close a big contract, or you’re giving a keynote, this framework delivers results. …and it has for (literally) hundreds of years. Here’s how you can begin using it for your next high-stakes presentation: 1. Start by acknowledging your audience's current reality (make THEM the hero). Begin your presentation by describing specific challenges your audience faces, using their language and perspective. Interview stakeholders beforehand to understand their frustrations, concerns, and goals so you can reflect these accurately. This demonstrates you understand their world before attempting to change it. 2. Create a stark contrast between this status quo ("what is") and the future they desire ("what could be"). Paint a vivid picture of what success looks like after implementing your idea or solution, focusing on concrete benefits and outcomes. Use sensory language that helps your audience feel, see, and experience the transformation you're proposing. Make this future state emotionally compelling, not just logically sound. 3. Toggle between these states throughout your presentation to create the BIGGEST possible gap between them. Deliberately alternate between describing pain points and their corresponding solutions throughout your presentation, rather than grouping all problems at the beginning and solutions at the end. This helps create tension and builds up your audience’s desire for the future you’re painting. 4. End with a clear choice: remain in the status quo or take action toward transformation. Conclude by framing a specific decision point that puts the power in your audience's hands. Make the call-to-action concrete and immediate - something they can do within the next 24-48 hours to start moving toward the "what could be" state. Remind them what's at stake if they choose inaction. Remember: Your presentation is only as effective as the action it inspires. And I’ve seen this framework deliver time and time again. P.S. I have a YouTube video where I break this framework down in far greater detail. I left a link in the comments. #BusinessStorytelling #CommunicationSkills #PresentationSkills

What most sales managers get wrong about underperformers When a rep is struggling, the default response is: “Let’s coach them. Let’s build a plan.” Sounds reasonable. But it often misses what they really need. I had a seller - missed target two quarters in a row. Still showing up. Still trying. They weren’t lazy. Or clueless. Just anxious. Hesitant. The spark was gone. And in sales, that’s dangerous. Because sellers live on momentum. When they stop feeling the win in their hands, they spiral. I didn’t jump to frameworks or action plans. Instead, I did one thing first: We sat down. Pulled up the pipeline. Found one real opportunity. And we worked it. Together. They closed it. And it changed everything. They stood taller. Spoke with certainty. Booked more meetings. Took more risks. Because now the job felt possible again. Sometimes, belief isn’t enough. You have to help them feel like a winner again. Then coach. Then rebuild. But first, give them the win.

If your CEO asks for deal updates in Slack, don’t expect reps to update Salesforce. You can throw all the tech, training, and sales ops resources you want at CRM adoption - but if leadership isn’t leading by example, none of it will stick. Here's the tl;dr: Reps don’t hate updating Salesforce because they’re lazy. They hate it because they know no one actually uses it. When leaders bypass the CRM - asking for updates in Slack, emails, or meetings - they send a clear message: “This system doesn’t matter. Your notes don’t matter. Just tell me directly.” And that’s how $100k+ Salesforce investments turn into glorified Rolodexes. So, how do you fix it? 1. Top-down adoption Start with the CEO. If they want deal updates, they need to ask for them in Salesforce. Chatter, Slack integrations, whatever it takes...but it has to flow through the system. 2. Make sales managers accountable Reps won’t change unless their managers enforce it. Run pipeline reviews directly from Salesforce dashboards. No exceptions. If it’s not in Salesforce, it doesn’t exist. 3. Quantify the pain Show reps how missing data costs them deals. Lost follow ups, misaligned hand offs, deals slipping through the cracks...all because the CRM isn’t up to date. 4. Reward the right behaviors Sales culture loves to celebrate closers. But what about the reps who close and keep a clean pipeline? Make data hygiene part of what gets recognized (and compensated). The reality is that CRM adoption isn’t a sales ops problem - it’s a leadership problem. If the top isn’t setting the example, the bottom won’t follow. And until that changes, you’ll keep throwing money at Salesforce while your reps keep their real pipeline in a Google Doc.

She was afraid she’d lose her job if she said this publicly. Last week, a top AE (3x SaaS Unicorns) DM’d me after one of my posts: “Almost all companies I’ve worked for enforce their ‘perfect’ sales process” “And if I don’t follow it like a robot, I’m branded ‘incompetent’” “It’s like I can’t use my brain or EQ” “What if I feel that deep discovery would hurt this call?” “What if I can’t access the DM but trust my champion?” “We’re ignoring how buyers buy” “And it’s costing deals” Wow. I spoke with 100+ VP Sales and CROs last year. And I get it. I really do. We all want consistency and predictability. But hard process enforcement is a VERY slippery slope… Real-life selling and buying are not that easy to 'hack'. The best sellers ‘dance’ their deals. They are experts in the buying process. They use the sales process as an anchor. But break it often. Too much enforcement can kill their intuition and creativity. And make them force a sales process on their buyers. Instead of facilitating their buyers’ process. But what about the more junior sellers you ask? Yes, they need structure. But that doesn’t mean burying them in CRM blockers or scripts. What if it makes them believe buying is linear? What if it makes them think less—and just comply? Over-enforcing won’t make them better. It only gives us leaders a false sense of control. So what's the solution? 1. Show ‘What Good Looks Like’ Make sure every rep has access to the best demos, best business cases, best POC/MAP frameworks, etc. Especially at large companies, this is a big mess, and deals are black boxes. 2. Enforce What You Must Stay strict on Qualification Criteria or Discovery Framework so everyone speaks the same language in pipeline and forecast meetings. But don’t overload your CRM with blockers that cripple your team’s agility. 3. Teach Sellers the ‘Why’ AND When to Break the Rules Don’t just hand them a checklist. Explain the reasoning behind your process and encourage them to adapt when the buyer’s reality requires it. Their creativity is their secret sauce, not memorizing a script. 4. Trust Frontline Managers to Coach, Not Micromanage Instead of forcing top-down compliance, empower your managers to do real coaching. The more they guide reps day by day, the more your process becomes a competitive edge—not a bottleneck. —— I get it. I’m a process geek, too I love having clean data and predictable forecasts. But going hard on enforcement is not the answer. It risks harming team morale. And your buyer’s experience. A sales process is an anchor, not a cage.

Pre-sales is dead. Post-sales is dead too. Whether you talk about an infinity loop, bowtie, Mobius strip or other geometric shape, what’s universally true is that companies are moving away from dated models that fracture between before and after contract signature. To this point, Jean-Charles Renoux, Ori Entis and I brought together several respected Revenue Operations leaders to talk about changes in teams, processes and technology to support a more integrated customer journey. We discussed org structures and it’s fascinating that there are multiple models, each with pros and cons: 1. Some put sales ops under a CRO and CS/CX ops under a CCO. This allows for strong functional alignment and autonomy. 2. Others have an integrated RevOps org under a COO with sub-leaders for sales ops and CS ops. This drives better integration across the customer journey. 3. Some put this integrated function under a CRO. Inevitably, since it’s 2025, we talked about how AI is being used in RevOps teams: * Creating simulations for sales reps to test their pitches in a “safe environment.” * Automating RFP responses. * Competitive research. * Route planning for their field agents. * 100% automated voice prospecting. I asked what was the biggest challenge they had in terms of aligning pre and post sales. Universally, the answer was the one that’s always been the challenge - “the handoff.” Some of the solutions were uber-creative: * Required Salesforce fields to capture the client’s goals before an opportunity is closed-won. * Automatically creating slack channels per region when a new deal closes - with the CSM, AE and TAM as members. * Assigning a CSM at the “commit” stage to allow for the handoff to be done well and giving the CSM the key to validate that the client is ready for a handoff. * Creating a deal room with a “mutual action plan” between the vendor and the client and then handing that artifact off to the CSM. * Inferring client objects from sales recorded calls. * Almost all of them automated pushing these objectives into Gainsight. One attendee shared that they found that deals that had goals filled out had a 2X higher customer satisfaction rate than those that didn’t! It’s so exciting that we’re moving beyond the silo-ed world of “pre-“ and “post-“ sales. And AI will help us get there! Thanks to Mandarachalam Aruchamy Franklin Fredrik Bayley Fesler Heidi Thompson Sonam Dabholkar Adam Josephson Shaun Martin Melissa Allen Beth Anne Altamura Justin Miller Patrick Sweny for adding so much to the dialog! What do you do to streamline the handoff between your Sales and #CustomerSuccess teams?

No one hit quota for 8 months straight. The VP blamed the economy. I blamed the VP This conversation happened in a conference room VP: "The market's impossible right now. Nobody's buying" Me: "Show me your quota calculations" VP: "What do you mean?" Me: "How did you determine each rep needs to close $200K monthly?" Silence I saw that quotas were set by taking revenue goals and dividing by number of reps, zero consideration for market capacity, no analysis of historical performance, no adjustment for ramp time or seasonality and mathematical quota setting without reality checks I ran the actual numbers: → Average deal size is $15K → Average close rate is 8% → Average monthly qualified opportunities per rep is 12 The math: 12 × 8% × $15K = $14.4K monthly Their quota: $200K monthly They were asking each rep to perform 14x above statistical possibility We changed everything realistic quotas based on market data, achievable stretch goals with bonuses, monthly coaching focused on process improvement Three months later 5 out of 8 reps hit quota, team morale went from toxic to motivated and pipeline quality improved Your quota should stretch your team, not break them If nobody's hitting numbers for months, the problem isn't your people It's your math Set quotas based on reality, not wishes P.S. Do you have problems with sales? Check out my newsletter

The average sales deck is 37 slides. Your champion shows 6 to their team. The average sales email has 9 paragraphs. Your champion forwards 2 sentences. The average demo covers 14 features. Your champion remembers 3. The average ROI model has 25 inputs. Your champion focuses on 1 number. This is why your deals die. Not because your product isn't good. Not because your pricing isn't right. Not because your competitor is better. But because your champion can't sell for you effectively. Think about it: You spend weeks perfecting your pitch. You create beautiful presentations. You write detailed proposals. You build complex ROI models. Then you hand it all to someone who: • Isn't a sales professional • Doesn't know your product as well as you • Is juggling 50 other priorities • Has never been trained to handle objections And you expect them to close the deal? This is sales malpractice. Your champion isn't failing you. You're failing your champion. Last month, I completely changed our approach: Instead of arming champions with OUR sales materials... We built them spaces where THEY could be the hero: • Interactive content they could customize for their colleagues • Simple visuals that made their recommendation look smart • Engagement tracking so they could see who needed more convincing • Anonymous Q&A where objections could surface safely The results? Deal cycles shortened 20%. Win rates increased 12%. Champions started calling US when deals progressed. Stop thinking like a salesperson who needs to close. Start thinking like a champion who needs to convince. Every piece of content you create should be designed not for prospects... But for champions to use WITHOUT YOU. That's how modern deals actually close.

A customer can ask for exactly what they think they need and still be wrong about the real problem.  That creates a bigger risk than most companies realize.  Because when your sales team takes the request at face value, they can build the right solution to the wrong issue.  A customer asks for more people.  The team starts designing a staffing solution.  But the real issue may be turnover, poor training, broken processes, technology gaps or customer experience problems.  A customer asks for a new system.  The conversation immediately becomes about platforms and capabilities.  But the real issue may be workflow, adoption, reporting or leadership.  This is especially important in technical sales, where teams can move quickly into specifications and solution design before the business problem is fully understood.  This is where strong sales organizations separate themselves.  They do not simply respond to requests.  They help customers understand what is actually driving those requests.  That changes the conversation.  It changes the solution.   It can change the economics of the deal.  And it changes whether the buyer sees your company as another vendor or as a strategic partner.  For CEOs, this is not just a discovery issue.  It is a positioning issue.  Is your sales team trained to respond to what customers ask for, or to uncover what the business actually needs? 

Your sales managers are drowning in data—but starving for clarity. I was on a call last week with a VP of Sales who showed me his dashboard. 47 different metrics. I asked him : "Which number, if it moved 20% this month, would change everything?" Silence. Here's what I see happening: Leaders know *something* is off. Pipeline isn't converting. Reps are busy but not productive. Deals are slipping. But they can't pinpoint the actual behavior or skill gap that's causing it. Here's how to actually diagnose what's broken (and fix it fast): —— Step 1: Pick ONE North-Star Metric Not 10. Not 5. One. What's the single number that, if improved, would cascade into revenue growth this quarter? Could be: → Connect rate → Discovery-to-demo conversion → Demo-to-proposal rate → Close rate Pick the constraint. Ignore the rest for now. —— Step 2: Work Backward to the Behaviors Metrics don't move themselves. Behaviors move metrics. Ask: What are the 3–5 specific actions that directly influence this number? Example—if your North-Star is close rate: • Multi-threading (are reps building champion + EB relationships?) • Next-step clarity (is every call ending with a concrete commitment?) • Objection handling (are reps folding on pricing or timeline pushback?) Now you have a target. You know exactly what behaviors to inspect and improve. —— Step 3: Inspect the Work, Not Just the Outcome Most managers live in lagging indicators. They see the deal lost, the pipeline gap, the missed forecast—after it's too late. Top leaders inspect leading behaviors weekly: → Listen to 2–3 discovery calls per rep. Score them on your behavior checklist. → Review pipeline hygiene: Are next steps clear? Are close dates realistic? → Check activity quality: Are reps reaching the right people, or just burning through volume? You'll spot the gap in week one. You can course-correct in week two. —— Step 4: Use BIPSY to Diagnose the Root Cause When a behavior isn't happening, most managers assume it's a skill problem and throw training at it. But the issue might be: B – Behavior: They don't know they should be doing it. I – Issue Diagnosis: We don't know the CAUSE of the problem. P – Process: There's no clear standard or it's not reinforced. S – Skill: They know what to do but can't execute it well. Y – You (Impact): YOU as the leader aren't doing the right things. Diagnose correctly, and your fix is 10x faster. Don't guess. Diagnose. —— Step 5: Coach the Behavior Until It Sticks One conversation won't change anything. Great managers build a weekly rhythm: Monday: Inspect the work (calls, pipeline, activity). Tuesday–Thursday: Coach the gap in 1:1s with real examples. Friday: Measure early proof (did the behavior improve?). Rinse and repeat. This is system force, not brute force. The Bottom Line: Your team doesn't need more dashboards, more meetings, or more motivation. They need clarity and specific actions.