Steve Moskowski

Sales was a mess. Then they handed it to me. Back in 2023, I was VP of Marketing and was asked to take over Sales as well. I stepped into a world I thought I knew well from the outside, but now I had to lead it. I kept reminding myself of something Udi Ledergor once said: “Marketing’s job is to make sales easier.” I wasn’t going to teach the team how to sell. I was never a salesperson, and we already had a great team of sellers. But I could make it easier for them to do what they do best. So I asked myself: How do I actually help Sales sell? Then I stepped in and saw the chaos: - Outdated one-pagers - Random follow-up emails - Clients lost in email threads - AEs juggling deals with no structure It was nothing like the structured world of marketing campaigns and cadences. Everything was manual. Best practices were tribal knowledge, if shared at all. I wanted to fix it. Systemize it. Make sure our AEs spent their time selling, and our clients had a seamless experience. The fix? We rolled out a digital sales room: Aligned A joint effort between Product Marketing and Sales Leadership. Now, every deal lives in a single digital workspace: - Pricing - Collateral - Mutual action plans - Engagement tracking - Clean. Shareable. Always up to date. The impact: - No more chasing PDFs or approvals - Internal champions close loops faster - Deals close faster with higher conversion rates The value of giving clients one professional, centralized place to evaluate us? Priceless. That clunky and messy buying process? Gone. Clients now feel more confident. More in control. More ready to buy. This post isn’t about a specific tool (though our sales team will vouch for Aligned any day). It’s a reminder: If you want your team to win, do not just ask them to grind through the manual work. Give them systems and tools so they can focus on what matters most: Selling. Make sales easier. Make buying easier. Hit your targets.

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🔥 Hot take: AI won’t kill sales — but it might kill good salespeople. I’ve been in sales long enough to remember when closing a deal meant actual conversation, real negotiation, and yes, human intuition too. Now? Feels like too many are outsourcing their edge to AI. Yes, AI is great. It can boost productivity, automate follow-ups, summarize meetings, and help you prep like a boss. But let’s be honest: closing a complex deal isn’t about reading a script generated by ChatGPT. It’s about trust, nuance, and knowing when 2+2 equals 5 in the mind of your customer. The real danger isn’t AI replacing sellers. It’s sellers forgetting how to sell. Just like pilots started relying too much on autopilot, we risk raising a generation of salespeople who lose their instincts.... So no, AI won’t be the end of sales. But bad salespeople hiding behind AI? They’re done. Use AI, but keep the magic. #ai #sales #chatgpt

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The #1 sales skill I still use every day in Customer Success? Listening. Years in enterprise sales taught me that the fastest way to a deal isn’t always the slickest pitch. It’s understanding what the client truly values, often what they don’t say out loud. I recently faced a situation where a key new client was quietly frustrated with how our team was handling their rollout. Most metrics were fine, but something felt off. Instead of jumping in with solutions, I spent time listening genuinely, without interrupting or trying to “fix” immediately. For that meeting, I brought along a couple of technical experts (including a senior sales colleague who understands the product capability better than many experts) and the project manager. Together, we listened to the client’s operations team, point by point. We identified most of the misalignments across the table, and for the remaining concerns, we understood their expectations and went back to our engineering team for feasibility discussions. We then returned to the client with clear yes/no answers and timelines for what could be done. Lesson: In Customer Success, as in Sales, listening first is the ultimate leverage. The client may forget the slide deck, but they’ll remember that someone truly heard them. How do you ensure your clients feel genuinely heard, beyond metrics and dashboards? #CustomerSuccess #EnterpriseSales #Trust #ClientExperience #Leadership #SMtalks #Coaching

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I’ve reviewed 100s of discovery calls. The #1 difference between AEs converting 40% and AEs converting 70%+ of first calls is the number of problems discussed. And the top reps discuss fewer. Reps that don’t convert go wide, trying to find anything and everything to tie their product to. They think: “The more problems I find, the better chance I have of solving some of them.” Reps that convert go deep into the most important problems uncovered. They think: “I need to attach to a problem worth solving.” I built a discovery capture sheet that will help “guide” your conversations to go deep, instead of wide. You can get it here in this blog post (ungated and no cost - just make a copy): https://lnkd.in/gCaUJ4ZD

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When quotas are hit, most leadership teams take that as proof their system works. But what if hitting quota is actually a red flag? In Varicent's 2025 SPM Market Spotlight, we surveyed over 1,400 revenue and operations leaders and uncovered a surprising contradiction: 90% of sellers say they expect to hit their quotas.  But only 31% of sellers believe those quotas are realistic. Why does this gap matter? When teams consistently hit unrealistic quotas, it doesn’t mean the plan is working. It means something else is compensating.  Often, that looks like a few top reps pulling most of the weight, rushed deals at quarter-end, or margin-eroding discounts.  It’s not a sign of sustainable growth. It's a sign of friction. High-performing organizations approach quotas differently: ● They align targets with actual market opportunity, using territory data, account potential, and realistic benchmarks.  ● They measure median attainment, not just the average, to see whether success is spread across the team or carried by a few.  ● They monitor the ratio of activity to outcomes to make sure seller effort translates into sustainable pipeline and revenue. Real growth is not about whether the number is hit. It’s about how it’s hit. If you're using quota attainment as proof of strategic alignment, it might be time to take a closer look. Access the research here: https://hubs.ly/Q03sG4kD0 The 2025 SPM Market Spotlight unpacks how top-performing companies are redesigning quota models to drive scalable, equitable growth. 

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We made a big bet on Enterprise Sales - and nearly pulled the plug. Then Dylan Steele hit 204% in Q2. Crushed it. ACV 2x’d. A $480K deal closed. That’s when we finally felt it: the system was clicking. But getting there? Not fun. Here’s what I wish we’d known sooner (and what actually worked): 1. Specialize Early We thought our senior AEs could handle all deal sizes. “We’re a small team, no time to specialize.” Wrong. Win rate dropped to 20%. Why? Because our AEs were stuck chasing 10 $10K deals or one $100K deal, and missed both. The context switch is brutal. Different buyers. Different tempo. Different stakes. Enterprise needs depth, not speed. Specialize early. Do it. Result: Win Rate >30%, ACV 2x’d in Q2, 100% of Enterprise AEs overachieved. 2. Inbound Misses Execs We’re 100% inbound. 1,000s of users sign up for our free plan or request demos every month. Our SDRs follow product signals and work their way up. It’s great for volume. But execs don’t fill out forms. We’d find champions. But without exec buy-in, deals died at the top. Now we blend outbound from day one and run exec-to-exec outreach. CROs on first calls. Result: In Q2, a big logo closed in 64 days with CRO & VPs engaged on day 1. 3. Upmarket Is a NEW Market Enterprise wasn’t just bigger deals. It was a different game: New personas, requirements, and entirely new competition. We weren’t just selling Digital Sales Rooms anymore; we were up against Sales Enablement giants buyers had used for 10+ years. Don’t assume what worked downmarket still applies. The playbook MUST be rewritten. Result: In Q3, we displaced 3 legacy vendors. 4. Weekly War Rooms Every week, we deep-dive into all strategic deals. I join these calls to help. These kinds of deals must be orchestrated, not sold to. We get requirement docs, uncover existing executive connections, tackle issues that require unique troubleshooting. Every AE has the entire team at their service. Result: Today, every big deal has an Exec Sponsor. 5. Protect Seller Focus Big deals don’t need more hours. They need better ones. More research. Better business case. Sharper strategy. Most companies buy tech to help. We’re building ours in-house, customized and soon productized. Agents that help reps prep, update CRM, raise flags, and move faster. Result: Every deal now has a Business Case using Aligned's AI. 6. Brand Brand Brand The more we invest in what we can’t measure, the faster we scale. When buyers already trust you, deals move faster. They loop in execs. They have fewer objections. They know your name. You can’t calculate the ROI, but good luck closing 6-fig deals when your AE is the only engine building trust. Result: We show up 10x per day in our ICPs feed. 700+ join our webinars. —— Stop hiring enterprise reps hoping they’ll fix your GTM. If the system’s not built, they can’t win. It’s not on them. It’s on you. Don’t blame the people doing the hardest job. What’s worked for you going upmarket?

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