Sales Assembly

Great CS isn’t about saying yes to everything. It’s about saying no in a way that makes customers trust you more. Some customers treat CSMs like a genie in a bottle. - Custom feature requests - Faster-than-possible implementations - Extra services (for free, of course) And if you don’t set boundaries? You become an overworked, under-resourced "yes machine." Until the customer churns anyway because they never got what they actually needed. ?? Anyway, saying no is an art. Here’s how the best CSMs do it: 1. Start with why. Customers don’t get mad because they hear "no." They get mad when they don’t understand why. Instead of a flat rejection, explain why something isn’t possible. - Offer a structured alternative. Instead of "we can’t do that," reframe: - “That’s not something we can build right now, but here’s what we can do in the meantime.” - “I can’t promise X, but here’s an approach that’s worked for other customers.” 2. Make trade offs clear. - "If we prioritize this, it’ll delay that. Which is more important?" When customers are forced to choose, they focus on what actually matters. 3. Back it up with data. - Example: "We’ve analyzed this request across customers, and what actually moves the needle is X. Let’s focus there instead." 4. Be brutally honest (when necessary). - Sometimes, the answer really is no. And that’s okay. Most customers would rather have clarity than false hope. Customers don’t want everything. They just want results. If you position your "no" in a way that keeps them focused on real outcomes, they’ll trust you more. And when you say yes? They’ll know it actually means something.

In 2025, we decided to take a fresh approach to Continued Education and Professional Development and that led us to partner with Sales Assembly. Huge shoutout to Jeff, Brad, Matt and the entire Sales Assembly team. They’ve been incredible to work with, and the subject matter experts leading the live programs have been top-notch. Excited to share the first (of hopefully many!) skill certifications I’ve earned through the Sales Assembly program. Looking forward to what’s next!

A new VP walks into their first board meeting…. They’re fired up. Confident. Ready to talk deals. Then the CFO starts asking about gross margin. The CEO wants a breakdown of sales efficiency. A board member asks about next quarter’s pipeline risk. And suddenly, that confidence evaporates. They realize: “I don’t know what I don’t know.” If you just stepped into a VP role...or plan to...here are 10 questions you need to be able to answer before your next board meeting: Revenue performance & pipeline: 1. What’s your current pipeline coverage, and how does it compare to historical conversion rates? 2. What are the top 3 reasons deals are slipping or being lost right now? 3. Where is your growth actually coming from...net new logos, expansion, or increased ACV? Sales efficiency & forecasting: 4. What’s your team’s quota attainment distribution? Are you top-heavy or middle-loaded? 5. What’s your current sales cycle length, and how does it vary by segment? 6. What’s your win rate by stage? Are there any drop off points that indicate a messaging or process problem? Financial & board level metrics: 7. What’s your company’s CAC payback period? Is it improving or getting worse? 8. How are your gross margins trending, and how does that impact sales compensation strategy? 9. What’s your team’s productivity benchmark (ARR per AE) vs. best-in-class SaaS benchmarks? Next quarter’s strategy: 10. What specific levers are you pulling next quarter to improve pipeline, close rates, or deal size? Most new VPs get caught up in individual deals and rep performance. In doing so, they miss the bigger picture. The board doesn’t care that one of your reps closed a big deal last week. They care about repeatability, efficiency, and risk. If you don’t have answers to these questions yet, get them. Because if you don’t know, someone else in that boardroom does. And they’ll be the ones making the decisions. cc Mor and Krysten per your request the other day. ?? Any questions you’d add that might bump one of these off the top 10?

Investing in Revenue team prof development: OLD WAY - Finance budgets $1,500 per employee for prof development/training - Leadership announces the availability of funds at Q1 SKO - Funds are available for any type of prof development (e.g. cooking classes) - HR advertises employee benefit in recruiting materials - Revenue team members delay (forget) tapping the budget - Little/no professional development takes place all year - In Dec a handful of team members ask their manager to approve Amazon book purchases - Company quietly reclaims unspent training budget. Investing in Revenue team prof development: NEW WAY - Finance reduces prof development budget in 2025 - Revenue leaders still have acute need to upskill team - Company lacks in-house resources to plan/execute year round prof development - Company pools budget and invests in annual membership to team-wide resource - Team members join functional peer groups and receive tactical, practical advice - New hires join certifications to ramp in role more quickly - VP/CXOs provided valuable networking opps with peers (Zoom+IRL) - Team accesses needed content and connections year-round If you’re a B2B SaaS company facing acute skills development needs and a tight L&D budget in 2025. Check out Sales Assembly. Great certifications.?? Great workshops.?? Great content.?? Great events.?? Great team. Best investment in skills training and professional development we've made 6 years running.

Here's the 5 objection types salespeople face: - Authority - Timing - Reflex - Price - Fit Here's 5 common mistakes that stop you from overcoming them: - Discounting Prematurely - Lack of Preparation - Not Fully Listening - Getting Defensive - Exaggerating Here's the 8 step framework I use to avoid the mistakes and stay in control: - Hear - Acknowledge - Explore - Isolate - Respond - Confirm - Repeat - Close Here's the 3 step simpler version that's easier to remember: - Acknowledge - Isolate - Answer Tomorrow at 11 AM EST I'm running a session for Sales Assembly breaking down the following: - How to get ahead of objections - How to respond to objections word for word - How to implement these frameworks on your next sales call Comment "SESSION" below if you're interested in attending, and I'll send you the details

Your buyer nodding isn’t the same as them understanding Most sales calls go like this: Rep: “Our platform helps streamline operations and improve efficiency.” Buyer: “Got it.” (They didn’t.) Here’s the test: Can your buyer repeat your value in their own words? If not, they didn’t actually hear you. Why does this happen? 1. Reps speak in vague, high-level benefits ("We optimize workflows") instead of specific, memorable takeaways ("Teams like yours cut admin work by 12 hours a week after switching") 2. Buyers are overloaded with buzzwords and slides but lack a clear, personal takeaway There's no emotional hook...no reason to care beyond “sounds nice” So, how do you fix it? - After you explain your value, ask: “How would you describe this to your CFO?” If they struggle, simplify: “The way we’d explain it is… [one-sentence takeaway]. Does that align with what matters to you?” - Tell a story: “One of your competitors faced [X challenge], and after switching, they [specific outcome].” Kudos to Mark Smyth for bringing this amazing guidance to a Sales Assembly course on Storytelling last week! If your buyer can’t repeat your value, they won’t repeat your name when it’s time to buy.

I am looking forward to partner with Sales Assembly, leading a session on driving product-led success in B2B tech!

Excited to lead this Wednesday’s Sales Assembly course on ???????????????? ??????????????: ????????????, ????????????????, ?????? ????????. Nailing these three elements is key to winning more deals and shortening sales cycles. Looking forward to sharing strategies that drive results. If your company is looking to upskill your sales team, check out Sales Assembly. #sales #coach

“How much will I make if I hit 110% of quota?” If your sales reps can’t answer that question without pulling out a spreadsheet - or worse, asking finance - you’ve got a comp plan problem. One VP I know walked into a similar mess: - Reps were overpaid for the wrong behaviors (hello, renewals getting the same commission as net new logos). - Leadership needed to shift focus to new business, but changing the plan risked mutiny. - The new comp plan? More lucrative if reps focused on new logos...but it looked complicated. So, what did the VP do? They built a simple comp calculator. Nothing fancy, just a basic tool where reps could plug in: - Their quota - Pipeline numbers - Expected close rates And boom: it showed exactly what they’d make at different levels of attainment. When reps saw that they could make more under the new plan (especially with accelerators kicking in over 100% quota), the pushback evaporated. Here’s why it worked: 1. Transparency kills fear. Reps don’t like surprises…especially when it comes to their paychecks. 2. Behavior follows incentives. Show them where the money is, and they’ll adjust their strategy. 3. Simplicity wins. Comp plans already feel like algebra - if a rep needs a PhD to understand their commission, you’ve lost. Moral of the story? A comp calculator isn’t just a nice to have. It’s a change management tool. Because when you’re trying to shift sales behavior, clarity beats complexity every time.

If your reps didn’t know how to prospect before, AI just helps them do it faster. And worse. Sales teams are racing to slap AI onto their prospecting workflows. Custom GPTs, intent data engines, AI-personality profilers…it’s starting to feel like MORE tech is the answer to FEWER responses. But here’s the thing: We all know by now that AI isn’t the magic bullet. Bad inputs = bad outputs. The folks I see using AI properly are doing the following: 1. Using AI to prep smarter, not spam harder. AI tools that analyze 10-Ks, earnings calls, and LinkedIn posts? Gold…if reps know what to look for. Example: Instead of “Congrats on your funding!” (the most overused opener ever), a rep could say: “Noticed your Series B is aimed at scaling product. We’ve helped [competitor] cut onboarding time by 40% - thought it might be relevant.” 2. Custom GPTs built around their data. Some teams are building internal GPTs trained on their closed-won deals, past proposals, and customer calls. The result? AI that mirrors their own voice, knows what messaging actually works, and avoids the generic stuff ChatGPT spits out. 3. AI-Powered research, human-powered messaging. AI should handle the grunt work, like digging through data, summarizing insights. But the message? That still needs a human touch. The best reps blend AI-driven intel with personality. Think less “perfectly optimized email” and more “insightful, relevant, and human.” What’s NOT Working? - Mass personalization at scale. (Spoiler: It’s not really personalized.) - Relying on AI to write the whole email. (Prospects can smell a ChatGPT draft a mile away.) - Using AI without strategy. (More data isn’t better if reps don’t know what to do with it.) The reality is that AI is making bad prospecting louder. The winners? They’re using AI to do what it does best, which is research, prep, and pattern recognition. But the messaging? That’s still where the real game is played. Prospects don’t want to talk to robots. They want value. They want Insight. They want a reason to respond. Use AI as your sidekick, not your crutch. Because at the end of the day, the best sales weapon is still the same: A rep who actually gives a damn.