Sales Process Optimization

I watched a company lose a $1.2M deal last quarter because they were still running MEDDPICC like it's 1996. They identified a Champion and an Economic Buyer. They documented Pain points. They were textbook perfect. The problem in 2025 is that no single Champion can get a deal done. Sales methodologies from the 90s weren't built for today's buying committees, consensus-driven decisions, and distributed authority. The modern sale requires a complete methodology upgrade. No more obsessing over a Champion. You need relationships with the entire team. No more chasing generic Pain points. You need Numerical Priorities linked to business outcomes. No more vague "Compelling Event". You need documented, financially-validated trigger points. No more hoping for Decision Criteria. You need to shape it with objective benchmarks. The best sellers still run a methodology, but it's evolved. They're identifying group priorities, mapping out competing initiatives, and anchoring everything in provable ROI. Try this on your next deal…instead of asking "What's keeping you up at night?" ask "What are the top 3 numerical priorities for your department this quarter?" Watch how quickly you can separate real deals from wishful thinking.

The ultimate guide to 0-to-1 sales with Jen Abel Jen and her team at JJELLYFISH have worked hands-on with over 300 early-stage startups, teaching them how to do sales, early customer discovery, and to set up a repeatable sales motion. In our conversation, Jen explains 🔸 What to do at step of the enterprise sales process 🔸 What three channels work best for outreach 🔸 What to say (and not say) on your first call, and subsequent calls 🔸 How to craft outreach messages 🔸 Where to find the good leads 🔸 How to maintain momentum with prospects 🔸 Strategies for navigating procurement 🔸 How to avoid common pitfalls in the sales process 🔸 Why founder-led sales is so crucial early on Listen now 👇 - YouTube: https://lnkd.in/g6hnrm2v - Spotify: https://lnkd.in/gxMKpiDs - Apple: https://lnkd.in/ghYK8RhJ Thank you to our wonderful sponsors for supporting the podcast: 🏆 Brave — A smarter way to search: https://brave.com/lenny 🏆 Vanta — Automate compliance. Simplify security: https://vanta.com/lenny 🏆 Paragon — Ship every SaaS integration your customers want: https://lnkd.in/geirC2qS Some key takeaways: 1. As a founder, you are the best person to sell your product in the early stages. No one knows your vision and product as deeply as you do. Use that knowledge to connect with potential customers. Salespeople can’t replicate the passion, vision, and insights you can offer. 2. The typical enterprise sales process includes: a. Initial outreach and qualification b. Discovery call c. Demo/proposal d. Co-authoring scope of work e. Procurement f. Signature and closing 3. When crafting outreach messages, focus on: a. Relevance to the prospect’s role b. Presenting a counterintuitive or novel insight c. Focusing on the problem, not the solution d. Keeping it concise (3 to 4 sentences maximum) 4. When reaching out to potential leads, don’t just tell them your product is “better”—show them why it’s fundamentally different. Share a shocking insight or counterintuitive observation that’ll make them stop and think. If they read your message and think, “That’s interesting,” you’re already halfway there. 5. In the early stages, founder-led sales should focus on learning about customer pain points, not just closing deals. Treat sales conversations as research opportunities to gather insights, validate problems, and refine your product based on real feedback. Look for “budding insights”—those subtle hints of deeper needs—that can guide product or pitch adjustments. 6. You may think cold emailing and LinkedIn DMs are your only routes to outreach, but cold calling is surprisingly effective. In fact, the response rates can be much higher than with email in some cases. So don’t shy away from picking up the phone—especially when you can deliver that personal touch that makes people want to engage.

Founder-led sales is the most dangerous drug in growth. It’s fast. Addictive. Convincing. You're closing deals. People are leaning in. You think this is working. And it is… Until it’s time to hire your first sales rep And everything falls apart. Suddenly: Deals stall. Pitches feel flat. The reps you were so excited about? They’re missing targets, second-guessing themselves, and asking you for answers you never had to write down. The problem? They’re not you. They weren’t there when the product was born. They don’t wake up thinking about your customers. And they can’t run on pure conviction. Because reps don’t run on passion. They run on structure. And if you haven’t built that structure, It’s like asking someone to run a race with a pulled hamstring. Even if they want to help Even if they show up with heart They’re still not going to win. Maybe they get lucky. But luck doesn’t scale. Structure does. So, what does real structure look like? ★ Crystal-clear ICP Not “anyone who might buy” but the exact buyer you win with and why. ★ Sales materials that actually help Talk tracks. Use cases. Case studies that answer objections, not just decorate a deck. ★ Real product training Not just features, but the actual value story from the customer’s point of view. ★ Defined sales process What good looks like, step by step. From first call to closed-won. ★ Coaching and feedback They need more than numbers. They need to grow in a system that teaches. You can’t scale on founder magic alone. It starts with it but it never ends there. If you're in that messy middle wondering why it's not clicking It's not the people. It's the structure around them. 👇 Seen this happen? Or lived it? Let's talk about what really works when you're ready to scale. 🎥VC: gcarralejo #SalesAndMarketing #RevenueGrowth #Strategy #CustomerExperience #JuddBorakoveStyle 

I've watched 1,000+ sales pitches fail for the exact same reason. After coaching some of the best AEs in tech, I discovered the real problem isn't what you're saying—it's the entire framework you're using. Most companies create pitch decks that brag about themselves. This NEVER works. Customers don't care about your products. They care about their problems. For years, I've taught my private coaching clients a framework that's completely transformed their close rates. I call it the 5 P's of Pitching: 1/ PROBLEM What high-level business problem do you solve? This must matter to executives—not technical teams. If you sell CRM, your problem isn't "manual data entry." It's "rep underperformance" or "missed forecasts." 2/ PRIMARY REASON Why does the problem exist? Nail the root cause. "Leadership has poor visibility to pipeline and no accurate way to predict which deals will close." Articulating this builds immediate credibility. You speak their language. 3/ PAIN What metrics are suffering because of this problem? Missed forecasts lead to plummeting stock prices, revenue shortfalls, and sales layoffs. This is where you make it personal for the decision maker. 4/ PROMISE How does your solution address the PRIMARY REASON for the problem? "Our AI-driven forecasting prevents inaccurate manual forecasting and low deal visibility." Don't list features. Focus on solving their specific challenge. 5/ PAYOFF What metrics will improve when you solve their problem? For CRM: improved quota attainment, rep productivity, and accurate forecasting—all driving revenue and profitability. The 5 P's framework works because it's centered on the customer, not on your product. The best part? It takes 15 minutes to build and dramatically increases your close rate. If you want a copy of the 5P's template I use with my clients, comment TEMPLATE below.

“You’re not scaling excellence. You’re just celebrating survivors.” Most sales teams aren’t following a process. They’re surviving one. I worked with a B2B sales org where three reps consistently smashed quota. Everyone else? Average at best. Leadership said, “Let them do their thing — it works.” But here’s what “their thing” actually was: – A jumbled blend of SPIN, Challenger, MEDDPICC, Sandler and instinct – CRM updated only when deals closed – Coaching sessions that relied on anecdotes, not systems When one of those top reps quit, the pipeline fell apart. Why? Because success lived in their head, not in the process. Here’s the uncomfortable truth: – If only your best reps can navigate your system, you don’t have one – If deal reviews sound different every week, your methodology is broken – If forecast accuracy depends on “gut feel,” you’re scaling luck, not learning ✅ Want to fix it? – Shadow your best reps — not for charisma, but for structure – Document their patterns in a step-by-step format anyone can use – Build coaching and CRM workflows around that structure, not in parallel to it 🎯 Psychological landmines to watch for: – Outcome Bias: Just because a deal closed doesn’t mean it was the right process – Survivorship Bias: Don’t replicate what worked for one without knowing why – Resistance to Codification: Top reps may resist standardizing what makes them feel unique Process isn’t about rigid steps. It’s about giving everyone a fair shot at consistency, especially your middle 70%. 📌 You don’t need 10 reps winning 10 different ways. You need 1 way that scales to 100 reps. 🔁 Repost if your top performers have become your entire process 💬 What happened when your star seller left? 📥 Follow for repeatable systems that scale skills, not just results

If I only had 3 months to grow B2B SaaS startup, here’s what I would do: Rules: - You have 3 months - Need to impact revenue - Spend under $200/mo Here's what I would do: 1. Create a “laser focused” account list: a. Go to Keyplay b. Build out Sales 200 → 200 companies I want to sell into c. Import the list into Sales Navigator and run a lead search d. That should give me ~700 people. 2. Analyze 10 Closed Won / Lost deals a. Upload the transcripts of 10 Closed Won deals into ChatGPT b. Prompt: Analyze the key reasons why prospects bought from us in these deals. Organize and rank them c. Upload the transcripts of 10 Closed Won deals into ChatGPT d. Prompt: Analyze the key reasons why prospects didn’t buy from us in these deals. Organize and rank them 3. Design a “mini-offer” (cold friendly) a. Use the two insights above to design a mini offer. A mini offer is something that your prospects see and say “I need this right now”. In the early stages, this isn’t usually your product. Your standard “book a demo” or “let’s get on a call” isn’t going to cut it (Some ideas to get you started are in the pdf 👇🏽) Once you have that, you can… 4. Outbound to get mini offer out a. Use lemlist or Closely to warm up some email domains ($100/mo) b. Create a sequence across LinkedIn, email and calling for three lists: > Warm companies > Cold folks that are 2nd degree connections to anyone at our startup > Cold folks that are not 2nd degree connections c. Manually send the sequence to warm d. Use Closely to send the sequence to cold prospects across LinkedIn and email 5. Content for air cover I’d pick LinkedIn as my primary “PR” channel. When someone sees something from you, the first thing they do is go to your LinkedIn profile and see what you talk about. To provide “air cover” for the outbound campaign, I would create inbound content across 3 pillars: > Value Driven Content > Curation Driven Content > Founder and Employee Led Content (details in the pdf below👇🏽) 5. Set up tracking, analytics and automation a. Set up Google Analytics, Hotjar and connect to CRM b. Use Miro / Funnelytics to map out the entire funnel c. Find and map out all the “dead-ends” d. Pick 3 key metrics to track across the funnel e. Automate follow up email, calendar scheduling and website chatbot -- Summary: 1. Create a “laser focused” account list: 2. Analyze 10 Closed Won / Lost deals 3. Design a “mini-offer” (has to be cold friendly) 4. Inbound for air cover 5. Set up tracking, analytics and automation — P.S. If you want to workbook below with all the exercises and tools, comment “canvas” and I will DM you the entire playbook on how to do this (must be connected or following)

I recently closed a six-figure deal with an enterprise client. While most deals this size take 6-8 months, I closed this one in under 60 days. Here's exactly how I did it: When selling to an enterprise company, it's easy to get trapped in long deal cycles. To avoid this from always happening, here are the 4 steps I take to expedite my enterprise closing process: 1. Subject Matter Expertise Plays    Most sellers pitch products. We pitch proven expertise in their space. This shifted the entire conversation from "vendor" to "expert." • Pitched as an industry expert, not influencer • Showed proven processes from our team  • Focused on vertical expertise vs following Expertise beats influence every time. 2. Multi-Threading     Instead of focusing on one champion, I built relationships across the organization. Each stakeholder had different things that made this a win for them. • Built relationships with seven key stakeholders • Sent a recap email to each buying department so everyone knew what was going on • Had notes for each department's goals and why they wanted to win Throughout the deal, I always asked who would feel left out if they weren't involved. Every time I found a new person, I made it a point to meet them. That means more allies for the deal to sell internally. 3. Weekly Momentum Building    Most deals need more momentum. That's why I keep the energy high. • Sent weekly videos to keep my POC informed • Highlighted each stakeholder's priorities • Highlighted work we were doing along the way Momentum beats perfection. 4. Procurement Fast Track This is where deals typically go to die. Not today my friends. This is where the party starts. As soon as I get introduced to procurement, I ask for a quick 15-minute call so I can quickly text edits as my lawyer goes back and forth. • Asked for concerns up front • Built solutions into proposal • Asked what do you people typically redline when they approach you Being proactive beats being reactive every time. Because doing the little things well will always yield great results. P.S. Have a favorite step?

When I started in sales, I thought success came down to the perfect pitch. Say the right words. Handle objections. Close the deal. But over time, I realized that’s not what separates the top reps from the rest. The real difference? Discipline. It’s not flashy. It’s not exciting. But it’s everything. And it can feel very lonely Here are 7 daily sales disciplines that compound: 1. Pipeline Hygiene, not just updates  → Scrubbing out dead deals weekly, re-scoring leads, and keeping the pipeline realistic, because false hope kills forecasting. 2. Pre-call intel  → Spending 10 –15 mins before every prospecting block digging into trigger events, recent news, and mutual connections. The difference between “generic pitch” and “you clearly did your homework.” 3. Post-meeting debriefs  → Writing down objections, exact phrasing prospects used, and tone shifts. Not just for memory, but to sharpen the next conversation. 4. Micro-touches that don’t sell  → Sending a relevant article, a quick voice note, or engaging with their LinkedIn post. Building context, not just chasing contracts. 5. Opportunity time-blocking  → Structuring the day so you touch every deal in mid-stage daily, even for 2 minutes. Deals die from neglect, not competition. 6. Daily deal strategy check  → Asking: “What’s the next step I own to move this deal forward?” If you don’t know, the deal is already slipping. 7. Self-review like a coach  → Replaying a call, listening not for the prospect but for your own filler words, missed buying signals, and talk/listen ratio. That’s how average reps become closers. These aren’t “big moments.” They’re small, routine actions. But when you do them consistently, they add up to something huge. The sales reps who hit quota month after month aren’t superheroes. They’re just the ones who treat the little things like they matter. Discipline doesn’t feel good in the moment. Discipline is often the loneliest part of the sales process and mindset But it’s what makes you great in the long run. 👉 What’s one small thing you do every day to stay disciplined as a sales guy?

We know all the legacy sales training methods, but we are also quick to plug problems with "the way we've always done it" without considering how they often don't address the problems sellers and leaders face today: 💡 Most methodologies were designed decades ago for starters, but many also talk to you about how to win the deal. Issue: your sellers are being KPI'd on prospecting and outbound, many of which have never received training on how. Consider the money + resources wasted + seller frustration by not helping them here. 💡 "We have intent for that!" Issue: If you're responding to buyer intent, so are your competitors. What will you do to stand out? 💡 Finding the right buyer is one thing, getting them to say yes to a meeting is (a really really hard) another. Issue: In the age of scaled-and-veiled automation that tricks buyers into thinking you made an effort and where our buyers are flooded with outreach, you have to find a way to stand out. Show Me You Know Me sets open rates and response rates through the roof. 💡 "I don't have time to coach." Issue: What doesn't get measured won't get done, so if you don't have KPIs here and those aren't tied to annual reviews... Not having time often = "I just don't know how to do it so I don't." 💡 "And in just 13 steps and 17 weeks, you'll see a win from this training!" Issue: We're in an age where humans need quick gratification to motivate change. Many of these legacy methods require a full change in process vs. quick wins that make big impacts. 💡 Theory + What To Do Issue: Almost all trainings do the above, but the ones that stick tell you HOW to do it. Method, timing, medium, socials, nurturing, multi-threading process and scripts. ********************************************************************** The cliche is true here - what got us here, won't get us there. Your sellers aren't looking for more theory or more product training. They're begging their brands to teach them how to succeed in today's market, not last decade's market. #samsales #SMYKM

Sales cycles grew an average of 27 days this year: - Cycles in H1 2023 were an average of 134 days (4.4 months) - Compared to the 107-day (3.5 months) average in H1 2022* *data from the excellent Capchase report, 'B2B SaaS Sales Cycles in 2023' Which is (obviously) a big problem. Because a 25% jump in cycle times is *the same thing* as having just 9 months to close 12 months of revenue. Like getting your 2024 quota… …then being told to hit that target in September. Not December. In other words: A whole quarter was stolen from most sales teams this year. Which is why 84% of leaders in the study said shrinking cycles is a priority. So, what’s the secret to cutting cycles times? Well it’s not about applying more force or pressure. It's about applying a little “WD-40” to cut out friction in the *buying* process. The trick is knowing where to apply it. _______ 1/ Update your pipeline stages to focus on specific *buying* behavior. 2/ Create specific exit criteria for moving deals from stage → stage. 3/ Look for the longest stage-to-stage time. 4/ Ask: what’s happening in the buying org? What's preventing them from moving forward? 5/ Pinpoint the doubt / uncertainty / confusion that's happening. 6/ Intentionally address the answer to # 5 in the prior stage. 7/ Repeat # 1 - # 6 above from the longest → shortest stages. _______ Here's a visual of what this could look like. Notice two big ideas: - You can’t troubleshoot what you can’t isolate. - Slowdowns are about what happens inside the buying org. Which are two big misses in most sales process design: - Stages are too clumped up, without clear exit criteria. - Stages are based on a seller's activity, not buying behaviors. And if you're an AE reading this, thinking, "Uhh, great, but I can't change our CRM stages..." that's okay. You can still take and apply the concept to the process *you* choose to design and run inside your own accounts. Which is the difference between deals closing in '23, vs. pushing to '24.