Jeffrey Gabriel

 Most deals don’t fail at closing. They fail way earlier because you chased the wrong prospect. 👉That’s why qualification is everything. I call it the 5-Step Deal Qualification Cycle: 1️⃣ Verify Pain 2️⃣ Confirm Budget 3️⃣ Map Decision Process 4️⃣ Assess Fit 5️⃣ Evaluate Competition If you master these, your close rate skyrockets. Stop chasing “maybe.” Start closing “must-have.” ➡️ Swipe the carousel for the full breakdown. ❓What’s the first question you ask when qualifying a deal? 👥 Follow me for more sales strategies that help you win smarter, not harder.

61

64 Comments

Seller ($50k deal) vs. Consultant ($5 million deal) Sellers run ‘sales cycles.’ Consultants deliver strategic consulting engagements. Here is the MASSIVE difference: Sales Cycle: - Prospect -> SDR pitches to mid level managers - Discovery -> AE ‘does a discovery call’ - Demo -> SE leads a demo (often brought in by AE with no context or prep) - Close -> AE tries to get a second meeting, often fails Result: 15% win rate, $100k average deal size Strategic Consulting Engagement: - Insight written by experts (read by executives who then bring them in for a deeper dive) - Executive Briefing delivered by experts to executive team - Analysis (paid) executed by experts ‘to get to the root cause’ - Results read out session - delivered by experts to convey findings to execs - Project established - execs buy in and are willing to pay big bucks given analysis results and reputation of consulting firm. Result: 50% win rate, $5M average deal size So these realities leave us with a few key questions: 1. Do you want to run a traditional sales cycle or a consultative engagement? 2. Have you become an expert in your space/domain? 3. Can you hold your own in a conversation with a senior customer executive? 4. Do you have experts on your deal teams? 5. Does your company have the internal capability to generate insights? 6. Is your average deal size where you want it to be? We are in the most difficult selling reality in a generation. If you aren’t rising to more advanced selling playbooks, you will fall into the abyss of transactional sales, which is the path to failure. Rise up. EDIT: P.S. Join 200+ enterprise tech sellers following the step-by-step playbook I used to close $160M in SaaS revenue: https://lnkd.in/dUgY78_R

255

135 Comments

Do you still give your SDRs call spiels? Do they still read aloud from a written script? And did you ever wonder why the quarter is already ending, but you’re not even half as close as your target quota? There’s your answer. In those “scripts.” Scripts are fine during the onboarding process. During the early stage, During the Getting To Know Each Other phase… But that’s just it. If you’re ramping up for an advanced campaign, it just makes more sense to bring along an equally advanced tool. The sophisticated, non-primitive tool your SDRs can bring when closing deals? It’s their supercomputer. It’s their brain and their power to THINK. When going off-script (which you will 100% do 100% of the time), what you need is a fast-paced, critical thinker who knows just what to say outside the spiels. Yes, there are buyer patterns, but they always unfold in REAL TIME. And if you’re head is not there, when you’re stuck in what is in your script, consider that deal lost. So, when training your reps, don't tell them what to say. Ask them what they noticed. "Why do you think they said that?" "What pattern are you seeing here?" "What would you do differently next time?" Force them to reflect. They should have the brain power to know just what worked and what didn't. They need to know how buyers actually think. Give them that, and you'll build a team that can sell just about anything, no sweat.

27

7 Comments

Most salespeople suck. Not because they’re bad people. Or lazy. But because sales is really hard. In 2023, across 650,000 opportunities representing ~$50B of pipeline, just 20% of reps delivered 80% of revenue. In 2024, that number fell to 14%. Just 14% of reps delivered 80% of all revenue in B2B tech! Want to know the funny thing? Those numbers haven’t changed much in the 25 years I’ve been doing this. 15yrs ago, we used Objective Management Group to assess our sales team. The numbers were the same. The assessment told us to hire 2 out of every 10 people we thought would be a good fit. And keep 2 out of 10 that already worked for us. The rest were unsalvageable. Time and again, it turns out that a small percentage of sellers generate almost all the revenue in an organization. The real question is: Are the other 80% redeemable? Perhaps a more precise question is, “Can we shift the median performance of the other 80% to warrant investing in development?” Research would indicate, YES. Investing in B players increases their odds of becoming A players by 63%. Can you afford to make that investment? Or better yet, can you afford not to? Let’s compare what’s more expensive... Investing in development or trying to hire only A players. INVESTING IN DEVELOPMENT - According to Spotio, the typical ROI of training is 3.53:1 meaning for every $1 you invest you generate $4.53 in return - Companies that prioritize training are 57% more effective than competitors - High-growth companies are ~2× more likely to provide ongoing sales training HIRING ONLY A PLAYERS - Hiring A players feels like the smart bet. Except it’s not. For two reasons: You’re not very good at hiring and performance isn’t portable. Previous success often depended on firm-specific factors — supportive culture, familiar products, internal networks — that don’t transfer to the new employer. In sales, this means a top 1% performer at Company A might struggle at Company B due to products, processes, or team dynamics. Harvard research calls this the “portability of performance” problem: star employees are “imperfectly mobile” resources. There are additional challenges with hiring stars: - High cost and ROI uncertainty: Top performers command top $ — not just in salary, but guarantees, bonuses, recruiting fees. If the star hits a slump or takes a long time to ramp, the investment may not pay off.     - Expensive mistakes: A failed sales hire can cost $500k — and more if you include lost revenue and morale drag. BOTTOM LINE: Most people are bad at their jobs. Most sales people cannot sell. You can invest in development and it will have some impact. You can try to hire only A players but you'll fail. The answer is probably trying to do both but quickly routing your best leads to people that prove themselves and creating a system that will look unfair but will drive higher productivity. Which means 10-20% of your reps will generate all your business. And maybe that's OK.

382

107 Comments

The answer to your outbound problems isn't: ⛔️ AI ⛔️ More volume ⛔️ SDR agents ⛔️ More relevance ⛔️ Dialers ⛔️ Better tools It's your OFFER. Let me explain... Most reps reach out with something like: “Just want to introduce myself and our company…” “Let’s do a quick call so you know your options when budgeting season comes around...” The problem? You have NOTHING to offer. If there’s no immediate need, there's zero reason to take a meeting with you. So you need a way to entice buyers to meet when they have a problem, but are not actively shopping. Here are three types of offers you can use to entice buyers to meet with you: ✅ Offer #1: Good - Pitch The Blind Date Position who the buyer will be meeting with. Hype up the AE, sales engineer, or yourself. Show them that meeting with you will be worth their while. Example: A client of ours sells an automated welding solution. The manufacturing industry is facing a massive shortage of welding talent. Their SDRs pitched it like this: “I’d love to introduce you to Eric. He’s worked with a dozen manufacturers like Caterpillar, Karavan, and more, who are all facing similar challenges. He’ll walk you through how they’re automating the most difficult welds and dealing with the labor shortage. Even if nothing comes of it, you’ll walk away with a better understanding of how the industry is solving this.” Even if the buyer isn’t shopping, they gain value from the conversation itself. ✅ Offer #2: Better - 1:Many Offers These are high-quality, reusable insights that still feel tailored. Think: competitive benchmarks, industry research, or best practice guides. Example: We have a client that sells to ecomm brands. They conducted a mystery shop of 400 competitors to analyze response times, customer service channels, etc. Their reps used those insights to open cold calls with: “Hey Katie, I submitted a ticket on your site, and it took about 48 hours to get a response. It was about 3x longer than folks like Patagonia and the North Face. Again, it’s Jason. Mind if I share more about why I’m calling?” That’s an offer that feels immediately relevant and valuable. It gets a conversation started immediately. ✅ Offer #3: Best - 1:1 Offers These are custom-tailored experiences or resources created specifically for the prospect. It’s you and your organization putting in serious effort to customize the offer. This works best at the enterprise & strategic levels. Examples: - A cyber risk analysis - A benchmarking analysis - A workshop - A personalized audit of a website checkout flow. - Visiting and experiencing the brand firsthand, then sharing insights. - Offering free data, licenses, or pilots. These take more work, but they convert like crazy. ~~~ You don't need better tools. You need a better offer you can deliver on to make meeting with you worth their time.

52

13 Comments

I audited 23 SMB AEs’ calendars + process last month. Some are stuck at $100K/year or less and platued. Others are earning $15K-$20K/month and getting promoted to mid-market. Here are the 3 problems keeping the stuck ones from breaking through: [Problem 1 - Unstructured Calendar]: They wake up Monday morning and think: "Who should I call today?" They update CRM between calls. They send recap emails whenever. They clean their pipeline randomly. Ask them what Monday through Friday looks like: "It depends." The $15K+ / month earners can tell you exactly what happens at 9 AM, 12 PM, 3 PM every day. The issue: Mixing revenue-generating activities with admin work all day long. The fix: Separate and prep. Revenue activities: → Prospecting (9-12 PM blocked) → Discovery and demos (1-4 PM) → Deal follow-ups (specific time blocks) Admin activities: → CRM updates (4:30-5:30 PM) → Recap emails (end of day) → Pipeline planning (night before) [Problem 2 - Small Pipeline]: They rely too much on inbound leads and SDRs. When it gets slow, they don't know how to build pipeline themselves. The fix: Block time for prospecting. Build pipeline from a familiar list: → Call existing customers for referrals → Reach out to closed lost deals from 6-12 months ago (timing/budget may have changed) [Problem 3 - Dead Pipeline]: What I found: → Average sales cycle: 14 days → Deals sitting in pipeline: 45+ days → Prospect status: Ghosting them They're forecasting deals that will never close. All that mental energy gets sucked into prospects who disappeared months ago. The fix: Clean, purge, focus. Know your average sales cycle Pull your CRM data. 14 days? 20 days? 30 days? Identify dead deals. Any deal open 1.5-2X your average cycle + no prospect response = dead. Send breakup emails: "Haven't heard back. Assuming this isn't a priority. Let me know if things change." Then mark it Closed Lost. Focus on what you can close NOW Structure your calendar. Build your own pipeline. Clean the dead weight.

66

11 Comments

Most trade "what will I do?" for "what happens next?". Every day brings endless business decisions: Raise prices or lower them? Add outbound or double down on PLG? Target enterprise or stay with SMBs? Build new features or fix what's broken? Start a podcast or run more ads? The paradox? The more options you have, the more tempting it becomes to do nothing. Just follow what others in your category are doing. Copy the leader. But following isn't strategy. It's compliance. You need to be able to answer 'why will we win', and that requires decisions about tradeoffs.

41

23 Comments

Follow this structure to increase your connect-to-meeting ratio and build trust from the first call: Cold calling that actually works: Most reps dial and pray. Top reps follow a system. Here’s a 5-step cold call script that sourced $2M+ ARR: 1. Trigger Don’t call out of the blue. Start with a recent event about their company to prove relevance. 2. Problem Frame a clear business challenge they’re likely facing. This makes them listen. 3. Validate Check if this problem is real for them. A simple “Is this something you’re seeing too?” keeps the call alive. 4. Handle Objections Expect “Not interested.” Stay calm, acknowledge, and pivot back to the problem. 5. CTA Don’t sell your product. Sell the value of taking a meeting to solve their problem. Stop spraying and praying. Start calling with a structure. This is how top sales reps get meetings booked consistently. 👉🏻 Follow Christian Krause for more such amazing content 👉 Follow Sales Tips for no-fluff sales tips.

49

10 Comments