Ryan Estis and Associates’ Post

When I was a VP of Sales, the 3 worst questions my AEs used to ask on their discovery calls before the demo that led to a 20-26% demo conversion rate: → "Can you tell me about your business?" → "Are you the decision maker?" → "What features do you need?" The problem with these questions is: ❌ They were asking something they could have been Googled ❌ They were insulting their authority, but also assume it ends with them ❌ They were not focused on solving the problem, and end up feature dumping We tore down those questions, and replaced them with these 6 ones: (this led to a 50-75% demo conversion rate) 1. CHALLENGE Q: "What challenges are you specifically having now that you think we'd be able to help solve?" I recommend this be your leading discovery question since it anchors the entire conversation around pain (exactly what you want). The prospect usually opens up fast about their problems, especially since the ending of that question assumes you may NOT be a fit (i.e. unselling them). 2. ALIGNMENT Q: "Every time I speak to a business like yours, they're usually focused on [SOLVING X], how aligned is that with your vision?" Ask this question if you know the exact buyer persona and buying scenario your prospect fits into (based on your historic deals). People want to do business with people they trust. Show them you understand their world and you'll earn their business. 3. GOALS Q: "Whether you go with us or some other solution, what would success look like to you in the first 90 days of implementation?" I usually like asking this question after I've found out the prospect's pain. This question is focused on the prospect's goals and expectations (something they typically keep hidden). The prospect will give you EXACTLY what they want, spoon-feeding you the deal. 4. EVALUATORS Q: "Assuming we'd still be a fit after you see the demo, besides you, who on your team would need to trial this?" We forget that 'end users' influence the entire decision. E.g. If your prospect rolls out new software for their sales team, but they unanimously hate it, they won't buy it. Remember, influencing leads to decision making. 5. DETRACTORS Q: "Who do you think won't believe you actually need this?" There's always someone in the deal that pops the air out of your opportunity. And usually, they're a 'hidden decision maker' or influencer. If you don't ask this question, you'll only find out when it's too late. 6. STATUS QUO Q: "What are the chances that you'll end up just sticking to what you've currently been using?" Your biggest competitor is status quo. It's easier to stick to what you know than to try something new (especially, when your job is on the line). Find out the probability of losing the deal as early as possible. **I ask all these questions on my disco calls today** P.S. 6,000 AEs are using this to ask smarter discovery questions (free) https://lnkd.in/eR69raD4

I am giving all my sales secrets away. But this won't be your normal boring webinar. I have partnered with Calendly to launch a masterclass called The Art of ‘Cold to Closed.’ We all know it’s a great feeling to schedule a meeting, but it's even better when you can close it. Here are the strategies I will be sharing to get you a big fat pipeline to close: • How to sell on LinkedIn the right way • Simple frameworks you can execute to schedule meetings with cold calling and email • Uncovering urgency in the sales cycle to drive sales These will be tactical sessions, during which I will share what I have done that has led to millions in the pipeline. You will be able to use the information right away to see results. Zero fluff over here. As one of my favorite quotes goes, "The more you learn, the more you earn." P.S. Do you agree having a big fat pipeline helps you close more? P.S.S. Sign up for the Masterclass here. https://lnkd.in/e9cZghE2

Why 83% of Sales Teams Miss Their Targets (And How to Be in the Top 17%) 🗒 Register and find out... https://lnkd.in/e6ERWUFs 🎯 83% of sales teams fail to hit their targets. But you're not going to be one of them. Welcome to Week 2 of our "Hit Your 2025 Sales Goals" series!   Last week, we kicked things off with a powerful tip to start building your "Voice of the Customer" database. (If you missed it, check your inbox!)   This week, we're diving deep into why strategic sales planning is your secret weapon for 2025 success.   Here's the shocking reality ▪ Only 17% of sales organizations use a formal, guided sales process ▪ These top performers see 28% higher revenue growth compared to their peers What's their secret? A rock-solid sales plan built on three key pillars:  1. 🔎 Clear Market Focus: Identifying and targeting your most profitable segments.  2. 🚀 Defined Sales Process: Creating a repeatable, scalable approach to closing deals.  3. 💪 Team Capability: Equipping your team with the skills and tools they need to excel. Let's look at a real-world example: Meet TechInnovate, a B2B SaaS company that was struggling to meet its targets. After implementing a strategic sales plan with SalesStar: ▪ Their win rate increased by 35% ▪ Average deal size grew by 28% ▪ Overall revenue DOUBLED in just 18 months Want to achieve results like these? You're in luck!   Our upcoming 45-minute webinar, "Build a Bulletproof Strategic Sales Plan for 2025," is just around the corner.    📆 October 17, 2024   🕑 2pm EST 👉 Secure Your Spot Here https://lnkd.in/e6ERWUFs   In this session, you'll learn:   ✅ How to craft a 1-Page Strategic Sales Plan that drives results   ✅ Strategies to win over C-suite decision-makers in complex sales cycles   ✅ Tactics to achieve measurable, predictable, and profitable growth   Not going to make it? Don't worry, we will send out the recording after the event, but you must be registered to receive it.  Sign up!   Can't wait until the webinar to get started? We've got you covered.   Book a complimentary 1-on-1 Strategy Session with one of our expert consultants. We'll help you lay the groundwork for your 2025 success plan.   https://lnkd.in/ebcVNR8f Here's to your sales success,

Your team: when will our 1st AE close their 1st deal? Reality: it's going to be a minute. Speed can actually be harmful. It's really easy to become a rep who is an inch deep and a mile wide on all topics. There's no sales enablement leader at the company to guide them. And when the rep feels pressure to perform, the natural inclination is to just get started. But it's pretty obvious when a rep doesn't know their stuff. That's why your 1st rep needs an intentional 30-60-90. Go slow to go fast. All activities should roll up to 1 of 3 themes: \ Learn our personas \ Become competent pitching our product \ Develop a rhythm with our team Then build in key activities. Due dates should create urgency, but be realistic. Learn our personas: - Ride along on founder's sales mtgs. Look at their calendar, ask to join. Take notes. Save questions to ask in a 1:1 after the fact. - Review call recordings, call notes, deal notes. If there are any. Pull out themes as you go, and ask team members about them in 1:1s. - Meet the team member who manage customer relationships. Have them walk you through 2-3 customers who have common profiles. - Ask for links to any relevant documentation. Add them to your reading backlog. - Ask the team what related news sources they like. Add them to your favorites. - Organize your notes from all of the above as a persona outline. Who they are, what problems they have, how they solve them today. This should look like a bullet point list, not polished collateral. It's purely a format to facilitate internal Q&A during your ramp up. Become competent pitching our product: - Review your founder's favorite sales deck. Take notes on their talk track. - Schedule a product walkthrough with any team member who knows the product well. Record the mtg, ask questions and take notes. - Review product documentation. If there is any. - Get a demo account and explore. You should know where every click leads without having to think about it. - Record a <5 minute pitch. Just slides, no demo. Share internally, ask for feedback. - Host multiple mock demos with team members. Get feedback. - Lead disco call(s) with the founder on the call to help if needed. - Align with founder on what else they expect before you hit the field solo. Develop a rhythm with our team: - Share 30-60-90 with team. Transparency builds trust and they can give you tips on what else to include. - Batch questions from all of the above to the most aligned team members. - Learn your v1 CRM data and report on what you're learning about the sales pipeline. - Create an prospect feedback landing page. Pin it to a shared slack channel. Every sales rep will have their own way of learning their job. But regardless of personal preferences, make sure they provide an intentional plan.

What's better than nailing a sales demo? Closing the deal! 🙌 My teammates at Calendly compiled their top tips on how to keep momentum high after an amazing demo. I personally loved their advice on how keep prospects engaged and beat the clock with timely & personalized responses! 👇

What's better than nailing a sales demo? Closing the deal! 🙌 My teammates at Calendly compiled their top tips on how to keep momentum high after an amazing demo. I personally loved their advice on how keep prospects engaged and beat the clock with timely & personalized responses! 👇

What's better than nailing a sales demo? Closing the deal! 🙌 My teammates at Calendly compiled their top tips on how to keep momentum high after an amazing demo. I personally loved their advice on how keep prospects engaged and beat the clock with timely & personalized responses! 👇

What's better than nailing a sales demo? Closing the deal! 🙌 My teammates at Calendly compiled their top tips on how to keep momentum high after an amazing demo. I personally loved their advice on how keep prospects engaged and beat the clock with timely & personalized responses! 👇

Jamal is "having more reps than usual in Q4 asking me to help them save their deals." His "naked truth is that if you are in the later part of the sales cycle and you are facing these challenges, there aren’t many levers left to pull. The trick with strategic selling is that it is very front-loaded: The magic happens at the beginning, not the end." Jamal is a great content creator. Is he correct? Yes and no. • Yes, "The magic happens at the beginning!" You set the stage with ICP qualification, meeting the buying committee, multithreading, and timeline alignment + expectation management. • No, "There aren’t many levers left to pull" - If you know how to execute the right way, you can still turn it around. Here’s What You Need to Do today: 1️⃣ Multithread—right this second. If you’re relying on a single point of contact or even 2, your deal is on life support. Reach out to their peers, managers, and decision-makers. Use LinkedIn, email, or calls—whatever it takes to build relationships across the organization. This obviously requires a smooth touch, in some situations, a deal that would have closed in Q1 will break because the rep handled this part poorly. 2️⃣ Reset the Timeline. When a deal stalls, call it out: “What’s changed since we last spoke? Are we still aligned on [timeline/goals]?” Talk to your decision committee individually(via LinkedIn, phone, email, text messages, or online chat) and get an idea of the actual situation. 3️⃣ Leverage Your Own Execs. Are deals stalled with the C-Suite? Bring in your own. A personal executive summary, a digital coffee this week, or a quick meeting with your CRO or CEO can create immediate momentum and demonstrate commitment. 4️⃣ Add More Touchpoints—Immediately. One email or follow-up isn’t enough. Flood their inbox (strategically and valuable), engage on LinkedIn, and provide value-driven insights. Make it clear you’re there to help, not to harass. Obviously, don't push to break. You should have a full understanding of what deals you can push this way. We can't make magic out of mud, neither me or Jamal. Key Takeaways for Teams Closing Q4: • Get Ruthless About Qualification: If a deal is low-probability or the buyer isn’t committed, cut it loose(for now) They can wait for Q1 if that's the plan. You can’t afford dead weight in your activity RIGHT now. • Multithread Like It’s Your Job: No single-threaded deal survives a tough quarter. Build relationships early and often. • Engage Executives Now: High-level touchpoints can revive stalled deals. Use them. The truth? You CAN turn it around. But scrambling and hoping won’t do it. The magic happens at the beginning—but it can also happen at the end if you know what levers to pull. 👇 Think I’m wrong? Prove me wrong below.

🏈 Here’s the play: Many inside sales teams are missing valuable opportunities by only following up on a fraction of leads, much like a football team that doesn't leverage every play to gain a first down or force a turnover. The scoreboard shows the outcome. There’s a misconception that once a lead reaches inside sales, they’re already in the red zone - when often, they still need some serious nurturing to get across the goal line. You need A-team starting players for this grind work. Otherwise, depending solely on purchased lead lists will result in frequent "3 and out" scenarios for your offense. Expecting a website’s lead form to qualify can be unrealistic too. Overloading forms with questions is like throwing too many passes - if it’s too complicated, prospects might drop the ball entirely. 📋 Consider these 3 strategies to boost your game: - Refine Lead Qualification: Ensure leads are properly vetted before they reach your sales team, maximizing your ROI. - Outsource if Needed: If building an internal qualification team isn’t in your playbook, consider outsourcing to effectively manage lead quality and credible intent. - Boost Performance: Properly handling leads increases pipeline volume, enhances customer experience, and drives higher conversion result$. 📈 How are you optimizing your lead flow and qualification? Share your winning strategies! #SalesOptimization #InsideSales #LeadQualification #BusinessGrowth #ROI