AMA: Cacheflow GTM Leader, Adam Wainwright on Discovery Tactics

An interesting first question, and one that assumes pain points and value language is completely understood - Let's do this insted. I'll give you my recipe for building a best-in-class pain/discovery process that you can use to either a) create a net new discovery process or b) tweak the one you're running in service of actually helping the customer, as opposed to running the customer through a marketing approved, but irrelevant discovery call. When creating a pain narrative that fosters a truly valuable conversation with a prospect, I always recommend focusing on understanding three key areas, in this order: the category, the language, and then the customer. Let me explain why. Understanding the Category First, why understand the customer last? It might sound counterintuitive, but when entering a new sales environment, the goal is to leverage trends and data effectively. Starting at the category level reveals general customer sentiment and overarching market dynamics that are otherwise easy to overlook. When researching a category, keep it broad. Understand the general language used and write down every emotionally charged phrase you come across. This is the key to crafting discovery questions that drive high-value conversations, prompting the prospect to acknowledge their challenges: "Yes, I do have those problems. Yes, I want to solve them." Some helpful resources include: * Gartner Magic Quadrant: It’s a staple for understanding vendor positioning, though analyst biases exist. Focus on the patterns in the language analysts use to differentiate vendors, not on any one company's score. * Forrester Wave Report: Forrester’s insights often forecast upcoming market shifts. Their analysis can help you anticipate what pains and language might resonate with buyers in the near future. * G2 Crowd: This is an effective way to understand customer pain through real reviews. Ignore the fluff and focus on strategic commentary that qualifies why reviewers like or dislike certain vendors. Understanding the Language Once you’ve absorbed information from analysts and user reviews, it’s time to develop a "Pain Menu"—a slide that showcases all potential pains that could be impacting your customer. The pain menu is a powerful tool for discovery because it gets the prospect talking, but make sure it’s concise and tailored to your audience. Here’s where it gets interesting: If you can present a compounding narrative—highlighting how different operational or tactical pains roll up into a bigger strategic challenge—you’ll get a richer discovery outcome. For example, detailing how disjointed sales processes hinder scaling can connect to broader themes of strategic inefficiency. This demonstrates that you understand both the practical and the big-picture implications of the problem, building credibility. Augmenting with Data Emotionally charged language draws prospects in, but you need data to substantiate the value of addressing the pain. My advice? Keep it simple. Find something that supports a 10x ROI—particularly in the current environment where financial leaders crave realistic yet compelling metrics. Use data to align with a strategic initiative, like "We’ll help you scale efficiently, enabling a 2026 at full revenue productivity." You can present "worst case, most likely, and best case" ROI scenarios. This helps financial decision-makers see that even the worst case justifies the investment. Make sure the worst-case scenario is both realistic and favorable, and position it as being tied to customer adoption success. For example: "Our worst case happens when customers don’t engage fully with our professional services and enablement. We’ve made big improvements in how we support adoption, including x, y, z." Finally, Understanding the Customer Finally, dig into understanding the customer. I leave this for last because it’s easy to get caught up in the day-to-day operational pains during customer interviews. To build a great pain menu, focus on developing pain content that connects the operational layer with the strategic vision of the business. Use customer interviews to pressure test your language. Test your pain statements with different personas and try to bucket the winning language with the appropriate titles—this ensures your discovery process resonates across both operational and strategic layers.

This is a critical question and often the root cause of inefficiencies and confusion when scaling a business development function. First Rule for Discovery Prep: Keep It Simple For SDR-led discovery, the primary focus should be on disqualification criteria. Define the minimum requirements to disqualify and make these the core of the SDR qualification process. Avoid asking SDRs to conduct complex, value-driven discovery calls with senior evaluators unless you are actively looking to transition them into a sales role. Their focus should be on determining whether a meeting should qualify as pipeline—nothing more. In situations where there's no SDR qualification and meetings are directly booked via web forms, adjust the process to streamline the first call. Replace the generic “You're all set to meet with us” email with a high-level qualification email that sets expectations for the call and prompts a response. This approach ensures AEs are equipped with enough context on the buyer’s pain points to avoid a cold discovery call. Example Email: Hi [Prospect], Thank you for your interest in [YOUR COMPANY]. Could you share 2-3 sentences on what prompted your interest or the initiatives you’re looking to solve? This will help me prepare and ensure we make the most of our time together. If there are others you’d like to add to the meeting, let me know and I’ll include them. This type of message invites the prospect to share their priorities. An engaged buyer (a sign of a promising deal) will provide details that often allude to specific pain points—a valuable signal that can help position the solution effectively during the call. * Pro Tip: When a prospect responds, cold call them briefly to clarify key points. Keep it concise, with just one or two follow-up questions to show curiosity without overstepping. The aim is to build rapport, not conduct a full discovery. Be brief, be bright, be gone—just enough to establish a connection and show value. With this approach, you'll head into the first call with confidence, having already created a personal connection and gained an early advantage over competitors. Building a Point of View (POV) To prepare for a successful discovery call, it’s essential to develop a robust POV that demonstrates your understanding of the customer’s account. For this, you’ll need: 1. A standardized set of attributes that helps you "know" your customer. 2. Tools that provide the data needed for this POV—such as Salesmotion, ZoomInfo, LeanData, CopyAI, Copilot, Warmly, or 6Sense. Attributes for an Effective POV: * Company Name: Identify the target company. * Attendees: List who will be present and their roles. * Purchase Motivation: Understand why they would buy your product. * Urgency Factors: Assess why they would buy now. * Pain Points: Capture any expressed challenges. * Meeting Goal: Define your primary objective. * Customer Expectations: Understand their desired outcomes for the meeting. * Key Moments: Identify key impressions you aim to leave. * Product Features to Highlight: Focus on relevant features for the discussion. * Potential Pitfalls: Be mindful of areas to avoid. * Company’s Offerings: Get familiar with their key products. * Growth Bets: Where are they focusing their growth strategy? * Business Themes to Align With: Important business statistics and themes. * Competitors: Be aware of their competitive landscape. * Success Stories to Reference: Use key wins to build credibility. * Discovery Questions: Prepare questions to understand their process and pain points. Leveraging this structured approach ensures that each discovery call is unformed, and better yet, meaningful, ultimately building trust with the prospect and effectively positioning your solution.

Before diving into the specifics, it’s important to establish the foundational role that Pipeline plays within an organization. Pipeline serves two primary purposes: 1. Forecasting Revenue: It enables you to accurately project future revenue streams. 2. Evaluating Business Health: It provides insight into the value and stability of your business, helping stakeholders understand how effectively you are converting opportunities into closed revenue. * Kick these deals back into the SDR blender and find a way to get them back into the funnel when/if it makes sense. This may simplify a complex topic, but it is necessary to identify where potential confusion might arise regarding the handling of Pipeline. Let me present two scenarios that illustrate different approaches based on organizational maturity. Scenario 1: Mature Revenue Organization For a well-structured revenue team with clearly defined segmentation, sufficient staffing, and the ability to measure revenue performance effectively, the strategy should be to avoid unnecessarily prolonging deals. In this context, the optimal path is to: * Develop a well-defined sales process that clearly outlines each stage. * Establish a rigorous process for managing “closed-lost” deals, allowing your team to focus on the deals that have a real probability of closing. By not dragging out unqualified opportunities, you prevent a misrepresentation of your forecast and ensure clarity in conversion metrics. Your team’s attention should be on driving the Pipeline that is likely to close—this will not only sharpen forecast accuracy but also enhance overall sales productivity. Scenario 2: Developing Organization For a growing business still finding its footing, closing out deals that aren’t moving forward may not always be the ideal course of action. Instead, it can be beneficial to: * Establish specific statuses or tags that allow you to categorize deals that aren't yet ready to be closed out or actively pursued. * Ensure these deals do not occupy the core focus of your sales team, whose priority should be opportunities likely to close within the established "days to close" window. However, keeping these deals in the Pipeline enables you to analyze patterns and define potential thresholds for Ideal Customer Profile (ICP) criteria—something critical for a scaling startup. This requires a collaborative effort across Sales, Revenue Operations, Marketing, and the Executive Team to jointly develop and own a process that drives insights from these inactive opportunities and informs future strategies. When raising, having more pipeline is better than having less. However, if you're still getting your footing on your ICP and feel like your in the "squiggly line" phase of your growth plan, it's not a bad idea to hold onto deals - you just need to be crystal clear in how you communicate managing pipeline expectations so it doesn't artificially inflate your actual forecast.

This is an excellent question, though providing a singular, straightforward answer can be challenging. Identifying root causes can range from straightforward to highly complex. Regardless, proficiency in the following areas is essential: * Customer Use Cases: Understanding ROI, persona-specific value, and the broader strategic context. * Value Mapping: If your champion understands the value but hasn't identified the root cause pain your solution addresses, it's your responsibility to reverse engineer this pain point and help align the buyer on how they will sell the solution internally. Sales Cycle Complexity: Understanding the complexity of your sales cycle is crucial. If you're operating within a shorter cycle with early involvement from decision-makers, root cause identification might occur swiftly. However, elevating the conversation to connect the champion's pain point to a broader strategic initiative will be key in securing executive buy-in. In strategic, enterprise cycles, the root cause may be more elusive. You'll need a plan to identify the people, processes, and work streams your solution enables or optimizes. The good news is that an enterprise strategic cycle is essentially a series of smaller cycles managed with a champion over an extended period. The following context will still apply, but understand that in a strategic cycle, you're always "on" and need to be hyper-aware of moving all evaluating parties through each step. This can be challenging if you're not accustomed to creating professional pressure. When pursuing root cause discovery in either scenario, consider the following: Uncovering Strategic Initiatives: To help your champion elevate the problem to align with organizational priorities, consider the following approaches: * Understand Executive Priorities: Ask your champion what their senior leadership cares about. If strategic language is absent, this may indicate that your champion lacks the seniority needed to push the purchasing request to the right stakeholders. * Leverage Company Messaging: Ask what is being communicated in company-wide meetings or all-hands sessions. Identify key themes or strategic initiatives that leadership is emphasizing. If the messaging is high-level (e.g., "We need to move faster"), determine who owns that initiative and gather additional context to position your champion's request accordingly. * Collaborate on Strategic Messaging: If your champion is more junior, you may need to brainstorm strategic root causes or initiative language together. This exercise can help them better communicate the value proposition in a way that resonates with decision-makers, framing the ask within broader strategic objectives. Now that you've aligned with you buyer on the larger strategic initiative, and hopefully aligned on pain. All you're doing is creating sales process that demonstrates the implication of said pain in the abscence of a solution AND the what happens on the other side of a sales process. I call this "selling value day." That is, we are usually spending the majority of our time selling the process, rather than the outcome, or even the pain. But in order to do this, I recommend that you come up with a few ways to standardize things that will help you maintain professional pressure, like: 1. 3 sentence Primary Business Objective statement - this is a succinct set of sentences that helps executives understand/get aligned on the solution presented relative to the "root cause" 2. 3 pillar Value slide - this is a pillar based representation of pain statements and desired outcomes each tied to business objective and is used to create some dimensionality to the previous Primary business objective. 3. From > To slide - If you're trying to create a sense of "pain: where we are" to "value: where we want to be" I recommend that you do a side by side slide that connects, very simply, the current state (1 sentence) and the desired state (1 sentence) PRO TIP: You want very few words on this slide, but lengthy, story telling context that you can elaborate on when presenting this slide later. PRO TIP #2: Best to reference customer stories here as well - bring these to life with real life examples. 4. Simplified Sales Process - Once you've tee'd everything up, you're now going to want to sell them on what they can expect in trade for their time. It's critical we make the process to getting into the desired state, easy. Or at least as easy as is reasonable

To manage a discovery process effectively, consider this approach: Condense the pitch deck into two focused slides: We do this because on our first discovery all we likely wont want to spend time in the pitch - However, you can use the contents of the deck to come up with a discovery guide. Later you can bring the pitch out for a larger audience and get them excited as well as beef it up with the learnings you've uncovered. For discovery, use the pitch to distill and create the following from it (add it to the top of your deck for future reference). 1. Pain Slide: This slide should tell a compelling story. It should outline both operational and tactical pains that, when discussed, reveal a larger strategic challenge. This narrative helps the champion articulate the issue to the broader buying committee and build urgency. 2. Sales Process Slide: This slide should outline the key tactical steps the buyer can expect during the evaluation. Limit this to 3-4 steps, with enough specificity to prepare your champion for next steps (e.g., needing to meet with the CRM admin to understand the current configuration). This provides transparency while setting realistic expectations. The key here is to use the Pain Slide to initiate a genuine dialogue. Reference use cases and tell stories that resonate. When executed well, the champion might respond with: “If you can address the first two issues, I can move forward; but if you solve all of these, I can easily rally support internally.” PRO TIP: When covering the Pain Slide, confirm alignment with your prospect’s pain points. It might seem obvious, but many sales reps make the mistake of assuming alignment without verification. Instead, break that pattern by directly asking: “If we can solve these challenges—specifically the one you highlighted—would you be in a position to champion this within your team?” The goal is to create moments that make the prospect feel the evaluation has genuinely begun. Without clear confirmation of pain alignment and the desire to address it, you risk simply discussing the product’s features rather than progressing the opportunity.

Integrating effective discovery into your presentation and demonstration process is the differentiator between consistently winning and struggling to close deals. Value-based selling demands that discovery is seamlessly woven throughout your engagement with prospects. When executed properly, this approach enables you to: 1. Deeply understand the customer's pain points and their broader implications. 2. Connect these pain points to relevant, successful customer stories. 3. Clearly outline tactical capabilities that address these pain points and confirm alignment with the prospect's needs. 4. Guide the prospect towards "value day" — the moment when they acknowledge the solution has resolved their challenge. By focusing on discovery, you control two critical outcomes: * Validation of the Customer’s Pain: Confirm the pain is significant, and that the prospect is committed to addressing it. * Demonstration of Value: Map pain directly to value, ensuring a tailored demonstration that resonates. Avoid generic, one-size-fits-all demonstrations. Instead, focus your demo on solving the customer’s most urgent pain points—the issues that generated genuine engagement during discovery. Key Execution Tips: 1. Customize Your Demo: Avoid "canned" demos—these are for marketing, not high-impact sales. Start with the pain point that resonated most with your prospect and build from there. 2. Demonstrate Pain-to-Value Continuously: Throughout the demo, take the opportunity to ask, "Can you see how [our solution] helps you overcome [specific pain point] we've discussed?" This ongoing dialogue builds clarity and reinforces alignment. 3. Drive Confirmation and Momentum: Repeat this process at least three times. It reinforces the connection between pain and solution, drives momentum, and elevates the prospect's confidence in you as their preferred vendor. Remember, winning is about understanding and empathizing with the customer's challenges, and proving your ability to solve them effectively.

The best reps, the ones consistently crushing quota, have a well-defined process for discovery. These reps enter discovery calls with confidence, having done their homework on the customer. This allows them to focus on building rapport while smoothly transitioning to the issues that matter most to the prospect. They keep the conversation natural and conversational but are ready to pivot into relevant slides that highlight the customer’s pain points—ensuring that the prospect feels the call was valuable and insightful. Top-performing reps never pitch the product during discovery. Instead, they show genuine interest in understanding the customer’s pain, hinting that when it’s time for the demo, "you’ll like what you see." PRO TIP: The key to a successful discovery is preparation, empathy, and restraint—focusing on the prospect's needs without rushing into a sales pitch.

Communicating value effectively isn't about having the perfect pitch. It's about having a system that enables you to drive credibility, identify real pain, and maintain momentum throughout the journey. Here are the core considerations to include in your system: 1. Establish credibility – Be someone worth listening to, early on. This means coming prepared, demonstrating expertise, and speaking their language. Credibility is earned by showing you understand their industry, challenges, and the outcomes they care about. 2. Identify & implicate pain – Discover the problem beneath the surface and highlight its impact. This is about asking the right questions to uncover hidden issues and then framing those problems in a way that connects emotionally with stakeholders. 3. Reference relevant use cases – Show them they’re not alone, and that others have succeeded with you. Share stories of similar organizations that faced similar challenges, and how your solution helped them achieve tangible results. 4. Map pain to value – Demonstrate clearly how your solution addresses their specific challenges. Create a direct line from the pain points identified to the value your solution provides, making it obvious why your approach is the best fit. 5. Sell a thoughtful evaluation plan – Guide stakeholders through a process where everyone knows their part and what’s next. A well-structured evaluation plan helps build confidence and ensures that all decision-makers are aligned on the steps to move forward. 6. Align on investment – Ensure they agree: this is a problem worth solving with time, energy, and budget. Make sure each stakeholder understands the cost of inaction, and that solving this problem is a priority worth their investment. 7. Establish ROI – Use value engineering to build an ROI model that lives across a worst case, most likely, and best case threshold. This will help quantify the value and show different possible outcomes, making it easier for the committee to see the financial impact of your solution. 8. Push professionally – Keep everyone focused and committed to moving forward, even when things get busy. Be respectful but assertive, maintaining momentum by setting clear expectations, follow-up actions, and deadlines. When selling to an executive committee, it's important to understand where the power lies in the organization and pressure-test your champion on their ability to wrangle team members to test your value story. The dynamics of a larger committee often mean multiple perspectives, varying priorities, and different levels of influence. Navigating this effectively requires knowing who holds decision-making power and ensuring that your champion has the influence to bring others along. Each time you're meeting with new decision-makers, you're running through the above system or process. You'll need to start a new mini sales cycle all over again. The objective is to align everyone who has power to get a deal done to your desired outcome, which, of course, will align perfectly with your champion's desired outcome. Value selling is an ongoing commitment. It’s not about pushing product—it's about helping others realize what's possible when real problems get solved.

Effective champions are crucial to securing a deal, especially when there isn't a direct path to an executive sponsor. However, if your champion is too junior or lacks the necessary influence, it becomes imperative to elevate the conversation quickly. To make meaningful progress, you need to amplify the perceived urgency around the pain points and advocate for expanding the evaluation committee as soon as possible. An unqualified champion can still be valuable if they can help secure introductions or arrange additional meetings with other stakeholders. Your objective is to empower your champion to be effective even when you are not present. This requires a deep understanding of how the executive team views their own strategic initiatives, particularly identifying any key initiatives that align with your solution. Positioning your offering as directly relevant to the company’s strategic goals can make your champion a more effective advocate within their organization. To achieve this, begin by uncovering the language, priorities, and key initiatives that resonate at the senior levels of the business. During your discovery phase, encourage your champion to orient you on the strategic imperatives that matter most to the executive team. Use this insight to craft customized value assets and pain-focused narratives that speak to broader organizational goals. Equip your champion with these tailored materials to help them socialize your solution effectively. The goal is to position your solution as an answer to the company’s most pressing challenges, ensuring that your champion can articulate its value in a way that resonates with senior decision-makers. By guiding your champion to align your solution with key strategic initiatives, you turn them into a conduit for executive-level engagement, significantly increasing your chances of success.

To effectively navigate objections, preparation is paramount. 1. Begin by deeply understanding your case studies through direct customer interviews. Develop a comprehensive list of the top three objections you are likely to encounter, and prepare structured responses that tie the discussion back to the broader challenges the prospect faces if they leave the pain unaddressed. * If objections reveal fundamental misalignment or indicate that the prospect is unqualified, consider whether it’s best to conclude the conversation. Winning fast and losing fast ensures you don't spend valuable time on deals that are unlikely to close. 2. When objections challenge your solution’s fit within their process, leverage relevant case studies to demonstrate success, and encourage your champion to articulate the long-term consequences of not solving the problem. Redirecting the conversation to the bigger picture and establishing relevance will help position you as a strategic partner. * Remember, discovery is about having a point of view informed by knowledge of their business, and using that to establish credibility as a trusted partner. 3. Handling objections well is critical to running a world-class sales cycle. Objections are opportunities to validate or enhance your position, and your responses should be rehearsed and ready. If you don’t have an answer, acknowledge it and commit to following up, but work to gain alignment on next steps during the call. Objections can be revisited if necessary—the key is maintaining forward momentum in the sales process.