Sales Prospecting Methods

A market map with 10,000 companies is impossible to prioritize. These are the 300 to know. I was a VP of Product in sales tech. And I was frustrated with the maps I found. So I've been studying the space and speaking with experts. Here's the players you need to know: — ONE - Core: Revenue Operating System This is your CRM, your system of record - where your sales operation begins. I break this into 3 segments: Enterprise Platforms → Built for large organizations with complex workflows and high-volume deals → Salesforce, Oracle, Microsoft Dynamics 365, SAP Growth-Stage Solutions → Designed for growing businesses that need scalable tools but with flexibility to adapt → HubSpot, Pipedrive, Zoho CRM, SugarCRM Modern CRMs → Startups and fast-scaling companies looking to move fast without rigid systems rely on modern CRMs. → Attio, Affinity, Close.io, Copper, Freshsales. — LAYER TWO - Engagement & Intelligence These tools power outbound outreach, automate sequences, and provide real-time data on prospects: → Outreach, Salesloft, VanillaSoft, Groove Engagement tools ensure your team hits the right prospect at the right time. — LAYER THREE - Revenue Acceleration These platforms shorten deal cycles: → Gong, Salesloft, Chorus.ai, Ebsta With real-time feedback and actionable insights... — LAYER FOUR - Data & Enrichment Your outreach is only as good as the data backing it. These platforms ensure you’re reaching out to right prospects. → ZoomInfo, Apollo.io, Clearbit, Lusha, Hunter io, Cognism — SATELLITE CLUSTERS - Modern GTM Stack These tools enhance parts of the GTM journey. AI-Enhanced Tools → Automate and personalize content creation at scale. → Writer, Grammarly, CopyAI, Jasper Product-Led Motion → Identify sales-ready leads through product engagement. → Pocus, Intercom, Breyta Sales Enablement → Equip sales teams with training, resources, and playbooks to perform at their best. → Seismic, Spekit, Allego Conversational GTM → Convert prospects directly through real-time chat. → Drift (now part of Salesloft) — SATELLITE CLUSTERS- Emerging Categories These are adjacent categories sales teams often still use. Product Analytics → Track user behaviors post-sale for better upsell and retention opportunities. → Amplitude, Mixpanel Customer Success → Ensure long-term customer retention and success beyond the initial sale. → Gainsight, Catalyst, Totango Workspace Integration → Enable seamless collaboration across sales and operations. → Notion, Slack, Airtable, monday.com Revenue Orchestration → Connect workflows across different systems to streamline revenue operations. → NektarAI, Tray.io, Workato, Boomi — This took a lot of time. Reshare ♻️ if you loved this post. What tools would you add?

For my first 16 years in tech sales, I averaged 240K/year. In my last 4 years, I averaged 720K/year. I did this by using an approach I call Yo-yo selling: 🪀 It’s how you win large, complex enterprise deals by building credibility with senior executives at the beginning of a sales cycle. This will save you months of spending time with mid or lower level Directors on a deal cycle, only to have your deal stall because it's not a priority for Executives. Here’s the concept: You start at the top, get senior level sponsorship for a deep discovery, drop down into the business, then bounce back up with a report of findings. This is the process I've used for nearly every 7-figure deal I've ever closed. Step 0: Research before outreach Before asking for time, I do deep strategic research. Earnings calls. Investor decks. Press releases. Executive interviews. I also spend time talking to their team to see if the problem that I solve exists in their company. Using that research, I build a Point of View that connects their top business goals to real execution gaps. This earns executive time. Today, AI tools like ChatGPT make this easier than ever. What used to take hours now takes minutes. If you skip this step, you lose your edge. Step 1: Prospect to the top and gain their sponsorship to engage Lead with your POV. The key is to teach them something new about their business which they aren't already aware of, and show them how it's putting their highest level goals at risk. If they lean in, offer up a deep discovery with your team and their team. Lock in a date to come back for a readout. Have them assign a project manager to help you coordinate Step 2: Drop down Once you have executive sponsorship, meet with their team. The key is to have the Exec sponsor send out a note to their team explaining what it's for. This will keep the assessment moving forward. Study workflows. Capture friction. Collect quotes. Do not pitch. Just listen. Step 3: Bounce back up Bring it all together in an executive summary. Show how their vision connects directly to what’s broken below. Present a focused business case. Build a custom demo. Create a roadmap and implementation plan. That’s where deals close. Real example from my career At Berkshire Hathaway HomeServices, we were told “no” on a point solution. Instead of walking away, I stepped back and asked what the company really needed. After deep research, I re-engaged the COO with a transformation POV centered on the experience of 50,000+ agents. The result was one of the largest new logo deals in Salesforce history. But Yo-yo selling alone isn’t enough. Because it's hard to execute and takes patience. Top performers also master their mindset, habits, and discipline. That’s why I put together a free masterclass for sellers who want to break into the top 1 percent. 👉 Watch the free training here: https://lnkd.in/eWD8mTqH If you’re serious about enterprise sales, this will change how you sell.

How I'd fill pipeline as an AE if I started fresh today. (Send this to your Slack group) Here is my plan: 1. Find Active Buyers The secret? Focus on prospects who posted in the last 30 days. Response rates are 2x higher from active profiles. Quick setup in Sales Nav: ↳ Create saved searches by seniority ↳  Build targeted prospect lists ↳ Update lists weekly for fresh leads Smart reps look for prospects who are active. 2. Strategic Outreach     Too many people say never do a cold dm, and tell you to sit back and wait. Please don't listen to this advice. Here's what I would do: ↳ Block 1 focused hour daily ↳ Send 20-30 targeted messages ↳ Be brief, brilliant, gone Example framework: "Reason I am reaching out [specific insight] → This matters to you because [direct benefit] → Imagine [concrete result/use ask] → CTA [simple, compelling next action]" The big fat pipeline is in the outreach. 3. Smart Engagement Don't just drop "Great post!" comments. Like real talk.. please don't do this. Start real conversations instead. The framework: ↳ Find a post ↳ Share specific insights from their content ↳ Ask one thought-provoking question Now if you did 20 messages a day check the math: 400 messages/month 10% conversion rate = 40 meetings/month There are no silver bullets. This is just an example, If you stay consistent what could happen. Stay prospecting my friends. ----- P.S. Mention someone who could benefit from this strategy. P.S.S. Which step are you going to use today?

I almost fired our best SDR last year. It wasn’t personal. He was a good guy, worked hard, and always showed up on time. But month after month, his numbers weren’t improving. Emails went unanswered. Calls never connected. Demos? Non-existent. We were both frustrated. I started to wonder if he was the problem. Maybe sales wasn’t his thing? Then one afternoon, we grabbed coffee. Instead of talking numbers, we talked openly. I asked him straight-up: “Why isn’t it working?” He took a deep breath and replied: “I’m following our playbook. I send hundreds of emails, but honestly, I’m just guessing. I don’t really know who’s ready to talk, so I try everyone.” It hit me like a ton of bricks. We’d built a system based on volume and hope, not precision. It wasn’t him. it was us. We’d given him the wrong tools, the wrong strategy. So instead of letting him go, we completely changed how we did outbound. We stopped guessing. We started paying attention to signals: Who’s visiting our LinkedIn profiles? (Tracked via Teamfluence™) Who’s engaging silently with our posts? (Tracked via Clay) Who’s spending serious time on our website? (Tracked via RB2B) Suddenly, our SDR wasn’t sending cold messages. He was following signals that said, “Hey, I’m interested. Talk to me.” Within a month, his reply rate doubled. In two months, he became our top performer. Today, he leads our outbound team. It wasn’t about effort. It was about timing and having a system that showed him exactly when to reach out and who to reach out to. Outbound isn’t about sending more messages. It’s about knowing exactly when and how to engage. If your SDRs are struggling, ask yourself: Are they failing you or are you failing them? It might change your perspective. It certainly changed ours. #Outbound #SalesLeadership #SDRlife #RevOps #LinkedInSales #SalesLessons #GTMStrategy #B2BSaaS #SmartSelling #GTMEngineering #AIOutbound #Teamfluence #Clay

Want to pitch someone on LinkedIn? Read this before you hit “send.” Every week, I get messages that go something like this: “Hi, I’m [Name]. I’ve built this incredible thing. It’s doing amazing work. Here’s why it matters. Can you help me/share it/connect me?” It’s not that I don’t care. I do. But these messages usually miss the mark and here’s why: They center the sender. Not the receiver. Here’s the truth: When you approach someone for the first time, you (and your project, product, or platform) are not the hero of the story. THEY are. If you want someone to care, start by showing that you care about what they do, what they stand for, what they’re building. Read their posts. Watch their interviews. Figure out what they’re trying to solve. Then ask yourself: how does what I’m doing help them win? Make your message less “I need,” and more “Here’s what I see in your work and how I can add value.” Additional tips: 💬 Keep it short. Long-winded intros are overwhelming. You’re not writing your bio, you’re opening a door! Three concise paragraphs is plenty (even less if you can). 🎯 Be specific. Instead of saying, “Let’s collaborate,” say: “I’d love to explore how we could align my youth platform with your mission to build stronger leadership pipelines.” People respond better when they know exactly what you’re asking. What’s your call to action? 🧠 Show you’ve done your homework. A thoughtful compliment goes a long way. “Your post on LinkedIn really made me think.” “I noticed you’ve been working on Y and I’m building something that could support that.” It shows you care enough to listen first. 🤝 Give before you ask. Share a helpful resource. Offer a useful intro. Tell them about an opportunity they might benefit from. Relationships are built on generosity. 📆 Respect their time. Instead of jumping into a call request, consider asking: “Would it be okay if I shared a 1-pager for you to skim in your own time?” People are more open when they don’t feel pressured. Please don’t immediately ask for a call. 💡 Think of it as planting, not picking. Your goal isn’t to “get” something, it’s to begin something. Not all outreach will lead to a project right away, but if done well, it can spark long-term relationships, ideas, and even unexpected opportunities. ✨ Bonus hack: I often ask my clients to count how many times they say “I” vs. “you” when they write to, present to or speak to their stakeholders. If the “I”s win, revise. It’s not listener-centric enough. Connection starts with empathy, not ego. Lead with curiosity. Offer service. That’s how collaborations are born. If these tips are helpful, check out Storytelling and Leadership for more. #Storytelling #AuthenticConnections #LinkedInTips #Leadership #PurposefulWork

Last month, I spoke with a VP Sales who built one of the most effective enterprise motions I’ve seen. His team wins $500K F500 deals at Seed with no marketing. Full STEALTH. This level of trust so early is almost unheard of. Sequoia just led a $45M Series A. Here’s how Trevor Messick from Nuvo did it: 1. Compelling message > Deck Enterprise is a battle of attention. Busy SVPs chased by 100s of AEs/SDRs and internal priorities need one thing – get to the (big) point, fast. A door-opening message so sharply researched it feels like a punch, whether it’s an email or a first call POV. And to approve $500K, punchy words that say "this is board level." Trevor didn’t spend his time polishing decks/proposals templates. He spent it on messaging – teaching his team how to build 6-fig stories. Priceless. 2. Turn customers into your marketing department In stealth, no brand means you start every deal in a credibility hole. Trevor's bet: over-invest in Customer Success until every customer becomes a trust-building marketer. White-glove onboarding, deep value-add, and post-sale check-ins. It all worked – referrals became their #1 pipeline source, while customer stories and proactive referrals (every deal!) drove trust no startup could build so early. 3. Make referrals a pipeline stage, not a wish Referrals beat cold outbound any day of the week – if you treat them like a deal stage. In late-stage negotiation, Trevor’s team asks: “If we deliver our promise, can we get 2 warm intros to peers?” They give a shortlist of lookalike accounts and track every intro like a must-win deal. Win rates crush cold calls because trust is already baked in. 4. Make buying from you feel like buying from a $1B vendor No brand? Make the buying experience your brand. With no big website or product marketing backup, Trevor designed buying moments that say: “wow, they’re real pros!” – using Deal Rooms (Aligned). All materials, timelines, and updates in one collaborative, smart workspace. No critical info buried in emails, out-of-the-loop stakeholders, or decision overwhelm. Buyers say it feels like working with a top-tier enterprise vendor, and deals moved faster. 5. Built a buying signal engine Half the F500 buying team never talks to reps. But their clicks, views, and activity tell the real story. Trevor built a signal engine in Gong (pushed to Slack) that pulls data from every Deal Room interaction (hidden buyers, content views, chat, MAP updates, AI assists) plus email and call data. It became their most accurate deal health score and deal execution decision center – letting them double down on engaged deals, tailor every move, and save at-risk ones before buyers went dark. —— Trust is the currency of enterprise. You can’t buy it. You can’t fake it. But you can design for it. From email-one to the $500K ask. That’s how a startup wins at the big table. P.S. Here’s free access to the Deal Rooms they use: https://lnkd.in/dwujpFvM

Mastering this skill is a sales superpower: Not pitching. Not persuading. But illuminating knowledge gaps, gently. Here’s what that looks like in the wild: ⸻ Prospect: “I ran a Monte Carlo and it said I have a 98% chance of success if I retire at 65.” Financial advisor: “That’s great to hear. Mind if I ask a few questions about how the analysis was set up?” Prospect: “Sure.” Advisor: “What inflation rate did the plan assume?” Prospect: “I’m not sure.” Advisor: “Did it factor in Roth conversions or strategies to reduce Medicare premiums?” Prospect: “Hmm, I don’t know.” Advisor: “What about charitable giving, did the plan reflect how much you’d like to give away at the end?” Prospect: “No idea.” Advisor: “Would it be worth getting a second opinion so you can see how the plan holds up under a few different assumptions?” Prospect: “Yeah… probably.” Here’s the psychology: When you tell people they might be missing something, they get defensive. When they realize it themselves, they get curious. You’re not challenging their intelligence. You’re shining a light on knowledge gaps. Complexity. That’s how trust starts. Not with answers. But with better questions. And when your questions illuminate knowledge gaps the close becomes a consequence, not a conquest. If you want to be a better closer, Be a better opener.

Most salespeople understand the sales process. Almost none of them understand the buying process. We know our stages. Pipeline. Methodology. CRM fields. But do we know what it feels like to buy? I'm a seller. I'm also a buyer. I lead teams. I get sold to constantly. If sellers understood buying, they'd be ten times better. Here's the journey: Unaware → Aware → Curious → Interested → Want → Justify → Buy In that order. Every time. Oh and underneath it all? Busy. Busy as hell. Most sellers skip straight to "buy." They pitch before the prospect knows they have a problem. They push for the close before the want exists. That's why deals stall. Your prospect isn't waking up thinking about your problem. They're living inside it. They don't know there's a name for it. They don't know your product is the answer. Your job: move them through each stage. Not skip to the end. I see most sellers get stuck at interested, but never get to want. They prospect is INTERESTED... but they don't actually want it yet, which is why things stall out. Before your next call, ask: Where is this buyer in their journey? What do they need to move forward? If unaware, help them name the problem. If curious, help them feel the impact. If interested but not wanting, show them what having it looks like. You cannot close someone who isn't at "want" yet. Want is emotional. Urgent. "I need this fixed now." Most reps pitch harder and hope the prospect catches up. They won't. Meet them where they are.

We never asked for referrals. Yet, 30% of our clients today came through word of mouth! 3 years ago: 0% of our clients came through referrals. Today? → 30% through referrals → 30% inbound → 40% cold outreach And here’s the wild part: - We never built a referral system. - Never offered commissions. - Never nudged anyone to “send someone our way.” But they did. Why? Because the referrals came from our existing clients. When people like working with you, they don’t just become clients, they become your advocates. Here’s what we do differently 👇 ✅ 1. We stayed obsessed with delivery. Most agencies obsess over getting the client. We’ve always obsessed over what happens after. We: - Send weekly updates & monthly reports - Educate client as to why we are doing what we are doing - Pro-actively respond to a question & keep smooth communication - Take ownership when something doesn’t work & tweak our strategy ✅ 2. We made our process visible. - I share BTS of how we do content for clients - We break down results (without bragging) - We write about the struggles we solve for our clients It builds familiarity. So when someone asks our client: “Hey, know someone who does personal branding?” We’re already top of mind. ✅ 3. We promise what’s realistic  In the early days, I’d panic if someone would ask “can you help us gain 100K followers in the next few months”? Now we educate. Instead of: “We’ll help you grow fast,” We say: “We’ll help you grow meaningfully.” → With better positioning → With content that reflects who you are → With inbound that brings the right people, not just more people And when someone experiences that kind of partnership, they talk about it. In their founder groups. In conversations. In passing. And that’s how we’ve built 30% of our current client base via pure referrals. Do you get clients through referrals? #PersonalBranding #Marketing #Instagram

🛑 Entry level applicants: Stop Asking Strangers for a Job Referral. Do this better thing instead (read on) Explanation: A common, counterproductive tactic we’re seeing in our DMs. Many candidates are sending messages like this to random people on our team: "I came across the [Role] and I feel it’s a great fit for my background. I’d really appreciate it if you could refer me for the position :)" If you are doing this, please stop. It's often bad advice that wastes your time and ours. ⏰ The Reality of Referral Program Integrity 🛡️ At dltHub (and most professional companies), an employee referral is a serious action backed by professional trust, often tied to a financial bonus. 💰 A True Referral Means: An employee is vouching for you—putting their reputation on the line because they have worked with you and believe you will excel. ⭐ The Problem: When you ask a stranger to refer you, you are asking them to falsely attest that they know you. This undermines the integrity of our internal programs and can be viewed as asking the employee to participate in a form of minor internal fraud. We advise our team against hiring candidates who employ this tactic. The solution: 🚀 Smart Outreach Strategy If you want to impress a Hiring Manager, put the effort into showing you care about the company, not just about getting an interview. The Golden Rule: Talk about their needs, not your own. 🎯 Instead of: "I need a job, can you refer me?" (Self-Focused) Try: "I noticed dltHub is scaling/hiring. I see a potential challenge in [specific operational area], and my experience [X] could help solve it immediately." (Company-Focused) The Best Way to Stand Out: 1. Apply Directly through the official careers page (this is mandatory). 2. After Applying, send a short, targeted message to the Hiring Manager or team lead. Show them you researched the company's challenges and know exactly how you can add value from Day 1. We look forward to seeing the applications from candidates who have truly done their homework!