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?

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?

Cold Calling Is Dying. Here’s What’s Replacing It. The numbers don’t lie: • Cold call success rates have dropped to 2.3% in 2025, down from 4.8% last year (Cognism). • 72% of sales calls never reach a person, and it takes 8+ dials to connect with just one prospect. • Only 28% of reps still view cold calling as effective. Meanwhile, high-performing teams are doing something different. Research-Driven, Insight-Led Outreach Wins: • Reps who thoroughly research their prospects are 3x more likely to succeed (Clevenio). • Prospect-specific research can lift conversions by ~30%. • Insight-led outreach builds trust before a call is ever placed. Email and Social Are Outpacing Phone-First Approaches: • Personalized cold emails outperform generic ones by 32%; average reply rates are 8–9%. • 78% of social sellers outsell peers, and social-enabled teams hit quota 66% more often. Takeaway: 1. The call is no longer the first touchpoint. It’s the third or maybe the fourth; it’s only viable once you have demonstrable engagement via other channels. 2. Buyers start with research—so should you. Start with research. Deliver value. Leverage email and social. Then—and only then—call with context. You’re no longer the teacher like when you were knocking on doors. 3. This is how modern sales works. And this is how trust is built at scale. Welcome to the future, my friends. 🙌🏾 #NervousSystemsStrategist #SalesLeadership #ModernSelling #ColdCalling #SalesDevelopment #InsightSelling #SalesStrategy #SalesEnablement

I built an AI agent that handles my entire inbound system. (And I used to be against automation). Here's how I did it: I used two tools: --> Make: For automation workflows --> Relevance: For AI agents Here's what my AI agent handles: When someone fills our form, it- --> Analyzes their LinkedIn profile --> Reviews their website --> Checks if they match our criteria --> Makes a decision in seconds For qualified leads: --> Sends personalized pitch deck --> Books discovery calls --> Handles initial questions For non-qualified leads: --> Sends a thoughtful rejection --> Explains why we're not the right fit --> Keeps the door open for future The best part? My team and I can focus on what matters - strategy and client success - instead of spending hours on admin work. No more: -Manual lead checking -Back-and-forth emails -Calendar scheduling headaches -Just high-quality conversations with pre-qualified founders. Want to know the biggest lesson? Automation isn't about replacing the human touch. It's about creating more time for it.

This is how 99% of people ruin LinkedIn outreach. They send a connection request—then instantly pitch their services. It’s awkward. It’s desperate. And it doesn’t work. Imagine meeting someone for the first time… and before you even shake hands, they ask, "Hey, want to buy my service?" That’s exactly what’s happening in most LinkedIn DMs. No trust. No conversation. Just cold, robotic pitches that get ignored. Most outreach doesn’t fail because of the offer. It fails because there’s no relationship. People don’t buy from strangers—they buy from those they trust. Yet, most salespeople treat LinkedIn like a cold email list, spamming connections instead of building conversations. Here’s what actually works: 1. Engage before you pitch – Comment on their posts, interact naturally. 2. Personalize beyond “I saw we have mutual connections” – Show real interest. 3. Lead with value – Share insights or ask thoughtful questions. 4. Earn the right to pitch – Once they engage, then start the sales conversation. LinkedIn is a networking tool, not a sales megaphone. If you treat people like transactions, they’ll treat you like spam. Build trust first—sales will follow. What’s the worst LinkedIn pitch you’ve ever received? Follow Evan Chi for more content like this. #prospecting #leadgeneration

Hey Salespeople: Do you truly understand the Challenger sales methodology (teach, tailor, take control)? It does not mean being aggressive. TEACH – Provide insights that challenge the prospect’s current thinking and help them see an unrecognized problem or opportunity. This approach positions the salesperson as a trusted advisor rather than just a vendor. Example: Instead of just pitching accounting software, show a CFO data revealing they're spending 40% more time on compliance than industry peers, costing them $200K annually in labor inefficiency. TAILOR – Customize the conversation to align with the prospect’s industry, company priorities, and individual stakeholder concerns. Example: When speaking with the IT Director, focus on integration and security features; with the CFO, emphasize ROI and cost reduction; with end-users, highlight ease of use and time savings. TAKE CONTROL – Taking control involves guiding the sales conversation confidently, addressing objections proactively, and steering the prospect towards a decision. This doesn't mean being aggressive, but rather being assertive and value-focused Example: After demonstrating value, saying "Based on what we've discussed, I recommend starting with our enterprise package at $85K annually. To hit your Q3 goals, we should begin implementation within three weeks. Does your team have the authority to move forward, or should we include someone else in our next conversation?"

Your startup story probably sounds like everyone else's. Traction, growth, success. Kurt Vonnegut, the famous American novelist, mapped why this fails: humans remember “shapes”, not facts. Without conflict and resolution, you're just noise in their inbox. Vonnegut drew stories as shapes on a blackboard - lines that rise, fall, or stay flat. He called "Man in Hole" the story people never tire of because it has the dramatic fall and climb that sticks: Character falls in hole. Character gets out of hole. We've loved this structure since the beginning of time because the brain prioritizes contrast. The fall creates tension. The climb creates relief. Together, they burn into memory while mundane details fade. Yet 90% of pitches are flat lines. Stuff like, "We help teams collaborate better." No tension. No relief. No memory. Compare that to Stripe's early pitch: "Every time you try to accept payments, you waste weeks on bank integration hell. With Stripe, just paste seven lines of code. First payment processes in minutes." Fall: weeks of integration hell Turn: paste seven lines Rise: processing payments in minutes Here's how to build a pitch that actually sticks: 1. Map the hole to a specific moment in their week Script for discovery calls: "Walk me through the last time this broke. What day? What were you trying to do? How long did it take to fix?" Write their exact answer. If they say "every Monday when we compile reports," your opener becomes: "Every Monday at 9am, you lose 3 hours to broken reports." Not "inefficient processes." Their words. Their moment. 2. The “turn” is one action that reverses direction Wrong: "Our platform automates workflows" Right: "Paste this webhook" (Stripe) Right: "Type instead of meeting" (Slack) Right: "Drag your file here" (Dropbox) Test: Can someone DO the turn in 5 seconds? If not, you haven't found it. 3. Show the slope change with their data Never say "you could save time." Instead: "Upload your last sprint's logs. See that pattern? That's 4 hours of debugging that disappears. Run it now." The shape creates urgency. Features create comparison shopping. A/B test template for cold outreach: Version A: Feature-first (what you probably use now) Version B: Hole-Turn-Rise (Man in Hole structure) Send 500 cold emails of each version to similar prospects. Measure reply rate. The “shape” version typically outperforms. Not because your product changed. Because the story's trajectory determines what sticks. Vonnegut knew: content doesn't drive memory. Shape does. Your product might be revolutionary. But if your story is a flat line, you're forgotten before they close the landing page.

Most AEs fail on the phone for one simple reason: They’re cold calling people who’ve never heard of them. In 2025, that’s just lazy. Here’s how I would book executive meetings without sounding like a desperate sales rep: I used to teach cold calling techniques. Tonality. Pacing. Objection handling. And while that still matters... It’s not the reason I consistently get meetings with C-level buyers. The secret? I never cold call anymore. I warm call. Here’s how I do it: Step 1: Start with a personalized, relevant email. Do some quick research. Make it about them. For example, if I’m reaching out to a CRO, I’ll highlight a drop in quota attainment from RepVue and explain how I can help upskill their team in tough times. Step 2: That same day—a few hours later—I call their cell phone. (ZoomInfo or LinkedIn can get you that. No excuses.) DO NOT call the office. DO NOT waste time dialing assistants. If you can’t get a cell, send a LinkedIn connection request with a DM or video message. Step 3: When I call, I say: “Hi, this is Ian Koniak—did you happen to see the email I sent this morning?” If they say no: “No problem. I sent it because I saw your team’s quota attainment is down since 2022. I think I can help based on what I’ve done with other clients. Do you have a couple minutes now, or should we find time to connect on Zoom?” It’s not a pitch. It’s a reference to something you already sent that’s about them. That’s what makes it warm. Step 4: If they don’t respond, wait 2–3 days. Then reply to the original thread with more context: – Mention the training or workshops you offer – Share real results (e.g., 20% increase in quota attainment) – Ask: “Is this something you’d be open to learning more about?” Always lead with interest, not a hard ask for time. Step 5+: Stack 6–8 touchpoints total. Each one builds on the last—adding more insight, examples, testimonials. Mix in: – LinkedIn videos – Client stories – Relevant frameworks Each message = more value. That’s how you break through. It can take 8-12 touchpoints to get a meeting. Most reps quit after 1-3 touchpoints. Or worse—just send the same “following up” message. No value. No relevance. No shot. This process works. It’s not magic. It’s just real sales effort with a real strategy.

Over the past 9 years, I’ve acquired 1,000+ clients for my agencies. If I were starting over today, here’s exactly how I’d land my first 10 clients: Step 1: Start with the right data The biggest challenge when starting out? Finding highly targeted prospects who are ready to buy. Here’s how I’d solve that: Google Maps. Yes, I said Google Maps. Why? Because it’s an untapped goldmine for qualified leads. With over 4,000 B2B categories, it’s packed with local businesses and SMBs often overlooked - or missing - from LinkedIn. These are hidden gems waiting to be discovered. Scrap (https://scrap.io/s/9MYK) transforms this goldmine into actionable leads by extracting from Google Maps listings: - Emails, phone numbers, & websites - Social media profiles - Website technologies - Even Google Maps ratings & reviews Filter and focus on your ideal targets in just 2 clicks. For example: - Restaurants with 4+ ratings but no Instagram. - Local businesses with websites but no ad pixels. - SMBs in specific niches or locations. Scrap’s real-time data extraction ensures you always have the most accurate info - and it’s available as a Chrome Extension for instant insights. Step 2: Personalize your outreach Generic outreach doesn’t work - relevance is everything. Try this playbook: - Subject Line: Use something attention-grabbing like “Quick question about [business name]” or “Idea for [service].” - Personalize: Reference their Google Maps reviews, website, or niche. For example: “Congrats on your 4.9-star rating - I can see why people love your café.” - Partner Up: “I help cafes like yours boost foot traffic through email marketing. I noticed a few opportunities I’d love to share.” - CTA: End with a low-pressure ask: “Does this sound worth exploring?” Pro Tip: Pair the emails from Scrap (https://scrap.io/s/9MYK) with LinkedIn outreach - connect or engage with their posts to build trust. Step 3: Stay consistent and scale your efforts Build momentum through persistence: - Follow Up: Most responses come after the 2nd or 3rd touch. Example sequence: Email → LinkedIn connect → Follow-up email → Call. - Track Metrics: Monitor open rates, replies, and booked calls. Aim for a 20%+ email response rate and 10%+ meetings booked. - Leverage Referrals: Once you’ve landed a few clients, ask, “Know anyone else who might benefit?” and share testimonials like, “We helped a local coffee shop grow foot traffic by 20% in 30 days.” - Automate: Use Scrap for fast lead gen and a CRM to manage outreach. Recap: - Use Scrap (https://scrap.io/s/9MYK) to turn Google Maps into a lead-gen machine for local businesses, SMBs, and niche prospects. - Personalize your emails with insights and a clear CTA. - Stay consistent by following up, tracking results, and leveraging referrals. - And remember: Your first 10 clients lay the foundation for scaling. #ScrapPartner

Many sellers inadvertently lower their status with their "rapport building". Want your prospect to actually respect you? Try this approach: The easiest way to earn your prospect's respect and get them to "like" you: 1. Show you respect their time 2. Show you know their business 3. Show you're prepared for the call To accomplish all 3, our team follows the 𝟵𝟬 𝘀𝗲𝗰𝗼𝗻𝗱 𝗿𝘂𝗹𝗲 in sales meetings: In the first 1.5 mins of the call, say something that SHOWS we prepped for the meeting and know their business. Examples: 1. For our newsletter sponsorships, we might comment on a new product feature they just released: "𝘐 𝘸𝘢𝘴 𝘱𝘳𝘦𝘱𝘱𝘪𝘯𝘨 𝘧𝘰𝘳 𝘵𝘩𝘪𝘴 𝘢𝘯𝘥 𝘴𝘢𝘸 𝘵𝘩𝘦 𝘯𝘦𝘸𝘴 𝘢𝘣𝘰𝘶𝘵 𝘵𝘩𝘦 𝘭𝘢𝘶𝘯𝘤𝘩 𝘰𝘧 𝘵𝘩𝘦 𝘢𝘶𝘵𝘰-𝘦𝘯𝘳𝘪𝘤𝘩𝘮𝘦𝘯𝘵 𝘧𝘦𝘢𝘵𝘶𝘳𝘦 - 𝘵𝘩𝘢𝘵'𝘴 𝘢𝘸𝘦𝘴𝘰𝘮𝘦. 𝘏𝘰𝘸'𝘥 𝘭𝘢𝘶𝘯𝘤𝘩 𝘨𝘰?" ^This is likely something they'd want to promote in a newsletter -- 2. For our Club Pass sales training program, we'll might comment on something we read on a job posting for an AE: "𝘋𝘢𝘯, 𝘐 𝘸𝘢𝘴 𝘳𝘦𝘢𝘥𝘪𝘯𝘨 𝘵𝘩𝘦 𝘰𝘱𝘦𝘯 𝘑𝘋 𝘺𝘰𝘶 𝘢𝘭𝘭 𝘩𝘢𝘷𝘦 𝘧𝘰𝘳 𝘵𝘩𝘦 𝘌𝘕𝘛 𝘈𝘌 𝘱𝘰𝘴𝘪𝘵𝘪𝘰𝘯. 𝘗𝘳𝘦𝘵𝘵𝘺 𝘤𝘰𝘰𝘭 𝘵𝘰 𝘴𝘦𝘦 𝘺𝘰𝘶'𝘳𝘦 𝘭𝘰𝘰𝘬𝘪𝘯𝘨 𝘵𝘰 𝘦𝘹𝘱𝘢𝘯𝘥 𝘪𝘯𝘵𝘰 𝘥𝘪𝘧𝘧𝘦𝘳𝘦𝘯𝘵 𝘷𝘦𝘳𝘵𝘪𝘤𝘢𝘭𝘴 𝘣𝘦𝘺𝘰𝘯𝘥 𝘫𝘶𝘴𝘵 𝘴𝘦𝘯𝘪𝘰𝘳 𝘭𝘪𝘷𝘪𝘯𝘨 𝘤𝘰𝘮𝘮𝘶𝘯𝘪𝘵𝘪𝘦𝘴. 𝘏𝘰𝘸'𝘴 𝘵𝘩𝘢𝘵 𝘨𝘰𝘪𝘯𝘨?" ^Selling into new verticals often leads to VPs wanting to upskill their teams. -- Done right, you differentiate yourself from every other crummy sales call they've taken this quarter AND get a chance to feel out how much they care about the thing you called out. If I get a lackluster response about the new feature release...I know that's probably not something they're going to want to promote in the newsletter, and I know not to waste time asking more about it! Don't waste everyone's time attempting to schmooze about the cold weather in Toldeo in an obvious attempt to butter 'em up...instead, find ways to demonstrate credibility and your calls will kick off so much smoother.