Darren Carter

outbound tip: identify specific, observable problems your prospect faces right now. not theoretical pain points from a buyer persona doc. actual problems you can see from the outside. property managers in october need gutter work. SaaS companies hiring 10+ salespeople need pipeline infrastructure. companies with broken DMARC settings can't reach inboxes. these aren't assumptions. they're facts you can verify before sending a single email. when you can point to something real and urgent, your outreach stops feeling like spam and starts feeling like help.

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Executives won't open cold emails, but they will open a package. This is my best advice for breaking into Tier 1 accounts... When we were trying to break into big enterprise accounts at Levelset, there was one approach that consistently worked. We sent our top prospects a gift in the mail. Most teams never try this. They send another cold email, another LinkedIn message, or another voicemail. Then they sit around wondering why nothing converts. When you’re going after companies that can change your trajectory, you have to operate differently. Start with the person you are trying to connect with. Before you buy anything, spend time learning about the prospect. Look at what they post. Notice what they care about. Listen for the problems they’re trying to solve. You’d be surprised how often people leave clues out in the open. AI is really helpful at pulling this together for you. It's important to understand what would actually matter to them. Pick a gift that shows you pay attention. It takes more effort to pick something thoughtful than it does to spray a thousand people with the same sequence. But you’re not going after a thousand people. You’re going after the handful who can meaningfully move your business forward. It doesn’t need to be expensive. It needs to be personal. Somewhere in the $25–75 range is enough to show you cared without feeling transactional. Include a handwritten card. Keep it simple. Three or four sentences. Tell them why you chose the gift. Tell them what it made you think about in their business. Then make a clear, easy ask. When everything else in their stack is automated, a handwritten note stands out. Send it in a bubble mailer. Nothing fancy. USPS works fine. A bubble mailer gets opened. People are curious. Just make sure the address is right. We double checked every single one. Full up after it arrives. Don’t assume they saw it. Don’t assume they connected the dots. Send a short email. “Just shipped you something. Should arrive this week.” Then follow up again after it lands. The follow up is where the meetings get booked. Did this work? At Levelset, this was our most reliable way to break into large accounts. The response rates were dramatically higher than anything we did through email or phone alone. And it wasn’t because we were clever. It was because we were willing to put in more effort than everyone else. Most reps won’t spend thirty minutes researching a prospect or writing a card. That’s fine. The ones who do will win the meetings with the best prospects. The Reality This work doesn’t scale. It’s not supposed to. You don’t run this play for your entire TAM. You run it for the hundred companies that would meaningfully impact your business if you earned their trust. For those accounts, a thoughtful gift is a small investment compared to the upside. And if you’re willing to do the work, you’ll end up in conversations your competitors never even get close to.

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This CS Agent just replaced a $200,000 SaaS tool 🤯 And it’s a sign of what’s coming. GTM was built in the image of SaaS. →One tool for every function. → Dashboards everywhere. → Disconnected workflows patched together by process. But the SaaS-Native GTM model is breaking: → Too many tools. → Too many gaps. → Too much headcount. → Too many teams stuck reacting - instead of moving with intelligence. And now AI is exposing the real issue. Because it can understand, reason, act and learn. But SaaS-Native GTM misses the context, intelligence and memory. Recently, we worked with a $250M ARR SaaS business - where Customer Success was struggling to scale: → NRR was falling → Retention weak → CSAT in decline → Just 20% of customers actively engaged → No visibility into product usage → Sales handovers were non-existent → No insights flowing to Product or Marketing → Playbooks untouched since 2023 → Support inbox chaos → CSMs firefighting and burning out They were preparing to hire 8 more CSMs. And they were already spending $200,000 on a well-known CS platform. But that platform couldn’t help. → It was disconnected. → Outdated. → Siloed from CRM, product, support, and the rest of GTM. So we replaced it. Not with another tool. With GTM Intelligence Infrastructure and an AI-native CS Agent. Here’s what changed: ✅ Context was unified - CRM, usage, support, and calls all connected ✅ Signals were identified - risk and expansion surfaced in real-time ✅ Agents orchestrated action - plans, workflows, follow-ups ✅ Memory was built - learning from every customer touchpoint ✅ Slack became the interface - insights and recommendations delivered where work happens The CS Agent didn’t just alert. It acted: → Detected risk or opportunity → Explained context and surfaced reasoning → Set objectives based on account maturity and goals → Referenced ICP, persona, and past plays → Generated a dynamic plan → Guided the CSM with meeting prep, follow-up, and next best action → Reported and escalated when needed → Monitored resolution and learned continuously → Shared insights with Product, Marketing, and Sales - automatically This is what a system that thinks looks like. And the results? → 45% increase in CSM capacity (more active customer conversations, zero added headcount) → 250% increase in expansion pipeline → $200K platform fully replaced → CS team re-energised, focused, and aligned with GTM And this is just the beginning. GTM teams don’t want another disconnected tool. They need infrastructure that adapts. Agents that guide. Systems that learn. We’re now replacing legacy platforms across sequencing, forecasting, ABM, and CS - with one GTM system powered by context, intelligence and memory. If you build the infrastructure now - You gain compounding insight, action, and advantage. 📩 Tired of legacy SaaS tools in GTM? DM me. ✉️ Building GTM with AI? Get in touch. 🔔 Follow for more insights as we we build AI-native GTM.

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You ran the heatmaps and session recordings, and BOOM: Zero clicks on “Talk to Sales.” Instead, they hovered over your product screenshots—looking for something you didn’t have. Health tech buyers aren’t waiting around for your SDR. They’re scanning your homepage, looking for a way to use your platform. If they don’t find it in 8 seconds… they’re gone. Decision-makers don’t want promises. They want proof. And they want it now, not after filling a form. That’s why interactive product experiences aren’t just “nice to have” anymore. They’re the filter buyers use to decide if you’re worth their time. Here’s how you can fix it: Interactive tools are the new first impression. Why it works: • Buyers want to self-qualify before speaking to sales. • They want control, not a guided tour. • They trust their hands more than your words. You can swap out a video demo for a self-guided product tour — and see your bounce rate drop by 30%. No one wants to feel “sold to.” Why it works: • Interactive demos remove pressure. • They feel like discovery, not a pitch. • Buyers stay longer, click deeper, and return more often. It reframes the product from pitch deck to playground. Time-to-value matters before the sale. Why it works: • Buyers are scoring your ease-of-use within seconds. • If they can't get it, they think their team won’t either. • Clarity wins over complexity, every time. Your homepage should show usability, not talk about it. Demo pages are triage zones. Why it works: • Buyers scan for proof that you “get it.” • They check if there’s a free trial, a playground, or a hands-on tool. • If they don’t see one, they assume the worst. If there’s no interactive element, you’re losing deals before discovery calls. Product-led isn’t just for PLG. Why it works: • Even demo-driven sales benefit from interactive layers. • It increases demo show-up rates and shortens deal cycles. • It turns curiosity into commitment. Product-first trust builds pipeline. Big takeaway: Buyers don’t need more convincing. They need more control. And if they don’t get it on your homepage, they’ll find it on someone else’s.

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RevOps isn’t a tool. It’s a commitment to reality. Most teams buy software to avoid discipline. Then nothing changes. If you want revenue to scale, install RevOps like an operator: 1// Define pipeline stages Clear entry/exit criteria. No vibes. 2// Assign next actions Every deal has a next step or it’s dead. 3// Track conversion rates Lead → call → proposal → close. 4// Run a weekly revenue meeting Scoreboard, pipeline, offer friction, commitments. 5// Clean the CRM every week If your data is fake, your decisions are fake. You don’t need another tool. You need a system that tells the truth. Follow Gerald Duran — in-the-trenches mentor to founders who are done guessing. Founders who want mentorship through CanaGlobal: start at 𝗖𝗮𝗻𝗮𝗚𝗹𝗼𝗯𝗮𝗹.𝗼𝗿𝗴 (click Start Here).

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Every week there is new AI hype, and I get it, it is tough to ignore the excitement of a silver bullet that will do all your research, map your entire market, find every contact you didn't know you had, then email them all before lunch... generating a mountain of actionable deals for you while you ski. Trust me, I live in Tahoe, I want this too. But let's level-set: 1️⃣ Yes Claude Code is fantastic. I've used it for over 15 hours this week alone and most serious engineering organizations today are implementing it because it finally moves the needle in development orgs 2️⃣ Yes it is easier than ever to generate useful code and small apps without having a fundamental understanding of software engineering (see Lovable, Replit, et.al) 3️⃣ Yes you can find thousands or millions of records and blast them with AI-personalized messages at volumes never before seen But also... 4️⃣ Outputs from zero-shot AI prompts and the vast majority of individual AI agents hallucinate, lack context, and fundamentally miss the best and most interesting opportunities without SME defined processes and thoughtfully defined governance, graphs and tools. 5️⃣ Disposable software has a place, but sustainable high performance sourcing operations require thoughtfully design stable systems, and software is a living breathing entity that requires continual maintenance for sustained performance. I know PE firms that have spent $3-5M (and more) to build software to realize their ongoing maintenance and operational costs quickly turn the equation upside down (one I've been talking to wants us to take over their full stack they spent a 5 years building). 6️⃣ Every one of us is experiencing feeds, inboxes, and text message folders filled with AI slop and we're all getting smarter about identifying it (and tools will get better at auto-filtering) I'm happy to be proven wrong as I'd love to ski more... But the world needs more intentional data-driven human-to-human connection leading to trust-filled transactions, not more thoughtless agentic blasts of AI slop.

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The coverage model is a churn machine dressed up as a CS strategy. Nobody says this out loud because the metrics make it look like it’s working. You know this CSM. Owns 80 accounts. Knows every client’s first name, their kids’ names, their renewal dates. Responsive to everything. QBR completion rate: perfect. Health scores: green across the board. (Health scores are always green right up until they aren’t.) Then Q4 comes and three of those accounts are offboarding. The thing the coverage model can’t produce isn’t effort. It’s access. The client who tells you the relationship is cooling before it becomes a decision. That conversation only happens with the CSM they trust enough to have it with — and that trust requires depth, not volume. Maile Collmer — a referral networking coach who rearranged how I think about this — said something I’ve been applying to CS ever since: stop thinking about what you want from the room and start thinking about what the room needs from you. The wide-net CSM is optimizing for the room. The deep CSM is doing something the coverage model has no metric for: becoming a genuine business partner. On Thursday’s episode, Anika Zubair said the CSMs driving 120% NRR aren’t managing the most accounts. After 14 years scaling CS teams at hypergrowth SaaS companies, her read is clean: the ones hitting those numbers are the ones their clients treat as actual partners in growing the business, not just contacts at the vendor. AI can write the QBR deck. It cannot be the person your client calls when something is going wrong before it’s officially going wrong. That’s the deep CSM’s job. You can’t do it across 80 accounts. Your coverage model didn’t create this problem. Your metrics did. #KarlTheBridge P.S. The wide-net CSM gets recognized at the SKO. The deep one gets the call at 4pm on a Thursday before the client talks to anyone else.

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SaaS companies are running signal based outbound only to fail Here is why Signal-based outbound isn't about using random signals. 👇 . Here's the brutal truth: The more people use these signal-based tools, the worse they work. Think about it. When everyone gets the same "congratulations on your Promotion job" template, nobody responds anymore. Even if you write an email that stands out, how do you know that "new hire" signal is something that shows buying intent? I am seeing that most people are randomly choosing signals and launching campaigns. This is not going to work. But here's what actually works: Researching signals and identifying the ones with buying intent. For example, you can find mentions of your competitor and try to identify people looking for alternatives. or Look for negative reviews and reach out to those people with personalized landing pages and explain to them how you can help them This is way better than chasing random signals: I've used this exact approach to close over $ 20,000 per month in deals. Not because I got lucky with a signal, but because I understood my prospect's actual situation. Signal-based outbound isn't about finding the perfect AI SDR tool. Everyone has access to the same tools anyway. Stop outsourcing your problems to the next shiny tool. Start building systems and signals that actually work.

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Most SDRs aren’t actually selling. They’re stuck at building lists, researching accounts, and switching between tools. That’s admin work, not revenue work. Hire a GTM engineer to handle qualification, scoring, signals, and CRM uploads. Now your reps start the day with ready-to-call leads. Less busy. More productive. Are your reps selling… or just staying busy?

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If I became CMO of a $5M ARR B2B startup, here's what I'd do in my first 30 days to 2x ICP pipeline: 1. Create a list of every target account in my ICP. I'd ask sales & CS about which factors make a great account. Then I'd bring in real-life data, analyzing all won/lost deals over the past 18 months to see which factors led to the highest expected ARR per 100 opps (equation: win rate x average ACV x NRR x 100). These factors would almost certainly include industry, company size, and geo. But I'd look to go a level deeper factoring in tech signals, hiring signals and other indicators of buying intent. 2. Identify all the most relevant contacts at those target accounts. I'd start with initiator and champion personas. Users, influencers, and exec buyers could come later. This data used to be hard to access, unreliable & expensive -- that has quickly changed. 3. Figure out where those target accounts are in their buying journey. If there were 1,000 accounts in my ICP, how many were we able to identify & market to? How many are aware of us (i.e. visiting the website, engaging with ads, opening emails, etc.)? How many are interested (i.e. viewing an interactive demo, visiting high-intent pages, starting a free trial)? And how many are considering a purchase (i.e. they're sales pipeline)? From there, the bottlenecks become obvious to the entire team. It's time to tackle them. 4. Build a pod around the biggest bottleneck. I'd spin up 10+ tests in the first week. The variables I'd play with: the account signal, the message, the channel, the offer, and the level of 1:1 personalization. (A manual approach would be fine to start with -- I can automate what works later.) The lowest hanging fruit is usually to convert aware/interested accounts into pipeline. This might mean warm outbound to convert website visitors, testing personalized video over LinkedIn, offering exec access, etc. 5. Create a 🔥 content asset that I know will resonate with my target accounts. My starting hypothesis: a State of X report featuring interviews & quotes from my ICP. I'd start with highly referenceable existing customers for social proof (low-hanging fruit). I'd then use the report as an excuse to message ICP prospects (the side-benefit: account-specific insights to personalize campaigns). I'd build this report in public -- creating a content <> community flywheel -- to already drum up interest from my ICP well before the report was published. -- Why this 30 day plan works: (a) it's focused on the best-fit accounts, (b) it brings tight alignment between marketing <> sales, (c) it creates quick wins -- earning trust to take bigger swings, (d) it's the best possible onboarding, and (e) it's aggressive -- setting the bar high. And, if it doesn't work, perhaps I'd propose another brand refresh 🙃 #marketing #icp #abx

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Stop hiring "Black Box" SDR agencies and hoping for the best. Most outsourcing models work like this: 1. You hand over your product materials. 2. They disappear for 30 days. 3. They come back with lukewarm leads that never close because the SDR didn’t actually "get" your value prop. It’s disconnected. It’s robotic. And honestly, it’s why most sales leaders are scared of outsourcing top-of-funnel. We’re doing it differently. Instead of a ticket in a system, we give you a teammate. We provide pre-vetted, high-performing SDRs who integrate directly into your Slack, join your daily standups, and learn your product nuance as if they were employee #1. The Data: • Deep Integration vs. Black Box: Embedded SDRs typically see a 35% higher conversion rate from meeting-booked to qualified-opportunity. • Ramp-up Time: Because they work within your ecosystem, ramp-up time is slashed by nearly half. • The Economics: Leverage elite, pre-vetted talent for up to 60% less cost than equivalent in-house hires, without sacrificing quality or control. You don’t need more vendors. You need more talent. Let’s discuss: What’s the #1 reason you’ve been hesitant to outsource your top-of-funnel? Is it the lack of control, fear of brand misalignment, or past bad experiences? 👇 Let me know in the comments.

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The fastest way to get ghosted? Apply to jobs selling to a buyer you’ve never spoken to. Companies don’t want to take risks right now. They want familiarity. Relevance. Proof. We posted a role last month at a company selling to MedSpas. 90% of applicants had never worked with MedSpas. Never even sold to brick-and-mortar. Just spraying. Guess who got interviews? The 10% who had relevant experience. I am a firm believer that the spray and prey approach does not work. I’ll show you how to do it right in this week’s paid RolePulse newsletter. Comments - do you agree?👇

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As an SDR I went from SMB to MM to ENT in 11 months, averaging 137% across all 3. Each segment was like a completely new role. Want to progress as an SDR? Here’s exactly how I won at each level. 1. SMB It is all about relevancy at scale. Your TAM is huge. You often have thousands of accounts so you don't have the time to personalise for each account. Instead, you should think how can I hit as many accounts with good messaging as possible? This is the process I'd follow. - Define your true ICP which companies to sell to - Define your personas, who to reach out to - Define the trigger, why to reach out - Define messaging, why now This sounds super simple but it works, in theory it would be like: Sales ATL + SaaS companies + Closed Lost. SMB is mostly high-volume sequences with you ripping dials, it’s quite simple. 2. Mid Market Now more of a strategic approach comes into play. Naturally, your time gets smaller because the companies you're going to be going after are bigger. Therefore, tiering accounts is much more important at this stage. A tier 1 account should represent about 5% to 10% of your total book with the rest falling into tier 2 and tier 3. And those tier 1 accounts are the ones where I would give them personalised relevant messages. Things like CEO mentions, key initiatives from the organisation, anything that could only be tied to that company, and that's what you should be referencing in your messaging 3. Enterprise This is where the real fun begins of true personalised prospecting. You could have a book of business from anywhere from 10 to 200 accounts you want to break into, so each account needs deep research. This is where you have to make it specific about the company but more importantly you have to craft a perspective to show how what you solve directly ties into a key business initiative. Enterprise is mostly timing. There's so many things they could be fixing. You have to show why this one issue you solve is the one they should be focusing on. Why this fire out of all the ones they could put out? 4. Processes & SOPs Rep, you should really be building out your processes for each stage because how you approach SMB vs. mid-market vs. enterprise will be completely different. I used to do all of this in Notion. It took me hours but tools like Tango can now make this 10x easier for you to just document what to do so you can do it at scale. Do your outbound as you would normally and let it record everything you're doing. You have a detailed breakdown of your system. The easier it is for you to focus on outbound, the more meetings you’re going to book. I think there's a lot of advice saying that you have to be personal but the truth is that only applies to the segment you're selling into. If you do an SMB focus on trying to be relevant at scale to the bulk of your accounts. If you do an enterprise, make it personal, make it one-to-one. Advice isn't one size fits all.

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Most outbound agencies or even list building services work like this: 1. You fill out an onboarding form with your ICP info. 2. They plug it into ZoomInfo or Apollo. 3. They hit export and call it a day. The result is hundreds of bad contacts, double digit percentage of completely dead dials. Leaves you paying for conversations with: – Wrong titles. – Irrelevant functions. – Out-of-date profiles. – People your reps will never sell to. Every data provider has broken tagging systems. No platform is ever going to spit out a perfect list. That’s why my team does it differently. We start with Sales Navigator (the most accurate source of “who works where, doing what”), then rip the data into a google sheet where I can manually filter out the junk titles and industries that software can’t catch efficiently. Otherwise you have to go through the search results page by page and filter out titles manually with exclusions. It's a nightmare. It’s more work upfront for us, but it means the final list is tight. There's IMMEDIATE payoff, because the rep ends up on the phone with 10-20 of the right people, rather than half of them being the wrong persona. Book more meetings this way. Trust me. That’s the philosophy behind the system I show in this video.

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When outbound scale becomes a liability instead of a growth engine At a certain point, sales and customer support stop being about effort. Teams work harder, call volumes grow, budgets increase, and headcount expands. Yet leadership starts noticing something unsettling: results no longer grow proportionally. Conversion flattens. Forecasts become less reliable. Quality varies from team to team. And instead of clarity, more activity creates more questions. This is usually the moment executives begin asking themselves uncomfortable things. Are we scaling revenue or just scaling noise? Can we trust what we see in reports? What actually breaks when volume doubles again? In large financial organizations, this realization comes fast. Outbound operations stop being a sales problem and reveal themselves as an infrastructure problem. That was exactly the situation when Alfa-Bank Ukraine engaged us. Outbound sales and customer support were already running at scale. The challenge wasn’t launching or experimenting. The challenge was sustaining performance over years, under strict regulatory pressure, with predictable outcomes and controlled risk. Over three years, we built and operated a long-term outbound and customer support infrastructure designed for durability, not short-term wins. The focus was never on call volume alone. It was on building discipline into the system. Clear KPIs aligned with business outcomes. Consistent quality control embedded into daily operations. Team structures that allowed growth without losing accountability or stability. The operation scaled to as many as 150 agents, handling over 10 million calls annually. More importantly, this execution led to more than 100,000 activated credit products. Not through aggressive scripts or constant pressure, but through repeatable, controlled execution that leadership could rely on year after year. The approach itself is not complex, but it is rarely implemented well. First, performance metrics must reflect revenue and risk, not just activity. Second, quality control has to be part of the process, not an afterthought. Third, team structures must assume growth and stress from day one. And finally, outbound should be treated as a core operational system, not a temporary sales channel. When organizations get this right, scale stops being a threat. It becomes a controlled advantage. If your sales or customer support teams feel constantly busy but increasingly unpredictable, it’s often a sign that scale has already arrived while the infrastructure is still catching up. That gap is where long-term performance is either built deliberately or quietly lost.

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Gangster outbound idea from an AE in Sales Assembly's peer group that cut through the outbound noise (and led to a ton of responses) with something dead simple: - They pulled up the prospect’s website. - Recorded their screen. - Spoke directly to a new initiative or signal. - Offered one clear, tactical idea. - Thirty seconds. No polish. No fluff. Response rate? Off the charts. So, why did this work? Well, first of all, because most outbound sucks. It feels manufactured. This doesn’t. It’s specific. It’s low effort. It looks like it was made for me...because it was. No generic “I saw you raised funding.” No gimmicky GIFs. Just: “I did the homework. Here’s the connection. Let’s talk.” So, how do you do this? Easy peasy: 1. Start with your top 20 accounts. 2. Use Loom or Zoom. Doesn’t matter. 3. Open the prospect’s homepage or press release. 4. Call out one relevant shift (new product, hiring signal, expansion). 5. Connect that to what your product actually solves. Keep it under 45 seconds. 6. Subject line: “[Company] + [Trigger] = quick idea” 7. CTA: “If this tracks, let’s talk. If not, no sweat.” That's it. This obviously ain't about being fancy. It’s about being relevant. Polished content gets ignored. Unpolished insight gets replies.

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Your inbox is leaking revenue. The average SMB loses $200K+ annually in deals that get buried in email. Leads are missed. Follow-ups are delayed. Opportunities slip through unnoticed. It’s difficult to stay on top of your inbox. And manual tracking isn’t sustainable. Every unanswered thread is a potential deal that might have been closed. This problem builds up slowly. But over time, it turns into real revenue loss. That’s where EVE comes in. ↳ It’s an AI Operator that connects directly to your inbox. → Finds potential leads hidden in your emails → Flags missed deals automatically → Helps you follow up at the right time with the right message EVE helps you turn forgotten conversations into active revenue. ↳ Most businesses recover $50K to $500K+ in their first 90 days. ↳ Without hiring more people or changing how they work. ⚡ Here’s what makes EVE stand out: 24/7 Lead Tracking → Constantly scans your inbox for new or stalled deals Smart Opportunity Detection → Spots signals like “Need demo,” “Budget approved,” or “Send pricing” Revenue-Based Prioritization → Scores each lead by potential value so you know where to focus AI Response Drafts → Prepares personalized replies based on your writing tone Unified Team View → Connects multiple inboxes for a clear company-wide picture 🎯 Here’s how to get started with EVE: Step 1: Schedule a demo at joineve .ai Step 2: Connect your Gmail or Outlook account in minutes Step 3: EVE scans your inbox and identifies hidden opportunities Step 4: Review and respond with one click If your inbox is full but your pipeline isn’t, it’s time to fix that. 📩 Try EVE today → joineve.ai 🔄 Repost to help others find deals in their inbox — #AI #Email #Inbox #Sales #EVEPartnership #SponsoredByEVE

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