Nathan Rawlins

Sales was a mess. Then they handed it to me. Back in 2023, I was VP of Marketing and was asked to take over Sales as well. I stepped into a world I thought I knew well from the outside, but now I had to lead it. I kept reminding myself of something Udi Ledergor once said: “Marketing’s job is to make sales easier.” I wasn’t going to teach the team how to sell. I was never a salesperson, and we already had a great team of sellers. But I could make it easier for them to do what they do best. So I asked myself: How do I actually help Sales sell? Then I stepped in and saw the chaos: - Outdated one-pagers - Random follow-up emails - Clients lost in email threads - AEs juggling deals with no structure It was nothing like the structured world of marketing campaigns and cadences. Everything was manual. Best practices were tribal knowledge, if shared at all. I wanted to fix it. Systemize it. Make sure our AEs spent their time selling, and our clients had a seamless experience. The fix? We rolled out a digital sales room: Aligned A joint effort between Product Marketing and Sales Leadership. Now, every deal lives in a single digital workspace: - Pricing - Collateral - Mutual action plans - Engagement tracking - Clean. Shareable. Always up to date. The impact: - No more chasing PDFs or approvals - Internal champions close loops faster - Deals close faster with higher conversion rates The value of giving clients one professional, centralized place to evaluate us? Priceless. That clunky and messy buying process? Gone. Clients now feel more confident. More in control. More ready to buy. This post isn’t about a specific tool (though our sales team will vouch for Aligned any day). It’s a reminder: If you want your team to win, do not just ask them to grind through the manual work. Give them systems and tools so they can focus on what matters most: Selling. Make sales easier. Make buying easier. Hit your targets.

162

30 Comments

"Our product is too expensive!" - Reps love this one as a loss reason. Really? You're sure? I pull the data. 12% got closed lost for price. TWELVE PERCENT. But that one loud rep has the whole team convinced we have a pricing problem. One of my favorite questions to as my leaders is this. Volume vs Volume. Is this a high volume problem that is just LOUD. Or is this a high volume problem that there is ALOT of it. This is what kills sales organizations. We chase the LOUD problems instead of the A LOT problems. The Loud vs Real Problem Reality Check: 🔊 LOUD: "The script doesn't work!" 📊 A LOT: Nobody's actually using the script (0% adoption tracked) 🔊 LOUD: "Marketing gives us garbage!" 📊 A LOT: 63% of MQLs never hit the right number of follow ups 🔊 LOUD: "The product is too expensive!" 📊 A LOT: Reps skip value discovery in 67% of calls 🔊 LOUD: "That competitor is killing us!" 📊 A LOT: Lost to "no decision" 5x more than any competitor Here's what happens in every sales org: One rep hits a weird objection three times. Suddenly it's "THE objection we need to solve." Meanwhile, 80% of your deals are dying in discovery and nobody's talking about it. Why? Because discovery death is quiet. It doesn't bang on your door screaming. The Data I Actually Look At: Not: "What are reps complaining about?" But: "What's happening in 100+ deals?" Not: "What's the latest fire?" But: "What pattern shows up in the numbers?" Not: "Who's yelling loudest?" But: "What does the scorecard say?" How to Stop Chasing Ghosts: 1️⃣ Track Everything If it's not measured, it's not real. Period. 2️⃣ Minimum Sample Size One rep's bad week ≠ a trend. Get 50+ data points minimum. 3️⃣ Follow the Math, Not the Mouth The loudest person in the room is rarely the most accurate. 4️⃣ Ask "By How Much?" "Leads suck" → "By how much did quality drop?" "Script fails" → "What's the conversion rate?" 5️⃣ Look for CHANGES - is anything new, or was it always that way. If it was always that way, it's not what's causing the drop. The Brutal Truth: Your loud problems are usually edge cases. Your real problems are boring and systemic. But we love solving loud problems because they're: Exciting to talk about Easy to blame Make us feel like heroes While the real problems quietly eat your pipeline alive. Stop managing by complaint volume. Start managing by data volume. The loudest problem in the room is rarely the one killing your quarter. Find the quiet killers. They're the ones that matter. Volume vs Volume ya'll.

155

82 Comments

Top revenue performers have options. If you want to attract and keep the best, you need more than competitive comp plans. 🎯 What actually matters: — Clear career progression. Specific paths and timelines, instead of vague promises. — Real-time transparency. Show performance metrics now, not in quarterly reviews. — Leadership that gets it. Revenue leaders who've done the job themselves earn trust. — Culture of winning. Celebrate success, learn from losses, and set aggressive but achievable goals. The bottom line: Treat revenue professionals like the revenue drivers they are. Give them what they need to succeed, and they'll choose to stay and perform.

79

2 Comments

One of the hardest things to get right in a revenue org is consistency. Every team has high performers. But too often, their success stays siloed. Craig Hanson makes a strong case for how AI can change that – by capturing what’s working and scaling it across the entire go-to-market engine. This isn’t about more dashboards. It’s about: - Turning proven behaviors into repeatable workflows - Embedding best practices into every deal cycle - Driving consistency across teams, not just visibility If you're thinking about how to operationalize what works – and do it at scale – this is worth your time. Link in the comments. Thanks for the insight, Craig.

180

14 Comments

So I joined a demo last week and the rep joined three minutes late, camera off, and the first thing I hear is "sorry, can you see my screen?" No, dude. No I cannot. Because you didn't test anything. This is the stuff that drives me bonkers. Everyone wants to talk about MEDDIC and value selling and consultative approaches. Meanwhile reps are fumbling the absolute basics that cost them deals before they even start. Here's what I mean: 1. Join the call 3 minutes early. Not on time. Early. Because early IS on time. Plus, remember that is so, so easy to be early. You literally have hours to do so, whereas “on time” lasts only for a single minute. Anyway, when you show up early, test your audio. Test your screen share. Make sure your background isn't your unmade bed. The prospect shows up to a room where you're waiting, composed, ready. That's how you signal professionalism before you say a single word. 2. Camera on. Always. Don’t worry, your hair looks fine. People buy from people, not from profile pictures and disembodied voices. If you're not willing to show your face, you're already communicating that you're not fully present. 3. Have your deck/demo queued up. Don't make them watch you navigate folders like you're Magellan searching for the East Indies. Have everything open in separate tabs. Know exactly where you're going. Confidence comes from preparation, not winging it. 4. Use their name. Correctly. I was on a call a few months back when a rep kept calling me "Mike" for 30 minutes. Name's Matt. It was on the Zoom screen, buddy. This is basic respect stuff. If you can't get someone's name right, why should they trust you with their budget? BTW - if you're unsure how to pronounce someone's name, simply ask them. "Hey I want to make sure I pronounce your name correctly - is it [NAME]?" 5. Follow up the same day. Not tomorrow. Not when you "get a chance." Ideally within 2 hours of the call. Send a recap, next steps, and anything you promised. Speed signals commitment. Look, I get it. This feels remedial. But you know what? There are reps that are fucking this up. And in a world where everyone's got the same deck, the same demo, the same pitch, these tiny details ARE the difference. Your buyer isn't comparing you to the perfect rep. They're comparing you to the last three reps they met with who showed up late, forgot their name, and never followed up. Do the basics. Do them every time. Hate to say it, but that alone will separate you from the pack.

499

197 Comments

MIT says 95% of enterprise genAI pilots are failing... TBH - doesn't surprise me one bit. This stuff is HARD. For the world I play in... the focus is AI Agents for CX, but what makes it hard? Getting to a working demo is pretty dang easy, but the last 20% of a production level build is a different story. -> You need to get transcription right: What about when a customer says "bye" or "by". The former you tell the AI Agent to hang up and the latter you wait to hear what's next. -> You need to get the edge cases right: To solve this most people just shove more into the prompt, but this is where regression happens and AI Agents start breaking process. -> You need to get APIs ready: True impact comes from automation of workflows and that requires touching a variety of systems. Many APIs are customer owned. My prediction? Many pilots will fail and a "hunger games" moment will transpire where only a few AI platforms will be left standing as the players who can actually drive customer value.

53

4 Comments

A month ago, I flew to NYC to speak at a MailCon panel with Nick and Taylor. Ours was the only B2B session at a B2C email conference, and that got me thinking: Cold Email is difficult. So when you’re stepping into it from B2C emails, you might be tempted to use some of your B2C strategies. But here’s what I’d say to someone who is planning to switch from B2C to B2B Cold Email: 🔷 In Cold Email, your offer, targeting and timing matter much more than volume. 🔷 Many marketers coming from B2C email might want to lead with their offer and features. But in Cold Email, that’s not the way to go. 🔷 The goals are different, and so are the main metrics we use to measure success: for B2C it’s open rate and clicks, for us cold email folks, bounce rate and positive replies are more important. 🔷 In Cold Email, you’re reaching out to people who don’t know you. They haven’t signed up for your lead magnet or bought your product. You need a reason to reach out specifically to the people on your list. 🔷 Cold emails are mostly plain text. B2C emails include html templates. 🔷 B2C and B2B emails need dedicated tools. A cold email tool won’t work for sending newsletters and mass offers. An email marketing tool won’t work for sending targeted cold emails. And that list could go on. But all in all, think of them this way: 👉 B2C emails are like you’re advertising by distributing flyers at a conference – anyone who wants to, can opt in to take a flyer and use your offer. 👉 Cold emails are more like you’re coming up to a specific person at that conference, and starting a conversation. There’s a place for both. Just don’t confuse one with the other. P.S. To everyone who came to our MailCon panel: thank you. And special thanks to Adrian, Taylor and Nick - it was awesome to speak with you at the panel, and hang out afterwards. 🙂

72

16 Comments

Yesterday Kyle Norton gave a refreshingly non-fluffy AI talk at Pavilion GTM 2025. One piece of advice I loved: over-invest in enablement and change management. There’s just *so much* change right now. If you can build a process to quickly “install” changes in your team, you’ve got a super power. I couldn’t agree more and I wanted to add something Kyle didn’t have time to mention. Front-line sales mangers are the highest leverage change agents in your GTM org. Each front-line manager directly influences 6-10 reps and, like it or not, they’re the face of any change you roll out. If you want to build a repeatable change management process, start with them. Get them involved, get them excited and changes roll out smoothly. Don’t do that and watch everything grind to a halt. I wrote a lot more about how most orgs are failing front-line managers—and what to do about it—in Uncharted Territory. https://lnkd.in/g2qVQNqJ

74

15 Comments

If you're leading Brand/Comms/PR at a large B2B tech company, and trying to activate your CEO and executives on Linkedin, you should be studying Meghan Barr. As VP of Brand & Comms at ZoomInfo, she worked with her CEO Henry Schuck to build his CEO Brand on Linkedin (81,000+ followers). While Henry is leading a $1.2B ARR public company, she helped him tell their story to ZoomInfo's customers, employees, and investors at scale. Few large B2B tech CEOs are doing it more successfully & authentically than Henry. And last week, Meghan joined me for an interview. Here's what we covered: -- Why Linkedin has become her #1 PR channel -- How to support a busy CEO to be active on Linkedin -- How to manage risk vs pushing the boundaries when it comes to storytelling -- What happened when they took out apology billboards -- Why Henry’s posts outperform ZoomInfo’s 240k follower brand page -- How to activate your other execs -- How Meghan transitioned from journalism to tech -- Plus much more Listen here: Spotify - https://lnkd.in/e7w7Ne7q Apple - https://lnkd.in/eBjfNmF6 Youtube - https://lnkd.in/e_PP5N6J Some of my personal takeaways: 1. Linkedin-native PR Two years ago, they made the shift to prioritize Linkedin-native CEO storytelling. Not a PR piece first, and then republish to Linkedin. Not writing a blog post, and then sharing the link on Linkedin. Why? They noticed that Linkedin has become the place where their customers, B2B decision makers, are talking, learning and finding news. So that's where they wanted to be. They realized that you need to have a Linkedin-first approach to content, which means eg. leaning into video. 2. Your CEO needs to value Comms Henry is a natural with content. He WANTS to be out there. He sees the value. The work between Meghan and Henry is collaborative, each brings in ideas, they discuss them, find the right balance between being spicy (Henry's tendency) and playing it more safe (Meghan's tendency), and draft posts together. If Meghan had to drag Henry's feet, it wouldn't work. 3. The power of comments Henry is very active in the comments. When ZoomInfo was getting a lot of customer complaints about data accuracy about 2 years ago, Henry was actively replying back to people's Linkedin posts complaining about the product, taking accountability, talking about how they're fixing it. It's how I first found him & became a fan. That authenticity and closeness is rare. 4. Linkedin as INTERNAL Comms If your CEO is talking on Linkedin about the company, the vision, the story, the product, your priorities - all of it is internal comms. For any message to sink in, you need to repeat it 100 times. And if your All Hands is only once a month or quarter, that's how often your CEO can repeat your core messages to everyone on the team. With Linkedin, everyone at the company can see what's in your CEO's head in real time, multiple times a week, in small bite-sized pieces.

64

14 Comments