Chris Armstrong

I stayed in SDR longer than I wanted. Turns out, it was the best thing for my career. I used to think SDR was just a step. Book meetings. Get promoted. Move on. So I focused on numbers: → Hit quota → Logged activity → Tried to look “ready” on paper But it wasn’t enough. Until someone told me: “If you don’t master SDR, AE will expose you.” They were right. I started treating SDR like it was the job, not the wait.  • Refined my messaging  • Practiced objections daily  • Treated every call like a rep  • Studied ICPs, pain points, and personas And I learned how to sell. Not just book. Not just qualify. Sell. So when I got promoted? I wasn’t guessing. I was ready. → Month 1 as AE: I booked 15 meetings → Month 2: I booked 12 more → Month 3: Hit 575% of my quota (ramp 66% of target) and closed a 154k ARR 1 year commitment deal Because the habits I built as an SDR didn’t disappear, they scaled. That foundation made me fast, focused, and fearless. If you’re in SDR right now, and you want AE? Don’t rush it. Master it. — Want to go from SDR to AE, the right way? Connect with me and add a note: “SDR to AE coaching”. I’ll randomly pick one person for a free coaching session on how to make the jump. Follow me @Jonathan for outbound plays that grow careers, not just calendars.

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Your CSM just renewed 95% of their book, but their expansion revenue was 3%. So you're paying someone $85K to be a really expensive customer support agent with a fancier title? Most CSM comp plans reward one thing: keeping customers from leaving. So that's exactly what you get. At the same time, more and more leaders are pushing their CSMs to focus on driving expansion revenue. If you want CSMs who actually drive growth, you need to pay them like growth matters. Instead of $75K base + 10% of renewals, try: - $65K base + 5% renewals + 15% expansion revenue. - $1K SPIFF for every expansion conversation that moves to proposal stage. - $500 bonus when they identify and introduce a new stakeholder to the AE. - Quarterly bonuses tied to account health scores that predict future expansion. Some teams add expansion readiness gates: - 80%+ of accounts with documented expansion opportunities unlocks 1.5x expansion multiplier. - <50% expansion pipeline coverage? Your renewal rate drops to 5%. With this structure (and the proper enablement), your CSMs will stop avoiding pricing conversations. They'll start thinking like account managers. They'll map org charts. They'll identify budget cycles. They'll become expansion hunters, not just churn preventers. One team we work with made this shift last year. Their CSM-driven expansion went from 12% to 43% of total growth. Same people, different incentives. If you pay CSMs to prevent churn, they'll prevent churn. If you pay them to drive growth, they'll start driving growth.

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I’ve reviewed 100s of discovery calls. The #1 difference between AEs converting 40% and AEs converting 70%+ of first calls is the number of problems discussed. And the top reps discuss fewer. Average reps cover a lot of ground in their discovery calls. They go wide, trying to find anything and everything to tie their product to. The logic makes sense: “The more problems I find, the better chance I have of solving some of them.” The best reps aren’t trying to uncover a lot of problems. They understand that: - No company has the capacity to take on a bunch of priorities at once - Discussing a bunch of problems leaves your prospect overwhelmed and not wanting to book more time - Deals are won by solving the biggest priority, not by solving a bunch of annoyances So they focus on finding and attaching to a problem worth solving. Monday morning, I’m sharing the exact question you need to ask in all of your discovery calls to validate you’ve found the right problem. I’m also sharing my “Discovery Capture Sheet” - a resource you can use to: - Know exactly what you need to uncover on a discovery call - Example questions to ask to uncover valuable insight If improving discovery is on your personal development plan for this quarter, you won’t want to miss my next newsletter. Join (no cost) at salesintroverts.com!

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SDRs - Getting promoted to AE is HARD. Here are 5 things I did to get promoted that you can copy too: 1. Choose the right company: DataGuard had a proven track record of promoting employees within the sales org from BDR - AE - Ent AE. 2. Aligned with an internal champion: Max Seidl made it very clear from the outset that he was looking to ensure I was promoted to AE as long as I hit my metrics. So we mapped out what success looked like and how to get there. Once it was clear I was delivering, Max was eager to run through walls to let other GTM stakeholders know of my promotion plan. 3. Regular check-ins: I'd check in with Max in my 121 on where I was in relation to my promotion goal and how I could improve. 4. Prepare for the next role: Whilst still delivering on my BDR duties, I found time to practice discovery and demo roleplays with my colleagues to prepare me for the role. Loyd Spillane and Ashish Gandhi thanks for the help! 5. Enjoyed the ride: Enjoy the journey as an SDR, the skills you learn in your X months in the role are the foundations of a successful AE. So soak up the knowledge and watch the months fly by. Anything you'd add? P.S Here's a picture of me doing the sunrise hike in Guatemala! Worth the pain lol!

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Why most SDR outreach is getting ignored in 2025 ? Buyers don’t answer cold calls. They ghost emails. LinkedIn messages go unread. Because every SDR is doing the exact same thing. ❌ Sending the same “Just following up” email ❌ Copy-pasting generic templates ❌ Relying on automation instead of personalization Buyers are drowning in bad outreach. So what actually works? >> Make it about them, not you. → Stop leading with “I’d love to book a call.” Instead, start with “I saw your post about [X] and had a quick insight to share…” >> Use multiple touchpoints. → Combine email, LinkedIn, video, and (yes) even voicemail. Buyers need multiple interactions before they engage. >> Follow up with new value. → Every touchpoint should add something new. A fresh insight, a relevant case study, a question that makes them think. The SDRs who stand out are the ones who put in the extra thought. Are you? We are teaching what works in 2025 in our live cohorts. Link to speak with me in the comments. #sales #sdr #outbound

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A few minutes of deep work on Sunday makes for a great week ahead. How to make this week wildly effective and productive as an AE: 1. Prospecting bucket: -Choose 5 net-new accounts -Find 3-5 contacts at each account -Develop 5 POVs for each account for why you want to reach out -Send 15-20 relevant & tailored emails, make 15-20 dials and send 15-20 LinkedIn connection requests 2. Active deal bucket: -Audit existing pipeline and de risk by asking "what is the friction in this deal and what could go wrong?" -Send 1 multi-threading email to each deal -Send 1 value touch to each champion 3. Low hanging fruit bucket: -Reach out to all closed/lost opps -Reach out to all people who have recently changed jobs from a past customer -Find 5 new warm intros from Sales Navigator 4. Personal development bucket: -30+ minutes of movement per day -Daily gratitude by writing 3 things down -Eliminate screen time during the work day -Live in alignment daily with your core values -Take action even if your brain is trying to convince you not to (discipline) Nearly impossible not to have a productive week if you fill each of these 4 buckets!

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One of the most overlooked traits when hiring SDRs is credibility, specifically, how quickly and naturally they can build it with a prospect. People don’t connect with scripts. They connect with real stories, authenticity, and lived experience. That’s where trust is built. The more complex the solution, the more credibility matters. How are you building your credibility?

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Most sales leaders focus on their top performers. But your best reps will crush quota whether you help them or not. Here's the uncomfortable truth about scaling revenue... Your top 10% will succeed despite you. They'll figure out how to sell your product and close deals even if you give them zero support, no collateral, and an undefined ICP. But you can't build a scalable revenue engine on top 10% talent alone. It's just math. Even with a rigorous interview process and strong recruiting brand, our 12-month retention rate at Levelset was around 55%. And that was GOOD. The key to scaling isn't finding more unicorns. It's raising the floor for everyone else. That means writing down exactly what success looks like. Not just hoping good people will "figure it out." I learned this the hard way. For the first 4 years (or so), we closed deals almost in spite of ourselves. No real sales playbook. No defined process. Just talented people working hard. When we finally documented our exact process - from first touch to close - our ramp time plummeted and consistency shot up. The uncomfortable truth? Most founders spend way more time recruiting than preparing to train and support their hires. Your playbook doesn't need to be fancy. Start with one document: "How to Run a Demo." Make it painfully detailed. Your top reps will hate it. Your new reps will love you for it.

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Salespeople… THIS follow up email scored me a meeting. Here’s the story and 3 things you NEED to do when following up with a prospect… Last friday, I cold called a rev ops leader who expressed some interest in my pitch. However, when I asked to set some time to further chat, he let me know that he would need to chat with his VP of Marketing before committing to a meeting. If you’ve done any amount of cold calling, you’ve definitely faced this.  In this scenario, I wasn’t able to overcome the objection, so I settled for sending him a video to share with his marketing leader. THEN… a few days passed. NOTHING. No feedback on the video, or how the conversation went, NOTHING. So, what’d I do next? I called him again, left a voicemail, sent the following email, got a response, and booked the meeting. Here’s 3 things you should do if you want to be successful in your follow ups. 1. USE THE PHONE. The biggest mistake a rep can make when following up? Not picking up the phone. A live conversation beats any email. So first things first, pick up the phone and give them a call. If no response? Leave a voicemail and use that voicemail to point to an email. 2. Make sure you have the RIGHT email. I’ve made this mistake WAYY too many times. I send a GLORIOUS follow up email, only to realize I had the wrong email in the first place. The way I get around this? Snov.io Snov.io has THE BEST built in email verifier out there. So before you waste your time and send an email to the abyss. Make sure the email’s been verified FIRST. Snov.io is the best way to do this. 3. SHOW the prospect it’s worth their time to respond. When sending a follow up message, it’s CRUCIAL you ask yourself, did I add anything of value in this touch point? If you have not - go back to the drawing board. In this email below, I leveraged conversations I recently had with this prospects' competitors, so that he’d WANT to respond/meet and see what his prospects had learned that he had not. Follow up is THE most important part of your sales game. Make sure you’re doing it RIGHT! Dariia, Noam, Ivan, Leah, Jeremy, Ryan, Adia, Brianna, Philip, Elda, Christopher Any tips on sending GOOD follow up emails?

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Every SDR leader knows the pain. You finally get your top performer humming, and next quarter you’re backfilling them with someone brand new. That new SDR is learning everything: product, personas, competitors, tools. All before they even get to the hard part…figuring out what to say. Smart leaders bake this ramp into their pipeline models. Some even add “phantom” headcount to cover the gap between fully-ramped reps and the reality that 30% of the team is still learning the basics. The new SDRs heads are spinning as they bounce between six different systems of truth. So it’s no wonder new reps move at a glacial pace. That’s where Roomie AI Spark changes everything. Common Room already brings all your GTM signals into one place. Spark takes it further by turning those signals into natural-language insights that tell reps exactly what’s been happening at an account. Picture this: A champion joins a target account. In the old world, your SDR digs through Salesforce, hunting for context from their last company and stitching together context about the target account. Then they try to Hemingway it into a relevant messsage. It takes 20-30 min per message. In the new world, they hover over the contact in Common Room and Spark instantly surfaces everything — who they are, what’s happened, even Gong call insights from their previous employer. If I’d had this when I led SDR teams, I wouldn’t have needed to model ramp time because ramp time would be cut in half.

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The strongest muscle in sales? The AE + SDR partnership. Too many AEs try to bench quota solo. Too many SDRs don’t get that every rep is prepping them to level up. SDRs: Know the accounts. Bring updates. Send prep. Follow up like a pro. AEs: If you’re not leveraging your SDRs, you’re leaving gains (and deals) on the table. Show up. Give credit. Talk them up. Respect the grind. SDRs are doing the burpees of sales - hardest reps, biggest growth. No one maxes out alone 🏋️‍♀️

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Your sales process will make you lose deals. One common mistake I see? After a call with 5 stakeholders, reps send 1 generic follow-up. They think they’ve covered everything. But it’s too broad to matter to anyone. - CFOs care about risk. - Ops care about process. - Enablement care about adoption. So instead of blasting the same email, I split my follow-ups: - Short, sharp recap per persona - Each stakeholder only sees what’s relevant to them - All hosted in one trumpet 🎺 Pod - so I know who’s actually engaging That visibility helps me capitalise on engagement - and ensure I re-engage the less engaged. That’s what helps win deals. Still sending one-size-fits-all recaps? You’re not losing to competitors. You’re losing to your own process. I’ve dropped an example follow-up structure in the comments - and if you want a cleaner way to share these with prospects (and track who’s engaging), you can get 25% off Trumpet here: https://lnkd.in/es5gippF #sales #followup #buyerenablement #trumpet

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The SDR Role, Tough, But Transformative 🎉 💡 Let’s be real, the SDR role isn’t easy. You face rejections, objections, and constant targets. But here’s the truth, it becomes easy when you own it. Own your numbers. Own your activity. Own your growth. What drives you as an SDR? 💬 Talking to different people every day. 🧩 Solving their problems. 🚀 Preparing yourself for that next step, AE, Team Lead, or Manager. This role teaches you discipline, communication, and resilience, the same traits that build great sales leaders. Yes, it’s tough. But it’s also the most powerful, rewarding, and high-energy role in the sales journey. Because when you truly love it, it gives back, in growth, recognition, and commissions. So if you’re an SDR out there show up, own it, and love it. Because this is where great sales careers are built. 💪 #SalesDevelopment #SDRLife #Motivation #SalesLeadership #GrowthMindset #CareerInSales #SalesTeam #ColdCalling #SalesJourney #Inspiration #Deel

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The invisible work that get SDRs promoted. → Reviewing your own calls—even when no one asks → Asking for feedback from your AE → Sharing what’s working with your team → Offering to present in a team meeting → Leading part of a huddle → Owning a mini project → Learning how to run a pipeline review → Bringing a new idea to your manager These aren’t flashy. But they compound. Your next title often starts in the way you show up before you get it.

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SDR leader: "I want to leave our only B2B contact data provider. What’s the best tool?" Me: "There's no one magic tool that does everything." Most outbound teams rely on 1 data source, thinking it'll give them all the data they need. But every data vendor has quality and coverage gaps. When the data isn't good enough, you churn and go to another provider. Then you do the same thing again. You waste time and energy. Your team efficiency suffers. Your reps spend time manually looking for phone numbers and emails instead of actually prospecting. You're paying $200-500 per rep per month but only using 1 data provider. If you are scaling outbound: Stop relying on 1 data source. Use different data sources for: - Account data - Contact info (email, phone numbers) Measure your data providers on 2 criteria: - Coverage - Quality Use Clay to bring all your account and contact data together: For contact data: - you might need a mix of 3 tools like Cognism + FullEnrich or ZoomInfo. - Every provider is different when it comes to data quality and coverage. - A tool like TitanX to have the best phone data. For account data: - Team size from Sales nav - Tech stack from Builtwith (if available) or job descriptions with Sumble or TheirStack Recently, I talked to a company selling to an industry where most companies aren't on LinkedIn and sometimes don't even have websites. You need multiple sources. Test each provider on quality AND coverage for your target accounts. Invest more in data than your outbound stack. Data is the biggest piece of your outbound team efficiency. The right data gets you better: - Scoring → so your GTM team spends time on the right accounts - Phone numbers → so your team doesn't manually hunt for numbers or call bad ones - Emails → so your team doesn't manually search for emails that bounce Today you can have all of this in the backend with tools like Clay. Your reps don't need to touch any of this anymore. They spend more time prospecting. Follow me 👨‍🍳 Elric, the Outbound Chef, for daily tips on scaling outbound.

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