Best Practices for Account Management

The most-important, overlooked metric in your CRM: → The ratio of Seller:Buyer activities. Too many sales leaders will look at a long list of activities inside an opportunity and think, “Wow, they’re all over this one. Nice job!” And totally overlook how lopsided the activity is. Those 10 emails and calls to a Stage 3+ deal… …got a single email reply with a few words in it. That’s it. Which is a 10:1 ratio. Pretty scary. Compared to a 2:1, or even 1:1 activity ratio for deal in the same stage? I’m putting my money (and reputation) on the more even, 2:1 ratio. A couple other signals to look for inside the activity history: 1/ Spacing between activities. Are replies & follow-up’s happening same day? Same week? Even longer to get something back? Tighter spacing between activities = stronger. 2/ Who’s initiating the activity. Is it always the seller? Is the buyer starting new threads? Proactive outreach from the buying team = better. 3/ High vs. low-value activities. Two deals could have the same activity ratio. But one may have more "below the line" activities. Above the line activity = stronger. 4/ Activities not in the CRM. A lot of high-value activity shows up in texts / Whatsapp. So if it's a late-stage deal, do we have texts from champions too? If not, I start to press into the details more.

Segmentation beats personalization. Personalization is terribly inefficient... (and oftentimes unnecessary outside of highly strategic enterprise selling). Think about the ads that really grab your attention. None of them have your name in them. Or mention podcasts you were interviewed in or posts that you wrote. These ads work because they're segmented based on patterns amongst small-ish groups of people. Outbound should be treated similarly. Pro tip: this approach works WAY better over the phone than via email. The expectation for personalization and quality is much higher in emails than over the phone. Here are a few ideas for segmenting your lists so you don't have to personalize so much: ✅ By region/location If you sell anything brick & mortar, SLED, etc—segment your accounts by geographic region. You really don't have to personalize much when you can: - Name-drop local businesses/organizations - Drop the location This sounds like: "Hi David, we work with Fit & Fashion right down the road in SLU. It's Jason with ________. Ring a bell?" ✅ By tech stack Let's say you sell a tool that enhances Salesforce. Or Jira. Or some other specific tool. Segment your accounts by tech stack. This sounds like: "Hi Katie, we're partnering with engineering teams who wish sandboxes were way easier to set up and use in Zendesk. It's Jason with ________. Got a min?" ✅ By persona Let's say you sell to ecomm solutions to SMB retail business owners. This sounds like: "Hi Tom, we're working with several retailers in the Seattle area. It's Jason with ________. Heard our name tossed around?" (H/T Armand Farrokh) ✅ By trigger This list gets pretty extensive. Hiring, job changes, customer/champion change, M&A, expansion/contraction, promotion, etc This sounds like: "Hi Dave, congrats on the promotion. It's Jason from __________. Was just talking to a new HR leader yesterday who's running into all kinds of complications scaling international hiring. That by chance something you're running into?" ✅ By niche One of my favorites. Take a well-recognized logo like Rippling. You could go after direct competitors, but it's even better to focus on non-competitive products selling to the same personas. This sounds like: "Hi Cierra, we're working with Rippling to help scale their product suite for HR leaders. It's Jason with ________. Thought you might want to hear how they've doubled ACV in the last 6 months. Have a min?" ~~~ Before you think of personalization, start with segmentation. Do the work upfront to avoid having to customize too much. Agree or disagree? We're training entire sales orgs at companies like Shopify, Rippling, Zoom, and many more on how to land more meetings with outbound. Interested in custom training for your team? DM or email me jason [at] outboundsquad.com for more info.

Your top rep just left. You're giving their $2.3M territory to someone who's never closed a deal over $50K. What could go wrong? 🤷🏻♂️ Territory handoffs are where good accounts go to die. Lots of orgs treat them like real estate transactions - here's the keys, figure it out. But ENT relationships aren't transferable assets. They're built on trust, credibility, and months (if not years) of relationship capital that walks out the door with your departing rep. The new rep shows up to accounts expecting them to behave like warm leads. Instead, they get treated like cold callers because the buyer has zero idea who they are. Active deals stall. Renewal conversations get pushed. New opportunities dry up because the rep is spending 6 months just rebuilding basic credibility. Here's what actually works for territory transitions: - 30-day overlap period where departing rep introduces successor on every active deal. - Account transition memos with relationship maps, not just CRM notes ("Sarah in Procurement hates surprises, always CC her boss Tom"). - Reduced quota for 90 days while new rep rebuilds relationships. - CS co-sells for first quarter to maintain continuity. - Departing rep records video intros for top 10 accounts explaining the transition. That last one is the gangster move, btw. Also, track these metrics during handoffs: - Days to first meaningful customer conversation. - % of active deals that advance vs. stall in first 60 days. - Time to first new opportunity creation. - Customer satisfaction scores during transition period. Throwing someone into a $2M territory with a spreadsheet is basically corporate Russian roulette. Your departing rep spent years building those relationships. Give your new rep the tools to actually inherit them.

I met a sales team that tracks 27 different metrics. But none of them matter. They measure: - Calls made - Emails sent - Meetings booked - Demos delivered - Talk-to-listen ratio - Response time - Pipeline coverage But they all miss the most important number: How often prospects share your content with others. This hit me yesterday. We analyzed our last 200 deals: Won deals: Champion shared content with 5+ stakeholders Lost deals: Champion shared with fewer than 2 people It wasn't about our: - Product demos - Discovery questions - Pricing strategy - Negotiation skills It was about whether our champion could effectively sell for us. Think about your current pipeline: Do you know how many people have seen your proposal? Do you know which slides your champion shared internally? Do you know who viewed your pricing? Most sales leaders have no idea. They're optimizing metrics that don't drive decisions. Look at your CRM right now. I bet it tracks: ✅ When YOU last emailed a prospect ❌ When THEY last shared your content ✅ How many calls YOU made ❌ How many stakeholders viewed your materials ✅ When YOU sent a proposal ❌ How much time they spent reviewing it We've built dashboards to measure everything except what actually matters. The real sales metric that predicts closed deals: Internal Sharing Velocity (ISV) How quickly and widely your champion distributes your content to other stakeholders. High ISV = Deals close Low ISV = Deals stall We completely rebuilt our sales process around this insight: - Redesigned all content to be shareable, not just readable - Created spaces where champions could easily distribute information - Built analytics to measure exactly who engaged with what - Trained reps to optimize for sharing, not for responses Result? Win rates up 35%. Sales cycles shortened by 42%. Forecasting accuracy improved by 60%. Stop obsessing over your activity metrics. Start measuring how effectively your champions sell for you. If your CRM can't tell you how often your content is shared internally, you're operating in the dark. And that's why your forecasts are always wrong. Your move.

Teams who take a “boil the ocean” approach to outbound will fail. Here’s how to fix it and build sequences that actually drive results: Step 1: Focus your team on accounts most likely to buy now, invest at a premium, and become long-term customers or referral sources. This means moving beyond “anyone who fits the ICP” and zeroing in on high-priority targets. Step 2: Create deeper, more meaningful segments from that refined group. Traditional segments are great for organizing territories but fall short for crafting sequences that resonate. Instead, you need segmentation that helps your team speak the language of specific sub-groups. Use multiple layers of data—firmographics, intent signals, and contact-level insights—to break your TAM into smaller, actionable groups. Step 3: Launch micro-campaigns that target those precise segments with messaging designed to feel tailor-made. When you take this approach, personalization becomes scalable because it’s rooted in segmentation. Your reps don’t waste time on one-off customization, and your messaging feels 99% relevant to the prospect. I've been teaching this process as #ValueBasedSegmentation for the better part of a decade. It’s the key to building sequences that drive higher CTRs, replies, and engagement without tedious manual effort. ➡️ With this approach, you’ll: - Improve email performance - Write copy that prospects actually care about - Give your team a clear roadmap for focused outbound 📌 How are you helping your team build relevance into their outbound sequences?

If I was running ABM at a fast-growing security company (like Wiz, Snyk, or Netskope), here's how I'd avoid wasting money on bad-fit accounts. 👇 AI Segmentation. Most companies segment by industry. They say something like: "We target Tech, Retail, and Hospitality companies with 1,000+ employees." Motel 6 and Airbnb show why this breaks. Same firmographic profiles. But very different business situations, needs, and priorities when it comes to information security (or any tech purchase). You wouldn't sell to them the same way. AI Segmentation helps you uncover and target the highest value segments for your business, beyond basic industries. Here's how I would do this for a security company: 1.) Segment on business situation (not industry). -- Analyze your best customers (high NRR, high ACV). -- Group by specific situations that align to your value prop. e.g. Security Maturity Level, Security Use Cases, Compliance Sensitivity, etc.  -- Find the *natural* clusters based on value, not generic industry labels. 2.) Identify segments with AI. -- Use Keyplay AI to categorize every account in your market. -- Backtest segments against historical data to find which segments have the highest NDR, ACV, and Win Rates. -- Find new ICPs, outside generic vertical groups. 3.) Action the data -- Create ABM plays at intersections with highest win rates. -- Develop content specific to each segment combination (e.g., "Cloud Security for Advanced DevSecOps Teams in Retail") -- Refine your segmentation models as you grow. This process can reduce non-ICP Spend (waste) by 20-30% and help you find thousands of net new target accounts. Don't just throw your budget at industries. Find the segments where your solution resonates most, where you win often, win fast, and win big. That's strategic segmentation. p.s. If you want me and my team to kick-start this process for you, we're offering a free strategic segmentation analysis to CMOs at SaaS security companies with >$20M ARR. Get your report here --> https://lnkd.in/gMezS4Zk #ABM #ICP

Over two decades I've trained thousands of salespeople and leaders on the art of connection—the single MOST important skill in business (and maybe life). Yet, when asked, most people struggle to pinpoint the subtle, quiet nuances that separate good communicators from the truly great ones. So, what are the underrated communication superpowers of the best leaders and sales pros? Here are seven that change everything: 1️⃣ Never flinching. No matter the objection, price concern, or even a moment of silence—they remain calm and unshaken. Their positive energy never wavers. This composure breeds incredible trust. 2️⃣ Asking questions that stop people in their tracks. The kind of questions that make someone say, “No one has ever asked me that before.” These are the a-ha moments where breakthroughs happen and connections deepen. 3️⃣ Reading the room like a pro. They don’t just hear words; they feel the energy of the room. They know when to pause, engage, or redirect—and how to make every person feel seen, heard, and valued. When they leave, everyone thinks, “That person really gets me.” 4️⃣ Perfectly matching communication styles. Whether it’s tone, energy, or body language, they align with others seamlessly—without losing authenticity. This isn’t mimicry, it’s creating connection. And when people feel understood, trust becomes inevitable. 5️⃣ Embracing silence like it’s a secret weapon. Great communicators don’t fear the pause. They know silence isn’t awkward—it’s a breakthrough catalyst. 6️⃣ Being disarmingly honest. They tell you what you need to hear, not just what you want to hear. But here’s the difference—they do it with care. You don’t just hear the honesty; you feel the deep empathy behind it. 7️⃣ Making the complex simple, without ego. They don’t care about sounding smart—they care about creating clarity. By cutting through complexity, they don’t just explain, they connect. It’s not about impressing others, it’s about communion. Here's another interesting fact: Almost no company specializes in training sales and leadership teams on these skills. That's why my partners and I started The Question First Group. Our mission is to create master communicators who lead with curiosity, inspire with authenticity, and connect deeply with purpose in every situation. So ask yourself: 👉 How many of these superpowers does your team already have? 👉 What could happen if they mastered all seven?

One of the best ways to create authentic relationships with your customers, get honest feedback on your product and surface game changing ideas is to create a Customer Advisory Board (CAB). Here are the lessons I’ve learned about how to create and run a successful CAB. Your personal involvement as CEO is critical. If you lead it yourself, customers will engage at a deeper level. They’ll be more honest, more vulnerable, and more likely to become evangelists for your company. No one else can unlock this dynamic the way a CEO can. Be clear on the persona. Is your CAB for buyers, users, or budget holders? At BetterCloud, our sweet spot was Directors of IT. Not the CIO, not the IT admin. Know exactly whose voice you want in the room and tailor everything to them. Skip the compensation, give them “status”. Don’t pay CAB members—it gets messy. Instead, make them feel like insiders. Give them a title, early access to roadmaps, VIP treatment at events, and public recognition. People want to feel valued and influential, not bought. Set a cadence you can maintain. I tried monthly meetings once. That was a mistake. Quarterly is the sweet spot. One in-person gathering per year—ideally tied to an industry event—goes a long way in deepening relationships. Structure matters. CABs aren’t just roundtables. They’re curated experiences. Keep meetings tight (90-120 minutes), show real products that are still in the development process (even rough wireframes or high level ideas), and create space for interaction. Done right, they become the ultimate feedback engine. Build real relationships. Your CAB shouldn’t just exist in meetings. Build one-on-one connections. Text, email, check in at events. Keep it small enough that people feel seen and valued. When they have a direct line to the CEO, they stay engaged—and they speak the truth. Done right, your CAB becomes more than just a feedback mechanism. It becomes a strategic asset. It can shape your roadmap, sharpen your positioning, and strengthen your customer relationships in ways no survey ever could. For a deeper dive and detailed tactics behind each of these, check out the full writeup on the Not Another CEO Substack.

3 Salesforce automations tech companies should implement today (If they want to scale without the busywork): Manual tasks are killing your growth. If you’re still assigning leads, chasing follow-ups, or leaving renewals to chance - you’re moving too slow. Here’s how to fix it: 1) Automate lead assignment When a new lead comes in, speed matters. Don’t waste time manually routing leads to your team. Set up automation to assign leads instantly based on: • Territory • Deal size • Product interest Your reps should know exactly who owns the lead - the moment it enters the system. 2) Automate follow-up tasks Manual task creation is a silent time killer. Your CRM should automatically trigger follow-up tasks when: • A new lead is assigned • A deal moves stages • A prospect replies No more guessing. No more forgetting. Just clear next steps, every time. 3) Automate renewal reminders Retention is revenue. Your CRM should automatically flag upcoming renewals to your team, so nothing slips through the cracks. Better yet: • Trigger upsell tasks based on customer activity • Automate renewal workflows to keep deals moving Retention revenue is the fastest win for scaling tech companies. Your CRM should make it automatic. The more you automate, the more time your team spends on what matters: closing deals and keeping customers. Don’t let manual tasks slow you down. P.S: Subscribe to my newsletter — I share proven ways to turn your CRM into a growth engine. Sign up here: https://lnkd.in/gBukTtJN

I just watched a rep lose a HIGH 6 figure deal in the first 5 minutes. Not because of price. Not because of product fit. Because of tonality. Here's what happened: Prospect: "Hi, nice to meet you. Just finished walking my dog..." Rep: "Great. What business priority brought you here today?" Prospect: "Um... we're just looking at options..." Call went downhill from there. The problem: Some reps have only one communication style. For instance: Direct and aggressive. But 60% of prospects need a softer approach to open up. Here's the framework I teach top performers: 1) Read the prospect in 30 seconds Fast talker, "let's cut to the chase" = match their energy Slow speaker, relationship-focused = dial it down 2) Adjust your questions accordingly Instead of: "Who's the decision maker?" Try: "Typically when companies evaluate new solutions, it involves a few people. In your organization, who would usually be part of that process?" Same information. Completely different response rate. 3) Practice the uncomfortable Yes, it feels fake at first. Your brain says "this isn't me." But you're not being disingenuous. You're adapting your communication style to connect better. The drill: Record yourself asking 5 discovery questions at different tonality levels for 20 minutes daily. Level 10 = drill sergeant Level 5 = curious colleague Level 2 = supportive friend When reps master tonality… Discovery calls run 40% longer Prospects share sensitive information earlier Close rates increase 30%+ One of my clients went from 23% to 31% close rate just by softening her delivery on budget and stakeholder questions. You can have the best discovery framework in the world, but if your tonality shuts prospects down, none of it matters. Sales leaders: This is coachable. Shadow your reps' calls and listen for tonality mismatches. Role-play different prospect personalities in team meetings. The reps who master this skill connect with every buyer type and consistently hit quota. P.S. DM me if you want to install this in your teams.