Kieran Flanagan

All the best CSMs I know have one thing in common... They’re great at demoing the product. Not because it’s their job. But because it gives them leverage. Most CSMs say: ❌ “That’s Sales’ job.” ❌ “I’m not confident with demos.” ❌ “I focus on strategy, not features.” I get it. But the ability to walk a customer through a real use case, live, in-product, is a superpower. Here are 5 moments where demo skills = influence: 🔮 Pitching a new strategy? Slides tell. Demos sell. Show customers exactly how to execute that strategy inside the product. 🤑 Introducing a new product? Want to land your “You’re ready for Enterprise” pitch? A contextual 3-minute walkthrough hits harder than a pdf. 🤝 A new point of contact joins? They need a quick walkthrough. You could say it's someone else’s job… Or you could own it and build trust fast. 💔 Renewal risk conversation? Showing what they have used and what they could use can reignite belief faster than any pitch deck. 👩🏻‍🏫 Coaching power users? These folks want depth. Demos = activation. Activation = Usage. Usage = Stickiness. Stickness = champions. You don't need to become a full-time Solutions Engineer. But if you can’t show the product in motion? You’re leaving influence (and revenue) on the table. Great CSMs don’t just know the product. They know how to show it. 🔐 And the real unlock? Doing it at scale. That’s why I love what Trupeer is doing. Last week I shared how impressed I was with the tool they built. With Trupeer, CSMs can: 🎥 Record sleek, professional demos once 💄 Personalise them at scale 🔁 Reuse them again and again And it’s a better customer experience, too. Instead of: → Waiting for a meeting → Seeing it for the first time live → Sharing the recording with folks → Meeting again for follow-up questions… The CSM sends the demo ahead of time. The live meeting is deeper, sharper, and more impactful. That’s how you wow customers, without burning hours. I said it last week, and I’ll say it again: Try Trupeer. It's *free* to start. [link below] You’ll be mind-blown. 🤯 #CustomerSuccess #AI #CSM #RevOps #Retention #CX

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Every sales org has a pipeline: Stage 1. Stage 2. Forecast. Commit. You can recite it in your sleep. But when it comes to renewals? Crickets.... There’s no real-time view of customer risk. No weekly trendline. No forward-looking model that projects retention. Isn't that kinda bonkers? You FORECAST growth, but you DISCOVER churn...usually when it’s too late to fix. The big mistake is presuming retention is a lagging indicator, when it would be more accurate to define it as a neglected one. Think about it...most CS dashboards read like a rearview mirror: - Usage metrics. - Ticket volume. - NPS. Useful? Sure. Predictive? Nah. Because churn doesn’t start when a customer says they’re leaving. It starts months earlier when their exec sponsor stops showing up. If you can spot the risk early, you can unlock more levers: - Re-engage power. - Reset the value narrative. - Escalate to commercial. - Offer roadmap visibility. - Re-map success metrics post-reorg. But none of that works if your team can’t see it coming, which is why you need a churn forecast...just like you do for revenue. Build a churn pipeline. Treat it like sales. Some things to build into this: 1. Define churn stages. Just like deals, risk evolves: - Stage 1 (Early): No exec alignment, lagging adoption, stakeholder turnover. - Stage 2 (Mid): Value not realized, weak champion, limited engagement. - Stage 3 (Late): Renewal live, buyer pushing back, pricing/legal blockers. Assign clear criteria. Surface it in Gainsight, CZ, or Salesforce. Manage it like opportunity stages. 2. Assign prevention plays. Each stage should trigger a play: - Stage 1 = exec outreach + roadmap session. - Stage 2 = commercial review + value plan. - Stage 3 = C-level call + tailored retention offer. Codify this. Don’t let reps improvise. 3. Forecast it weekly. Revenue leaders inspect pipeline weekly. CS should do the same with churn. Ask: - How many accounts moved stages? - What’s projected retention by segment? - What % of at-risk logos have exec visibility? Also, share your churn forecast with the CFO. If the CFO sees new logo pipeline every Monday, but doesn’t see churn risk until Q4? That's no bueno. Start sending a weekly churn report with: - Total ARR at risk. - ARR by churn stage. - Stage progression. - Active recovery plays. - Forecasted retention (with confidence levels). This reduces surprises while also forcing accountability. Why? Because churn is rarely a CS failure, but it's often a product gap, pricing mismatch, or sales promise that aged poorly. When churn is forecasted, it becomes EVERYONE'S problem. Which it is. tl;dr = you don’t “discover” churn. You forecast it. You stage it. You act on it. Just like sales.

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It doesn't have to be complicated to run customer success in HubSpot. 🌶️ CS platform implementations take months because everyone's trying to fix their data AND run 15 plays they don't really need... Spicy take from Jeff Kushmerek? The reality is he and the Infinite Renewals team have the deep CS experience to back it up... Investing $30k plus in a dedicated platform will get you some fancy features...but taking a fundamentals-first approach in the HubSpot Customer Success workspace is more likely to drive impact and protect revenue this quarter. Here's the 3 back-to-basics plays Jeff told me every CS team actually needs: 1. Risk: Identify and address issues before they impact renewals and revenue. → Set up automated workflows triggered by health status changes 🧡 HubSpot Features: Health Scores, Workflows, Actions + Alerts in the CS Workspace, Tasks, Reports, Lists 2. Renewal: Start the process the moment a customer signs → Automate a renewal playbook that starts at least 90 days before contract end 🧡 HubSpot Features: Deal Pipelines, Workflows, Actions, Alerts, Revenue Tab in the CS Workspace, Tasks, Sequences, Reports 3. Relationships: Structure consistent engagement cadences → Create playbook templates for different customer meeting types and communications 🧡 HubSpot Features: Sequences, Email Templates, Snippets, Playbooks The best part? Implementation takes a weeks, not months, and doesn't require another full-time admin to maintain. Customer success teams deserve one less task on their todo list so they can stay focused on protecting revenue not implementing complex software. p.s. I started sharing playbooks for running customer success in HubSpot way back in 2022, before even HubSpot was really talking about it as a realistic use case. Seeing CS leaders like Jeff get so excited about the platform is a huge deal for all the companies debating if it's really possible to connect all their customer teams in one place 👀 p.p.s A full interview with Jeff and a deeper dive into some of the Infinite Renewals playbook for implementing CS in HubSpot will be in the ConnectedGTM newsletter tomorrow morning. Happy Friday ✌️

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How to make your next CRM your last Wild stat of the day: In MarTech’s annual Replacement Survey, 17–23% of businesses change CRMs every year. That’s a huge churn rate for what’s supposed to be the core of your engine. Switching systems comes with high costs for a company: Time, data migration, setup fees. But to build long-term relationships with your customers, you need to have a long-term relationship with your CRM. Most businesses change CRMs because they want better results, like improving customer loyalty and core metrics like CLTV/ABV. And they want better features to help them do this. Failed CRM projects aren’t usually about features. It’s about the foundations. Here’s how to choose a CRM you can bring home to the team. 1. Don’t shop for features, shop for solutions The “Ferrari trap” is real, choosing the flashiest tool with the most bells and whistles… that nobody ends up using. It’s easy to check a feature off a list, but that doesn't always mean it’s usable or even necessary. You should always plan a use-case round in your process to see how things translate from paper to reality. Before approaching any vendor, map out how you generate business and identify what’s not working. Is CAC too high? CLTV too low? Once you have your “what”, ask vendors to show you the “how.” You can always ask for a case study or reference call on top of a demo. 2. Understand the flow of data Companies are eager to fix their problems and improve their KPIs (fair enough) and hope a new CRM will do the trick. But CRM failures are often data problems. Audit your current customer data flow. Where it starts, how it moves, and where it gets dirty. Then, ask CRM vendors how they can help you centralize and normalize your data. What connectors are available? How often do data syncs happen? What does the dedup process look like? Clean data is rocket fuel for your CRM. 3. Involve your whole team A great tool with a poorly thought-out strategy and a hasty implementation will make even the perfect CRM fail. User adoption matters as much as software.  If you can make beautiful campaigns but you can’t plug product data into them without the help of IT, then your static product recommendations are weak compared to your competition. The best CRM is one your team can use. When identifying problems with your current system, bring in stakeholders from all teams that use the CRM. During evaluation, get daily users involved so they can test options and you can ensure they champion the tool post-implementation. 4. Future‑proof by choosing open architecture (dev-friendly APIs, webhooks) and reviewing the vendor’s roadmap and financial health (headcount growth, profitability). A partner who scales with you prevents another costly switch. So pick a CRM that aligns with these guidelines, and you won’t have to pick again. Following a structured walkthrough of the RFP process can set you on the right path. Here’s to finding your forever CRM. 

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