Steve Brian

Interviewing for a Customer Success Manager role? Most CSMs wing it. Top performers come prepared, with STORIES. Here are the 7 most common CSM interview questions I ask (and how to stand out when answering them) 1️⃣ How do you define and measure success in your role? Talk about metrics like NRR, adoption, and product usage, but also strategic wins like building trust and creating value. Get specific, don’t just say that you had a 100% NRR rate. Talk about the details underneath, how much of that was driven by expansion, churn and what the total portfolio was you held. 2️⃣ Tell me a story of how you grew seat utilization or expanded an account. Be specific. Walk through the signals you saw, the conversations you had, and the value you delivered. 3️⃣ How have you handled a renewal that was at risk? Show commercial acumen. What data did you use? What stakeholders did you engage? What was the outcome? How did you plan the strategy out, did you multi-thread and how… 4️⃣ What are early warning signs that a customer might churn? Mention things like drop in engagement, exec turnover, missed QBRs, and how you take action fast. Show that you have a bias towards action. 5️⃣ What’s your playbook when an account goes dark? Go beyond just “follow-ups.” Think multithreading, value emails, and reactivation campaigns. How are you really adding value for your customers? 6️⃣ How do you partner with Marketing or other teams to drive advocacy? Share a real example of a case study, webinar, or customer story you co-created. 7️⃣ What’s one way you’ve sped up time-to-value or onboarding? Show your process thinking. How did you reduce complexity, improve documentation, or drive engagement early? Which of these would YOU want to be asked in an interview? Let’s hear your strongest story in the comments.

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Today, many teams are kicking off Q4. A quick framework I’ve used for quarterly content meetings that the PMMs actually enjoyed: For context, when I was leading content strategy for Sales Cloud at Salesforce, we had a VERY cross-functional team. PMM, creative, demand gen, and content/editorial all had their own stakes in the game when it came to our quarterly planning. Lots of cooks in the kitchen, and recent reorgs prompting a need for clarity on roles. Everyone developed an integrated planning template, and my team adapted it for a quarterly content planning and reporting meeting. We even had some of the PMMs start to tell us it was their favorite meeting. 👀 Here’s what we would share quarterly. REFRESHER: What is this meeting? I find that a lot of meetings jump right into the subject matter without establishing what success looks like in the next X minutes. RULES OF ENGAGEMENT: Do we want questions at the end? Questions in the Google Meet Chat? Say how we want folks to engage. WHAT’S NEW? Everyone gets excited about innovation! What’s new since the last time we met? People updates are key. We shared things like new website and blog updates, team member changes, new authors or featured speakers, and a new top-performing social post to amplify (bonus points if people repostes during the meeting). PERFORMANCE: Quarterly and rolled up annual metrics. Show how we are performing against goals and, more importantly, what we will do differently and optimize because of the results. One of my favorite things to share in a quarterly performance update is “an anatomy of a great blog / social post” section. Pull up one of the team’s favorite top performers (can be a video, article, whatever you’re focused on) and point out all the things that made it great, whether that’s a strong hook, visual, and so on. INTEGRATED PLANNING UPDATE: Has the messaging changed? Are we still aiming for the same audiences? Share any cross-functional updates that change the high-level direction for the team. Another key thing to highlight here is roles and responsibilities. We did this in a “four wheels of a car” slide where we showed how PMM, content, creative, and demand gen were all critical wheels of the car to make it go. We showed a few quick bullets of what each team was responsible for to reduce confusion about swim lanes. CALENDAR UPDATE: Show what’s coming up next in the integrated plan! This is your roadmap for the quarter and the big bets everyone should know. In this section, you make all the high-level strategy real. Making it real is what leaders and practitioners alike get excited about. How do you run your quarterly planning sessions? I’m working on developing a couple frameworks around this for my new professional chapter, and would love to hear!

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Vendor Consolidation vs. Best-of-Breed Tech Stack No doubt, a HOT topic for Enablement leaders facing the quagmire of proving defensible value in the face of increasingly scrutinized budgets. Spoiler alert: this post won't settle that debate (at least today... sorry!), but it sure provides a polarizing caption. Rather, this post is about effectively securing the MOST impact for your internal teams evaluating tools while simultaneously pressure testing how much your external vendors actually want to invest in your success. The answer: propose a win-win onsite vendor day. CASE STUDY: - WHAT: a few months back, we proposed collaborating on an in-person "Gong Day." In exchange for flying Pigment's Enablement team to Dublin (Gong's EMEA HQ) and dedicating an entire day's worth of mindshare, Gong would organize a "Gong on Gong" showcase of how they internally utilize their platform for IC's and leaders across BDR, AE, and CSM personas. - WHY: 1) Pigment's Enablement team, much like many others in B2B SaaS, was not yet harnessing the full value included in its tech stack, 2) Pigment's Enablement team, much like many others in B2B SaaS, aspired to infuse bleeding edge AI-functionality into its GTM motion. - HOW: [see screenshot below] Pigment met Gong halfway in co-creating an eight-hour mutually-beneficial agenda: we walked away with Gong's battle-tested playbooks, and Gong walked away with critical insight into deepening its customer traction. In sharing this story, Enablement leaders should A) feel empowered to make this pressure-testing request of existing (or potential) vendors, because B) this exercise benefits BOTH parties. Perhaps how vendors respond will clarify the conundrum of consolidating vs. renewing. Kudos to Lesley Ronaldson, Karen Carroll, Arne Branagh-Schmidt, Mounir Boulazreg, and the entire Gong EMEA team for exemplifying an unwavering commitment to customer success.

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Predictive Enablement is transforming how we equip our revenue leaders. No longer just about delivering content or training on demand, predictive enablement leverages data and AI to: * Anticipate Skill Gaps: Imagine knowing which reps are about to struggle with a particular objection, product feature etc before it impacts a deal. Proactive, targeted coaching and training. RingCentral's enablement & Ops teams Kelly Molkenbuhr are launching The Revenue Standard which will be the framework to do just this. * Proactively Deliver the Right Resources: Instead of reps searching for answers serve it up. This is where Ringo I've talked about before is coming in for RingCentral. * Optimize Coaching & Training: By analyzing vast amounts of sales data – from call recordings to CRM activity – AI can pinpoint patterns in successful interactions. We are leveraging RingCentral's RingSense and Aviso AI to power this. * Accelerate Onboarding & Time-to-Quota: New hires can be brought up to speed faster with personalized learning paths and simulated scenarios Heather K. has a lot on deck to do just this! * Improve Forecast Accuracy: Account planning, opp planning and deal planning with AI Ratnadeep Chatterjee, MBA Michael Throssel and I have a few things up our sleeves to roll out in Q3! Predictive enablement isn't just a buzzword; it's a strategic imperative powered by AI and robust data analytics. It moves us from reactive problem-solving to proactive performance optimization, ensuring our go-to-market teams are always one step ahead. CC: Akshay Srivastava Joe Jacob Joe Fahrner Ayub Mohammed Amir Hameed Brandon Thomas Are you already exploring predictive enablement within your organization? What impact have you seen, or what challenges are you anticipating? #PredictiveEnablement #SalesEnablement #RevenueEnablement #AITech #Coaching #GTMStrategy

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For decades, enterprise sales were seen as a grind. Quota-chasing, cold-calling, transactional. Today, it’s something very different. In tech especially, carrying a number has become one of the most aspirational seats in a company. Modern sales means directing complex gtm systems that move billions in enterprise spend. Our recent blog maps out this tectonic shift: the unbundling of sales tech, and the rise of GTM automation platforms that rebundle not around features, but outcomes. Here’s a sneak peek 🧠 : ~ A breakdown of the MAPE-K loop, turning workflows into self-tuning systems ~ The business model reshaped: vendors get paid by outcomes, not seat counts ~ Why the role of SDRs is shifting, from execution to revenue engineering If you care more about revenue than tools, this is your new North Star. 💫 Read the whole piece here: https://lnkd.in/dCtg36GJ

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Want to break into Customer Success? Cool. But stop following bad advice. I've been recruiting a lot lately. Here’s what no one tells you, but I will. When I pivoted into CS leadership, I was already at the top of my game in Support. I didn’t “start over.” I translated what I already knew from my years of experience: - Solving messy enterprise problems - Reading between the lines when customers don’t say what they mean - Innovating on process and being a creative problem solver - Analyzing data to build scalable, repeatable success That edge didn’t disappear. I sharpened it. But I also had to unlearn a few things. Here are 4 rookie mistakes people make trying to get into CS and how to do better: ❌ “I’m a people person!” That's great, but that’s not the job. ✅ Be a translator, someone who can listen, understand a customer’s goal, and map it to product outcomes. 📤 “I submitted my CV. Fingers crossed.” Nope. ✅ Show how your skills transfer. Tell them why you’re the one for this company, not just any company. This one. Float above the noise. 📽️ “I’ll demo every feature to show how much I know!” That’s not impressive. It’s chaotic. ✅ Show you can listen, adapt, and curate. What matters to this customer? Why these features? 📚 “I skimmed the website, I’m ready.” You’re not. ✅ Go deeper. Know the product. Know the users. Show why you get it more than the next 10 candidates. CS is not a vibe. It’s not just a step up from support or other roles. It’s a shift in mindset. But if you’ve got the instincts, the resilience, and the ability to connect dots. You’re already halfway there. That’s what I learned making the switch. 👀 What skills from your past job became your secret weapon in CS? Let’s give the next wave something better to work with👇

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