AMA: ScaleUp CS Partner, ScaleUp CS, Nina Wilkinson on Developing Your Customer Success Career

Hard skills (must haves): Strong Excel and data fluency. Not “I can sort a column.” I mean comfortable building forecasting models, churn analysis, capacity plans. You will fight for headcount, budget, and tooling more often than you want to. Data is your weapon. Narrative building. You have to take what’s working, what’s broken, and what you need next, and tell that story to leadership in a way that lands. Most CS leaders can describe their team. Few can sell their team. That’s the gap. Managin ...Read More

There isn’t one. That’s the honest answer. I’ve hired people into CS from sales, support, product, implementation, consulting, ops, and one excellent CSM who used to teach high school chemistry. I’m an art history major with a master’s in museum management. None of my education was tied to selling, account management, or software. What’s carried me through is the ability to write. I spent years in school learning to construct an argument and tell a story, and that skill has done more for my care ...Read More

A few I keep coming back to: Vitally’s webinar series. Practical and tactical. Good for ICs who want frameworks they can use Monday. SuccessHacker. Strong programming overall and a good entry point if you’re newer to the space. Gain Grow Retain. Active community, real CS practitioners debating real problems. Sharebird. Yes, this one. The AMAs and Q&A archive are gold and you can search by topic. CS Insider newsletter. Weekly read, low effort, decent breadth. One thing I’d avoid: don’t pay fo ...Read More

Five tactical skills I look for: Discovery and listening. Most CSMs talk too much. The best ones ask better questions and follow the thread. If you can’t surface a customer’s actual goal in 15 minutes, you can’t drive an outcome. Look at your gong recordings, your customer's should be speaking between 60-75% of the call, not your CSM. Project management. Every account is a moving project with stakeholders, dependencies, and timelines. The CSMs who hit their numbers run their book like a portfoli ...Read More

Increasingly, yes. With tools like Claude, ChatGPT, and Second Brain, you no longer need to code to build useful things, but you do need curiosity and a willingness to learn how the product actually works. What “technical enough” looks like in 2026: You can read API documentation and explain it back to a customer. You can write a basic SQL query, or know enough to ask for the right one from data. You can use AI tools to build a workflow, a small dashboard, or a custom prompt that solves a real C ...Read More

Honestly, this hits harder for me as a CS leader than as a CSM. The thing that drains me most is constant change at the exec level. When leadership turns over every quarter, you spend an enormous amount of time re-litigating the same conversations: why CS matters, why your team needs the headcount you’ve already justified, why this metric is the right one to measure against. Every new exec wants to put their stamp on post sales, and you’re starting from zero on relationships, context, and trust. ...Read More

Three things in priority order: Ownership. If you’re crushing your current role, ask for more. Take on a piece of team reporting. Own the EBR template. Own onboarding for new hires. Own the renewal forecast for your segment. Director level work is owning outcomes that span more than your own book. Start practicing now. And as a leader I can't tell you how much I love sharing my legos with folks who want to take on parts of the job, it frees me up to do other work which is super rewarding. If you ...Read More

There are several paths and none of them require a CS background. I came in through account management that evolved into CS. I’ve hired plenty of folks from sales (SDR, jr AE), support, and implementation. Each path works. What’s becoming non negotiable is comfort with technical concepts. You don’t need to code. You do need to be fluent enough with APIs, SQL basics, integrations, and how your platform actually works to do initial diagnosis and triage before you escalate. That fluency also makes ...Read More

It depends on stage. The KPIs change as the team matures. Early stage teams (under ~$10M ARR): anchor on GRR and LRR. You’re proving the product is sticky and that customers want to stay with you even when their headcount or budget changes. Later stage teams: shift to NRR and LRR plus expansion opportunities created or Closed Won. You’re proving CS contributes to growth, not just retention. For tooling, here’s what I’d actually recommend: Vitally: my go to. Easy to implement, strong dashboards, ...Read More

Short answer: AI is replacing parts of the job. It is not replacing the job. The CSMs who get cut in 2026 are the ones whose work product looked like AI output already: copy paste QBRs, surface level account notes, status updates dressed up as strategy. Operators and people who think in an operational format will thrive in this new environment. What is getting automated: tier 1 reactive work, health scoring, call summaries, first draft EBR decks, churn signal flagging. What is not (yet): judgmen ...Read More

Depends on what you actually like doing. Here’s how I think about it: AM (account management): Right move if you love commercial conversations and relationship work but want clearer revenue ownership and bigger upside. Tradeoff: more transactional, less strategic depth on the customer’s business. RevOps: Right move if you’re the CSM who lives in spreadsheets, builds the dashboards, and gets energized by systems and data. Tradeoff: fewer customer relationships, more internal stakeholder work. Sol ...Read More

Most PIPs are not recoverable. I know that’s hard to hear. The data inside companies is usually that 70-80% of PIPs end in exit. In 15+ years in leadership roles, I've done ~12 PIPs, 4 folks have not only gotten off of them but thrived afterwards, it can be done, it's not necessarily fatal. That said, your job in the first 48 hours is to figure out which kind of PIP this is, and then run two tracks at once. Day 1-2: Get the success criteria in writing. Specific, measurable, time bound. If your m ...Read More

This market is brutal and I don’t want to sugarcoat it. I’ve reviewed reqs with 600+ applicants for a single CSM seat. You have to be deliberate. What is actually working right now: Referrals beat cold applications by an enormous margin. Spend 70% of your search energy on warm intros, not job boards. Find 5 CS leaders a week on LinkedIn, comment thoughtfully, ask for 15 minutes. You'd be shocked how often this works. Tighten your resume to outcomes, not activities. “Managed a book of 80 accounts ...Read More

Both paths are valid. They are not the same job, and a lot of people pick management because it sounds like the next step, then hate it. Don’t do that. Management isn't always the highest paid track and if you don't like coaching, it's not fulfilling. Here’s the question I ask my CSMs: what work energizes you more? Negotiating with a c-suite exec on a complex renewal, or coaching a teammate through their first tough EBR? Both are valuable. They are wildly different days. Lean toward what you’re ...Read More

If your team isn’t there yet, it will be. The era of “CS is a cost center, sales owns the revenue” is mostly over at strong companies. The teams I’m building today own renewals, expansion, or both, and the variable comp comes with it. How to get comfortable: Reframe what selling is. Selling expansion to an existing customer who loves your product isn’t cold calling. It’s articulating the next outcome, sizing it in their language, and asking for the meeting. You already do half of this. Shadow yo ...Read More