Lessons Learnt: Building CS Orgs from the Ground Up

Having built new Customer Success teams from the ground up multiple times, there are many lessons I have learned and would employ when doing it again. Here's 10 of the best.

Building things from the ground up can be pretty scary if you have never done it before. There's a temptation to take your time and over analyse, for fear of getting it wrong. But speed is key. The faster you can act, the faster you can succeed (or fail) and reap the benefits.

Having build Customer Success teams multiple times over now, there are invaluable lessons I have learnt along the way that I've made note of, so that when I do it again, I can move quicker. Every business, market, product, company, culture is different.

Note: these are lessons specific to building a Customer Success organisation from the ground up. Whilst they may not be wholly owned or led by CS, as a leader of the CS org I am seeking to influence these things. Sales, Marketing, Product, Support... will have their own lessons. Some may overlap.

After all of the things I've learnt, here are the first 10 lessons I would prioritise and repeat to myself again and again...

1. Tools can wait

Having too many tools creates distraction and unnecessary disconnection, not to mention operations overhead and wasted money on underused subscriptions.

Avoid the temptation to buy lots of tools because you think you need them, or because they are the cool tool to have, and they are popular.

There are some tools which you obviously need straight out the gate. Not all tools will be owned or managed by the CS team, but the CSMs will need access to them;

• CRM (Salesforce, Hubspot)

• Support (Intercom, Pylon, Plain)

• Comms and Colaboration (Notion, Slack, Zoom)

• Product insights (Pendo, Mixpanel, Amplitude)

• Call recording (Grain, Chorus, Gong)

If it’s not essential, wait. It's better to figure out what your processes are and get to the point where you can't live without them, than go impulsive shopping. Once you grow and get more mature in your GTM motion, you'll start thinking about other tools for your stack. I have happily added many of the following tools to my stack, but in some cases added them too early and just didn't make the most of them. I eventually used them, but spent a small fortune having them sat on the shelf in the meantime;

• Contact engagement and outreach (Outreach, Salesloft, Apollo)

• CS Platform (Gainsight, Planhat, Churnzero, Totango)

• Onboarding/Adoption (EverAfter, Appcues, Userflow)

• Forecasting (Clari, BoostUp)

• Project Management tools (Asana, ClickUp, Monday, Trello)

• Subscription Analytics (Profitwell, Baremetrics)

• Data Analytics (Retool, Mode, Looker)

• Best of the rest... Loom, Miro, Canny, ProductBoard

Start with as few tools as you can get away with, and focus instead on building tight, repeatable workflows that are tool agnostic. Once you understand the rhythm of your CS team's day-to-day, you'll be in a much stronger position to identify where tech genuinely adds leverage. Don't be swayed by vendors promising a silver bullet. In most cases, process maturity trumps tech complexity.

2. Data, Data, Data

Without data your CS org will be flying blind. Commit to being data driven, with a coherent strategy and tools. Invest time and money.

Data is going to be the life blood of running and effective and impactful post-sale team. Without product, user and associated usage data your team will literally be flying blind.

To begin with, it doesn't matter where the data lives or who owns it, but make sure that you have a strategy for data and that it is visible and accessible to everyone in the company. All too often there will be different versions of the truth because different teams will invest in their own tools. When it comes to presenting to the customer, or even internally, discrepancies in data will cause confusion.

Beyond product and usage data, Sales and Marketing data (in their respective systems), and finance and billing data is also critical for the same reasons.

Investing in data tools and strategy too late amplifies the pain. You find yourself scrambling for the information. The doubt and unreliability that brings takes a long time to overcome because people in the org have built up an inherent distrust that's difficult to dispel.

Getting a clear picture of the customer journey starts with agreeing on the source of truth. Misaligned metrics kill cross-functional collaboration and erode confidence. You can’t drive retention or expansion if you're debating dashboard discrepancies. Build shared data definitions early, and prioritise enabling your team to self-serve insights without needing a SQL degree.

3. Take care of the pennies

Knowing where your subscription revenue is coming from is essential for smooth renewals, expansions and win-backs. Both the internal and customer-facing experience will be effected without it

You've heard of the saying "take care of the pennies and the pounds will take care of themselves"? It's true. It seems like such an obvious thing to say, but make sure the billing system and CRM/Sales data is reliable and accurate.

If you're using a billing tool like Stripe or Chargebee, make sure every subscription has accurate details of billing contacts, terms, prices, seat counts etc

All subscriptions and contracts need to be accurate and correct, and sounds obvious, but it takes a concerted effort to ensure that you accurately record it and track it in a way that scales.

If you don’t know who bought what and when, you can’t serve your customers. Clean data and tight alignment between CS and Finance aren’t just operational hygiene, they’re revenue enablers. If CS doesn’t have clarity on term dates, payment status, or what was purchased, you’ll lose time chasing answers and miss critical renewal cues. A well-maintained customer record is your safety net when things get busy or messy... and they always do.

4. Build a GTM pod model

Use this super power for as long as you can. It won't last forever, but will be your greatest force in serving the customer with agility, creativity, speed and success.

When you are small and have very few people in the GTM org, everything is smoother and fast. In this stage you can build out a 'pod model' where you have 1:1 alignment between AE, CSM, and BDR. This will be your biggest GTM strength.

Each pod may be organised around a country/region, an ICP or persona, a segment/ industry. Where 1 AE, 1 CSM and 1 BDR only have to talk to each other, they will talk more often, make faster decisions, there will be less distractions, and the harmony that comes from knowing and trusting in each others work will quicken with every rotation, like the proverbial flywheel. Best of all, it cuts down on unnecessary communication.

These early pods aren't just a structural tactic, they shape culture. When Sales and CS are side-by-side, learning from each other daily, you're building empathy, trust, and a shared understanding of what customer success really means. That muscle memory stays with you as you scale, even after the pod model breaks apart under headcount pressure.

The GTM pod mode will, at some point, be a victim of it's own success. It will perform so well, that the business will grow and you'll take on several more people. At this point it won’t be possible to maintain the same working ratio and you'll need to structure differently. Mainly because Sales and Customer Success headcount rarely (if ever) grows at the same pace and one will outnumber the other.

5. Document what works

Documenting ways of working helps you scale faster and plan better.

Don't get sucked into the trap of thinking that nothing you do is repeatable, or that everything you do is ad hoc, one of a kind, unique to every customer. Also, don’t underestimate how often people will ask “what’s the process for this?” Having a lightweight but accessible playbook isn’t about bureaucracy, it’s about reducing noise and context switching.

Documenting ways of working early gives you clarity. It also gives you the ability to evolve and build new processes. The overhead to update them is there, but this documentation will become part of your standard operating procedures for the company and will build a culture for the future.

If you document even the simplist of tasks and processes it will pay itself forward as you scale. As you collaborate with others outside of your team, it helps to bring them along the journey and innovate with you. Navigating repetitive actions becomes faster, onboarding new starters to the team gets faster, but the best part is that finding and fixing faults in your process gets more effective.

Take time to 'sharpen the saw' and document as you go. That documentation should be publicly visible and searchable. My strong recommendation is that is done in Notion, and NOT in a GoogleDoc or Dropbox Paper doc.

6. Maintain an Ops backlog

It will inform the planning roadmap, future goals and strategy, and ensure you don’t slow down.

When building a new org, the list of operational items seems to go one forever. Some will be quick wins, some will take many quarters, some may even depend on the evolution of the org and can't be done until later. If you try to plan and execute based on whats in front of you, or the biggest fire or priority at the time, you'll always be chasing your tail.

Instead, build a visible backlog of things to work on, that grows and gets added to as soon as new things come up. Categorise the items on the list by operational area (tools, people/HR, process, customer, finance/billing, product) and give them a priority, status and planned/required completion date. Not only will this become your artifact for planning and aligning to company goals, OKRs, KPIs, but it will also give you a record of progress and achievements in the quarter.

Your backlog then becomes a strategic tool. It’s a running pulse of operational debt, opportunities, and ideas. It helps you push back when you’re asked “what’s CS working on?” and makes it easier to show progress even when outcomes take time. Treat it like a living document, not a dumping ground, regularly prune and prioritise.

As the team grows, others in the company will see and understand the value and impact of the Customer Success org. Make the CS Ops backlog visible to everyone in the company and make it such that anyone in the company can contribute to it. You may be susceptible to blind spots, that others can see would warrant a solution or some focus.

7. Hire behind the curve

Hire CS people when it’s too painful to operate without them.

When you built your GTM teams from scratch, there are some speculative roles that you have to hire ahead of the curve, even if you don't have many customers. The obvious one is Sales. If you have a PLG self-service motion then this might look slightly different, but generally rings true.

Being lean forces you to design roles thoughtfully and build scalable practices before people. When you eventually hire, those people will step into clarity, not chaos. Resist the urge to solve every problem with headcount. Early hires are culture carriers, not just capacity. Choose people who thrive in ambiguity and have a builder’s mindset.

Customer Success team members should be an early hire but you can't over-hire. In the early days you can’t afford to hire people because you think you’ll blow a number out of the water, because if you don't hit the heights, then you will likely have built redundancy into your machine. It's a fine balance and timing is everything because once you do decide to hire, it could take 3-6 months to find, hire and onboard the right people.

Hiring the right people is such a crucial thing to get right in scaling the CS org (I will save in-depth musings for another lessons learnt post). My takeaway here though is it is better to be behind the curve in hiring CS people, because in the short term their efforts will have to be picked up by Sales and Support, but just know you won't get as dedicated focus on customers until you do hire CS.

8. Meet EVERY customer

Your early customers will be your longest customers and your biggest advocates.

When you have high value customers you naturally gravitate to them and spend time with them, and you should. My advice would be to try and meet EVERY customer you have. Regardless of size, value, use case, expansion potential. Talk to them all.

When you reach out to every customer, go beyond your main contacts; the economic buyer, the procurement person, the senior leader/exec sponsor. Those people are super important, but further and deeper value will come from speaking to the average Joe and Sally on the street. They use your tool, they know what they need, they use it in unique ways that you'd not thought of, they have pains and needs, and their insights will be worth their weight in gold.

As you speak to anyone and everyone, those conversations not only help define what customers need from your product, but importantly you will hear common and repetitive themes that will help you to understand what processes to build, what works and doesn't with how they interact with you, where their experience with you as a vendor meets expectations or differs.

Early conversations uncover nuances that never show up in metrics. They help you build champions and detractors into partners. Even a short check-in can surface gold. If you listen carefully and follow up with intent, you'll turn users into allies and insights into advantage.

Investing in customer conversations will have untold future benefits. I've seen it time and time again, your early customers will be your longest customers and your biggest advocates. They will move companies and take your product with them, so whilst you're growing, treat them like the priceless gems they are.

9. Product Team are your BFF

Help the Product team with anything they need to be successful.

The Product team is your most important internal stakeholder. There is a mutually beneficial outcome that Product and Customer Success can have from partnering closely with one another. Without each other, neither of you can do your best work. Together you can make customers fall in love with you.

The Product team relies upon customer insights conversations to validate prototypes, PRDs, strategic roadmaps. They can of course go out an find customers for themselves, but because Customer Success has a closer intimacy with customers, the right users, the use cases, the introductions and relationships that Customer Success Managers make are always more valuable.

Be generous with signal. Don’t just report bugs and feature requests, offer patterns, pain points, and the “why” behind customer asks. Involve CS in product retros and let CSMs hear the roadmap rationale firsthand. When Product feels supported by CS rather than pressured, they’re more likely to reciprocate.

Few things are more crucial than getting reliable and swift feedback from the Product team on feature requests and the roadmap so you can close the customer feedback loop. With the insights and learnings you get from close relationships Customer Success is also better able to talk to customers in terms of the company's strategic vision and pains being solved, rather than presenting a list of recently released features.

10. Observe, Learn and Change

Don’t get stuck doing things that don’t work.

'Sunk cost bias' is a dangerous malady in growing an organisation. Don't get sucked into thinking that because you have spent time, effort, or money on something that you have to stick with it. If it's not working, change it. The one exception might be tools and team members where there are contracts and obligations to honour.

Regularly review process, strategies, tools, approaches and note what is working, what is not, and what needs to be done to reach a more effective velocity. The common 'start, stop, continue' exercise is a healthy quarterly introspection that can prevent you from persisting with the wrong things for too long. You haven’t got time to get sentimental about something that was a great idea once upon a time.

Iteration is your greatest advantage. Big companies get stuck in inertia, but you can try things quickly, learn fast, and shift course without bureaucracy. Build a culture that values curiosity over ego. Reward learning, not just outcomes. The best CS orgs I’ve built weren’t the ones that started perfectly, they were the ones that got better every month.