What It's Like to Lead Customer Success at a Startup

Over the course of my career, I’ve worked exclusively for startups.

It’s a challenge, but a worthwhile one – startups offer so much to learn and experience.

If you're considering doing the same as a leader, here's what I learned, chaos and all!

😵‍💫 Embracing the chaos

Priorities can change rapidly at startups. Managing each change with finesse requires an even head and an eye toward what you can control.

I would often put a lot of effort into a project only to realize priorities had shifted and we needed to start over. I found it difficult to reconcile and not react negatively, but once I looked at the bigger picture, I realized every step at a startup counts as progress and learning.

Even though we were changing directions, I could still apply what I learned moving into the future. I found it helpful to think of these situations as 'course corrections' rather than 'wasted effort'.

✅Takeaway: Don't get too comfortable or take things personally. Embrace the chaos and learn along the way.

And this brings me to my next point…

⭐ Not letting perfect be the enemy of good

My first job as a Customer Success leader was outlining processes that could be quickly implemented, one of which was customer onboarding. I needed to do this fast and nail it since we were basically starting from scratch.

However, a major reality check was waiting for me.

Despite having created a supposedly comprehensive onboarding program, many customers weren't even starting their onboarding, let alone completing it or getting value from our product.

To top it off, this lack of onboarding was contributing significantly to churn!

Ouch and OUCH!

I was dismayed – I thought I’d captured all the necessary steps needed to get our customers effectively onboarded.

On paper, I had a ‘perfect’ onboarding process.

What went wrong?

When I evaluated the steps leading up to our onboarding process, a couple of things occurred to me:

• Our Sales to Customer Success handoff was disjointed in that new customers were not shown how important our onboarding process was to their success.
• Since these new customers did not yet have a relationship with Customer Success, they were less likely to respond when their CSM contacted them to start their onboarding.

To fix this, we decided to have the to-be CSM join at least one pre-Sales call with a prospect when it became apparent that we were going to close a deal. The purpose of this call was for Customer Success to begin to form a relationship with this almost-customer and to walk them through the onboarding process as a necessary bridge towards meeting their goals with our product.

We found that this pre-Sales time investment from Customer Success was worthwhile, and we began to see more customers start to onboard. We also found and addressed other gaps in the onboarding process as we learned more over time.

✅ Takeaway: You’ll never be ‘done’ setting up a ‘perfect’ process, you’ve got to iterate constantly as your product, company, and customers evolve.

🤝 Forming strong cross-functional bonds

Even though outlining structure is an important first step in a chaotic startup environment, it is only effective if all relevant stakeholders are involved.

At another previous startup, our Customer Success team identified incomplete configuration as a leading indicator of customer churn. No surprise here.

So to combat this, we partnered with Engineering to alert our team whenever a customer’s setup was stalling.

While these alerts were helpful to an extent, we realized that we didn’t have all the required information to help customers actually fix their setup issues. So as part of our Customer Success-Engineering interlock, I set up a process for our Engineering team to provide us with more specific information that would help us get more customers set up.

However, with Engineering’s more ‘free-form’ way of working, we were still not getting all the information we needed to close the loop with customers.

It was discouraging – I thought I had built a clear enough process but something was amiss.

Here’s where I went wrong:

• I didn't start with the 'why' and convey the importance of setting up this process to the Engineering team.
• I wasn't being adaptable, especially when there were more stakeholders involved than just myself, each with different ways of working.
• I wasn't acting as a partner when setting up this process and instead was giving orders.
• I didn't understand our constraints, including Engineering's bandwidth and their other competing priorities. Engineers are a busy bunch!

Moving forward, I set up a follow-up call with Engineering to go over the ‘why’ behind the process and offered some ways to make it easier on them as well. I also prioritized building a relationship with the key stakeholders on the team which in turn helped boost knowledge sharing and collaboration.

✅Takeaway: True cross-functional collaboration only happens when all relevant stakeholders are involved and bought into the same vision.

⛹️‍♂️ Playing and coaching as you grow

You are often both a player and a coach in startups. Startups typically grow at a breakneck pace and they don't always have the staff to keep pace.

As a Customer Success leader at a previous startup, I had to own accounts while managing and building my team. But in the process, I became reactive rather than proactive, getting lost in the weeds and glossing over my big-picture responsibilities.

In order to improve my management skills and have time for strategic priorities, I began blocking off a couple of hours at the end of each day.

It can be tiring, but here are the questions I ask myself before calling it a day:

• How were my team interactions today and over this past week?
• What could I have done better? --> This leads to research on improvement areas for me as a manager.
• What are some of our inefficiencies? How can we avoid spending time on these so we can focus on bigger-value projects? --> This leads to broader strategic considerations on how we can improve our processes and better meet our needs.

There are some fantastic podcasts I love to listen to such as Women in Customer Success, Gain Grow Retain, and Planhat’s Customer Success podcast that are excellent resources for this.

✅ Takeaway: It's ok to switch roles based on what's needed most. Just don't forget that you are a coach first and a player second.

⏰ Knowing when it’s time to hire

Startups offer many learning opportunities where you get to wear a lot of hats! But when does this start to become detrimental?

A good rule of thumb is to hire if you find your priorities are all over the place. To quantify this, goal-set at the beginning of the quarter (here’s INC's guide to help you do this) – if you find yourself missing all your goals by end-of-quarter, it’s time to hire.

✅ Takeaway: If you realize you're drowning in work and aren't hitting any of your goals as a leader, the time to hire was yesterday.

👩‍🍳 Preventing too many cooks from spoiling the broth

Have you ever been a part of a group project where everyone assumes everyone else will do the work? In the end, these types of projects never get completed.

Yikes.

I’ve been in similar situations working at startups, only to find myself or others scrambling to finish the job.  This is a tough situation to be in, especially in a startup where resources are limited.

One cross-functional project I worked on recently suffered from analysis paralysis. We were constantly going in circles in ‘brainstorm sessions’ with no clear tasks, ownership, or next steps. This was an important project and critical for us to complete.

At some point it became clear that we were going in circles, so another department lead stepped in to reformulate our project plan – with their guidance, we divided the project into small chunks with clear stakeholders, deliverables, and timelines (a useful tool to establish this is MOCHA).

With each of us having clear decision rights and responsibilities, we were able to make quick work of the project.

✅ Takeaway: If everyone is responsible for the same things, no one is.  

🎯 Maintain balance while pursuing outcomes

In startups, projects move rapidly, and employees are eager to see things through to completion.

Yes, that was me as well! It wasn't just that I was eager - sometimes I was impatient as well.  In being so, I was inadvertently aggressive, driving a little too hard on deliverables from other internal stakeholders.

This was certainly a lesson learned the hard way and I quickly understood the importance of keeping a balance and working harmoniously with others.

✅ Takeaway: You can't control how other stakeholders perform. Focus on what's in your control and always be mindful of others’ bandwidth.

⚠️ Don’t forget these three things

I’ll leave you with some key learnings that have enabled me to be successful in startup environments:

• Always share the ‘why’ behind a project with other stakeholders and be persuasive. Telling a story if you can is great – people may forget graphs and data but will always remember a compelling story.
• Don’t dictate, collaborate! People will not know how to prioritize their tasks if they don’t understand the importance behind them.
• Set reasonable expectations on target dates for deliverables. No assumptions = No surprises.