Meet the CS Leader: Lisa Robinson, Gusto

We are excited to bring you a conversation with Lisa Robinson, Customer Success leader at Gusto. Lisa shares her insights on making Customer Success strategic and proactive, how the organization has evolved over time, and the challenges of prioritizing tasks for Customer Success managers at Gusto.

Thanks for making time to connect with us today! To start, we'd love to hear about your journey into Customer Success.

I actually started in a Finance role at Intel. After Intel, I went to Stanford GSB for business school, where I became really interested in startups. But ultimately, I decided that spending a couple of years honing my strategic skills in consulting would be the right next step. After 2 years at Boston Consulting Group, I made the leap to startups.

The first startup I joined was an early stage with only six of us in the beginning. As a result, I was able to do a bit of everything. Things like: how do we set up the customer experience? How do we market to our customers? What should our sales team look like?

That startup eventually led to Gusto, because they were both businesses that served small businesses, and I just fell in love with the space and Gusto’s mission. When I started at Gusto, I was in Marketing. But I quickly became interested in how much our customers really loved Gusto – and I wanted to dig into understanding how we served our customers. That’s how I moved over to the Customer Experience (CX) side of the house.

My role in CX was leading our CX Insights & Operations team. We were thinking a lot about how to continue delivering the same great service to a growing customer base. One idea was that a Customer Success motion could be really valuable and helpful to our customers. And about 3 years ago, that idea of Customer Success grew into a team.

I didn’t know this path would lead to Customer Success, but I’m glad it did!

Something we often hear is the importance of making Customer Success strategic and proactive. What does that look like at Gusto?

We’ve taken a very lean, scaled, intentional approach to CS. We have over 100,000 small businesses that we work with at Gusto and a relatively small team of CSMs, so we knew that we had to be pretty strategic about who we reached out to, when we reached out to them, and why.

Let’s make sure that touchpoint provides value to our customers.

We also run a lot of experiments. I like to say that we’re hypothesis-based and data-backed. When we do have hypotheses or insights about what we should try, we partner closely with our data teams to back that up and really refine that strategy.

How has the organization evolved since the early days at Gusto?

It’s grown a lot. We started a little over three years ago with 1 person – and now the team has scaled up to serve more of our customers.  

When we first got started, we knew we’d have to be very focused. We asked ourselves: what could we experiment with that would feel like a clear win for customers? We didn’t want to boil the ocean, so we went after one small hypothesis at a time.

The way we approached the growth of the org has been really driven by customer adoption and customer value. Are we helping customers adopt the features that are right for their business? If we do that right, we give our customers a reason to stay longer at Gusto. As we’ve been able to show value across adoption and retention, we’ve continued to grow the team.

What could we experiment with that would feel like a clear win for customers? We didn't want to boil the ocean so we went after one small hypothesis at a time.

As the Gusto customer base has continued to grow and scale, how has the CS organization approached high-touch vs low-touch customer engagement motions?

We work with smaller customers compared to an Enterprise SaaS business. So when we looked at building out our Customer Success motions, we had to think through whether a high-touch model across the board would make sense not only for the company but also for our customers.

Today, we use more of a low-touch model for the majority of our customers. This allows us to be very intentional about which customers we proactively reach out to - and also enables us to reach more customers than a typical CS model.

Ultimately, small business owners are very busy. So when we reach out, we want to make sure that conversation provides value to them and their business.

One thing we hear regularly from CSMs is that they have ton to do across a wide variety of focus areas. What does a day in the life of a CSM at Gusto look like and how do you help the team prioritize what's most important?

We’re really guided by the lifecycle and needs of our customers. At any given time, there are a few initiatives our CSMs drive on an ongoing basis – for example, reaching out to customers to introduce new features. Each CSM has a dashboard for every customer that helps them understand the context about the customer and helps guide the conversation

Fundamentally, it’s really about quality as opposed to pure quantity of activity. At the end of the day, what we’re really focused on is: Are we introducing new features that meet the needs of our customers and their business? What was the quality of the conversation? What happened as a result of that conversation? Looking at that is essential, rather than solely tracking the sheer quantity of calls or connections.

It sounds like a well oiled machine – would you describe it that way?

We’re getting better every day, but there’s always room for improvement! There’s still a lot behind the scenes that happen manually, but I do think we’ve come a long way from the early days.

At the same time, I like that we’re not perfectly oiled. The team has stayed very comfortable with experimentation and trying new things. Some of these experiences have been super successful and become part of our ongoing activities. And we try to continue improving and iterating on those.

I like that we're not perfectly oiled. The team has stayed very comfortable with experimentation and trying new things.

How do you think about when it's appropriate to make bets or run experiments versus continuing the same activities and initiatives?

We have a good mix. It feels like we have the fundamentals down in many ways – there are things we definitely know how to do, and know that they work – which actually gives us more confidence to try new things.

We’ve built a strong muscle in being comfortable in not knowing the outcome of these new initiatives. Ultimately, we’re trying to take the insights that we hear from our customers and the signals we’re seeing in the data and use both of those to drive actions for what to do next. Sometimes we hit the mark, and you know, occasionally we don’t – and that’s okay.

It’s okay that sometimes things don’t work. That’s how we learn.

How do you balance the scale needed to run a big CS machine vs the quality, focused nature of the conversations you mentioned earlier?

In many ways we need to do both in CS: have quality, focused conversations – and also do it somewhat at scale. This means reaching out to our customers, not just 1-to-1, but also using a 1-to-many approach such as email or digital. It also means we have to make sure that the insights we are collecting – the voice of the customer – are being heard by the right teams. To power this feedback loop, we partner closely with our product, marketing, and sales teams.

At the most basic level, we’re not afraid of doing something non-scalable in the beginning. That’s where innovation and experimentation start. Sometimes, that zero-to-one just takes a little bit of pure grind. It’s worthwhile. It’s also fun. Our goal is to help the customer, and if we help the customer, we’re doing the right thing.

Are there any open roles at Gusto that you'd like to shout out?

Yes! Gusto is a modern, online people platform that helps small and medium businesses take care of their teams. On top of full-service payroll, Gusto offers health insurance, 401(k)s, expert HR, and team management tools.

You can check out our open roles at

Thanks again to Lisa for sharing his insights and experience with us. Have follow-up questions or topics? Reach us below – we'd love to hear your feedback. 💙