Laying groundwork for customer success that scales with John Henwood
A-Z guide to hiring, scaling, and growing customer success while staying cash efficient
I spoke with customer success leader John Henwood about his experience scaling customer success at SaaS startups starting with his experience at Hootsuite and most recently at Productboard.
John shared a ton of valuable tips and his advice on when to start building customer success (hint: sooner than you think), a key thing founders must do before building customer success, and strategies that allow teams to scale while being cash efficient instead of over-hiring.
John’s journey into customer success
Lyndsay Tell me about your background. How did you get into customer success and customer success leadership?
John Henwood I've been in account management and then customer success for about 13 years. I started out in account management and partner management for four, five years selling corporate training to enterprises globally and partly in a channel type role.
In 2013, I first went into a customer success role where I was the lead for enterprise customer success at Hootsuite, a late-stage social media software company. I grew that into a team lead role where I managed a team responsible for our biggest customers.
I progressed from there into a manager role around 2016 and then into director where I was managing North American customer success and management. We had about 25 CSMs (customer success managers) spread across three teams.
From there I came to Productboard (product management software company). We were at the precipice of the scale up phase and I was tasked with taking the customer success team from zero to one.
We’ve had 10x growth in the last three years and really gone team's gone from what started as two CSMs at the time to now 35 plus across multiple disciplines. We’ve built the segmentation, the team structures and a whole group of leaders underneath.
It's been a fun journey over 13 years and I’m looking forward to 2023.
Lyndsay Awesome. Super helpful background and a lot to dig into given all of your experience in customer success.
Why building customer success early pays off
Lyndsay Let’s start with the basics. When should a founder start thinking about customer success?
John The short way of thinking about it is if you're at the point where you're even debating starting customer success, it's probably late enough where you should be starting customer success.
Once you've gone past product market fit and you've got enough customers, it's too many for you as the founder to actually directly engage with to deliver value. You see some of the things online which might say that you need to have at least $2 million per CSM to make that an investment worth making. I might not even wait until you have that.
The reason being is when you think about customer success early on, there's a lot of value you're going to get beyond just the direct interactions with customers as it relates to learning around what makes customers successful.
There’s value in getting success feedback into the product, understanding what drives new customer acquisition and makes future customers more successful.
CSMs play such a broad role early, I really would make that investment as soon as you possibly can.
The key thing founders must do before building customer success
Lyndsay What do early stages of investing in customer success look like? Is that hiring dedicated reps or beginning to make CS part of others’ roles?
John It's a great question. The first thing you need to do before you implement dedicated customer success is figure out customer support. If you don't figure out customer support and a way for your customers to be able to reach out and have their technical questions handled in a timely fashion, then most of what your customer success team ends up doing is customer support and they get relegated to that activity.
Early on, as with any startup, a customer success person is going to wear multiple hats, so they may play a customer support role to start, but then beyond that you likely want them to start doing proactive work with customers beyond the reactive nature of support.
Customer success managers need to interact directly with customers over key moments in the customer journey. Onboarding, adoption, through to renewal would be the three life cycle stages that I would think about as having basic plays around within customer success.
This is probably managed through the title of a CSM to start where they play all of those functions and, depending on the organization set up, if you don't have dedicated support, they may also undertake support interactions early on too.
The other thing I would think about earlier than is usually advertised in most thought leadership is to build scaled programs as a foundation from the start. Depending on the complexity of the product and the market you're in it’s helpful to have a CS marketing or programs function. They sit on the operations side as someone who can drive customer success programs at scale.
That may be someone who's building a tech touch journey or automation with email and in product campaigns, assuming the product or marketing team doesn't already own that.
The CS marketing person is going to be someone who looks at data, builds content, distributes that content across the user base in programmatic ways. That would be the other type of role I would think about very early, that way you just build a foundation of scale from the beginning and rather than having to hire six - eight CSMs to solve all problems.
Lyndsay So those early CSMs can be more productive if they have customer support in place and working and customer marketing in places working.
What to look for in early customer success hires
John Yes. When we think about those early people and what you’re looking for, it's really about learning and building.
When it comes to initial customer success hires, you're looking for someone who’s a builder, someone who has clearly been able to show that in their previous roles, they've been able to identify things aren't working properly, can build a process, can build a workflow, can build a new system. Someone who's process driven, who's very adaptable.
They’re doing lots of different things. You want someone who's a great listener, good at doing customer discovery and problem-solving because these are your most early people interacting with customers and you want them to be able to uncover the deeper problems customers are having.
That knowledge should then get recycled back into how we tell the value story to customers and prospects.
Early hires need to include someone who's a really good verbal and written communicator. You're going to be trying to build scale programs and from the start that probably means documentation, documenting best practices and use cases for customers that you can go share with them at scale.
Again, often the above might be handled by one individual playing a broader role that builds a recipe for who a successful customer is, what makes them successful and how the business needs to orient itself to capture and retain more of those customers.
Lyndsay Okay, great. And so just to round out how people should think about hires at this early stage, once you have customer support all set and you have customer marketing all set, what seniority level should those early customer success hires be?
John At the start you could take it one or two ways. So one, you're going to want someone who is willing enough to get their hands dirty and play lots of different roles. For that reason you don't need a VP of customer success straight out of the gate who's maybe not willing to do all of that range of motions. It could be someone who is earlier in their career just to get the zero to 0.5 off the ground.
Beyond that particularly as it relates to the tech touch motion and once you've got foundations in place, having a leader who's been there and done it before to help you then scale that team out once you are beyond a couple people is going to be really important.
For the first couple you're probably okay on the more junior side, beyond that, start to think about a more senior person who can then go scale that out.
For any net-new function you’re creating I like to have someone who’s “seen the movie before” - if you as a leader have that relevant expertise you might be able to afford to go more junior, but if it's a domain where you don’t have any knowledge then I’d lean more experienced. Once you’ve got the experienced individual you can hire more junior profiles thereafter.