I'm James Gill, Co-Founder and CEO of GoSquared. AMA!

:wave: Hi everyone!

Thrilled to be here on Relay for my first ever AMA.

GoSquared is beautifully simple marketing software for small businesses. We’re based in London, and started many years ago when my co-founders and I were at school. We have thousands of customers of all shapes and sizes who use GoSquared to grow their business.

We’ve built GoSquared into a profitable, sustainable business, and we’ve been going strong since 2006.

I’m excited to chat about all things product, design, content marketing, writing, remote working, building a SaaS business outside of SF, bootstrapping, and more.

I’ll be here on Thursday 7th May, 17:30 – 19:00 London time, and I really look forward to speaking then! :tada:


Note: This AMA is closed for new questions, but you can check out the existing conversations below.

In this AMA, we had James Gill — the co-founder of GoSquared which he started right after school and has now been heading for the past 14 years — share his thoughtful insights on thinking about your product’s vision, hiring senior people, understanding customer experience, and more. Dive in!

AMA Index (James’ brain-pickings) :brain:

(founding insights, opinions, and observations; deftly examined and articulated)

The three founding decisions “if made differently would almost certainly mean the company wouldn’t exist today”
The gains that accrue from being power users of one’s own product
How product and pricing are “totally intertwined,” why thinking in software categories is outside-in, and how GoSquared keeps the customer front and centre
“We find it crazy that it’s in any way considered ‘different’ to be building a profitable, sustainable business”
The maker/manager conundrum and how James thinks about career progression
How the GoSquared team did their exceptional bit during the COVID crisis
What keeps James anchored in London; “I believe the future of work doesn’t give a damn about geography.”
How they’ve sought distinction in the crowded analytics market
Notes on GoSquared’s 14-year-in-the-making evolution
Content as an acquisition channel; what has (and hasn’t) worked; “content has been great, but that obviously doesn’t mean ‘do more content!’”
More notes on internal progression and how James deals with the fact that most good hires aren’t looking for jobs
What James has learned about onboarding experienced people
How James views changing SMB marketing priorities post-COVID

Further reading/listening/pondering from the interwebz :open_book:/:headphones:

(Other insightful excerpts drawn from blog posts, interviews, and conversations)

On thinking about your product’s vision:

“You can take a very business-focused approach and say, ‘this is the category we’re in, and we’re going to take this much market share.’ Or you can think about it a little bit differently and just talk to customers, to go beyond this software ‘category’ definition of things. Move into more, ‘what are we trying to help customers do and why are they coming to us and moving with us?’ It’s totally against the advice of focusing on one thing but I actually really take issue on that advice, I think it’s totally fine to focus on one thing but what matters is, how do you define that thing, are you focusing on a category of product? The way we see it is to focus on one problem, which is turning visitors into customers. And so we just build the stuff to help you do that.”
Source: How 3 Teenagers Turned GoSquared from a Hobby Into a SaaS Business – with James Gill

On hiring senior people:

“I think this is a common mistake that a lot of people make. Not hiring senior enough people, especially after taking some funding. You always need doers. ‘We need someone to put out that fire and that fire.’ But then if you don’t have someone in a more senior position to overview, set goals, and set processes up. Things can get so messy, so quickly.”
Source: SaaS Stories with GoSquared’s James Gill

On simplicity and its power:

“Many people equate ‘simplicity’ with terms like ‘beginner’, ‘basic’, or even use phrases like ‘it’s a toy’. But ‘simplicity’ can benefit everyone – even the most advanced and accomplished users of a product or system appreciate and value simplicity. The more advanced a system becomes, the more important it is for the system to have originated from something simple and elegant.”
Source: Simplicity is a war

On being your own customer:

It’s not hard to know what your customer experience is like, but it’s very easy to think you know it.”
Source: Be your own customer

Stay in touch: :sunny:

You can follow James to stay updated with his discoveries and insights:

  1. James on Twitter
  2. James on LinkedIn

Hey James,

Thanks for taking the time! :slight_smile:

So great to learn about a team that’s been building a fine product on their own terms, for over 14 years now. It’s incredibly inspiring! I have a favorite question to ask, looking back, what are some of the key decisions that you wouldn’t go back and change.


Hi James

Do you use GoSquared internally? If so, has your internal usage given you any insights on your product that you may not have discovered from your customer interviews (i.e. latent needs)? Would love to hear your thoughts on the value of internal vs external customer feedback in the context of your product’s evolution over the years.


Hey James,

Glad to have you on Relay!

You touch on something really interesting in a podcast interview. That thinking around categories is outside-in. Zooming out to assess the ecosystem and identifying one’s place in it, is considered critical. But (surprisingly) I’ve rarely seen it being juxtaposed with knowing what customers might want. I’m curious to learn:
— With this lens, how do you think about product and pricing decisions, given that GoSquared thrives in some really competitive categories (live chat and web analytics)?
— As you serve some big enterprises like Canon and J.P. Morgan, and thousands of SMBs, how does this variance in the customer base affect how you think about categories and differentiation?

This caught my attention:

Whether you sell a piece of software, you run a government department, or you’re putting on an event, it’s all too easy to think you’ve catered to your customer’s needs. But step into the shoes of your customer and you might just change your mind.

How do you teach your team to learn to step into the shoes of the customer? You can build an incredible amount of context by doing that.



Hey James! Congrats on all your success to date!

1 - How did you decide you wanted to be profitable versus what many others are doing – raising huge chunks of capital and then burning money to grow more aggressively.

2 - What are the best ways you’ve found to cost-effectively grow your business?


When do you switch from ‘Doers’ to ‘Thinkers’? Or should you convert your doers into thinkers?


Hi James :wave:

I know you’ve been very responsive as a business to helping during the COVID crisis - what do you think has been making the most difference, what have businesses been doing that has impressed you? What do you think are some of the biggest risks we are going to be facing in next 6-12 months due to this terrible disease?


Hi James,

Thanks for your time.

Now, analytics is crowded market. How did you inform/attract customers about your USP?



Hi James,

Thank you for doing this AMA!

How has your product evolution been since the time you started? Were there pivots or is this what you sought out to build?

Who were the early adopters of your product? How did you go about identifying them?



Hi James,

Thanks for taking the time.

In your 14 years of existence, what were your biggest shifts in terms of customer acquisition channels?
How did you handle such changes?



Hey James,

Had another one in mind. :slight_smile:

Heard an interview of yours where you touch upon the importance of hiring experienced operators in the early days of a startup. What advice do you have for young founders for integrating them into the org and setting them up for success — what lessons do you carry from those first few experienced hires? And what are some of the lessons you have when it comes to retaining existing people to adjust to the new reporting structure?


Another question James- With many many years of solving for SMBs marketing challenges, I think you would have great insights here. What are some of the early trends you see in this space as an impact of COVID? How do you see the reshuffled priorities of the SMB marketing teams post COVID?


Hi James,

Thanks so much for doing this AMA. You have certainly had a very impressive journey, congratulations!

I have a couple of questions

  1. Our organization is trying to scale and we are finding that we have more doers than thinkers. The challenge before is this, how do we convert more of the doers into thinkers? As a follow up, if we bring senior people in how do you evaluate them to make sure there is a cultural fit as well as an ideological fit where you want to take the organization?
  2. I love how keeping things simple has brought you tremendous success. We are bootstrapped so far and have considered looking for funding at some point primarily to attract senior people. Was it a challenge to attract the senior people that you wanted when you were still scaling and how did you overcome it?

Thanks so much.


Hey James, a fellow London bootstrapper here. Have you considered or felt pressured to move over to silicon valley or establish a permanent North American presence? What keeps you anchored in London? Any geography based tips for London startup with a global customer base?


Hi Krish,

Thanks so much for the question – I’m hugely in awe of what you’re doing at Chargebee, and I’ve always had a really positive experience every time I’ve met someone from the Chargebee team.

I could talk all day about things we’d do differently, but this question is great – what calls would I make the same if I could revisit them?

There are three really fundamental decisions we’ve made in the history of GoSquared, and each of them, if made differently would almost certainly mean the company wouldn’t exist today:

1. We started the company when we were still at school.

We didn’t know what we were doing. We knew NOTHING about running a company.

But we had an urge to create something, and to follow our hearts, and we went for it. Generally, in life, I have learnt to not regret taking action – the easiest decision is to postpone and delay and find excuses not to start something.

So I don’t regret for one minute that we started early, we made a ton of mistakes, and we grew a business from a young age. If we’d waited we would barely have been any wiser, but instead have wasted years in indecision.

2. We were had a critical decision to make when leaving school and heading off to university.

We were approached by angel investors with an offer. The condition was to drop out of university that we had barely started and build the business in London. 50% of everyone I spoke to said I’d be stupid to not go to university.

The other half of everyone said I’d be stupid to say no to the opportunity. I think my main conclusion is that everyone I kew thought I was stupid :joy: – ultimately, we made the jump. We didn’t particularly want investment, but we certainly wanted to grow the business and take it to the next level. I am so glad we did – if we hadn’t, I believe GoSquared would have fizzled out, and be a footnote of my life so far.

3. We were offered the opportunity to sell the company more recently, and we said no.

It was another extremely difficult decision to make, but one that we were honoured to have the opportunity to even consider answering.

It made us think long and hard about what we wanted GoSquared to be, and I truly believe the outcome has made GoSquared stronger and the team wiser. I couldn’t bare the idea of writing one of those clichéd blog posts announcing we’d be acquired, and that we’d be stronger than ever, only to see the company fade away and be forgotten.

I also don’t know if I’d make a good employee! I have no regrets about the decision we made to not sell – and that played a factor in our decision at the time – we didn’t want to look back for the rest of our lives and ask “what if we had stayed the course and built GoSquared by ourselves?”

I hope those are of interest, Krish. Happy to expand as much as I can on any of them if wanted.


Hi Puneet!

Thanks so much for this question and for joining this – it’s my first ever time doing an AMA, so I hope I can keep up with all the amazing questions from people like yourself!

We absolutely use GoSquared internally – in fact it’s pretty core to our product’s evolution, and part of what motivates us to make the platform better every day.

We highly value customer feedback, and I am more than happy to share more on how we gather, digest, and ultimately address customer feedback, but we absolutely look at our own usage and use that to drive the platform forward.

A few key benefits we’ve seen from using our own product

  • We are a very product focused team – we all have a desire to build a great product, so everyone – whether they’re a developer, owning marketing, or in operations, everyone has an opinion on how the product can be made better. This is exciting and creates a bubbling melting pot of ideas.
  • We catch many tiny details about the user experience internally that we know customers may never care about to the point where they would tell us. We know about these issues only because we use the product obsessively.
  • We feel the frustration of customers when the platform can’t do something that we also want it to do – everyone wins when we deliver on those needs.
  • We can often bring features to life that customers have not asked for, but we know we want. We can often deliver features to customers without them asking, because we understand their cases so well, by doing them ourselves, so it can often feel like we’re reading our customers’ minds.

A few challenges that come from using our own product

  • It’s not all roses and rainbows though – as I’m sure anyone who uses their own product will know – you can sometimes risk prioritising features that you yourself want, over other improvements that can impact more customers. We try to avoid this by thoroughly researching the impact of product changes before committing to them.
  • Sometimes we are trying to perform an action with the platform that, gasp, we haven’t built yet. We haven’t built everything on our roadmap yet! So, for example we may want to run a report that doesn’t exist in the GoSquared Analytics product (yet). This is really frustrating because it means either: we find an alternative tool to do something we believe should be possible in GoSquared, or we must delay completing that task until we build that functionality. It’s often an opportunity to see what other products are doing, to learn from them, and to fold that back into our own platform over time.

I hope this helps answer your question, Puneet. Happy expand further on any of this if you’d like me to!


Hi Rajaraman,

Thanks so much for this question, and for taking the time to listen to a podcast I was on – a true honour!

I love this topic – the hardest thing is trying to condense my thoughts on it, as there’s so much to say. I’ll try to answer each of your key questions as best I can.

How we think about product and pricing decisions
I think product and pricing are totally intertwined, and thus everything that spawns from that – it’s all integrated, and hard to separate out.

A lot of the mistakes we’ve made over the years have been around treating them as isolated disciplines – e.g. setting prices higher while still having a low-touch SaaS model, or on the flip side, building functionality at higher price points and seeking feedback from free tier users.

So these days we tend to make sure we look at things as a whole. For example, we’re working on a huge new part of the platform, that we’re calling Automation, and it’s all about helping our customers act on the customer data they have in the platform, and ultimately to engage with their own customers in dramatically better ways.

With this new product, we’re very conscious that we’re in a competitive space, and that our customers have many alternatives available to them. But we’re working on this product because we know our customers can be more successful with the platform by doing it in GoSquared, we know that it fits our wider goal of helping businesses grow online, and we also know we can offer a product at a very competitive price point.

Pricing is such a hard thing to test and experiment with. We are certainly not the experts, but we’ve tried many strategies over the years, and it’s always a trade off of a few factors:

  • Are we competitive in the market?
  • Are we making enough money from our customers?
  • Can our customers understand the pricing – is it simple enough?
  • Can we implement the pricing structure / system without eating away at our time dedicated to delivering more value to our customers?

How our customer base affects how we think about categories and differentiation

We feel extremely fortunate to work with businesses of all shapes and sizes.

The breadth and depth of our customer base has been a huge asset to us as we have seen so much of the world change this year. Some of our customers have grown tremendously, while others have struggled. By not being too dependent on any one segment, we’ve been able to offer help to those who need it, and we as a business have been well positioned to handle a lot of change.

We don’t spend much time thinking about categorisation of GoSquared, other than when we need to list ourselves on review sites. I’ll be first to admit, that we haven’t 100% nailed down the category we exist in today – we believe there’s something new, that is yet to be defined, that is greater than the sum of parts that make up our feature set.

What drives us forward, and enables us to differentiate, is by listening intently to our customers, combining their needs and feedback, with our own vision, and focusing on solving really big meaty problems. It sounds so damn obvious, and I know everyone and their dog tells you this is how you should do it, but it’s incredibly difficult to execute this over a prolonged period of time in practice.

We believe that by delivering better for our customers than anyone else, we will help those customers grow, we will grow because of them, and they will become our best marketing department.

How we teach our team to learn to step into the shoes of our customers

Anything about working with our team comes from step one: hiring fantastic people, and not lowering that bar. Without having great people, that you have a solid trust base to build on, then everything else is difficult. I love our team, and every day I feel hugely honoured to work with them.

In terms of keeping the customer front and centre, and truly understanding their needs, there are a couple of practical things:

  • We use our own product, and so we are a customer of ourselves. This drives a lot of new ideas and product thinking.
  • Part of the GoSquared platform is GoSquared Inbox – a shared team inbox to enable you to respond to your visitors and customers.
  • We have a rota, and every member of the team – in any position – spends some time using Inbox to respond to customers on a regular basis.
  • The rota means that not only does everyone experience our own product, but they also spend time on “the front lines” helping customers and hearing their feedback first hand.
  • I don’t think anything can replace first hand experience – no matter how well you think you understand your customers, you can always understand them better!
  • Beyond this, we also are always evolving our frameworks for how we believe we help customers – moving away from the features we build, to thinking about the problems we solve for them, and where we are strong, and where we suck at solving those problems for them.

I hope this is helpful, Rajaraman. Happy to expand further on anything here if you’re interested!


Hi Jessica,

Thanks so much for asking this, and it’s great to chat with you – huge fan of what you’re up to at inDinero!

Profit vs investment

I don’t know if we’re crazy, perhaps we are, but we don’t get too excited by investment opportunities right now. Perhaps that will change again in the future.

We have taken money before, and been very fortunate to work with some great people. But right now, we are very focused on building a great business. A business we want to work in, and that we will be proud of for years to come.

We absolutely could grow quicker if we took more investment, and we have that as an option, but we also love being in control of our own destiny. We know we want to do things that might be quirky, that might not make sense, that might be trade-offs between growth-at-all-costs, and other things that mean a lot to us.

If anything, we find it crazy that it’s in any way considered “different” to be building a profitable, sustainable business.

Besides, I find it very hard to sleep at night knowing the only way to survive to seek further investment.

How we’ve grown cost effectively

To grow sustainably, we’ve certainly had to make some tough decisions.

A few things that have helped:

  • We spend every penny as if it’s our own – because it is.
  • We are very clear about what is valuable, and what is not. What is: our people and our tools. What is not: free beer and ping pong tables.
  • Being outside of bubble that is Silicon Valley. London isn’t cheap, but the culture around expectations is also very different.
  • Having co-founders that balance out your thoughts. I perhaps will more quickly spend to address a situation, but having co-founders that have a different perspective, and that are also good with numbers, helps to reduce the likelihood of poor decisions.

I could definitely go on for more here, Jessica! I hope this helps and happy to follow up with further info.


Hi Shruti!

Thanks for this question, and I hope I can do it justice!

Everyone on our team is, in my opinion, both a “doer” and a “thinker” – but I guess the pie chart of balance between those depends on the role and the context of any given task / day.

As the company and team have grown, I have found myself perhaps moving more into the category of “thinker”, but the thinking doesn’t help much unless it’s acted on – so I still do a fair bit of “doing”!

I firmly believe that ideas and inspiration can come from anywhere – often where you least expect it. So everyone is encouraged to contribute ideas and suggestions for how we can make the platform, and the company better.

I just try to spend as much of my time listening. Listening to customers, to the team, to other founders, and then I spend my “thinking” time digesting those thoughts and seeing how they fit against my existing concepts and thoughts, and establishing the action to take from that.

I also believe that everyone is different. Some people love to do – to create, to build, to write. Often career progression is perceived as “becoming a manager” (which perhaps could also be related to your definition of a “thinker” – sorry if I am misunderstanding), but I firmly reject the idea that climbing a career ladder should involve going from maker to manager.

I believe some people love to create, and given the opportunity can grow to become world class at whatever they create – and we strive at GoSquared to make that feasible, rather than to force people to change their focus away from creating to develop their career.

Hope that helps, and definitely can elaborate more if you like.