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

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.


Hi Bridget!

Thanks so much for stopping by – it’s an honour to see you here asking away!

What we’ve been that’s making the most difference to businesses during the COVID crisis

We’ve been incredibly reluctant to shout too much during this crisis. I believe that for most people, the last thing they want is another email from another CEO explaining how much they care.

I care, deeply. And I feel so so deeply for the people on the front lines, and for the people in far worst situations than me right now. Heck, my sister is on an NHS ICU ward right now in her PPE helping to keep people alive. When I talk to her, I feel… so removed from the reality of what is going on.

So this has pushed me to re-evaluate how much I can help – I can’t begin to help in the ways that others can. But, can we help in our own small way? Hell yes.

So we have been reaching out to customers that we know are struggling, and working with them – especially those that are less technical, to see if they need help on the tech side.

But primarily, to be blunt the single biggest thing that we have been able to do to help our customers has been offering them discounts and free service to get them through this. We know our platform can help them, and we can’t survive forever by giving GoSquared away for free. But we don’t want customers to worry that their GoSquared bill is another problem. We can remove that from their list of problems.

We firmly believe that it’s the right thing to do for the customers that are struggling, and we know they can make it through this, and we can’t wait to return to normal with them. We’re in it together.

What businesses have been doing that has impressed me

I find it a lot easier to look at the ones that have not impressed me.

It makes me feel physically sick to see how many mainstream brands have jumped on the opportunity to make us feel squishy inside about them, by sharing heartwarming video calls of normal people getting through this, and chucking their brand name at the end of the ad. I’m looking at you, Facebook.

I also admire Google and Apple for the work there doing on contact tracing APIs. I wish it could move faster, and from the outside, it seems their skills in marketing and communication could be better used to tell the world what they’re doing and why.

There are probably many more brands I want to list here, but it’s been a long day and I am struggling to think straight!

Big risks in the next 6-12 months

I think the biggest risk to me is the question of how long this goes on for. I don’t think any of us know, and I don’t think anyone can say until there’s a vaccine widely available.

Everything gets a lot easier for everyone if they have more certainty about how long lock down will be, how long the world will be tipped upside down for. I can see the world gradually finding balance again, but I think we’ll be redefining “normal”, and we’ll be a long way from that definition of normal for at least the rest of the year.

I hope that comes vaguely close to doing your questions justice, Bridget. Keen to expand further if you have any questions on this!

Thanks as always :raised_hands:


Hi Neil!

I love this question!

To move to SF or not? I have asked myself the question too many times to count.

I’ve been to SF many times, and I always feel inspired by the place – to be around the giants, and the companies we all look up to. It’s always refreshing to see, at the end of the day, these great businesses are made up of people, just like the people in London. They’re all humans, they’re not some mythical creature.

A few factors for us as to why we’re in London:

  • We love London, it’s always been my home.
  • I don’t currently want to live in SF – I much prefer London as a place to be(!)
  • The costs of being in SF for office space, living, and hiring are astronomically higher.
  • Our reduced dependence on investment means we don’t feel we’d take maximum value of the ecosystem there.
  • Everyone’s currently locked in their homes behind a Zoom video call. It’s never mattered less where you are in the world.
  • I believe the future of work doesn’t give a damn about geography.

Hope this helps! And v keen to expand further if you like!



Hi Lucky, thanks so much for this question – it’s a great one!

Absolutely – analytics is an incredibly crowded market!

As I have alluded to with other answers here, we try not to pay too much attention about categorisation, and we try to focus our energy on understanding our customer needs better than anyone else can.

Analytics is where we started – many many moons ago.

Back then, the world of analytics was very different. I don’t know if I even knew what “SaaS” stood for!

Back then, web analytics was hit logging tools, greyscale graphs, Flash charts, daily processing jobs, and horrid interfaces.

We always believed it could be better, so we built our first Analytics product – LiveStats – to show you in real-time who was on your website. To remind you that every visitor to your website is a human, not a bot.

That human element, combined with the real-time, fluid interface, was what got people’s attention early on. It was so different to what came before it, that it was barely considered an analytics tool – it was something entirely different.

I hope this helps for now! Happy to expand further, Lucky!


Hi Anush, thanks so much for this question – I love it!

There have been so many evolutions in our many years of business – I always need to cut some to ensure I don’t speak all day!

When we first started GoSquared we were building websites for other people, and trying many ideas out. It was only when we built our first Analytics product – Live Stats – that people started to get excited. We finally knew we’d found something that people wanted!

Key evolutions were really around each product we’ve built as part of the platform: Live Chat, Customer Data Hub, and soon, Automation.

Each evolution has been primarily driven by our desire to do a better job for our customers, and responding to the ever changing markets we operate in.

Our early adopters have always been (and continue to be) technically minded – often folks that build website for fun, and get a kick out of new technology. These people are picky, and we love that.

What has been difficult is assessing who our early adopters are – who are the product obsessives that try everything new we build, that give us hugely valuable product feedback, and who are our core customers – the people and businesses that drive the commercial side of the business. They’re not necessarily the same, but are both essential for us to build a great platform and a great business.


Hi Jeremy, thanks so much for this question!

It’s funny, I was talking to our head of marketing today about this very topic.

One thing that I realised on the call – I have never referred to them as “channels”. I don’t know if I am just delirious or if I am speaking any sense at this point, but I have often found channels to be a misleading way to look at our marketing mix.

Because, if we look at our “content marketing” channel – I would say as a whole that’s been the bedrock of our growth from the start. But within that channel, only a few things have worked, and then a whole lot of it has been totally useless and wasted effort and energy.

So as a channel, content has been great, but that obviously doesn’t mean “do more content!” – it means, to me, we need to establish exactly what actions and projects we should take on within the broad channel of content that work.

A few things that don’t work for us (or, I believe, anyone):

  • Getting people to write about topics they’re not deeply familiar with.
  • Hoping people will read a blog post and adopt our product in the same session.
  • Pushing visitors to convert too early.
  • Writing “SEO” content without a substantial good human readable core.
  • Telling ourselves that anything in content will have fast or obvious results.

A few things that have worked for us:

  • Building a trusted name, that is synonymous with quality.
  • Taking customer questions and support requests as a source of inspiration for blog content.
  • Asking customers where they heard about us, rather than relying on cookies.
  • Running a weekly newsletter for over 200 issues.
  • Sharing other people’s content, not just our own.
  • Building an inherently viral product – every customer can drive 100s more.
  • Continuing to find time for the founders to write and contribute to our content efforts.
  • Never letting our quality bar slip on content, writing, design.
  • Building a network of awesome people, and helping them, building trust, and only sharing what we believe will be valuable to their network rarely.
  • Working really really really hard.

I hope this helps a little Jeremy, of course happy to expand in any way you want here :wink:


Thanks so much for your kind words, Ravi!

I feel under qualified to offer you too many answers on these questions, Ravi, but I’ll do my best to share my own experiences here, and you’re free to take whatever you want from them!

Converting doers into thinkers

I feel very fortunate to have an amazing team around me.

I have not previously made this separation between thinkers and doers as I believe the two can coexist within one person.

I am more familiar with going from a “maker” to a “manager” – a process I have been through with mixed results.

I think first, as I alluded to in answering another question, not everyone wants to be anything other than a doer – they want to be freaking amazing doer, and ideally you can accommodate that.

In terms of having great managers, I think the best advice to start that I have been given is “manage yourself first” – most of us struggle with that, so we end up making pretty poor managers of other people.

I also would say that my approach to managing people is to aim to set a vision and goals as clearly as possible (they can always be clearer), and to be there to listen, and to address the blockers people face from achieving those goals. Other than that, I try to get the hell out of the way.

Early on I mad too many mistakes by getting too involved, by mixing the making and the managing. You have to learn to let go – I am still learning this.

Finding great people to join you

It is always a challenge to attract talented people. I spend a lot of my time talking with people a lot smarter than me. I think most founders hope hiring will happen very quickly, but I look at companies like Stripe, and take a lot from their philosophy on hiring – good people are not usually looking for a job.

So finding good people for roles relies on having a big existing network of really great people. And you don’t build that over night. So in terms of finding and persuading people to join your team, I would look less at the money, and more at your network, and your own vision and why it’s so compelling that the smartest people you can think of should join.

When you’re small and early, the biggest thing you can offer is the potential of what could be – if you can’t sell that convincingly either to others or to yourself, then I’d push to figure that out, before worrying about the financial constraints. The smartest people definitely have financial needs, as do we all, but they will also need to understand the upside and risks of joining you.

Hope this is valuable – let me know if I can expand further, Ravi.


Thanks James for the thoughtful and open response.


Thank you for sharing all these learnings. I definitely understand.
Congrats on playing “the long game” and getting the results of all these efforts.


Hi Krish, I am so sorry for not getting back to this question until now – I hope you can forgive me. I know it’s a slow one, but I really wanted to respond because it’s a great question!

I think we made a lot of mistakes in our early days where we hired people that weren’t more senior than ourselves, and so we all ended up making a lot of mistakes together – it’s never a good situation when you run into problems for the first time yourself, and it’s very refreshing when you have people on the team who have “seen it all before” and can at least offer guidance on how to tackle problems, so you’re not always learning from scratch with every issue that comes up.

I think key to bringing experienced people in is to treat them as such – there’s no point bringing amazing, experienced people in and then to tell them how to do their jobs(!)

So underlying this, for me, it’s really critical to have the “foundations” solid:

  • The goals of the company
  • At least a short to mid term plan
  • The roles and responsibilities and how they break down between everyone – avoid overlap and gaps
  • To always assume good intent – it helps when anyone screws up (and we all do)

And in terms of existing team members, it depends on the roles and who is in what position. I think it’s very hard when / if you need to hire someone “above” an existing team member, but hopefully this never comes as a surprise to either party.

Also – if you’re bringing on anyone more experienced – this is almost certainly a step in the right direction, assuming they’ve been hired based on the right decisions and rationale. So everyone on the team should be thrilled – it’s someone to learn from, to gain experiences from.

Somewhat tangential, but I also think there is tremendous value in the early days of any business in naivety – in not knowing everything. That naivety can drive radically different thinking and seemingly crazy bets, and that thinking, and lack of “playing it safe” can be as transformative as it can be dangerous. It’s great if there can be a balance of naivety and experience, and for an appreciation on both sides of what the other brings to the table.


Hi Anushree,

I am so sorry for not responding to this sooner – I wanted to make sure I didn’t leave any of these questions unanswered, and my weekend got in the way. I hope you can forgive me!

Re SMB marketing priorities I think some of the changes have been pretty clear to me:

  • Ditching budgets for in person events.
  • Re-evaluating whether those budgets made sense in the first place – only time will tell. My opinion is that in person events will always be an effective channel and have been put on pause, but will perhaps change in focus.
  • Adoption of Zoom / webinar software to do more online video – particularly for education to existing customers.
  • Further push towards “Product Led Growth (PLG)” for SaaS business, because folks are forced to not have in person meetings, and a lot of traditional sales pipelines are far less predictable than before.
  • A lot of people in SMBs – whether founders or marketing folks – no longer have a commute. I personally have seen this as a tremendous opportunity to look at how I spend my time, be more creative, and also more deliberate with where I spend my morning time.

I think “post COVID” is a long way away, and I think we will not return to “normal” – we will have seen a forced push into the future on a lot of marketing approaches.

Some stuff will be different, but the stuff that was good, that was genuine, is always timeless: building something people want, being authentic, obsessing over your customers, making something so great they tell others about, getting people to not just buy, but to LOVE your product.

Hope this helps, Anushree!


Thank you so much @jamesgill for finding time to share such a thoughtful response! :slight_smile:


Hey @jamesgill,

Thank you so much for taking the time out to answer all the questions in such a generous and candid way. Akash and I have been marveling over the depth and substance in your responses. Absolute gold here!

I loved your perspective on using the product internally to build empathy; and your point about why culture is a lot more than free beer and ping pong tables resonated very deeply with us.

Thank you, again, for sharing your lessons and insights with us. So glad we could host you!

And a big, big thanks to your sister for being on the front-line saving lives. Sending her all the strength and hope she stays safe. :raised_hands:

Hope to host you soon again. :zap:


Also, thank you @puneet, @JMah, @wingman4sales, @bridget, @lakshmikanth, @Anushree, @Jeremy, @raviramani, and @ncameron for joining in and asking some amazing questions.

Hope to have you join us for the upcoming AMAs as well. Stay tuned! :zap:


Hey James,

Love that! That’s an in-depth blog post of a response.

It’s a true pleasure and honor to host inspiring and generous founders like you. And your response shows such sincerity.

I absolutely agree. For us, too, a lot of those early mistakes spawned as a direct result of the process of understanding how deeply intertwined product and pricing really are. Also, there’s so much to learn from the inside-out way of thinking about categories and how it can cue us in to what really matters: serving and helping customers grow. To what extent companies pay heed and relegate decision-making to third-party definitions and references is certainly worth discerning.

And this is a truth we could all tape on our desks:

“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!”

And I can relate to this as someone who always built context about the customer problems by responding to support questions.

Thanks for sharing that thought and also the systems that GoSquared has instrumented to ensure that customer empathy has many sources to surface and prevail.

Thanks, again, for taking the time!