An update: Wow, this earnest and thoughtful looking-back at the past decade of a most (universally) admired SaaS company, has been truly fascinating to watch unfold. 
@timorein is away for some time and will be back to address the rest of the founder questions, later in the day.
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Hey Ravi, thank you!
Yes, at least 2 days for any role.
15% of the total staff.
It has definitely had its impact over the years.
- First, doing support creates more awareness about the impact of not building the right features and helps tighten the bridge between product and operational teams - quicker feedback on customer wants and needs and better preparation ahead of any launch.
- Second, it helps marketeers better understand our customer personas and communication style.
- Third, roadmap will be impacted especially when there’s something off with a specific feature that requires improvement.
- Fourth, product organization now has access to support conversation categories and knows in a quantitive way what product related questions and topics are coming in. That is always being accounted for during any product roadmap discussions.
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Thank you, Abhi - you’re too kind!
I actually don’t think it’s that much connected to these metrics. I would say it would be more important to somehow test if your organization is ready for such moves. Run a pilot with just a few more upmarket customers which gives you a good understanding of what you’re capable of and where you’re lacking. Maybe you discover you’re ready and should commit, maybe you find out that there are areas that need to be tightened up or completely studied before doing the move, and maybe you realize you don’t want to sell to upmarket 
.
It’s obvious that new roles are needed along with new approaches and skill sets. So, hiring is one change, it’s important to have at least someone more senior with relevant experience for starters. This brings a different sales process, different targeting and lead gen practices, less of a blanket approach and more of a sniper’s one.
, I don’t know. I would ask Pipedrive’s current product and sales leaders how they’re currently doing it but I’m unable to do so at this hour, I’m sorry. Maybe I can get back tomorrow with some information.
I’d love to give that advice but I don’t think I’m the best person - even though we started to transition during my tenure in Pipedrive, I would not be able to explain how it’s been going during the past year, for example, as I’ve been away from day-to-day business and updates. It sounds like I should get back after asking for comments from one of the leaders in the organization. It would provide a more accurate and honest response.
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Hey Divyansh,
It really made me think. Here’s what came up:
- From “I’m just a guy who can sell” to “I can build and run a global software business”. Took years to change.
- From “This is ⅓ of the product and should not enter the market being so incomplete” to “This is ⅓ of the product but ok to enter the market if customers find it useful as is, we’ll just continue developing while being used.” I needed other co-founders to convince me that it’s a good way forward, and it sure looks like it was .
There were others I’m sure but I guess less harder to change then, I’m happy to change my mind and habits .
Don’t know if it helps but that’s the hardest one to reflect on for me at this point.
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Thank you, Vengat, that’s great to hear!
I think there’s an answer to the first one in one or two other responses I’ve given today, hopefully you can browse through them and find out that it’s the case.
I believe we’ve been extremely lucky while we’ve also worked very hard. The luck part is rooted in the fact that so many customers of ours have consistently found us on their own and then advocated us to their friends. We provided support, and worked the hell out of ourselves but they did the actual selling. When you think about it in business terms that dynamic alone lowers acquisition costs dramatically and fuels growth while offsetting the high churn on the other end. A prime example of this is that we had no one in Brazil working for us for nearly ten years while we had thousands of Brazilians working for us for nearly ten years. In other words, no employees + thousands of customers = 10% of our business worldwide and 2nd largest market.
The hard work part meant that we took a lot of time to learn sales through practice in different settings, be it enterprise or door-to-door. We spent years prior to Pipedrive on this. It shaped me to be able to know which concepts work for salespeople when it comes to such tools and which won’t. The co-founding group was very good at recognizing that many things go into a successfully scaling business:
- raising money early on and learning from investors who had seen success,
- hiring the best people we can get and giving them a chance to build up important parts of the business,
- setting up systems for smooth global operations even without local presence,
- staying true to simple/useful in order to win the minds and hearts of massive numbers of salespeople worldwide (often at the expense of losing larger businesses to competitors),
- quantifying our efforts and results in daily and hourly data that we can use for insights, problem recognition and decision making,
- being business oriented when it comes to goals, customer-oriented when it comes to promises and deliveries, and employee-oriented when it comes to company.
I’m not saying we were incredible in all these things but I liked that, as a group, we found these things important enough to pay attention to and do something about them. By the way, this here is all my account - I’m sure my co-founders have different takes on what worked and why but that’s part of having a little larger group.
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Thank you all for your questions, and best of luck in your businesses and lives! Stay curious, naive and persistent while looking for your light .
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Some insider intel as we conclude this amazing session. :)) Over a month ago, in a wonderful stroke of luck, our outreach note slid past @timorein’s email channeling system. Responding with a kind note, almost immediately, and christening that cold email of ours ‘a sign,’ he generously agreed to do this AMA.
And what an invigorating one this has been! Timo has spent way more than the scheduled 90 minutes (which, we always admit, in itself, is a tall ask on a founder’s time) to address every single question here with admirable depth; responding to some, post midnight.
Each response glimmers with clarity that a decade of building and introspection brings, each of these speak for how many of those founding decisions may elude expectations yet how one must persist, learn to see things as they are, and open up to what’s possible. And all typed in with incredible humility, coming as they are, from what has been a decade-defining SaaS run. Inspiring! 
Thank you, @timorein, for your time, attention, and perspectives! 
And, thanks, as always, to our ever-thoughtful Relay founders, @ncameron, @Akhilesh, @aditi1002, @cathching, @aloarro, @raviramani, @aballabh, @navydish, @Vengat for joining us! 
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Thanks so much, Timo! This has been wonderful.
I loved this bit among others 
:
Again, I think our path was better for our co-founder group, which is why I believe a good reflection of experiences, instincts, motivations, and desires is necessary to find and settle on the right model. Funnily, we sometimes, not knowing the makeup of our competitors, didn’t fully understand why they would go upmarket so early on their journey. Then again, that might have suited their makeup much better.
That’s such a profound insight. The idea of founding-team-model fit is rarely evident from the outside and sometimes even remains unaccounted internally. Which results in misreading competition, but worse, our own selves. You’re right. It’s so critical to reflect on one’s own motivations ever so often.
Thanks, again, for doing this with such detail and care! 
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Wow, Timo, you actually went back and listened to that podcast!
Your account of this process is so perceptive. I’ll make sure to share this way of thinking on assessing the ‘environment’ of customer problems with product people on our team. Can see how that team-wide attention on specific user pains, not as mere feature requests or even potential solutions, would reinforce, widen, and inspire great customer-centricity.
Thanks so much for all your thoughtful responses, here! 
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