Krish, thank you for your kind words! I think it’s not only a good question but also a good and necessary reflection point for any founder. Who are you confident in targeting? Which approach will give you the best opportunities for growth?
I came into co-founding Pipedrive with more than a decade of personal enterprise sales experience, and so we could have also easily built a sales system and team with enterprise targets. Easier said than done, of course 
. Importantly, over these years, I also had learned the pains and needs of people in sales - salespeople lacked a user-friendly and actually useful tool while executives lacked a tool that would help them forecast results and control people’s efforts.
So, based on these insights and other co-founders experience from attempting to build SaaS products, our decision was to
- target salespeople (not executives) because that’s where we saw the gap in the market, and we didn’t think there was a quick and quality way to address the needs of executives without solving the needs of salespeople first.
- approach the global market from day one (because the customers would be predictably small, volatile, and only a large number of them would result in healthy revenues for us),
- and do so in the lowest-touch fashion possible (because that felt like the right cost-effective way to reach, generate and serve a global base of small customers).
The decision, while it surely was to take us into many unknowns, felt natural and hence, not too difficult to make. It caused weird feelings sometimes (i.e. "can we properly grow without a sales team?, “can we sustain growth without 100% of control of the sales process?”) but those passed as we drafted and executed systems to attract and acquire customers in our own way.
In hindsight, I would not do it differently, given our co-founder team makeup - I think we were primed to build this product and execute this model. Could we have grown quicker with a different target/model? Possibly, especially early on (based on requests from larger companies were kept turning down), and maybe equally later on (based on a stronger brand awareness and reach). So yes, there could have been a way to reach higher ARPA and expansion and lower churn, but we liked our chances with higher mass market potential, lower acquisition costs, and better WOM more. 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.