Good question. In the early days we’d go for the coolest tools regardless of maturity of the company. That had to change as knowledge of the tools became an important skill to hire for e.g. our early CRM was early pipedrive but then we switched to Salesforce. Started with Pardot and then switched to Marketo. Or we started with support on Intercom and then had to switch to Zendesk for better reporting and routing. For SaaS analytics we used to use ChartMogul, but eventually needed more sophisticated BI and implemented a stack with ETL in Keboola, Snowflake DW, and Looker on top. Design - I started in balsamic, then Keynote, then Sketch, and now Figma.
Some that lasted - Stripe was a good bet as the functionality continued to grow and we were able to iterate our pricing, revenue recognition, etc. on top of it. We’ve been happy on Slack and obviously all our Product collaboration is in Productboard 