What challenges have you faced in integrating third-party services and solutions into your platform, and how did you address them?

Build vs buy is a common PM dilemma. As for my own challenges, a couple of examples come to mind:

1. Support & reliability - at Carta, we use Mandrill as our email service provider (ESP). The service was brought in a long time ago and, over the years, became an unsupported offering from Mailchimp. Problems included downtime, unresponsive support, and no major product updates. When we started to evaluate alternatives, we realized that the cost of change was too high, so we decided to add layers of fallback, such as an internal queue. This way, even if the service is down, we queue emails internally and resend them when the third-party service gets back online.

2. Cost - AWS & Circle CI cost was fine for us in 2020, but during the economic downturn, companies, including ours, started focusing on spend. Commonly, the cost of cloud infrastructure is some of the highest expenses after headcount, so our engineering teams naturally started to focus on optimizing the efficiency of our deployments, CI pipeline, etc.

3. Extendibility - Readme & OpenAI are the latest services we've used that offer great baseline functionality, but then we quickly ran into limitations with customization and developer community support (Readme) or rate limits and latency (OpenAI). Often, teams can engineer solutions that remedy the lack of desired functionality; however, staying on top of this with a CSM informed a better decision-making.

IMO, procuring a new service is like bringing a new member on your team - they could be a huge multiplier or a detractor. Don't take shortcuts studying the candidates and doing reference checks.