Technical Ops and Compliance — From Bootstrap to Scale with Richard Crowley.
You haven’t sold into an enterprise until you run into compliance and SOC II audits. At boldstart, our founders are facing these issues earlier and earlier in their life cycle and if managed correctly and taken care of in advance, it can streamline your sales process and minimize disruption.
Given this huge need, we reached out to friend and advisor Richard Crowley who built Slack’s technical operations and compliance from scratch. He joined Slack as the 22nd employee initially helping support a user base of its 35,000 simultaneous users. During his time at Slack, Richard built the technical operations team as the company grew to over 10,000,000 simultaneous users and 2,000 employees.
Richard now runs Source and Binary bringing his Slack experience around scale and compliance to his clients. While there are so many lessons to be learned from scaling the infrastructure alone, I focused our discussion on all things compliance and extracted a few key insights below.
- Talk about risks and SLAs with your customers. Compliance isn’t just “something to add,” it’s a series of choices. Understanding your customers needs can help you pick the right compliance strategy.
- Deciding what you should buy. Every team is faced with the crucial build vs. buy decision, and Richard shares his framework on how to make those decisions.
- From centralized to distributed operations. Early stage operations teams work well as a group, but over time Richard recommends embedding site reliability engineers (SREs) into product teams.
- Avoiding the everything bucket. As an organization scales, optimizing for shared working knowledge as well as ownership is key to avoiding one group from becoming a catch-all silo of information.
- Bonus: What comes to mind when I show him👇 blast from the past in our bonus round 😂
I’d like to extend huge thanks to Richard for generously sharing these valuable lessons scaling one of the fastest growing messaging platforms. At boldstart we like to say it takes a village to start a company, and we’re fortunate to work with an amazing family of experts, operators, advisors, and angels who support our portfolio companies from day one to scale.
If you’re new to the boldstart community, please check back soon as we share more learnings on the first 180 days of the startup journey from other experienced operators in the fastest growing developer and SaaS companies.
