S5 Bonus: Greg Ratner, Troops

Episode Summary

Executive Summary: Greg Ratner, co-founder/CTO of Troops.ai, explains how the company began with a scrappy, non-scalable MVP to prove that sales and revenue teams wanted workflow help inside tools like Salesforce. The conversation centers on rapid experimentation, hiring for entrepreneurial technical talent, learning from failures, and evolving Troops into a platform that automates customer-facing workflows in Slack, Teams, and other systems.

Main Topics: Troops.ai’s origin and product vision (Priority: 5/5): The company was founded to make enterprise software more actionable and user-friendly by meeting workers in the tools they already use, rather than forcing them into clunky legacy systems. The first MVP and proof of value (Priority: 5/5): Troops validated demand using a no-code, manual workflow: users texted CRM updates and Troops staff entered them into Salesforce behind the scenes to test whether the concept saved time and created value. Experimentation and product culture (Priority: 5/5): Greg emphasizes that early products were treated as disposable experiments. The team moved quickly, shipped rough versions, gathered feedback, and was willing to kill ideas that did not show strong signal. Roadmap evolution through customer feedback (Priority: 4/5): Product priorities were shaped by real-world adoption and customer enthusiasm, with features that generated repeated requests and strong usage becoming the basis for future investment. Hiring and team-building philosophy (Priority: 5/5): Troops invested heavily in hiring people who were both technically strong and entrepreneurial, even if it took a long time, because the company needed builders who could adapt and stay mission-aligned. Scalability and infrastructure decisions (Priority: 4/5): Because the company was iterating so quickly, it deferred scalability in early stages and used cloud infrastructure elasticity to buy time while figuring out what truly needed optimization. Lessons from a major product misstep (Priority: 5/5): The team made one large product bet that consumed significant time and engineering resources but produced limited adoption, reinforcing the importance of small, validated steps.

Key Arguments: The core Troops thesis is that enterprise work should happen where employees already communicate, such as Slack or Teams, instead of requiring them to navigate heavy legacy software. A fast, manual MVP can be enough to validate customer demand before building a scalable product; Troops used texting and manual Salesforce updates to test the market. In early-stage startups, nothing should be considered precious; products should be treated as experiments that either prove value or get discarded. Shipping to production continuously enabled faster learning and more reliable roadmap decisions because the team could observe actual customer behavior. Hiring should prioritize people who are both highly technical and highly entrepreneurial, since they must build quickly, adapt often, and care about business value. Overinvesting in a large, year-long product bet can derail a startup; incremental validation is safer and more effective than relying on big assumptions. Founders should focus on speed of learning, reduce ego, and surround themselves with strong peers rather than hero-worshiping individual celebrity entrepreneurs.

Data Points: Time to launch early team: almost a year to hire six people - Greg describes how selective and time-intensive the early hiring process was. Manual MVP rollout speed: a matter of days - The first MVP could be deployed quickly to prove demand. Large product bet duration: over 10 months - An engineering team was dedicated to a major product initiative. Additional polishing time: 4 or 5 months - Further iteration followed the initial build of the large product bet. Feature adoption outcome: just a handful of customers - The large swing ultimately produced limited adoption. Market maturity horizon: six years ago - Greg notes that continuous deployment was less common at the time they adopted it. Customer impact: saves them tens of hours every single week - Troops’ automation across many workflows produced substantial time savings for customers. Product ideas launched per quarter: five products last quarter - Used as an example of how multiple experiments informed roadmap choices. Feature success ratio: one of five products performed strongly - Greg contrasts several weak launches with one standout feature that resonated. Platforms referenced: Slack and Microsoft Teams - Primary messaging interfaces where Troops delivers workflow actions.

Pivotal Quotes: "Nothing is precious. Anything that we build is an experiment." — Greg Ratner: Describing the Troops product culture and willingness to discard work that does not prove value. "We would start with a small experiment, it would ship it to customers... and very quickly get their feedback." — Greg Ratner: Explaining how Troops used rapid iteration to validate or kill ideas. "The most important thing is keep going, keep learning." — Greg Ratner: His advice to young entrepreneurs at the end of the interview.

Implications: The episode highlights a startup playbook built on rapid validation, tight customer feedback loops, and hiring for adaptability. For teams building workflow software, the future lies in embedding automation inside daily communication tools and proving value before scaling.