How Strategic Wealth Designers CEO Matthew Dicken grew to $9M revenue with a 90 person team in 2024.

Qobra

Qobra is an AI-first sales compensation platform founded in 2020 by Antoine Fort (CEO), Axel (CTO), and Tongue (CPO). The company automates end-to-end commissions, replacing spreadsheet-based workflows for sales organizations. Fort co-founded the business almost immediately after graduating, drawing on relationships with senior sales leaders to understand the problem rather than personal experience as a commission-earner. Qobra has grown from a 100K pre-seed round and its first customer in 2020 to approximately 8M in ARR as of May 2026, serving more than 250 customers at an average ACV of roughly 30,000 per year. The company broke 1M ARR in 2022, reached between 4M and 5M ARR twelve months prior to the interview, and is targeting 10M ARR by end of 2026. Total funding raised stands at 5.7M across a 111K pre-seed in 2020 and a 5.5M seed in 2022, supplemented by a 10M Series A in late 2023 and 2M in debt financing. Investors include Singular and Brieger. The team has grown to 49 people. The single most interesting strategic inflection point is Qobra's bet that AI agents will allow it to capture dollars currently flowing to implementation consultants and external firms. The company is launching three agents, called the Analyst, the Architect, and the Coach, in June 2026, with the Architect able to build and deploy compensation plans in minutes instead of weeks. Fort frames this as turning a 6-dollar services market into software revenue, citing Sequoia's thesis that for every dollar spent on software, six dollars are spent on services.

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Astra Security

Astra Security is a privately held U.S. & India based cyber security company. Backed by Techstars, Astra offers a Pentest Platform that helps organizations become proactively secure. The Pentest Platform uncovers more than 30,000+ vulnerabilities for its customers every month, saving its customers millions of dollars in potential loss and thousands of developer hours. The company has earned several accolades including ‘The Most Innovative Security Company’ by Prime Minister Narendra Modi at the Global Conference on Cyber Security (2017), one of the top 50 emerging cybersecurity companies at ‘Emerge 50’ by NASSCOM, the French Tech Ticket under which Astra Security got rewarded by the President of France under the La French Tech program. In 2021, Astra Security was also named as a CyberTech100 company. Astra is a trusted security partner to some of the well-known brands like Muthoot Finance, NIIT, Goldcast, ITC & more. Our flagship product, ASTRA, brings together an extensive feature set of manual/automated penetration testing tools, while performing a comprehensive vulnerability assessment and proactively responds to threats.