How Heartland IT Consulting CEO Patrick Donlin grew to $8M revenue with a 15 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.

Chattermill Analytics

Copilot transforms the way you interact with your customer data. With the power of generative AI, you can get answers to all of your CX, product, and marketing questions, improving team alignment, efficiency, and productivity. Have questions? Just ask!

Sentisis

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SPOT

Provider of a cloud based measurement software designed to make cloud computing more accessible and practical through simplicity and technical resources driven by the community. The company's cloud based measurement software uses artificial intelligence and machine learning to capture and analyze the data of the real world through video to predict and establish more precise marketing strategies, enabling businesses to optimize processes and gain competitive advantage.

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Tauri

Developer of a cloud based cyber security platform designed to provide effective and secure services to business across all places. The company's cyber security platform stores and safeguards confidential and classified information from threats and enables only the sender and recipient have access to encryption keys that are used to open communications and other files through web browsers, mobile phones, Windows and Mac, enabling organizations to handle communication, scheduling and file management in a secured way.