"The “Dos & Don’ts” of Building Winning SaaS Companies with G2 Crowd

17 Apr 2019 · 28 min
27:37

In this keynote, seasoned SaaS entrepreneur Jason Lemkin shares a candid, decade‑spanning chronicle of founding, scaling, and exiting multiple cloud companies—Big Machines, SteelBrick, G2 (formerly G2 Crowd), and the newer 3Kit. He frames his advice as a series of “dos” and “don’ts” learned the hard way. Lemkin begins with personal roots—his German‑American upbringing, early exposure to entrepreneurship through his father’s pump business, and a pivot from mechanical engineering to the dot‑com era. He recounts the birth of Big Machines, a cloud CPQ platform built to help his father sell pumps online, and the brutal early years of massive venture capital burn, near‑bankruptcy, and personal crises (premature twins, anxiety). The turning point came from relentless perseverance, a focus on a single market, and a strategic partnership with Salesforce that turned Big Machines into a leading cloud CPQ partner. Lemkin then describes the next venture, SteelBrick, emphasizing a narrow product focus (CPQ for software companies on Salesforce), rapid growth, and acquisition by Salesforce. He explains the creation of G2 as a platform to amplify the customer voice, replacing costly reference calls with public reviews, and how that model accelerated sales. Lemkin also introduces 3Kit, a 3‑D AR SaaS, highlighting how a tight‑knit team can spin out across companies. Throughout, he distills four core pillars for SaaS success: (1) Commit to a “summit” – a passionate, clearly defined market; (2) Master sales with storytelling, demos, and a repeatable playbook; (3) Build a winning, loyal team culture that scales across ventures; (4) Prioritize personal health and authenticity to sustain the founder’s journey. He weaves in concrete tactics—pricing discipline, annual upfront contracts, leveraging small partners, writing 100‑page sales playbooks, and using the V2MOM framework for alignment. The talk ends with a personal reminder to breathe, run, and stay authentic, underscoring that founder wellbeing is as critical as product‑market fit.

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