Reppy Award Winners

Born out of a single software solution designed to help MSPs gain control of their help desk and billing, ConnectWise has grown into a robust platform of software built for technology solutions providers (TSPs) to run their entire as-a-service business. With products aiding in business management, remote monitoring and management, remote control and access, quote and proposal automation, and cybersecurity risk assessments, integrations with hundreds of key vendors, plus the largest and most engaged community in the industry, ConnectWise has built a platform for The IT Nation.

KnowBe4 is the provider of the world's largest security awareness training and simulated phishing platform, which is used by tens of thousands of organizations around the globe. We enable organizations to manage the ongoing problem of social engineering by helping them train employees to make smarter security decisions, every day. We recognize that our base pay is slightly below what some sales reps expect; this is by design. Our Chief Revenue Officer knows that providing a compensation plan with a larger variable component allows top performers to earn a higher income. In other words, if you have a 90% base and 10% variable plan, your upside is very limited. However, a plan that is 30% base and 70% variable allows significantly more earning potential. Because of our uncapped commission structure and our exceptional product-market fit, many of our reps are able to significantly outperform their pay from previous jobs. Recently, our top SMB rep made over $160,000, and our top enterprise rep made over $500,000 in a year. OTE for SMB sales reps in their first year is $85,000 - $100,000, though many of our brand new sales reps earn much more! We also have a monthly bonus plan after the first 90 days of employment in which each employee can earn between $0 and $2,000 per month based on overall company production. Since 2015, the lowest bonus has been $7,500 per person in a year and the highest has been $17,800 per person in a year. KnowBe4’s work environment was built by sales professionals for sales professionals. When the company was in its initial stages, Stu, our CEO, asked Lars, our Chief Revenue Officer, to put together a list of all the worst experiences he had as an individual contributor in sales. They used this list to build a sales culture that protects our sales reps from having to deal with the same issues Lars had to deal with. Instead, they’ve created a positive sales environment where sales reps love to come to work and excel at their jobs.