B2B software sales has one of the lowest barriers to entry and the highest income ceiling of any career you can start without an elite degree. Top reps clear $300K to over $1M a year. But the same things that make it lucrative also make it brutal. This post breaks down honestly why software sales pays so well, why it's so hard, and who it's actually right for.

There is no shortage of advice on hitting $300k as an account executive. The problem is most of it is noise from people who have not done it. This is the AE career path broken down by two people who have: what changes as you move from SMB to mid-market to enterprise, how your skills have to evolve, and the macro factors nobody talks about.

Should you take the SDR offer at AWS or jump on the AI startup making noise on LinkedIn? It is the most common question we get inside Higher Levels right now, and the answer is not what it was three years ago. The market has shifted, AI has changed who hires whom, and the trade-offs between startups and big tech are bigger than ever. This post breaks down salary, promotion paths, training, culture, and job safety across both, so you can pick the side that actually fits your goals.

"Tell me about yourself" is the question that decides whether your interview goes well or falls apart in the first 90 seconds. This post breaks down the exact framework I've used in every interview throughout my decade in tech, scaling my income from $65K as an engineer to over $290K in sales. It's the same framework thousands of Higher Levels students have used to break into tech sales. If you're trying to break into tech sales in 2026, this is for you.

Cold call simulators went from a novelty to a core part of sales enablement in under two years. The problem is that most teams pick the wrong one. They optimize for org-wide rollout and end up with bland AI roleplay that does not actually move rep performance. This guide breaks down the seven most credible cold call simulators in 2026, who each one is built for, and how to pick the right tool depending on whether you care more about top-down consistency or actual individual rep capability. Written for sales managers, enablement leaders, and founders evaluating tools to level up their team's cold call performance.

Every tech sales interview mistake in this post is a real story from a real candidate. Some of them still keep us up at night. The good news: every single one of these ended with the person in a better spot, because they learned from it and moved on. If you're preparing for a tech sales interview at the SDR, AE, or any other level, these are the exact traps to avoid so you don't learn them the hard way.

Most cold call practice tools go easy on you. This one does not. I built the hardest cold call simulator in the world inside Rithim.ai, set it to max difficulty, and ran a live cold call as a HubSpot rep calling the CMO of OpenAI. Six minutes of getting torn apart. Here is what it exposed.

If you're exploring a career in sales, you've probably come across two paths that dominate social media right now: high ticket sales and software sales. This post breaks down the real differences so you can make the right call for your career.

Market sell-offs flip narratives fast. Six months ago tech sales was the golden ticket. Now people think it’s dead. Layoffs are up and fear is everywhere. Reality is more complicated. Here’s what’s actually happening and what smart reps are doing now.