Let me tell you a bit more about Katie, the woman I worked with who recently signed a deal for $230,000 + a bunch of RSUs at Harvey. If you’re even vaguely aware of the game, you should be aware that Harvey isn’t the average startup to work for. It’s like joining Databricks in 2019. Stripe in 2014. It's resume gold. I could go on. But let’s get back to Katie. She emailed me on June 12th of this year asking a few questions about how to find good companies to work for. I’ll discuss this in more...
8 months ago • 1 min read
I’ve been teasing something big for a few weeks now… Here it is. Katie (name changed for privacy), joined my Summer Career Accelerator at the end of June… And she recently signed an offer with Harvey, the AI Legaltech startup, with a £170,000 OTE + RSUs. If you’re making USD, that’s ~$230,000. And for you Brits, don’t let anyone on Twitter tell you there are no high salaries to be found in the UK. All it took was ~6 weeks of focused execution with tight feedback loops working together. When...
8 months ago • 1 min read
The raw number of salespeople that startups need to hire is far higher than you think. Let's take an example, with a hypothetical sales team that is doubling in size from 20 → 40 reps in one year. For the sake of this exercise, we're going to assume that the sales team is 50% SDRs and 50% Account Executives. Sales Development Representative Attrition You can expect an SDR to stay in their seat for a year. You might be able to extend this a few months longer, say to 14-15 months. Go beyond...
about 2 years ago • 3 min read
The average software salesperson doesn't want to leave their current role. After all, they're swapping a whole lot of knowns for a whole lot of unknowns. Yet I've made a career of talking with 5-15 reps every week for almost 8 years now. Most of them are currently employed. Occasionally I hear a novel reason for looking around, but usually they are leaving for one of the following reasons. You've changed the comp plan on them There's been a lot of territory shifting / management changes The...
about 2 years ago • 1 min read
Over the Christmas break I took some time to reflect on the trends I’ve been seeing in hiring salespeople in late 2023. 1: Reps are more focused on quota attainment than ever before Quota attainment across the industry was bad last year. I've seen numbers saying 60% of teams missed quota last year. I've seen numbers saying 90% of teams missed quota last year. Regardless of what the numbers were across the industry - one thing is clear. Quota attainment last year wasn't anything to brag about....
over 2 years ago • 3 min read
“Show me the incentive, and I’ll show you the outcome” It’s a very human tendency to assume that other people are playing the same game as you. But that’s a dangerous assumption to make. If you’re reading this, you’re likely in the startup world. The Startup game If you found a startup you’re playing a game where your long term path to riches is a bet that you can build a company that’s valued (and ultimately sold or publicly traded) at a multiple to earnings. That’s one game. I’m in a group...
over 2 years ago • 3 min read
Every startup is a bit different, but they almost all sound the same when it comes to how they pitch candidates. Here are a few things that you’ll commonly see: We’re a startup! We got funding from Sequoia Andreessen Horowitz led our Series A Equity 🤑 Uncapped commission 💰 Here’s the core problem: you’re offering that. So is every other startup. I searched through Crunchbase for startups that: Have raised at least $5m, Were founded in the last 10 years Are still alive Have 51+ employees And...
over 2 years ago • 2 min read
Hiring twenty accountants to complete your tax returns I was talking to a CEO the other day. He wants to hire 1-2 Account Executives ASAP. He asked me "my sales advisor says I should sign on lots of contingent recruiters (no win, no fee) and see what I get through the door" It's a curious way to approach the problem. Imagine hiring 20 sales advisors to build your outbound sequences, with the person who gets the job done fastest, getting paid Or hiring 20 accountants to do your tax returns,...
over 2 years ago • 2 min read
Over the last few years salespeople have been burned time after time by startups. They’ve been promised enormous OTEs, riches through equity and inbound leads… all to find themselves selling a half baked product that no one really wants, entirely through outbound. This is partly a case of companies baiting and switching, but it’s also partly the fault of the salespeople for being sloppy at doing their due diligence when joining companies. Let me take you back to the 2017 for a moment. I’m in...
over 2 years ago • 4 min read
