$119k OTE • $70k base

Entry level sales role at startup with great traction, training, and compensation/career potential.

What we do

Letterdrop is a profitable YC-backed startup.

We sell competitive intelligence. This helps CROs understand:

• who their competitors are prospecting
• who their competitors are actively selling to
• which of their own customers are being poached by competitors
• how to inform their GTM strategy based on segments competitors are going after

We can reveal 38% of a competitor’s active pipeline on average. 25% of the high priority accounts we flag are actual competitor opportunities.

Nobody else can do this.

This is a strategic board level problem that you can sell to CROs, sales and marketing leadership.

Our Team

Our sales team is 2 people and growing so you’d be on the ground floor.

We’ve closed enterprise logos like HubSpot, Datadog, Mountain, etc along with fast growing startups like Rillet, Clay, and Persona.

We know the talk tracks that work. Our last BDR booked 18-20 outbound meetings/month with GTM leadership consistently through cold calling and LinkedIn.

About you

• You are a high potential recent grad OR someone who wants to change careers and get into sales (we love both profiles)
• You are really driven, you want a lot out of your professional life
• You just make things happen, you find a way to be successful in whatever you do
• You enjoy and are good at learning new things/figuring stuff out
• You can have an intelligent conversation with a CRO on their priorities (we’ll train you, obviously)

Who is this for?

Someone who wants to get into sales and knows in their bones they can be successful at it. We have (1) a sales process that already works and (2) the ability to coach you really well, we just need someone who wants to work really hard to help us grow this company! If you do a great job, you’ll get promoted and do really well from a compensation perspective.

Who is this not a fit for?

• You can’t work hard right now. If you have big priorities that would limit your work to strictly 9-5, it won’t be the right fit for you.
• You don’t have the drive and aptitude to learn to sell at an actually world class level.

If the above makes you even more excited, let’s definitely talk. And if it’s not a fit, we appreciate you giving it a look anyway.

What will you do?

• Book 15 qualified sales accepted opportunities per month that meet with us
• Most entry level sales roles suck because they require a ton of manual work, clicking pointless buttons, wasting time. But we are very good at automating that manual work. So in this job you will spend the VAST majority of your time actually selling
• You’ll make lots of cold calls (a great way to learn to sell), post on LinkedIn 3x/week to educate the market and build trust, send personalized DMs, and anything else creative or innovative you want to try
• Become a public expert in our space to bring leads to you using Letterdrop
• Build relationships with CROs, Sales, Marketing leaders, and RevOps

How to apply?

• Practice the job starting now.
• At the very least, send Ryan a 1 min video (using Loom or any other tool) pitching why you’re the right candidate for us. I receive 50 applicants with ChatGPT/Claude messages everyday that I don’t look at. Stand out. You can find our Sales lead, Ryan, here. Send to him directly or call him at 847-471-4453
• Prospect Ryan. You can call, email, LinkedIn; do whatever to grab our attention.

Requirements

• Remote, based in North America
• Bachelor’s degree (but if you don’t have one and are confident you’re still a fit, that’s fine)