Your first remote sales job: go in with your eyes open, and know when to walk away

This guide is for juniors: 0-2 years in sales, or in an SDR, BDR, opening, discovery-only or appointment-setting role. Part 1 covered how to choose the right role. This part covers what to expect once you're in it, and when to get out.

Sales jobs aren't like other jobs

What do I mean by going in with your eyes open? A lot of salespeople are naive about how sales jobs work. I certainly was.

Sales jobs aren't like other jobs. They're more transactional, because in the end you have to earn your own salary, plus the cost of your seat. And your seat usually costs much more than your salary: think of the leads they send you, for example.

You're a profit centre for the business. In IT support, closing tickets fast and being a nice guy will get you a long way. In sales, that counts for almost nothing. You're either profitable or you're not, and if you're unprofitable for too long, you'll get fired.

So know the game you're playing, and your part in it. Your job is to make the company money. Do that, and only that. It's what you're there for.

If you're remote, this is even starker. Nobody sees you grafting at your desk: all anyone sees is your numbers. The CRM is your reputation, so log everything, and keep it accurate.

Who's taking the risk, you or the company?

That brings me back to something I touched on in part 1: who's taking the most risk, you or the company?

Many jobs put all of it on you, whether you're an employee or a contractor. In effect, they say: here are some cheap, basic tools (HubSpot, Slack, a seat in the management and sales meetings), and the rest is up to you. Your job is to bring us leads, by hook or by crook. We'll give you a bit of advice, but not much else.

With no basic, all the risk is yours. Your seat costs them less than $50 a month, so they don't care whether you sink or swim.

Be wary of these roles, and know when you're in one. Then use it as leverage: you're carrying more risk than usual, so push for higher commission or performance bonuses.

Is your sales training any good?

Judge the quality of the training and guidance you get. That's hard if you've never worked in sales, or haven't for long. And I've seen some absolute imbeciles running sales teams: people who clearly couldn't close a door, let alone a big deal.

If you smell a rat, compare what you're being told with the sales guides out there, like this one. If they're training you to do bullshit, you're not going to learn anything. Don't walk out, because you can learn from their mistakes. But start applying for other jobs.

If you're remote, bad training is easier to hide. You can't watch the top closers at work, so ask to hear them: call recordings, or sitting in on live calls. If nobody's calls are ever shared, be wary.

The red flags

• No basic, cheap tools, and "the rest is up to you".
• Training that contradicts what good sales guides tell you.
• A sales manager who clearly couldn't close a door.
• Nobody in the CRM earning the OTE you were promised, or only one or two senior people.
• You're on commission only and can't see how you'll pay your bills.
• Pay that turns up late, or not at all.
• No way to hear how the top closers sell: no call recordings, no sitting in on calls.
• Being asked to pay for anything: training, leads or a starter kit.

When to walk away from a sales job

This can be really hard, because salespeople are tough, determined people who hate giving up. As a junior, and even at mid-level, I stayed too long more than once, and I paid the price.

I've already covered the red flags that show you're probably in the wrong place. Here's when to start thinking about your next move.

When you've learnt everything you can

When you feel you've learnt everything you can in the role (and never be arrogant about that), start thinking about:

1. a promotion
2. a move up to another company
3. leaving.

Some of those overlap, obviously. There's more on getting promoted in part 3.

When you're earning well

Earning well makes it very tempting to stay, and that's fine. But a word of caution: at this stage of your career, think of it as getting paid to learn. You're not the finished article yet. Make sure you're earning, but put learning first. It's an investment in your future.

When the job was missold

Very often, maybe most of the time, you'll be lied to at interview about how much you can earn. Then on day one you'll look in the CRM and see that literally nobody is hitting the OTE (on-target earnings) you were promised. Or one or two senior people are, because mugs like you feed them great, warm leads.

That doesn't necessarily mean you should quit. Move somewhere else and, most of the time, it'll be no different. But if the role was completely misrepresented, especially if you're on commission only and can't see how you'll pay your bills, bow out graciously, and as soon as you can.

Never burn bridges. You never know how or when it could come back to bite you.

If you're remote, it's tempting to just stop logging in, or quit by Slack message. Don't. Tell your manager on a call, confirm it in writing and hand over your pipeline properly. Sales is a small world, and remote sales is even smaller.

Read next, part 3: Your first remote sales job: how to succeed and get promoted to closer