How to choose your next startup sales leader role

When it’s time to make the next step in your sale leadership career, how do you choose where to go? Peter Crosby, who has recently been in this situation, tell us how he does it.

In June we staged our first Sales Confidence conference at HereEast, in London’s Olympic Park. We called it SaaSGrowth2018. We had over 200 SaaS professionals in the audience, watching more than 30 of London’s foremost SaaS experts share their knowledge. Even if you couldn’t make it, we want to share the inspiration and education with you through our SaaSGrowth2018 articles.

If you’re looking for new career opportunities in SaaS sales, check out Sales Confidence’s all-new hiring site.

Peter Crosby

Peter Crosby is CRO at Ometria and a long-standing friend of Sales Confidence. He previously spoke at our Canary Wharf live event and brought the house down. Peter is also the current holder of our UK’s Top SaaS Sales Leader award, although he doesn’t like us mentioning it, so keep it to yourself!

Peter recently moved jobs, from Triptease where he was also CRO, to Ometria. As part of his talk titled ‘What it takes to grow SaaS sales from £0–10m ARR in London’, he talked about how to choose your next role. After all, you can’t grow ARR to £10m if you’re not there in the first place.

‘Scaling from £0–10m isn’t just about you and how great you are. It’s about choosing the right environment.’

Here are 3 things you should consider when selecting your next sales leadership role.

1 — The founder

When you are considering whether or not to join a SaaS company, one of the most critical things to think about is the company’s founder. The founder dictates the direction of travel for the business. When your career and security are at stake, you need to make sure you are hitching your wagon to an organisation that is moving in the right direction.

‘Do you believe in the founder? Do they know where they are going? Do they know what they need to get there?’

2 — The metrics

If you’re being courted by a new company looking for you to join them, they’ll tell you all kinds of things. The truth is in the numbers. Make sure you see all the company’s key metrics before you join. Be bold and ask them to send you the figures over, then dissect them to find the story. Where do you think you can make a difference?

‘Any company that won’t show you their KPIs and metrics in their entirety is hiding something. Ometria sent me theirs within about 5 minutes. The story was good. They are doing what they say they’re going to do. If you can’t get that, do not go there.’

3 — Your network

If you’re at a level when you’re considering CRO or equivalent roles, you’ve probably got a pretty good network. You know a lot of people with a lot of experience. When thinking about whether to join a new company, get opinions from people you trust. Don’t just trust the judgement of the founder or VC trying to recruit you.

‘A VC might want to hire a VP of Sales around Series A because they don’t know what they’re doing and they want someone to fix it. They’ll never tell you that though!’

Use your network. Ask for advice from people whose judgement you value. Take that advice.

Look before you leap

Peter spelt it out brilliantly. It sounds simple, but it’s essential. Take his advice. Don’t compromise. Don’t go for 2 out of 3. Make sure everything is in place before you take on that sales leadership role. Your reputation, earning power and career depends on it.

For the best opportunities in SaaS sales, make sure you check out Sales Confidence’s brand new hiring site.

Over to you now. What else should you think about when moving into a new sales leadership role. Leave us a comment to let us know.

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