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How To Be The First Salesperson At A SaaS Startup

Last month, we staged our first Sales Confidence live event in Central London. We were privileged to hear some of the best sales Founders and leaders in the SaaS industry speak. The nuggets of insight and advice we received were invaluable, and everyone left buzzing with ideas. Based on the talks at the event, we’ve put together the Sales Confidence Skills Series. Even if you couldn’t make it, you can still share in the knowledge.

Ask me anything

After our guests had done their separate talks, and I’d asked a couple of questions to get the ball rolling, I asked for questions from the audience. You can read the answers to one of our questions, about how to speed up the process of SaaS sales, here. Our next question came from Ben.

‘How easy, or difficult, is it to be the first salesperson at a startup, and be the person who is going to build a team?’

The panel reached a quick consensus on ‘Bloody hard!’, but soon expanded on that insight.

Neil Ryland

Neil Ryland, CRO at Peakon, kicked things off. He’s been in this situation twice, and while it’s hard, it’s ultimately rewarding.

‘Every challenge is an opportunity.’

Neil offered that the key to making it work is confidence in yourself and your way of doing things. If you’re going to be a success running sales on your own, at least to start with, you need to be free to make decisions. The Founder and the other top team members need to know that, and support you.

‘When you’re on the frontline, you’ve got to have the confidence to say what you think. If in the early days, you go with the flow of what the management is saying, but you’re the guy getting all the problems, you need to find a way to clearly articulate what you need to be successful.’

Neil also mentioned that a robust system of accountability, for you and for the management, is necessary for a smooth sales operation.

‘Put things in tables. Create a table of who does what by when. Focus and discipline.’

Simon Kelly

Simon Kelly, who has led sales teams at Microsoft, LinkedIn and more, found that when he was in this situation, his main problem was finding time to build a team amongst all the other things you have to do.

‘You’re in the firing line. You’re the guy responsible for everything, but eventually, something’s got to give. You think, ‘I should’ve started my recruitment way before.’

Simon makes an interesting point. When you’re the only salesperson in an organisation, you have the whole of London, or even the world, as your patch. You have leads coming in. You have outgoing calls to make. If the startup grows quickly, which is what everyone wants, you’re going to be very busy indeed.

‘Raise the alarm early and get the recruitment process started.’

Chris Tottman

Chris Tottman, an ex-sales leader, now a Partner at VC firm Notion Capital, recommended not to assume you know it all, that every startup is different.

‘The key is to apply everything you’ve learned in the past, all the mistakes you’ve made, to that specific situation. Don’t just roll out the old Salesforce best practice model.’

Another interesting point. To earn the role of sales leader at a startup, you’re likely to be extremely experienced in SaaS sales. However, you can’t replicate your past success doing exactly the same as you did before. The SaaS world changes so quickly. If you stand still you get left behind.

Approach this role as a learning opportunity, rather than a chance to show everyone how great you are.

Seize the day

The common theme to all our sales leaders’ answers is that being the first salesperson at a SaaS startup is hard work. You have to keep the management happy, build a team, plus implement a sales process that works, all at the same time.

However, it’s such a great opportunity, and if you’re ever offered the chance to be salesperson No1, you should grasp it with both hands. You get to carve something in your own image, working the way you believe is the most effective. Do it right, and the whole world is yours. Good luck!

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