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Written by Catherine Pearson Content Writer
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10 Jul 2019  |  Moving Upmarket

Putting Together a Sales Team for Growth: From Starting Out to Outgrowing Your Initial Set-Up

11 minute read

Every founder has the same big questions starting out. What do you need to set up a successful initial sales team? What does a strong initial team look like? What processes should I have in place from the start? You want your sales team to grow with you, too, so a little later down the line you’ll need to consider what processes no longer work and need to adapt to fit your new needs. We speak to our VP of Sales about structuring and scaling a sales team for success.

We ask our VP of Sales the big questions

What you’ll learn about setting up and scaling a sales team

  • The advantages of setting up a sales team
  • What you need to start selling in a startup
  • Why you need a sales process and how to establish it
  • Understanding your audience
  • Signs your team is outgrowing its initial set-up
  • What most startups change in the growth stage
  • The biggest scaling mistake a sales team can make

Why is it advantageous to build a sales team in a growing SaaS business?

Before we even begin looking into the people and processes that create a successful sales team, we ask our VP of Sales Adam Kay why you would want to build a sales team in the first place.

Meet our VP of Sales

Adam Kay is responsible for the sales organization and new business growth at Paddle. In short, he’s the man responsible for creating a sales process for the business that’s scalable, predictable and repeatable. When asked what takes up the majority of his time on a day-to-day basis, however, it’s clear that people are just as - if not more - important than process.

People come first

“The majority of my time is spent around the people and development side of things. This involves running training, supporting the team’s learning and development and creating courses and initiatives for people to improve. The people side is pretty intensive and that’s not just within the team I manage - that’s across the executive team as well”.

He’s seen how other sales teams work

In terms of Adam’s previous experience in sales within a startup environment, he’s seen sales teams at different stages in their growth. “Paddle is probably the first time I’ve inherited a team that’s been growing really really fast year on year and the role is either to maintain or exceed that” he shares.

“In my last role I was VP of Sales at an enterprise contact centre solution for digital messaging and I inherited a team who were really struggling to maintain the highs of years gone by. The mandate was to come in, shake up what’s going on and get back to growth. That was actually slightly less pressure, simply because I inherited a sinking ship and if I turned it around I was the hero! It always felt a bit safer than this - and thankfully it was the former, I was able to turn it around back to really strong growth both here and in the US”.

There are similarities between startup sales teams

Adam recognizes that what he’s seen in previous sales teams and what he’s currently experiencing as VP of Sales at Paddle indicates that startup sales teams often share a number of qualities. “In both roles I was presented with a very young, inexperienced sales team made up of intelligent, hungry people who had just been repeating a process that once worked for one person and so they’ve tried to scale it in that way. Both needed some outside thinking around the buyer journey to create a scalable process”.

What do you need to start selling in a startup?

If only there were some hard-and-fast rules to setting up a successful sales team. As with so much of the startup experience, it’s an iterative process to create something that works for your company and product. Adam shares his experience of early-stage sales teams and discusses whether the systems and structure or the people in the sales team should come first.

What do you need to establish in your sales process from the start?

Why have a sales process?

Adam believes it’s crucial to first think about the ‘why’ before considering how to establish a process within a team. So why have a sales process in place at all?

“The process isn’t necessarily something you just go away, put on a piece of paper and roll out to the team. It’s got to ultimately reflect the buyer journey. That’s the absolute objective. The whole purpose of the sales process is so that you can do something that is repeatable where you can identify separate, distinct stages of the buyer journey and understand what it takes to move somebody along this process, where you typically fail and how you can improve velocity and reduce resistance along this journey”.

Know your audience

“In order to establish a sales process, it’s really important to understand how your typical customers buy your type of software. For instance, at Paddle we have quite a technical solution. It’s not a pure, out-of-the-box, deploy-and-go solution - we’re an underlying infrastructure change. In order to win, we need to prove to our prospective clients that technically there aren’t going to be any challenges. The process to get up and running has been mapped out. Each sales process really needs to reflect how these companies buy and ultimately who in those companies is going to be making those decisions”.

How to establish a process

Once you know the ‘why’ behind a sales process and you know your audience, you can begin to establish a sales process. “It’s something that is likely to require continuous iteration”, Adam explains. “The stages of your buyer journey should be broken down into steps that are digestible enough that you’re able to get value from them individually. For instance, if you have a discovery stage that is around understanding your customers’ requirements - where you effectively ask ‘what’s it going to take to win this deal? - it’s important that the elements supporting this stage are in your CRM. This helps you to identify what you got at that stage that led you to success or, if unsuccessful, what you didn’t get or manage to achieve”.

Signs that your team is outgrowing its initial set-up and the issues of not scaling

When your sales team has been up and running for a while, it’s important to keep an eye out for indicators that your initial processes no longer work for your growing team. Adam considers the first sign that your team is outgrowing its existing set-up and the first issue you’ll likely encounter if you don’t adapt your way of working.

What do most startups change while in the growth stage?

It can be valuable to learn from those who have come before you and felt the same growing pains you’re experiencing. Adam has seen a number of sales teams encounter the pains of outgrowing their initial set-up and has seen what does and doesn’t work when trying to scale.

Change your attitude

“I think there’s a philosophical approach that people need to maintain when they’re scaling up or starting up: embrace failure. Where I’ve seen most businesses face this challenge and unsuccessfully overcome it is perceiving failure as a failure. It’s a cliché quote, but it’s true: ‘you don’t fail: you either succeed or you learn.’

“Businesses who say, ‘we’re going to fail fast, we’re going to iterate, we’re not going to make the same mistake twice’ have (albeit counter-intuitively) a really positive approach. You can read all the books in the world but really seeing the feedback from the market is going to be your best source of information and direction. It’s ultimately what you do with that information and direction that counts. For instance, if you are presenting your solution to the market in a way that yields zero results, you’ve got to look at that to understand why you didn’t get the results you wanted. Is it the product? Is it the way you’re presenting the product? Is it the market? You’ve got to be able to tweak your process in order to rule things out. Unfortunately there are rarely quick wins that enable you to go to market with the ideal product and process in place - it’s all about iterating quickly”.

Tweak your team

In Adam’s experience, another important thing to get right (and change when growing, if necessary) is the people in your sales team. Finding the right type of sales people is crucial.

“I don’t just mean hiring people with great experience in closing deals but making sure they’re a cultural fit as well”, Adam clarifies. “I’ve always tried to avoid hiring people who boast on their CVs that they were at a big sales company earning millions of dollars a year for the business because I like working in startups - and I know from working in startups what that means. That means rolling up my sleeves and not being afraid to do the dirty work, knowing that following the same process every time will not necessarily yield the same output and not expecting (and unfortunately not having) that many resources to support me in the role of sales person”.

What makes an ideal sales person?

“I think confidence is a big part of sales. When you go onto a call with a prospective customer and you don’t truly believe you’re going to be successful in your efforts, the prospect can hear it. I think it even goes further - even in an email they can sense confidence. Sales is 90% conviction and 10% persuasion and if you’re not showing that conviction and belief in yourself and your ability then how is the prospect going to feel about it? Sales in itself can be quite a demoralizing role; you are rejected or ignored more than you win so you need mechanisms in place to celebrate successes to break up the continuous, compounding pain of being rejected. It’s important to fail fast and work as a team”.

What’s the biggest scaling mistake a sales team can make?

Adam tells you what to avoid in the growth stage…

We’re all going through it…

You’re not alone. Here at Paddle we’ve experienced the pains and upheavals of being a growing startup and still have new challenges to face each day. When Adam Kay joined the team as VP of Sales, he was the last person to come on board at the end of a big hiring spree. We had a team of 24 sales people, supported by 5 managers, and it became clear to him that a shake-up in the distribution of roles was vital for the sales team to succeed. Some tough decisions had to be made when restructuring the team, but with the aim of doubling our sales team by the end of this year we’re still aggressively hiring!

What we’ve changed since our initial sales team set-up

Our sales team has seen a number of shifts in order to grow and evolve with Paddle’s needs.

“The sales process and the role of the Account Executive have definitely changed since the start”, Adam shares. “When I first joined we’d recently built a Business Development Representative team, so up until then the Account Executives were responsible for all outreach and pipeline generation. They were also responsible for implementation once a prospect had signed an agreement with us. For me, that was a massive deviation from what is already a broad job, so we created the Account Manager role to take that responsibility off them”.

“In terms of the types of deals we’re doing now, I believe these have changed too. When I first joined I felt the team were very reliant on the product to win us deals. This is fine when you’re operating at a very low-value-high-volume level, but we actually got validation from several large prospects that our product was a great fit for them, so I’ve been trying to get our sales team to go after some larger value clients now. Of course, with this comes a change in approach, structure and process; we’ve had to be a bit more strategic and value-based, asking ourselves “what is the reason people want to buy the Paddle solution?” 

Why indeed? Try our demo to see how Paddle can save you time so you can focus on scaling your business.

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