How to scale a sales team from 1 to 50?


Scaling is not the same as growing. 

Scaling is a slow and steady approach to adding new hires to your organization. 

Scaling should have a thoughtful, data-driven approach that sets new hires up for success.

  1. Growth is increasing revenue directly to the number of resources being added to a project or team. 

  1. Scaling is about increasing revenue at a rate faster than the costs that operations incur.

Our sales team at Jiminny is scaling upwards and we want to share the processes we are looking at to get to a team of 50. Plus share some insights on things we want to avoid.

Processes need to be scalable

  1. Devise  a system that is ready to increase its capacity

  1. Have a winning and repeatable sales process  (Find out how we can help Sales Leaders use intelligence to improve the effectiveness of your sales team here)

  1.  Key performance indicators will note the benchmarks that salespeople must reach during a specific time period to keep scaling in the right direction

Why are you hiring? And what type of sales forecasting have you done to show when and why you need to hire?

  1. Is it to fuel long-term growth?

  1. Is it to win new customers?

  1. Is it upsell to existing customers?

  1. Is it to earn more revenue consistently?

  1. Is it that your existing sales team is hitting their quotas and now you need more people to do the same?

  1. Is there a shake-up in your industry or the economy that means the timing is right?

Recent new hires at Jiminny were because we answered YES to all the above. We have grown our sales and marketing teams with new roles like Business Development Representative, Customer Sales Representative, Product Manager Growth Marketing Manager, Engagement Champion in addition to new positions in the engineering, software, finance and leadership teams. Find out more about Jiminny here

10 Tips To Plan The Recruiting Process 

Before you even start the interview process consider the following: 

Who will you hire and what will you pay them? 

Do you reward by commission or bonus-focused compensation plans, plus a basic salary? Or something like that?

We have worked with recruitment agencies and had input from all in the leadership team and advisors in the board to help us make a concrete plan.

  1. Who is our ideal candidate (skills / qualifications / experience / qualities)

  1. How will you interview and evaluate candidates?

  1. Who is responsible for hiring candidates?

  1. How will the new hire affect the team/organization?

  1. How to find candidates? Job boards / referrals / sourcing (eg. FB/LinkedIn campaigns) / agencies / company branding

  1. Use automated tools to respond to candidate applications and keep records post interviews

  1. Create a clear job description of the new role and include all responsibilities and activities involved

  1. Remember some candidates might not be right for you now but could be right in the future

  1. Revise and get feedback on your process so you know where and how to look for your next hires in the future

  1. Usually, there will be a probation period for any new hires. During this period you can access if things are moving in the right direction for your business and take a view when it comes to seeing if they will fit in the longer term

10 Things To Consider Or Avoid When Scaling?

  1. Do you hire in rounds during the year or all the same team? Planning this out can have an effect on your onboarding, training and recruitment time and costs

  1. How will you onboard your employees? How will this be different if you are working remotely? Design an onboarding process that will make your new hires want to stay. Get feedback from new hires after onboarding so you are ready to improve with the next phase

If you view new hires as an investment (as they should be) you will spend time on the onboarding process. Research by Gallup shows that a good onboarding experience can make a positive difference to employee productivity and retention

  1. What type of company culture do you want? Every new person will help define the culture

  1. What seniority or type of role are you recruiting for? For example, you could use a “bottom-up” for sales product adoption where you might offer a given product for free - OR - try a “top-down” approach - where sales promote the value of a product

Salespeople can demonstrate the importance of features, including pricing and packaging that unlock more of the value the product is creating for an organization. The result is greater penetration into the enterprise, higher product appreciation, and more revenue from a given customer. OR do you combine both approaches by layering a formal sales function that yields the best results?

  1. Aim for each sales rep to bring in at least 5x their total compensation. The sales-driven SaaS companies that are very capital-efficient generally end up at 5x or greater as a ratio of average quota attainment / average on-target earnings

Intercom believes that a sales professional should bring to the company five times what they earn in compensation and commissions. The logic is that such revenue will allow for positive cash flow, keeping the business in the black. 

  1. Develop a sales process that repeatedly works. Sharing a playbook of customer calls amongst the sales team and having well-documented data with actionable insights on how to improve will teach new and existing hires how to succeed by using a winning process that repeatedly works. 

  1. Coach and train your sales team to grow. Ongoing support through peer-to-peer training or coaching to tackle individual needs can help work on specific areas to get the best results. This keeps all the team focused, up-to-date and constantly refining their knowledge and skills

  1. Create a model for your sales team eg: a six-person sales pod would be composed of three SDRs, two AEs, and one customer success rep

  1. Find out what are the similar characteristics of the best sales candidates. For example is it coachability, curiosity and work ethic? All candidates should show passion, drive and grit for the business if you want them to succeed

  1.  Hire salespeople who can understand and use modern communication tools. To be more productive, finding ways to automate easy, but time-consuming tasks and a good CRM is a must to scale. Find out more here

What lessons have we learned so others don’t make the same mistakes when scaling?

  • Challenging every assumption you have. Sometimes you need to unlearn things that you’ve been doing for years and do something different

  • Hire the right sales leaders and reps for your business.  If you hire someone that turns out not to be a good fit, then learn quickly and find someone else

  • Have accurate and up-to-date data all the team can use. This is important to how you move forward. It's so important to get all colleagues using the systems and updating as and when so everyone has the freshest content. This really is a time saver!

  •   Use forecasting intelligence for analysis so you can learn from to grow

  • Make sure the various teams or departments are collaborating and sharing information to keep them working toward the same goal. For example, keep the Sales and Marketing departments closely aligned. 

  •  Continue to learn, adapt and make insightful changes to grow 

Poor management can lead to scaling causing problems: 

  1. Lack of a system to handle new situations

  1. Organizational hierarchy disagreeing on adjusting to a mid-long term plan 

  1. Prevent growth due to business operations losing control

How are the first stages of scaling different from getting towards a team of 50?

The first handful of people in your sales team represent your business. They need to be a perfect fit for you and the marketplace. They will find out all the initial research about potential customers and their community so you can learn and give feedback to the product team. 

Nothing is more important than learning from the target customer. We often hear in sales about learning from our first 100 customers and going back to them for feedback on the products so we can learn and grow. This is the foundation for future scaling. See how Uber, Airbnb and Etsy did it here

In the first stages, the focus is less on the financial result and number of sales. Instead, it should be on the indicators like what are the prospects saying after x number of meetings. 

The initial hires need to be resilient and ambitious. These salespeople aren’t just in the game for the money but the opportunity of where things could go. They want ownership and responsibility to perform well. These sales reps will also really care about the business and the future. They want to share ideas and make suggestions that will get listened to. It becomes more difficult to get heard as the company grows. These sales reps are always proactive.

As your company starts to scale up larger sales teams may have different motivations for joining the company. Find out what is driving each team member? What are their values?

Establishing guidelines and a staff handbook for growing employees becomes more important. Hiring operations is really important. In the first recruits, you don’t want to have specialized roles but when the demand requires you might start to branch into finding other expertise. These people will need to work well with others doing a different job. For example, a designer might sit with the sales team and listen to customer calls to understand how to develop the product. 

Other specialized roles as you are scaling might be for a Growth Marketing Manager or Business Development Representative. The marketing person can now help you tell stories on how your customers are getting value from your product. 

You continue to find people that can adapt to new strategies and your business. These people should always add value at every step of the way.

Tracking is crucial to know how effective your scaling efforts are. Collecting meaningful data to analyze this can then outline key areas that might need tweaking. When you are growing your team you need to constantly gather data that shows if your process and planning are effective and revise the plan as you continue to scale upwards.

If you want to share your story of how you grew your sales team, we would love you to share in the comments or contact us here