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How to scale a sales team from 1 to 50

  • Jul 11, 2022
  • 7 minutes

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.

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


Processes need to be scalable

Devise a system that is ready to increase its capacity. If you’re trying to work out how to scale fast, your fundamentals need to be right.

  • Have a winning and repeatable sales process 
  •  Key performance indicators will note the benchmarks that salespeople must reach during a specific time period to keep scaling in the right direction

How to scale a team

First ask yourself why you are hiring. And what type of sales forecasting have you done to show when and why you need to hire?

  • Is it to fuel long-term growth?
  • Is it to win new customers?
  • Is it upsell to existing customers?
  • Is it to earn more revenue consistently?
  • Is it that your existing sales team is hitting their quotas and now you need more people to do the same?
  • 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. 


11 Tips To Plan A Recruitment Process 

Before you even start the interview process consider the following: 

#1 Who will you hire and what will you pay them?

#2 Ask yourself - Who is our ideal candidate in terms of skills, qualifications, experience and qualities?

#3 Work out how you will interview and evaluate candidates. You need to be clear on what the process and the timelines are to be able to plan to have the right number of heads in the right time.

#4 Assign who is responsible for hiring candidates. No responsibility means no accountability. Next thing you know you're six months down the line and nothing has happened.

#5 Consider how the new hire will affect the current team. Particularly if you want to scale your team quickly, give this some thought before jumping in and causing damage. 

#6 Think about how you will find candidates. There are plenty of options - job boards, organic marketing, referrals, paid ads, agencies… but they’re not all right for everyone. Think about your company values, who you want to attract and how much budget you have to allocate. 

#7 Use automated tools to respond to candidate applications and keep records after interviews. Scaling a sales team - or any team for that matter - needs to be a streamlined and organized process, so employ tech where you can.

#8 Create a clear job description of the new role and include all responsibilities and activities involved. This is your chance to sell the company and team candidates could be joining so paint a vivid picture, but be honest about what to expect. 

#9 Remember some candidates might not be right for you now but could be right in the future. Create a process to keep tabs on people that you may want to revisit. 

#10 Revise and get feedback on your process so you know where and how to look for your next hires in the future. Ask recent hires how they found the process. If you’re new to all of this, research scaling processes at other startups - connect with others in the industry to learn about best practices. 

#11 Define the probation period and your criteria for success. Ensure you can make the most of this time to assess if things are moving in the right direction for your business and take a view when it comes to seeing if the candidate will fit in the longer term.


10 crucial things everyone forgets when scaling

#1 Hiring cycle. Do you hire in rounds during the year or all the same team? Planning this out can have a huge effect on your onboarding, training and recruitment time and costs - so don’t get carried away.

#2 Onboarding. 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 and get feedback regularly. 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

#3 Culture. What type of company culture do you want? Every new person will be a part of defining the culture, so think about your end goal or dream culture and work backwards. Below, Tom and Shelley share the culture and values we’ve worked towards as we’ve scaled.



#4 Check and double-check your requirements. What seniority or type of role do you actually need to recruit 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?

#5 Set viable targets. 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. 

#6 Develop a sales process that works repeatedly. 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. 

#7 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 the team focused, up-to-date and constantly refining their knowledge and skills to remain competitive. Check out our group coaching guide if you're new to this.

#8 Create a model for your sales team based on data, targets and structure. Eg: a six-person sales pod would be composed of three SDRs, two AEs, and one customer success rep. 

#9 Think characteristics, not qualifications. Find out what are the similar characteristics of the best sales candidates - or of your existing top performers. 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

#10 Hire salespeople who can understand and use modern communication tools - especially if this is how you already run. 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 about conversation intelligence.


Lessons we learned when scaling

Challenge 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 who 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 crucial 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 it 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 causes scaling problems. Lack of a system to handle new situations, organizational hierarchy disagreeing on adjusting to a mid-long term plan - before you know it you’re your own worst enemy. 


Early-stage scaling vs 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.


Want more on hiring? Check out our guide on hiring for coachability here. 


Tom Lavery is the CEO and Co-Founder of Jiminny, the leading conversation intelligence and sales coaching platform that helps companies maximize their revenue. With over 15 years of experience in high-growth VC/PE-backed SaaS companies, Tom was previously SVP at Reward Gateway, now sharing his wealth of knowledge as a speaker in the conversation intelligence space.

Shelley Lavery is the COO and Co-Founder of Jiminny, the leading conversation intelligence and sales coaching platform that helps companies maximize their revenue. With over a decade of experience in coaching B2B sales teams, Shelley was previously Group SVP of Sales at Reward Gateway now leading the conversation intelligence discussion with expertise and insight.

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