Hold on tight, this is it! You’re heading towards 100 people! 🎢 This is a really exciting, but potentially chaotic growth spurt for a lot of companies. Around this stage, if you’re VC backed you’re likely under some pressure to really start scaling quickly. All the processes and people you’ve put in place up until this point will be tested to their limit.

This phase will see you start heading away from having a lot of great ‘generalists’ in your team to needing to specialise and hire people who are more linear experts in their field (Finance, People, Talent, Ops… even IT/Legal?). Your sales team will start to break up into specialised teams too; sales people will go from all-rounders to dedicated Account Managers and Customer Success Managers.

You’ll find yourself really growing up as a business. But being tested when it comes to your ability to expand properly. Your Talent team needs to be up and running by now so you’re ready, with hiring process, tooling, and onboarding all in place. By now you’ve got employees in the business who are probably passing their 1 year mark with you and no doubt banging on the door 🚪 for promotions and pay rises, again testing your current frameworks validity.

The growing number of new people in your business will test your culture heavily too. By nature performance problems will increase as numbers grow too- so is your performance management up to scratch?

Success in this phase rests heavily on how well you’ve done to set up everything along the way. Of course things will still go wrong, and lessons will be learned but you need to make sure you are ready for this point - Large changes now will be slower, and harder to achieve.

What you need to focus on:

• Talent Strategy & Team
• Candidate Experience
• Org Structure & Development Frameworks
• Performance Management
• People Team
• Stay Calm & Stay Close

Why Now?

• 🔎 Talent Strategy & Team You’ve hired your first 50 employees, but the next 50 will mostly likely come thick and fast and you’ll probably start to the feel the pressure of getting the right people in, but doing it quickly to meet the demands of your growing team, customer base and investors. But don’t worry, you’ve no doubt already got your processes running fairly smoothly by now end to end so it’s just about making sure you’re set up for whats to come.

You may need to add an extra head into the Talent team. Your business / hiring needs will dictate what that looks like, but no doubt your Talent Partners will start to be more specialised, and it’s important they can handle the more specialist roles you are more likely to be hiring for between 50-100.

New jobs will be created that haven’t been created before so making sure job descriptions are thorough and well created is vital. Managers must play an active part here. You need to make sure you have the right tooling in place to source candidates, and possibly will be due an upgrade on your ATS at this point.

Important point here to remember, is don’t over commit to permanent headcount in the team because you’re feeling the pressure to scale. One day hiring will slow, so this is a delicate balance. At this size I’d suggest 1-2 permanent Talent Partners, or even 1 Talent Partner complimented with a very good external agency you can turn to if and when needed or consider adding in an embedded Talent Partner from an embedded agency- super flexible and you can turn the tap on and off as you scale which is perfect.

• 🥰 Candidate Experience As companies grow, even with the best will in the world, mistakes happen and things slip. It happens. But one thing that tends to break very easily when companies are hiring at pace is candidate experience. Teams and processes get overwhelmed with volume of candidates applying to roles and people get forgotten. Many of these candidates end up having a bad experience with your company and this can greatly impact your employer brand.

At this point you’ll likely have a Head of People and a Talent Partner in place, so this is a job for them to own, but you need them to be fully accountable for that candidate experience from the moment candidates see your job advert, to the point at which they’re hired, or rejected by you. They should be breaking down every step of this process and considering the touch points with candidates and how they can make this the best experience ever, regardless of outcome.

There’s a heap you can automate here to help growing, under pressure teams.

• 📈 Org structure and development frameworks Your business is really starting to change now, which can be both exciting and scary. You don’t just have a ‘sales’ team now, you probably have a Sales, Account Management and Customer Success team. Your marketing team is possibly starting to become quite specialised, and you’re really having to start thinking about layers and reporting lines.

Your bigger functions should probably have a ‘Head of’ in place as you approach 100 people. Most likely Sales, Marketing, People, and of course Engineering/Product depending on your business. As before you must think carefully about how and who you put in these roles. There’s a very good chance your employees who joined at 1-20 are still with you but have they proven they can move from being great all-rounders and executors to being people leaders who can manage specialists?

It’s very likely you’ll feel pressure again to put your loyal team members into top jobs here, but be careful. Sadly, you will most likely face some very tough decisions and conversations at this point, and likely see some attrition within some of your original team. Even if one does get promoted, there will be others who had their eye on ‘that’ role for a while and may have to leave to keep furthering their career. Don’t be downbeat, this happens. But how you handle it, and communicate it really defines how the situation unfolds.

It’s super important that you also have your Development Frameworks in place too. Lots of companies tend to be too slow at this. And with all these new roles being created you likely wont have frameworks to lean on. But you should, in theory be able to talk about what someones progression and development path looks like in a new role before you hire them. So if you have a new role to hire for, get that framework done too.

• 🎯 Performance Management As alluded to just now, some of your longer standing team members may well be struggling to keep up the pace at this point, which might feel ironic given the superstars they seemed in the old days. The fact is, some people operate well in certain environments, and helping to get a scrappy start up off the ground is a huge skill, but not always one that translates into operating well in a maturing scale up. More process, structure, linear roles and less communication with you the founder can lead to people either falling behind or feeling a little lost. You may find that you need to say goodbye to some early members, which again can be a really strange, sad moment, but it’s part of the journey you go on as a startup, and if you communicate this well and make sure you talk openly about how this could happen whilst you are growing it will be less of a hit to the team when it does happen.

Aside from this you’ll absolutely start to get more requirements come up for managing performance, both good and bad. There’s some great tools out there to use for setting goals, OKRs etc which I would 100% advise putting in place so that you, and managers can look after this properly. Equally you’ll need to make sure you have the correct policies and procedures in place when it comes to managing out any underperforming employees. Don’t forget, some of your earlier team members might have passed the two-year mark with you, and at that point, it becomes much more delicate as to how you exit someone from a business.

• ❤ People Team Given the last point, you need to make sure you keep investing in your People team. A big mistake lots of companies make is they hire someone operational to handle things in the earlier days, but assume that will most likely do for a long time. Given all the above, you really need to make sure you have a more strategic head in the business to handle org design and planning, performance management, frameworks and development etc. I would advise somewhere between 50-100 that you’re hiring a Head of People. This person, supported by a People Ops person, with Talent reporting into them too will most likely be ok for now. You don’t need to worry about a Chief People Officer for a while yet.

You may still be working with a Fractional CPO too, in which case you may start to think about whether you still need that help if the Head of People settles in and is able to handle everything themselves. How you transition one in and one out is key, but as always, get it sorted before you start growing like mad. Whichever one oversees this will need time to plan ahead and be ready.

• 🧘‍♂️ Stay Calm & Stay Close OK final point from me. You will f**k up along the way to 100 people. If you don’t I highly suggest you document your journey and go and make millions writing a book to tell others how to do it perfectly. But the chances are things will go wrong, and there will be moments of panic, and doubt and times where you think the world may end.

Stay Calm. Don’t rush or panic.

You have to keep trust in this team you’ve built. If you’ve done everything as best you can, set the right values, behaviours, culture, hiring process, promotion and leadership decisions etc, then you should have an incredible team who are right behind you and ready to solve challenges.

Use them.

They are your allies, and your team mates, and you’ll solve a heap together if you just continue to trust them and give them autonomy, and treat failures as a chance to learn and improve.

And you must still find a way to stay close to everyone in your business. Don’t ever pretend there’s an excuse to step away at this point of 100. 1000 maybe it becomes harder, but at 100 people you should still be incredibly connected to every team member- you know each and every one, you’re tapped into whats going on in their lives, their roles, etc. If you lose this, then that is one of the biggest indicators that your company, despite it’s growth, is starting to struggle culturally.