Brilliant Business Scaling Advice

What have been your challenges to scaling?

We’ve tried many different ways to align our team around shared goals. We’ve tried to implement systems like Objectives and Key Results. We’ve even tried doing no goal setting which I wouldn’t recommend. Nothing stuck with our company in the past. We recently landed on our current best way which is informed by a lesser known book that was recommended to me: The Art of Action by Stephen Bungay. The general idea is that you write an “Intent” document which gives backgrounds and specifies outcomes that you want. Other leaders in the company then translate that in to intent documents for their teams. People have the freedom to decide how to achieve an outcome, and know how it’s connected to the rest of the organization.

What would you do differently now you know?

Invest in my own learning around strategic thinking earlier. At the beginning of 2020 I went away to do a deep dive in many different strategy books. There’s not a great curriculum for what leaders need to know at different company stages. I often find I’m scrambling to fill gaps in my own understanding.

What are your next challenges to continue scaling?

Every challenge in a business can be fixed by having great people. So that’s where I try to focus. How can we attract or recruit a diverse, global pool of applicants when we have an open position? How do we support people who join our team and have great onboarding, clear career paths, and opportunities to grow within the company? If we succeed at those things, we’ll be able to overcome other challenges.

What have been your challenges to scaling?

Getting the right people. There are people available with great technical skills in the jobs market.

The challenge is finding the right fit for us. Finding the people who are going to take the ball and run with it, rather than keep passing it back. Then having found the right people making sure they act responsibility and are accountable.

What would you do differently now you know?

Stronger employee involvement in defining the issues and bringing solutions. Better empowering each person by setting clear expectations and clarity for their roles. Empowering them to take responsibility, so each person identifies issues and ensures they are managed.

Breaking down and making objectives SMART (specific, measurable, attainable, realistic, timebound). Particularly the clarity around deadlines. Often people leave deadlines unclear and everyone has a different perception of what critical, urgent, important, early next week or ASAP mean! Add to that our global work and time zones, end of the day isn’t clear either.

What are your next challenges to continue scaling?

Overheads and Administration. We want to remain lean and not top heavy. It’s an incredibly competitive world and to grow with more employees, we need more overheads to support the growth.

The challenge becomes getting the right structure, KPIs for management and processes. Processes to make the business easier to manage. Processes that avoid the need for the time and effort associated with on the fly decision making.

As the business gets more complex we need to avoid that creating a need for lots of extra overheads.

What have been your challenges to scaling?

Accepting that my role is now about working through other people and not about my own personal contributions. Now that my company is over 50 people, it’s far more important that I take an overview and steer the strategy and teams without getting distracted by detail.

What would you do differently now you know?

I would invest more money and attention on building effective KPIs for the whole sales funnel.

Being able to measure the funnel at every stage, from marketing spend, through initial visitors to the website and sales engagements then onto the final closed won (and lost) sales allows much better allocation of budgets, and allows issues in the funnel to be addressed in a really targeted and effective way.

What are your next challenges to continue scaling?

We’re now at the stage where all departments are getting big enough that they need to be split into several teams, so our next change is to promote or bring in team leaders. With that, we’ll need to make sure that our organizational software tools are also working well, including bringing in new project management tools.

What have been your challenges to scaling?

As we’ve continued to grow we’ve been through inflexion points, 10 people, 25 people and now 50 people. The most recent challenge was getting the structure and executive team moving from being player/coaches to coaches. Delegating and elevating to handle the growth.

Then changing the executive leadership team to be thinking and looking out, planning and predicting 6 to 12 months ahead with middle managers taking care of the everyday to next 90 days.

My role is increasingly becoming looking out to the horizon. Keeping clarity of vision and that the business is executing successfully on that.

What would you do differently now you know?

I’d have started planning for the current inflexion point way sooner. Getting the right structure right 6 to 12 months ahead of needed. Rather than getting there first and then having to slow down to speed up.

What are your next challenges to continue scaling?

Making sure the operational side is ready to bring in more people. Getting the processes, tools, structure right so that as we bring people in they can start working immediately.

People are a huge investment, it’s important to get them productive quickly so you can get the value you expect from bringing people in.

Another challenge is getting the right data in place to be able to run the business effectively.

What have been your challenges to scaling?

Talent is consistently the number one challenge I’ve found in scaling. The identification, recruitment and onboarding of the right talent, with the right cultural fit is always critical! When it comes to the commercial talent, so sales, account management, marketing, delivering these in line with the business plan timing is critical. In SaaS, if you don’t have the people in place and productive when you planned to, you don’t fuel the machine at the right level to deliver the ARR you want!

What would you do differently now you know?

Take a strategic approach to the investment in talent, best practices and systems to support the development of a strong and cohesive performance led culture, alongside effective processes for onboarding and reduced time to productivity. I would encourage establishing experienced people leadership earlier in the scale-up cycle and build an in-house talent team, blending one’s own talent resources with partners.

What are your next challenges to continue scaling?

Identifying and investing in coaching skills, to utilise expert resources internally and externally, applied at improving individual, team and functional performance; so the people and therefore the business can be the best it can be front to back.

What have been your challenges to scaling?

dotDigital is a 400-person company and we’ve needed to break through the ceiling at several stages during the growth.

We’re continually expanding with more offices internationally, first New York, then LA, Sydney, Melbourne, Singapore and now Amsterdam. The international challenge is structural. Locally getting the balance between being part of the larger enterprise whilst having freedom to act like a small entrepreneurial business to crack the local territory.

That means taking all the benefits at the core of dotDigital and working within a framework. The UK teams need to understand the regions when and why they don’t fit 100% into dotDigital processes.

For example, in the UK it makes sense to have an internal trainer, external trainer, sales trainer. Whereas in local regions you get one person to do it all whilst the operation is scaling.

Scaling is all about finding the right people.

When you’ve got the right people with the right skills, then delegate to them, giving them ownership and control.

I’ve always joked I want to find someone who can delegate my tasks on my behalf!

With the right people and structure then its down to making sure the right KPIs are in place.

What would you do differently now you know?

At dotDigital we didn’t raise money. We did convert to a public company. That came with a whole load of different challenges.

Looking back, perhaps I would do the timing differently. I’m working with and helping several entrepreneurial companies and I give them the same advice:

Hold out for as long as you can before raising capital.

There seems to be an idea in smaller entrepreneurial businesses of “we’ve got to go and raise money, we’ve got to do this, we’ve got to do that”.

I’m an investor too – one of the nice ones – but the reality is if you haven’t shown you’ve got a viral product, if you haven’t shown you’ve got partnerships, if you haven’t shown you’re making any dollar, then you’ll have to give a big share of the company.

Any investor is going to need a big share because of the high risk, you’ll end up giving up much more of the company than necessary.

Just put your nose to the grindstone and make some dollar. Show some progress!

Do that and you’ll raise a ton more money and face much less dilution.

If you get money too early and growth doesn’t go smoothly, forcing the need for more money, more dilution, then as the founding entrepreneur you become marginalised quite quickly.

Don’t raise money until you have a solid plan. Why you need it and what you’re going to do with it. Have demonstrable proof that if you do X you’ll get Y return.

What are your next challenges to continue scaling?

Onboarding new people and continuous training in the post COVID world.

Firstly, finding the right person. There is almost too much choice, whereas before it was selecting 1 from 100 it might be 1 from 10,000 now.

And figuring out integrating home working. The world has changed, many people are never going back to office-based work. The likes of Facebook, Twitter, Shopify have all said they’re never going back.

Previously you could hire a new salesperson. That person would sit with the rest of the group. They are learning and picking up on things as they listen to the rest of the group talking to prospects. How do you do that with home-based working?

Just like management by osmosis and water cooler conversations the unstructured training that happens in an office doesn’t exist in the home environment. We must find new ways of getting the same benefits.

And as the business is scaling giving people the opportunity to grow and develop. Like, how do you elevate someone into a managerial role for the first time when people are largely at home? How are you going to do it? It’s going to be interesting.

Another challenge is marketing. Millions were spent on flights and events to help drive leads. With no or fewer physical events how are you going to do it?

Everyone is doing webinars. But how can we differentiate? How can you make your digital events stand out?

We had great partner session with a company called Something Digital. A wine and cheese night. They sent everyone the same wine and cheese, we got to taste it, someone walked us through it.

That made me want to attend, because they physically delivered something. It was a bit of fun and we had the business chat after the tasting. So much better than a typical webinar with a message being rammed.