Our 8 key insights from last year of the Scaleup Valley podcast

2019 is coming to a close, just as we’ve reached the 100th episode of the Scaleup Valley podcast. This momentous milestone has got us thinking about this past year and all of the insightful conversations that our CEO, Mike Dias, has had with some of the leaders of the world’s fastest growing scale ups. 🤔

If you haven’t been able to keep track of these conversations for yourself, we’ve got you covered. 

As our early Christmas present, we’re giving the Scaleup Valley community a round up of our top scale up insights that we’ve gathered over the past year. Plus, the questions you should be asking yourself this year that can help you better align your team for scale. 

Starting with one of the most prolific SaaS companies out there, that this year reached the $200 million revenue mark. How’s that for scale?

  1. Box – A key scale up lesson from the Chief Product Officer

What drives a company to scale all the way from 100 million to 1 billion? 

According to Jeetu Patel, the Chief Product Officer at Box, the key ingredient that’s gotten them to acquire over 95,000 customers is the fact that, despite having 2,000 people on their team, that they still think like a startup.

This means that they allow innovative energy to flow through the company, earning them the right to serve their customers every year. 

Key questions for next year: Would you say that you continue to foster creative energy in your company? Is it built into your company culture? Every quarter do you feel like you earn the right to serve your customers?

2. Gainsight – A key scale up lesson from the Chief Operating Officer 

This leading customer success platform received its Series E funding of $52 million and has shown no signs of slowing their scale. 

Speaking with the COO, Allison Pickens, we discussed the importance of sticking to the rule of 40, meaning that a company’s combined growth rate and profit margin should exceed 40%. 

But Pickens takes it even further with her insight that it’s not smart to be burning tons of cash, even if your company is growing. Because we’re grown so used to the abundance of capital, the trend is to feel that we have the ability to burn cash. But, for companies to really scale, it’s crucial to change this way of thinking and put a deep consideration into the feasibility of each move from a cost perspective, despite a high-growth rate.

Key questions for next year: Are you guilty of burning through capital despite your rate of growth? Do you stick to the rule of 40%?

3. Starling Bank – A key scale up lesson from the CEO

In October, it was announced that this mobile-only challenger bank had raised an additional £30 million in funding. Anne Boden, the CEO, shared what she found to be a crucial aspect of her position that is often overlooked in the scale up process. 

Boden highlighted the significance of looking after yourself – not just physically, but also in how you balance out the difficulty of your. With each conversation that you have, you must be very analytical and honest with yourself about what you’re getting out of the conversation. 

CEOs spend their time having both nice conversations and difficult conversations. Both are pertinent to the job, and both need to be in balance with one another. If you spend all of your time having difficult conversations, then you’re not only going to burn out – but you’ll be overlooking the opportunity to bond with your team and give yourself the space to reflect. 

Key questions for next year: As the CEO or member of the leadership team, do you practice balance? Do you spend more time having nice conversations or difficult conversations? How can you improve the way that you take care of yourself within this role?

4. Mews Systems – A key scale up lesson from the CEO

This year, Mews closed their Series B round with $33 million to fund their future growth. As the CEO, and a first-timer, Matthijs Welle.

While Welle got used to covering every job (including replacing the toilet paper in the bathrooms) during the early stages of Mew Systems, at the scale they’re growing now – he’s had to let go of that. Moreover, he said that one of the key strategies when letting go of tasks is to give them to specialists. 

When you look at your leadership team, it’s important that you have people that aren’t just good at what they do – but knowing how to scale it, too. If they know more than you about their sector, then you’re in good shape. 

Key questions for next year: Are you bringing in specialists as you scale up your company? When you look around the room, do you see people who know more than you about their specific field?

5. Telefonica – Key scale up lesson from the Global Entrepreneurship Director

Miguel Arias, the Global Entrepreneurship Director of Telefonica, is in complete agreement with Welle. But for him, the true art – specifically as the COO – is knowing when to pass the baton on to the highly capable operators, or specialists, that you’ve hired to fill each position on your team. 

You’ve already made sure to hire people that know more about their field then you – so you have to learn how to let them be the specialists and use your time doing more productive things. 

Key questions for next year: Do you give the leads of each team the space to make their own calls? Do you trust their judgement? Have you handed over the baton?

6. Workboard – Key scale up lesson from the CEO

This year they raised their Series B Round to $23 million making their total capital raised to about $35 million. 

For the CEO of Workboard, Deirdre Paknad, true alignment is only achieved by declaring what you’re trying to accomplish and the measurements that prove you got there.

Once it’s been declared, the pressure to keep up each week is there, ensuring that you’re continuously achieving scale based on the numbers. Their OKR system has been working for the Workboard team, but anything that works to keep you aligned is important. 

Key questions for next year: Are you putting in the time and effort to properly analyzing everyone’s performance? How useful are the metrics you use to measure? Is there a better way that you could measure alignment?

7. Scalyr – Key scale up lesson from the CEO

For their Series A, Scalyr raised $20 million for their super-fast log reading tool. 

Taking Paknad’s idea one step further, Christine Heckart, the CEO of Scalyr, says that she works to ensure that each member of the leadership team can answer – with clarity and conviction – the key questions about the company and their journey scaling up. It may sound simple – but after actually implementing it into your leadership team and culture with commitment, you will feel the difference in alignment!

Key questions for next year: Have you defined your company’s key questions? Can each person on your leadership team (and perhaps even further down the ladder) articule the answers to these questions clearly and concisely?

8. Collibra – Key scale up lesson from the Chief Technology Officer

This SaaS unicorn raised $100 million and surpassed the $1 billion valuation milestone. That’s truly beautiful scale!

When we spoke with Stijn “Stan” Christians about his key insights as the CTO, he told the Scaleup Valley community that the most important thing to keep in mind is flexibility

Having Co-Founded Collibra and eventually taking on the role of COO, Christians was always ready for new challenges, so much so that he boldly shifted roles to become the CTO when the company required it. This also came with a move to NYC and a whole new set of skills, challenges, and lessons to learn. 

If we can learn anything from him, it’s that flexibility is necessary if you want to see your company go from $1 million to $10 million to $100 million and beyond.

Key questions for next year: Could your time be better spent elsewhere in the company? What are you overlooking and how can you take on that space?

Each and every one of these leaders had a million and one more things to share about scaling up on their episodes of the podcast. If you haven’t checked it out yet, we highly suggest that you do. 

Then, keep scaling up!