Skip to main content

Coaching Scaleup Companies Around the World: Meet Roland Siebelink

Roland Siebelink is a 25+ years veteran of Internet business, entrepreneurship and digital marketing. He is a former landslide winner of the Silicon Valley Founder Showcase (2011) and the only person who has lived through three 10-1000 FTE scaleup journeys in a row. He lives in San Francisco and coaches scaleup companies around the world.

Startup founders know that product market fit is the “pot of gold”. But what happens after? In this podcast, Dominic and Roland take founders through the Silicon Valley Roller Coaster and the different stages they will have to scale to reach product market dominance.

On today’s podcast:

  • Why it’s better to avoid hiring executives that come from big corporations if you’re a scaleup
  • Helping companies become more robust while keeping the entrepreneurial spirit alive
  • How to hire the right people
  • Going from early market to mainstream
  • Dimensions to consider: followers, strategic focus, follow through and flow
  • Roland’s book recommendations


Don’t hire executives that come from big corporations if you’re a scaleup

Roland is a scaleup ally for tech founders. He is based in the San Francisco Bay area, the Mecca for tech companies. His clients are both in the Bay area but also in other areas around the world.

One mistake many scaleup companies make is to hire people that come from very established organizations as executives because they assume that these people will bring structure and reliability to their organization.

People that had all their lives been in very stable, mature organizations are not well suited for the work of a scaleup company that’s still trying to find its way in the marketplace.

Helping companies become more robust while keeping the entrepreneurial spirit alive

Roland loves the potential of making a company much more robust while keeping the entrepreneurial zeal alive. It became his mission in life.

Trusting your employees and only hiring the best talent is the precondition for not turning your company into a bureaucracy. For Roland, a bureaucracy is the antithesis of trust.

You also need to have a set of solid values and you need to be able to take tough decisions when it comes to sticking to your values. For example, allowing a customer that’s not aligned with your values will eventually create a lack of trust.

Values are just a tool to let people make the right decisions by themselves, so that you don’t have to prescribe everything as a manager.

How to hire the right people

For Roland, an A-player is someone who both really fits the company culture, and also outperforms the average of their position.

Early stage scaleups may have no clear performance objectives defined. Very often they equate “this employee performs well” with “I personally like him/her”.

Companies need to move away from the purely subjective standard of “do I like them?” and make it explicitly about “does this person fit with our values and our purpose?”

From early market to mainstream

Early market companies need to build their entire marketing and sales strategy from scratch in order to build the mainstream market.

This may often mean starting to think afresh about “What does the mainstream customer need? What are new features that we may not be excited about but that the customer might expect?”

Typically this involves a complete shift from focusing on the core technology to expanding it to supplementary assets around the technology. The new market might not care so much about the core technology, they might just want it to be complete.

Dimensions to consider: followers, strategic focus, follow through and flow

There are a few dimensions Roland is always looking at:

  • Followers (including employees and investors). You need to make sure you tend to them so that they keep following you as a leader. Ask yourself:
    • Am I still happy with the people I have on board?
    • Are these people holding themselves accountable?
    • Are they actually performing?
    • When it comes to team dynamics, especially at the executive level: Are we trusting each other? Are we holding anything back? Are we holding each other accountable? Are we more focused on results than on status?
  • Strategic focus. A good strategy should focus on the areas where you really have a realistic chance of winning and establishing full dominance in the sector.
  • Follow through aka the discipline around execution.
    • How do you make sure that you execute your plans?
    • How much follow up do you need to do as a leader? Can you just rely on the team to deliver the assignment?
  • Flow:
    • The simple flow of the processes
    • The flow of cash. It’s important to be aware of how much money is being spent. The valuation of your company can be extremely influenced by your management actions.

Book recommendations

What books does Roland recommend?

Multipliers, Revised and Updated: How the Best Leaders Make Everyone Smarter by Liz Wiseman

Scale Your Technology Business

Answer 10 challenging questions and discover if your business is going to crush it or get crushed.

Get your own growth report with customised insights that will help you to identify the main challenges that may prevent your business from scaling up.

Take the Scorecard

    Discovery Call | Business Growth Strategy Session

      Discovery Call | Scaling Up Master Business Course