Simon Johnson: Customer Success, Leading Global Teams, Falling into Tech

What a winding career into tech can teach you about leading well

Simon Johnson did not plan a career in tech. As a teenager he wanted to be a physiotherapist. He liked movement, he was surfing and doing a lot of fitness, and he liked the idea of helping people recover. Then his final school results came in, the marks were not there, and the degree he had his eye on was gone. He spent a few days moping around the house until his dad told him, in so many words, to get a job or enrol in a course and get on with it.

Three decades later, Simon is Senior Director of Customer Success for Asia Pacific and Japan at DocuSign, leading a team of around 35 people across the region. His path ran through Macquarie Bank, JP Morgan, MYOB, EMC, Google and Okta. What is striking, listening to him, is how little of it was strategic and how much came down to a few habits he kept repeating. For mid-career leaders and managers wondering whether a messy start or a winding route counts against them, Simon's story is a useful corrective.

A rocky start is information, not a verdict

Simon is candid that he was not a strong student and did not get the marks he needed the first time. What stayed with him was not the disappointment but the lesson underneath it.

“Most of the time you get what you deserve.”

He means it both ways. Work hard and earn the result, and you deserve it. Fall short, and the result tells you something too. It is a lesson he now tries to pass to his own children. The useful move for any leader or manager is to treat a setback as feedback rather than a ceiling. A knockback early on did not decide Simon's career. What he did next did. When you or someone on your team hits a wall, the more helpful question is not whose fault it was, but what the result is telling you to do differently.

Customer success is about value, not just renewals

Simon's whole field is built on a simple idea that is easy to say and hard to do: make sure people actually get the value they paid for. He uses the image of a gym membership you sign up for full of good intentions and then never use. A customer success manager is the person who notices you have stopped going and helps you get the value back. Get that right, he says, and the commercial result follows on its own.

“If we can see customers getting value and the customer recognises the value that they're deriving from the solution, then the renewal event often becomes a byproduct.”

The lesson travels well beyond software. Whether you lead a team, manage a client relationship or run a service, the durable version of retention is value, not pressure. If you want people to stay, stay close to whether they are getting what they came for. Renewal, loyalty and goodwill tend to be byproducts of that, not things you can force at the point of decision.

Get one layer past small talk

Asked what has made him successful, Simon points first to building rapport. He is quick to say it is not about being slick. It is about making a genuine connection quickly, especially with people you have just met. His method is practical. Respect the thread someone gives you and take it somewhere real rather than batting back the same line about the weather. And look for the thing a person clearly cares about.

“It's hard for people to not talk about things they love.”

He describes walking into a customer's office, sometimes a hostile one, and noticing a guitar on the wall or a photo on the desk, then asking about it. The guard comes down. For managers, the same approach works internally. Building real connections with the stakeholders around you, before you need anything from them, is what makes the difficult conversations possible later. Curiosity about other people is the engine underneath it, and it is a skill you can practise, not a personality you are stuck with.

The advice that compounds: do what you said, consistently

The best career advice Simon has been given comes in two parts, and both are quietly demanding. The first is about reliability.

“Doing what you said you would do is important. But being consistent with that means that you build some real credibility and trust with the people that you've got around you.”

Anyone can deliver once. The trust comes from doing it again and again until people stop wondering whether you will. The second part is about feedback. Simon makes a habit of asking the people he works with, and his own team in particular, what he could be doing better as a leader. Both habits are unglamorous and both compound. If you want one thing to take from this episode and start on Monday, it is this: be the person who reliably does what they said, and who asks their team how they are finding your leadership.

About Simon Johnson

Simon Johnson is Senior Director of Customer Success for Asia Pacific and Japan at DocuSign, the agreement management company best known for its e-signature product. Over a 25-year career he has held customer-facing and leadership roles at Macquarie Bank, JP Morgan, MYOB, EMC, Google and Okta. He thinks in terms of work life blend rather than balance, and is based in Sydney.

Listen to the full episode

Hear Simon Johnson's full career story on Career Stories, the podcast for mid-career leaders and managers that combines real leaders' stories with practical leadership and career advice. New episodes every Wednesday. Listen wherever you get your podcasts: https://pod.link/1873863711