Meet the Masters - Kirsten Wolberg, Public & Private Company Board Director

KIRSTEN WOLBERG

We caught up with Kirsten Wolberg for this week’s Meet the Masters interview series. Sarah Noyce, Director at The Up Group, spoke to Kirsten about her experience of moving from an executive career into a non-executive career and her thoughts on what makes a great Board Member.

Tell us about the experience of moving from an executive career into a non-executive career. What has it been like for you? Have there been any key learnings or surprises for you?

One of the things that I love most about being a leader in an enterprise is leading teams. The biggest shift between an operating role and a board role is moving from running those, sometimes, very large teams to being an individual contributor on a team. That’s been a big shift for me.

In the board context, they talk about ‘toes in, fingers out’ and needing to provide ideas, questions, and expertise, but doing so at arm’s length; reminding yourself that you are not management, you are on the board and having to understand where that line is. As I was first stepping into being a non-executive board member, as I am sure many other first time board directors have found, I oftentimes had to remind myself where that line was, so that I am being helpful to the management team whilst not being intrusive or trying to do their job.

From that perspective, there is a difference between a private company board and a public company board. With private company boards, I feel I have the opportunity to dig in a little bit more, and that’s generally because the private companies are at an earlier stage from a maturity perspective so there is a greater appetite and interest on behalf of the management team to be getting the best experience and background from the board members.

I find myself having more of an affinity towards the private company boards for that reason, as it’s a micro step closer to that operating role. As a leader I love workshops, problem solving with cross-functional groups and strategic thinking, and with private company boards there is a greater opportunity to have those moments.

I have managed to find the right balance between private and public company boards that still feeds my inner operating executive whilst keeping me aware and conscious that my role as a board member is not the role of an operator or management, and I need to be able to keep that appropriate amount of distance and assistance without meddling.

In your opinion, what are the three top attributes of a great Board Member?

I think number one is the ability to listen, and then to bring what you’re hearing into context. The beauty of diverse boards is that you then have a wide variety of contexts, so everyone is listening according to their own situation and can bring responses based on what they heard, individual to their own perspective.

I think the second attribute of great board members is to really understand and bring risk into the conversation. But that risk must be within the context of the company’s risk appetite. For example, if you’re working with a younger company from a maturity standpoint and it’s trying to rapidly gain market share and a footprint in the market, they are going to have to take relatively big risks to achieve that strategic outcome. As a board member, the ability to think through those risks within the context of that particular business is really important.

Finally, the ability to be open, honest, and direct in your communication whilst still being constructive. A lot of people think that being honest is the most important thing, but within that honesty if you’re being destructive or delivering messages that people can’t hear, that is often not helpful and can be hurtful to relationships and the group dynamic. Delivering messages and direct feedback to the management team in a constructive way is an important trait.

What are some of the highlights of your executive career? How have these impacted you as a leader?

In 2008 when I first joined Salesforce, at a time when no one knew what Salesforce did – people joked that I worked at a temporary staffing agency! – a lot of what I needed to do as a leader was convince enterprises that running applications in the cloud was safe, secure, scalable, and cost-effective, as well as a solution that could work within their complex environments.

When I came in, Salesforce were running the majority of their applications still on premise because at the time that was the only option in the marketplace but more applications for the portfolio were starting to become available; for example, we were the third implementation of Workday at Salesforce. We found ourselves not only being the early adopters of all the Salesforce technologies but also every SaaS based technology that was on the market as we had the vision to show other enterprises that you could run in the cloud. By the time I left Salesforce, more than 85% of our applications were running in the cloud.

I talked about considering risks as a board member; we took a lot of risks during that time, but again, in the context of what we needed to achieve as a company. Being honest, it was painful because many of the modules rolling out from SaaS applications, Salesforce included, were not ready for prime time use so as a team we had to find all the problems with the applications before our customers did – we were the canaries in the coalmine. It taught me that I really needed to coach my team about being risk-takers and the understanding that there is a lot of benefit in failure. There is benefit in finding these problems early and fixing them, in having the courage and fearlessness of jumping into aspects that are unknown. High-risk, high reward.

For me personally, I then had the ability to tell the story first-hand to other executives about our experiences, what we had found and the mistakes we had made. It gave me a lot of credibility as a leader and as a partner to the sales team, as I could talk from experience rather than hypothetically.

In your opinion, why does diversity matter? Do you have an example from your career where you’ve seen tangible business impact from increasing diversity - maybe within your team or across the broader business?

I am sure everyone has seen the academic research that quantitatively and qualitatively shows that you get better business outcomes with diverse teams. I have certainly lived that experience and lived those facts in my career.

A good example is from my time at PayPal, and one of my proudest achievements during my tenure was how we transformed the way we built product at PayPal. Broadly, we did this by moving from a waterfall approach to an agile way of building product. We had a large cross functional team leading the transformation as the shift required changes in the product and technology architecture, the product development process, and the roles and skills needed.  

What we found with this change to agile, is that we then had intact teams made up of seven to 10 people and we had the ability to track their velocity, in terms of how much product they were turning out in a set period. In the teams that had even a single woman, we saw that their productivity was 10-15% higher than those teams who had no females involved. We then had the quantitative metrics to prove that greater business outcomes are possible with even just a little bit of diversity amongst teams.

Every time I have come into a leadership position across the course of my career in financial services and technology, I have been faced with leadership teams that have not been particularly diverse – predominantly white and male. I am proud to say that in all my leadership roles, Charles Schwab, Salesforce, PayPal and DocuSign, I left those organisations with teams that had a 50/50 split of men and women, and broad ethnic diversity. I fundamentally believe that by doing so, the organisation was in a much better position to be able to achieve its business outcomes. 

The challenge in my last operator role at DocuSign was the concept of belonging, within the context of inclusion more broadly. How as a leader do you create a sense of belonging and a place where everyone feels like they are seen, heard, and appreciated for everything they bring to the table?  

I think employee affinity groups are important in creating spaces where people have others that they can relate to, and colleagues who support them. The role that recruiting and hiring plays, in making sure your slate of candidates is diverse and, importantly, the interviewers themselves. If people see others like themselves, they have the sense that they can belong. That’s the mindset that I bring to diversity and inclusion, and I am trying to implement it across my board work.

Are there any books or platforms that have influenced your career or leadership style that you would recommend? 

Brian Johnson has created a website called Heroic, a ‘training platform for heroes’. It’s about how to become your best possible self, whether that is in the context of leadership, personal health, wellness, or relationships. I am constantly trying to find ways to be a better ‘everything’ and as a leader it is my job to help inspire and motivate employees, board member peers, and my management teams on how to be better versions of themselves too.

From the platform, I learnt about a book called Atomic Habits by James Clear. Atomic Habits is about how to make better behaviours that optimise our performance into regular habits – how do you make exercise a habit? How do you make eating right a habit? How do you make being a good leader a habit? This is a book I live by and recommend regularly!