Meet the Masters - Iain McDougall, Yapily

IAIN MCDOUGALL

‘Ultimately, a great commercial leader will know that their people are the key to success. As I continue my career, particularly in early-stage companies I have found that you are nothing unless you surround yourself with curious, smart, engaged, and energetic individuals’. James Burrows spoke to Iain McDougall, for this weeks Meet The Masters interview series. Iain shares his insight into what he has learnt from his role as Yapily’s Chief Commercial Officer.

In your opinion, what are the top attributes of a great commercial leader?

To be a great leader in any function, I think a key skill is recognising the greater need to put the customer at the core of everything you do. A good commercial leader would start from there and work backwards.

At a more granular level, attributes that a commercial leader needs to have will vary at different stages of company growth. There are certain characteristics that can help you to accelerate, for example. One of those is a willingness to roll your sleeves up and get stuck in with the customers, the deals, and the teams. If you have the relevant experience, knowledge, and can advise your teams on the best and quickest path to desired outcomes, it keeps people focused and accelerates the rate at which those skills and behaviours become embedded within the team.

Commercial leaders also need to have the vision and ability to articulate the plan to the rest of the team. It is not always self-evident what the priorities are, and so the ability to clearly explain how and the time horizons is important.

Ultimately, a great commercial leader will know that their people are the key to success. As I continue my career, particularly in early-stage companies I have found that you are nothing unless you surround yourself with curious, smart, engaged, and energetic individuals.

What killer questions do you ask to separate a great commercial leader from a good one?

In an interview, I am very focused on the initial understanding of how much effort a person has made to get to this point in their career, and how much they want to work for this company specifically – to me that is a great indicator of what type of person they are.

I often ask people what they need to know to work out whether they will be a good match for the company and a good match with me as their manager. More often than not, their answer speaks volumes on how much homework they have done, how much they have thought about the role, and how much they want to be in this industry. In the same vein, I also ask people what they are going to do if they do not get the role as it helps me to understand how committed they are to working for that specific company.

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?

There are a set of logical links that I make when I think of diversity. As a general statement, groups make better decisions. I am a big believer that consensus-based decision making with the right people is incredibly powerful and often results in decisions that organisations will support.

The extension of this is that if the number of viewpoints is larger and more diverse, then in my mind, that ultimately helps you to uncover where the pitfalls are that you may not necessarily have anticipated operating in an echo chamber. Whilst gender is by no means the only diversity factor at play here, I do believe it presents a significant issue within the tech industry particularly.

Where diversity translates the most for me is the hiring process. On countless occasions I have seen the value of diverse points of views when hiring an individual, helping to surface attributes of a candidate that may otherwise have been missed if there was a more congruent set of people making that decision. It has often been the case that it is the diverse voice in the room that sees the key attribute, which then turns out to be the reason why that employee becomes a stellar employee for the company.

What advice do you have for your peers and other executives on prioritising D&I within their teams?

Put simply – be explicit and deliberate about doing it. Resist the temptation to take the easy route and hire without considering diversity and inclusion.

It is all about maximising your pool of quality candidates to help overcome that challenge. I am a strong believer in hiring based on aptitude and potential rather than experience, so I look at previous trajectory, quick promotions, and additional responsibility gained over a short period of time. If we just look for raw experience, we are limiting our way of thinking about who the right candidate might be.

What has been the biggest challenge to your leadership style over the course of the pandemic?

Part of my role is to create a sense of community across the whole company, by making connections and building bridges between teams. Amidst the pandemic, this has undoubtedly been the most difficult leadership challenge that I have experienced in my career so far. 

How do you create a high-performance culture?

It starts with ambition – setting ambitious company-level goals and getting the team excited about the level of success we will all share when we reach them.

People then need to know what their individual measures of success are and have a clear line of sight as to how their performance scales up to the company’s goals. In an early stage and mission-driven company that tends to attract people who believe in the company vision, it’s about making sure that there is a palpable link between what they do on a day-to-day basis and how the company is going to achieve its ambitious goals. 

Companies also need to ensure that they are celebrating the role models who are embodying that high-performance culture and its values. It helps others to gain a sense of how they should be performing and behaving. It also needs to be backed up with clear and decisive approaches to managing under-performance.

What is your career highlight to date?

 The pivotal milestones for me have always had a correlation between breaking new ground on a project that, at the outset, seemed a risk or near impossible, and then seeing that come true.

The best example was moving from IBM, a traditional enterprise technology company to Google, a modern internet company – organisations at opposite ends of the continuum. I went to Google at a time when cloud computing was being conceived, and there was limited belief that it would work or be able to surpass the cornerstones of the tech industry. But trusting a hunch and having faith in the process meant that I was lucky enough to see that risk validated.

Looking at my time at Stripe, a parallel path to my journey with Google, playing a role in scaling a company that has gone on to be super successful is incredibly rewarding from a personal perspective. I’m excited to be working in another high-growth, early stage FinTech environment at Yapily and am hoping that this will be the next career highlight for me when I look back in years to come.

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

‘Multipliers’ by Greg McKeown and Liz Wiseman talks about the theory that there are two kinds of leaders: multipliers, who want to maximise and unlock their teams’ potential, and diminishers, those that are not focused on maximising the potential of others. This has significantly influenced how I think about leadership and my own style over my career. ‘The 7 Habits of Highly Effective People’ by Stephen Covey is also one that I read early in my career and the principles have stuck with me ever since.