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7 Questions on Leadership with Enshored CEO, Ian Jackson

Before co-founding Enshored in 2014, Ian was a successful FinTech executive. From 1994-2005 he helped drive digitization and the move to real-time financial information for investment professionals. From 2007-12, following his MBA, Ian built business management products for the world’s top investment bankers.


Following a move to California in 2012, Ian rediscovered his passion for working in and for disruptive start-ups. At Enshored he leads strategy and sales. He continues to be led by a belief that given the right opportunities, people with energy and drive can achieve much more than they can imagine.


1. What have you found most challenging as a leader?

The most challenging thing for me, is recruiting senior leadership. I’ve failed more times with this than I am happy with.


I’d read and heard it was challenging but it has been harder than I believed it would be. I think I met many colleagues when I was a middle manager that I enjoyed working with, and assumed it would be similarly easy to find and gel with a senior leadership team.


I have now become more accustomed to the challenges and have to accept that there is more risk in hiring at a senior level, and I continue to adjust my practice.


2. How did you become a leader? Can you please briefly tell the story?

I’d always considered myself a decent enough manager, but was generally happy to follow the great leaders I was lucky enough to work for. Then after founding Enshored I lost my co-founder Jeff Bauer, who died following a brain aneurism only 3 years into our journey together. I had to take on all the leadership, and quickly, at a time of great stress and sadness.


I’d seen that Jeff was very charismatic and had been happy to sit a little behind him as leader to that point. I emerged when I had no choice as the conscience and driving force of the company. I have surprised myself with how well I have done, and some of the challenges I anticipated actually haven’t been all that bad. I believe I have a good moral compass, some great confidantes to help and coach and push me when needed. We’ve grown the business more than 30-fold since I took over sole leadership and I think that speaks to my suitability to the position.


3. How do you structure your work days from waking up to going to sleep?

I generally get some physical exercise in during my early morning, as I am a firm believer in healthy body healthy mind, plus I love cycling. I am generally thinking about the key challenges of the day or week and working through them mentally as I work out, then tackle them in order of urgency and priority through the day. As a 24×7 team with global clients we have meetings at various hours of the day and these often dictate what I do and when.


Evenings are still often finishing finance and admin tasks that need doing, but I try really hard to always be available to be with my wife and kids to sit down and eat together, and support the kids with driving them to and from their sports.


10 years into our journey at Enshored it is fair to say my schedule is normalized a bit more, and more predictable, but even if I am nominally out of the office I am generally checking in still fairly regularly.


4. What’s a recent leadership lesson you’ve learned for the first time or been reminded of?

There have been a few instances recently where I have been reminded how important it is for your team to get exposure to how you do things. I’ve been at the company since day one, none of them have, and that experience needs to be leveraged.


I have been helping coaching some of the senior team and finding that in some cases they were second-guessing how I might handle things, and it was leading them to be less effective than they could be. I have never been a micro manager, and have generally been someone more interested in the result than how my leaders get there.


This hasn’t helped them on their journey though, so I am trying to be more involved in the complex decisions, to be there as a coach more. I am thus trying to carve out more time for those in the organization who I think have the biggest runway and growth opportunity. This needs to be done proactively, as these leaders generally are not the ones who come looking for help, or ones whos objective performance leads to you checking in on them more.


5. What’s one book that has had a profound impact on your leadership so far? Can you please briefly tell the story of how that book impacted your leadership?

Shoe Dog, by Nike founder Phil Knight, really had a big impact on me. There are aspects of his leadership style that I really related to. The Nike journey involved lots of involvement in and working with Asia, which is a big parallel to me, and trying to work out what will be the same and what will be different in dealing with different cultures.


More than that though, Knight talks a lot about when he was challenged with questions he found it difficult to answer, and how he wouldn’t let these dominate his days, and how it was OK sometimes not to have the answers.


My team know that I wont knee jerk respond to complex questions, nor will I take a stance I don’t firmly believe. And this isn’t being wishy washy, it is acknowledging that some business decisions can be very complex and need time and thought to answer. Leaders in business don’t need to respond reflexively like is needed from wartime generals.


6. If you could only give one piece of advice to a young leader, what would you say to them?

Surround yourself with smart people – at your company, in your network, wherever you can find them. With the right peers and coaches you can be open and learn. You should know as a young leader that you are not the finished article so get surrounded by people who can help you be better at every step of your journey. This requires a good dose of humility, and I think it is really hard to be a successful leader in business without that.


7. What is one meaningful story that comes to mind from your time as a leader, so far?

We are in the B2B space, and I believe it is critical to treat every new client opportunity like it is the major opportunity that can turn your company’s fortunes around, regardless of the size as it is initially presented to you. If you treat some opportunities as lesser, and get behind them less, and don’t put your A team on them, you will fail, and not grow.


We have a major client with a very large team with us at Enshored, and the first time we met them, I recall going into their office in San Francisco, and it was a Class C office, classic small start up space, in a walk up building in Chinatown. The team was working like crazy, and they told us they just need help with one small piece of their business. Fast forward 5 years, a takeover, and multiple leadership and business changes and pivots and they are a very important part of our company and a trusted partner.


The lesson here was very similar to the famous “10 commandments” codified by John Whitehead at Goldman Sachs from the 70s – which I still like to refer back to as I work out how best Enshored can grow and be successful.


7 Questions on Leadership series on Consult Clarity features interviews with various leaders who share their experiences and insights on leadership. Jonno White is an Executive Team Retreat Specialist and CEO Coach known for his unique approach to leadership development and team dynamics. 

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