Kristen Shannon is the founder and CEO of Highliner a consultancy that helps high-growth businesses scale across people, systems and processes.
Connect with Kristen
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Highliner Technology
Additional resources
Rocket Fuel
Blitzscaling
Listen to the full episode here.
Company Growth Inflection Points: When Everything Changes
Brandon: What's your take on this thresholding of 50 employees and what happens after that? I know that Kristen is talking from 50+. I read an article years ago talking about how companies change when the number starts with a 1 and a 3. So 1 person to 3, 10 people to 30, and then 100 people. This has actually struck me as very true.
Bethany: I tend to join companies when they're about 30 people, and there's clearly a point there where you need some specialization. Then 30 to 50, I haven't noticed a massive difference, but when you get to about 100, the wheels start falling off if you don't have these processes in place. Interestingly, at least for me, around 300 is when I stop enjoying the job. I've always wondered if I stop enjoying it because it's 4 to 5 years in and I'm bored and overwhelmed and ready for a new challenge, or if there's actually something at 300 people where it becomes much more performative and less around knowing everybody in the organization. That is what I don't enjoy.
Building Trust in Leadership Teams: The Foundation of Scaling Success
There are 3 core tenants to set up organizational scaling success, regardless of whether it's 50, 100, or 300 employees.
The first one is building a good structure and ways of working around the leadership team specifically - and in particular, trust within the leadership team. Each individual functional leader needs to be in a position to share concerns they're having with their function, share concerns with other functions within the business, and do so in a way where they clearly feel the other team members have their back.
Bethany: It's challenging. It's not just challenging because you need to build trust within the organization or within the management team, but also you tend to have everybody being a specialist. They feel personally responsible for what their team does, and then there's also a certain amount of "don't step on my shoes, this is my patch."
It's not just around building trust, but there's also a lot of needing to let go of ego. So that you can listen, not feel threatened, and realize that you're in a room full of bright people who might actually be able to help you.
The Power of Informal Leadership Conversations
Brandon: What I've tended to find is that having an informal chat with a couple members of the SLT, usually the C-suite individuals, on a weekly basis where you're out of the company, you're having coffee, it's informal, there's no agendas... having this organic conversation around concerns or wild thoughts you're having around the business is incredibly useful in ways that I don't get from an SLT meeting.
Bethany: I had that type of experience at NuVoice Media because we were in the office probably 2 to 3 days a week altogether. Some of the best work and thinking and progress was made in those informal conversations. At Peak, we never really managed it because we have such a dispersed team, and I just think in Zoom it's hard to replicate.
External Coaching for Leadership Teams
Brandon: I've always found it very useful for SLT members that don't have experience in the phase that you're in - so let's say you're in a Series B round - to really give them access to outside coaching and counsel with someone that has been there and done that.
Bethany: Do you need experience in the phase to be successful? No. Will it take you a lot longer and will you make a lot more mistakes and could you have done it better with some outside experience? Yes. You can do it, it's just might not be the most efficient way.
We're having Pete Crosby on in a couple weeks, and what he did at his company was everybody on the SLT had to have a mentor who was 18 months ahead of them. It was their responsibility to source a mentor, see them regularly, and learn. Part of their SLT meeting monthly was everybody getting together and sharing what they learned from their coaches.
Meet Kristen Shannon: From Hiring 75 to 800 People
Brandon: I am thrilled to welcome Kristen Shannon to the show. Kristen is an expert operator and has been COO at multiple high growth companies. In one of her roles, she actually hired 800 people in a single year. Kristen is now CEO at Highliner, a consultancy that helps high growth businesses that have just raised their series A or B scale effectively.
Kristen: The 800 is interesting, because actually, when I started in that organization, we were hiring 75 people a year. The most interesting part was seeing when I got back from mat leave and we were hiring at that scale, some of the same systems and processes we had put in place for 75 were still being used at 800.
I remember asking the team, "Why are we running this particular selection process for this type of candidate?" Someone said it was super important, we've always done it this way. I looked at them and said, "That's not true. I had a really difficult senior manager who ran that unit years ago who insisted doing it that way, but there's no necessary reason to run the process this way."
"We've always done it this way" is the scariest thing to hear, or the best trigger to know that you need to make some change. If you're doing things the same way you did when you were hiring 75 people, it inherently won't work as it gets bigger.