Five Growing Pains You Will Have To Navigate As You Expand

Thursday, October 27th 2020

Sometimes - in the rare quiet moments between the sales meetings, conferences, presentations, and the rest of the hustle and bustle that comes up on a daily basis - we like to reflect on the changes we’ve been through with Shyft (and Surveybot, and Crater) over the last 5 years.

And although we’ve been on a phenomenal rollercoaster ride, from a three-person team of founders at Crater to a triple-digit international headcount with Shyft, we’ve experienced some pretty hefty growing pains along the way.

We’ve found a way through a series of brick walls, and we thought sharing some of the hardest of them might help.

Here are five of the biggest growing pains we ran into as founders scaling our business.

1. Underestimating Your Product Scope 

When we started Crater we didn’t realize the opportunities that would come 200,000 video surveys later.  As we talked to people across the industry and became more familiar with the issues moving companies and transferees were facing, we realized our SurveyBot video surveys were only scratching the surface to be a meaningful part of the value chain. Be ready to evolve and diversify your business model quickly to maximize your product’s scope and exploit the unexpected opportunities that will fly your way.

2. Getting The Right Hires To Scale Effectively

Attracting the right talent in the early days is tough, especially at the c-suite level. Not only do you lack brand recognition but also the financial stakes of making a wrong move are higher for you. So focus on what you can offer from your unique market position. Whether that’s autonomy, the opportunity to create and lead their own team, or the chance to have their ideas implemented quickly in your iterative timescale. Tread carefully, do your due diligence on new hires, and don’t rush into decisions. There’s a level of vulnerability needed to cultivate a world-class team. It starts with a desire to hire people who are smarter than you. 

From a broader commercial perspective, you lack brand recognition and the financial stakes of making a wrong move are higher for you. So focus on what you can offer from your unique market position. Whether that’s autonomy, the opportunity to create and lead their own team, or the chance to have their ideas implemented quickly in your iterative timescale. Tread carefully, do your due diligence on new hires and don’t rush into decisions. 

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3. Not Delegating Fast Enough

Closely related to the above is the pitfall of not delegating quickly enough. There are personal and operational costs to not delegating enough. Not feeling able to pass on responsibilities at the right time will lead to you being stressed and overburdened at best and fully burnt out at worst. Your business is your baby, but - just as it takes a village to raise a child - it takes a dynamic and diversely skilled team to scale a business. 

Operationally, the logical conclusion of not delegating is that you’ll be doing tasks better suited to someone else’s time and skills. And the logical conclusion of that is that you’ll spend less time where you should be: on growth, strategy and defining and refining your corporate goals. Essentially, you’re not valuing yourself highly enough.

4. Scaling Communications 

On any given day, our Shyft Team could be working anywhere from San Francisco and New York to Belgrade and Beijing, and across 15 or more timezones. Four years ago, we were 6 feet away from each other. So you can imagine the challenges we faced scaling our comms, not only scaling them but also ensuring everyone feels like part of the same team, no matter where they are in the world. We had to build a robust comms structure and schedule, fuel it with the right software, and create a culture of openness and transparency, where everyone knew what was happening and where they could get the help they needed. From frequent feedback sessions and weekly all-hands meetings, to an open, approachable exec team and lively Slack channels, think about your comms now and how those methods change as you grow.

5. Raising Capital

There are no two ways about it: raising capital can be a grind. But at the same time, it’s almost inevitable if you have any kind of serious ambitions for your startup. We built up resilience quickly during our Series A funding round, although handling repeated rejections of the business you’re so positive about takes strong reserves of bouncebackability. You’ll quickly polish your pitch and get solid responses to the most challenging questions. In the meantime, network, network, network. Build up a solid LinkedIn circle of potential introducers for your Series A, create your company sizzle, and start your research on investors that might love what you’re doing.