How to Ease the Transition from Startup to Enterprise

Startup culture is fun, aggressive, and fast-paced. Discover some pros and cons when it comes to transitioning your startup into a full-scale enterprise.
Reading Time: 7 minutes

Ping pong tables, drones gone rogue, and an annual game of Office Olympics…these are just a few of my fond memories of Sapper as a start up. Since then, we’ve scaled dramatically. Our team is still lean and still scrappy, but as we’ve transitioned from start up to enterprise, a lot of Sapper has changed. From culture to process, we’ve evolved into something brand new…and the growing pains have been real. 

Start Up Culture

The best way to describe start up culture is ‘building the plane while flying it’. From role responsibilities and process development, you figure it out as you go. You break things, move fast, and learn from your mistakes. Start up life is aggressive and fast paced, but can offer very real opportunities for growth and personal accomplishment. Below are the pros and cons I noticed in Sapper’s startup phase. 



Tight-knit Community

Probably the most notable benefit of working at a startup is the tight-knit connection you build with your coworkers. With long hours and aggressive goals, it’s easy to foster a ‘we’re in it together’ mindset. Because you feel like you’re part of a community, the struggles are more bearable and the wins are more satisfying!


In the early stages of a startup, you likely won’t have many processes in place. ‘How’ you do your job is less important than meeting your goals. From working on patios to DIY workflows, whatever gets the job done will usually result in a green light. For those that prefer freedom at work, this can offer a huge advantage. 

Role Ownership

In addition to flexibility on how you work, developing your role can feel like a Choose Your Own Adventure game. If you’re a go-getter, you can easily direct your growth within your role and within the company. As Sapper has scaled, I’ve seen many of my coworkers transition into new roles, rapidly move up the ladder, and grow their individual contributor positions into entire departments.

Company Contribution

With a small company in a startup environment, decisions are often a group initiative. Leadership wants input on company changes, re-orgs, etc. Not only do you get a say in how your work changes, you also feel included and valued on the team. 

Cons – 

Flexibility doesn’t Work for Everyone

While all of the above can be pros of growing a startup business, if you thrive with structure and struggle without it, the flexibility of a startup can impact your workflow. Startups come without much routine, direction, or supervision. For some people, this simply doesn’t work. 


Prepare to Wear Many Hats

Again, depending on your own preferences, this could be a benefit or a disadvantage. While the company is scaling, you’re working lean. Your title might be ‘Strategist’ but that may also include content writing, list building, party planning, and talking your clients off of the churn ledge. Startup life is not for the faint of heart!

High Stress, High Workload

Limited resources mean it’s time to get scrappy….because hitting your goals are non negotiable. Late nights, long hours, and googling how to do aspects of your role are far from unheard of. While smart companies praise their hard-working contributors, working at a startup requires discipline, perseverance and a laundry list of sacrifices. 

Enterprise Culture 

Over the last few years, we’ve grown to over 100 employees. We’ve traded our singular lunch table for a bougie coworking space and our small ‘family’ to nothing short of the Brady Bunch. We still call ourselves a startup, but let’s be real; that title doesn’t really fit anymore…(we have a handbook and everything). 

We now come fully equipped with multiple departments to meet our goals. With our increase in revenue, we also have more access to technology, perks, and resources that we didn’t have prior. And with more power, comes more responsibility. Below are the pros of our scale to enterprise.


Growth Structure

If you want to move up in the company, there’s a clear path to get you there. It’s no longer a guessing game. You need to hit exactly X KPIs for exactly X quarters to level up. For many, this framework is empowering and provides clear direction on setting and executing priorities.

More Perks

FREE SNACKS! That was the perk we’ve all been gunning for… Additionally, we grew our office space, took company trips, and developed a full tech stack. Not only do these perks help to incentivize the team, they’ve also made us more efficient and better at what we do. 

New Departments, New Opportunities

I remember once (or maybe thrice), I pitched to our CEO that I should be in a wellness position. We needed more yoga in the office! While I’m still not our Chief Zen Officer, we’ve seen tremendous opportunities open up for our team. From an onboarding team to a marketing department, our company roles have expanded.


More Red Tape

Ah yes, the dreaded red tape. No longer are last minute planning and half baked ideas enough to start a new project. Whether you want to host an end of the quarter celebration or change a clunky process, there are certain boxes you have to check first. For some, this is a breath of fresh air; but generally decision making takes longer and you may face more obstacles than you did in the startup phase.

You Might Not Know Everyone’s Name

As companies scale and departments grow, you may not know everyone you work with intimately. In fact, you may not even know all of their names. As a company with a culture that was built on inside jokes, this has been a huge change in our environment to have new people coming in each month. While we’re so thrilled to have each and every new face involved, it’s simply more challenging to get to know 100+ people in an organization.

More Linear and Structured Approach to Work

Again, this is a blessing or a curse depending on your workstyle. In short, the bigger your team, the less autonomy you likely have. By the time we’d scaled to be an enterprise organization, we had robust systems in place. Each project now has a process, each team has a workflow, each decision has checks and balances. If you prefer to dictate how you do your work, having a more structured approach may feel stifling.

Less Involvement with Company Changes

At 30 employees, we often had group discussions on company changes. While we still have employees weigh in on decision making, we more regularly rely on focus groups to keep us informed. We strive to be transparent in all that we do and as we’ve scaled, we’ve had to rely more on our leadership to make decisions on behalf of the group. 

Harder to Stand Out as a Top Performer 

We like to think of our team as the best of the best. And with 100 team players competing to be number one, it’s harder to be noticed. In short, it’s easier to be a big fish in a small pong – but once you move to the ocean, it’s a whole other world. From feeling appreciated on the team to making a move up the ladder, the environment is more competitive. 

Biggest Challenges in the Transition

As we’ve shifted our structure, the culture and work changes are not always going to suit everyone involved. There are pros and cons to both, but the transition from startup to growth comes with challenges.

Things break. Processes, tech, and structures that once served you will become irrelevant or ineffective. You’ll Lose employees due to unavoidable culture and work changes. Great employees will feel the added stress as you flex into new systems.

But the growing pains don’t last forever. You can make your transition easier by communicating your vision from the beginning. Sapper was always planning to scale and we talked about it regularly; it was no surprise that our team and company was growing. Make sure you ask for feedback on what’s working and what’s not. This will not only keep you informed on the experiences of your frontline employees, but will also help you to prioritize changes needed in your organization. Finally, expect discomfort. Discomfort and uncertainty are inherent parts of scale when growing a startup business. Hold your vision and keep going.

Scaling through COVID-19 has come with its own set of challenges. Learn how we recession-proofed our business and surpassed company records during a pandemic here. 



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