6 Months, 10 Lessons: What I've Learned So Far at Our Startup

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Discover what the first six months at a startup can teach you. By Tessa Greenleaf (Happiness Lead, CloudPeeps)

This post originally appeared on the CloudPeeps blog.

I’ve been a part of the CloudPeeps team for six months now, and time has flown by in ways I couldn’t have imagined. Before another six months passes, I’d like to share the top ten things I’ve learned in my time here, and how working at a startup has challenged me to grow both personally and professionally.

1. Agility is Key

Especially when you’re working at an early stage startup you have to be able to move fast – and move often. Over the last few months, we’ve been building out our platform and testing our product-market fit as we go.

What’s great about being in a small team is that you have the ability to move quickly, but you have to be flexible as well so that you don’t get set on one way of doing things. Being open to change is crucial to innovation and product improvements.

2. Embrace “Other Duties as Assigned”

Working as a part of a small core team can be challenging, as you always have several things on your plate to take on in a single day. While I joined the team to predominantly oversee customer and Peep happiness, this didn’t exclude me from getting my feet wet in accounting, legal and product development.

The great part about being needed in a number of areas is that you get a firsthand look into bigger picture goals, and understand more of what needs to be accomplished on a daily basis for the company to be successful.

3. Speak Up

During my first couple of weeks I developed the “newbie mentality,” where I felt I didn’t have the klout to speak up and share my opinions. I soon learned that I was selling myself short, and that the team not only valued when I spoke up, but yearned for it.

Now, I’m in a position where we’ve brought on new team members and I understand firsthand the importance of hearing from people with fresh eyes.

4. Speak Often

Members of our team at CloudPeeps are currently distributed between San Francisco, New York City, Seattle, Miami and Berlin – which means we’re rarely in the same place at the same time. What has been amazing to see is how we all keep in touch and work together using tools like Slack, Skype and Hangouts.

It’s especially important among a distributed team to speak up and speak up often. The more vocal you are throughout your day and what you’re working on the more of a collaborative environment you create.

In all honesty, I sometimes feel more connected with my team now than I did when I was sharing an office with teammates in the past.

5. Take Initiative

My background working in the public sector meant that I was used to going through multiple levels of approval and clearance before any action could be taken. That environment did not set me up for working in a startup culture.

Working with an extremely agile team means that you won’t have time to sit around waiting for approval. On the contrary, you’ve got to establish trust between one another so that you can be independent members of a team with a unified goal.

6. Build Trust

Spring boarding off of my last point, one of the most crucial aspects of working in a startup is building relationships based on trust. Since you (more than likely) won’t have time to run every piece of content, every product update, and every tweet by each member of your team, you need to trust that what they’re doing relates back to your overarching company goal.

7. Make Mistakes and Learn from Them

I’ve made numerous mistakes since I’ve started with CloudPeeps, and I’m not ashamed to admit that I haven’t been perfect — no one is. The important thing is that you identify the mistakes you make along the way and learn from them going forward.

8. Embrace Uncertainty

Working in an early stage startup comes with a high level of uncertainty. When I came onboard, CloudPeeps had only existed for eight months, and I was very aware of the risks associated with joining such a young company.

While success is never guaranteed, I trusted our founders to point us in the right direction for positive growth, and knew that I wouldn’t have been offered my role if they weren’t in a position to expand their team.

9. Establish a Schedule

Very early on, I realized just how much work was involved in joining a recently built company. I could very easily sit at my desk for 12 hours a day and fill each hour with meaningful, productive work — but that isn’t healthy for anyone involved.

Although we work as a remote distributed team with each person having the flexibility to set their schedule (some of us work well at 5AM, I am not one of them), a proper work/life balance is crucial. If you’re putting in strings of 12 hour days, you will burn out very quickly.

I started to set my hours similar to how I was accustomed to working in the past, in 8-9 hour chunks.

10. Keep Your Eye on the Bigger Picture

It was easy for me to get into a daily rhythm once I had been working on the team for about a month. However, that rhythm didn’t lend toward active growth.

We have a Trello board — our chosen project management tool — we use to map out our big picture goals at CloudPeeps. It’s important for me to visit that board daily to remind myself of where we are, but more importantly, where we’re going.

Each startup has its own set of culture values, and those values will have a big impact on your role within the company. What I’ve loved about being member of the CloudPeeps team has been the overarching encouragement that we provide to one another on a daily basis. We’re all new to building this, and we’re all learning what works best as we go.

The important thing is that we trust one another to build it together.

Photo credit: enterlinedesign via Shutterstock.


About the guest blogger: Tessa Greenleaf is a Matching Specialist at CloudPeeps. She believes in the future of remote work, and is excited to be a part of a movement toward a more distributed workforce. Find her on Twitter at @TessaGreenleaf.