A Designer's Transition into Startup Life: 7 Hard-Earned Lessons

A Designer Transitions Into Startup Life

If you’re anything like me, you graduated from college with a portfolio full of blood sweat and tears. You developed every skill needed to land a job working for Don Draper in the tough and prestigious world of the agency. 

You could print, cut, and assemble packaging mockups at lightning speed. You could create logos that captured the essence of any client's company. After all, those were the things you needed if you wanted to enter into the client world and the skills your teachers gave you most of their advice on. If you wouldn’t be delivering awe-inspiring pitches, what else were you going to tell your friends you did, right? 

I asked myself that same question after working in advertising for a couple of years and feeling like I was missing out on something. I knew designers were making a big impact in the tech industry, but I was clueless as to how they fit and worked inside many of these fast-growing companies. Could my future as a designer lie somewhere beyond the agency life? I wanted an answer, so I decided to look into a change. 

On New Year’s Eve of 2014 my husband and I drove 17 hours from El Paso, Texas heading west. We crossed three states and ended our trip on January 1st, driving across the Bay Bridge as the sunset welcomed us into our brand new lives in San Francisco. 

I accepted my job as a designer at HelloSign with confidence in my craft, my skills, and my process. But I was unfamiliar with how in-house design teams (of all sizes) operate, strategize, and execute. I also wanted to experience how different it was from the client-agency dynamic I was so used to. 

Major companies such as Airbnb, Facebook, and Google have already come to embrace and empower in-house design teams that gain as much recognition as any great agency out there. 

If you’re looking into joining a design team in a startup, I’d love to share some insight that might help you transition more easily into the mindset of a product-focused company.

Lesson #1: Put that timer down, you ain’t billing no one no more

When a client would approach the small agency I worked for in Texas, the end deliverables would always be figured out very quickly. Whether it was an entire identity system, an ad campaign, or a brochure, at the end of the day there was always a proposal or an invoice that listed out what the agency had to deliver to the client and the amount we were getting in return.   

In the startup world, no matter what your position is in the company, the success of the product depends on what everyone is ultimately working on. Departments such as, Marketing, Engineering and Creative develop strategies that seek to grow and improve the reach and value of the product. 

Designing in an in-house team means that the amount of time you spend on a design is not influenced by trying to stay within a certain number of billable hours. Work-in-progress is shown often in a more casual manner and feedback is delivered faster from the parties involved since they are – most of the time sitting – in the same office.

Lesson #2 Your Product is your main client

Knowing the product, just like getting to know a client, is essential to make work that is truly impactful and successful. My very first task at HelloSign (and one all new employees do) was to use the product for an entire week. I completed use cases and recorded very honest feedback, an invaluable resource that can only be provided by new users. Then, I spent the first month learning the ins and out of the product, which allowed me to feel confident as I began completing tasks and contributing to projects of increasing complexity. 

As a designer, the types of tasks you’ll work on will vary depending on the size of your organization and the size of your department. Bigger creative teams usually employ designers that have honed particular skills, like say, interaction design. But at HelloSign, our Creative department is still rather small – though eager – so we happily take the lead on tasks that span from print design and illustration to UX/UI and Motion Graphics. Although it can be somewhat intimidating to work in projects that stretch our areas of expertise, I find it extremely rewarding to constantly learn by involving myself in different areas of design. 

Being a designer at a startup exercises your ability to collaborate with others and identify where your talents are needed the most. Whether it’s a set of icons, a new interface, swag for conferences, or ultimately your insight as to what design challenges will come as the product and company grow.

Lesson # 3: You'll never meet all your users. But you'll always be working to improve things for them.

Back in my agency days (and I’m sure it’s still the case), there was nothing worse than finishing a presentation with a client whose work had kept the team very busy for weeks, only to have him or her produce a frown of disapproval. “I don’t like it,” he or she might say. When asked why, they’d often reply, “I don’t know.” 

Projects of many different kinds come in through agencies’ doors every day and just as varied are the clients who request them. The truth is, although designers work hard at balancing form and function in every piece they work on, many of us have made some dreaded revisions that have felt unnecessary or even detrimental to the design. In many of these cases, these revisions were the result of our team compromising with our client over an aspect of the work that was deemed by him or her, non-negotiable. 

Although there is an assumption that the client knows their product and audience the best, he or she typically doesn’t participate in the processes leading to the final product, other than to reject or embrace what your team has created. This divide between the agency and the main stakeholders can pose a challenge when presenting work. With limited time to communicate the thought process behind so many decisions that affected the course of the piece, it becomes especially difficult to advocate for the ones that aren’t embraced by your client. 

At HelloSign, making our users awesome is a constant goal. Our product enables individuals and businesses to easily fill out, legally sign, and send agreements online in a matter of minutes. Many of our customers sign and send mortgage documents, offer letters, contracts, and NDAs while also requesting signatures from other parties. It’s a challenging task to constantly improve the experience for thousands of people, who use and rely on our product to make important business and financial decisions (and you won't usually get to meet the majority of them!"). Collecting feedback and other metrics from our users keeps us busy since this data is crucial in the process of rapidly changing and evolving our product

For this reason, startups have made design a resource so indispensable that outsourcing it to an agency simply makes no sense in the grand scheme of things. 

As a designer at a startup, I iterate fast, I talk to multiple stakeholders, and participate in design decisions in their most basic form by helping strategize what needs to be or not be designed.

Lesson # 4: Done with a project? Just call it v1.1

When working at the agency, there was a finite amount of time I could work on a project. Once it was presented, revised, loved and turned in, it was considered finished (tip: always keep samples for your portfolio!). 

This was definitely a useful workflow coming right out of college because it taught me to work fast and allowed me to polish my craft and be versatile in different styles and mediums. Also, there’s a level of adrenaline and pride that comes from targeting projects like this, knowing that you have to work within a framework of things such as budget and an agreed deadline. 

Later in my career, I noticed that the time limitation of hard deadlines wasn’t allowing me to explore design strategy as much as I wanted to. Working at a startup has given me the opportunity to collaborate with larger teams, work with longer timelines, and even lead self-started endeavors. 

And while we still operate under deadlines, they’re not designed to constrain creativity. It’s an environment that constantly supports new and better versions.

Lesson #5: There will be a lot of prioritization. A lot.

Just like many companies, our year is broken down into quarters, and updates to our product are grouped by release. This allows departments to prioritize tasks, coordinate goals with others, and be able to track users’ responses better to any product improvement. Of course when a project is set to go out over a longer period of time, or broken into releases, keeping momentum and focus is key to success. 

To stay updated on the many things everyone is working on, the entire company meets weekly. The format of the weekly meeting changes often, as we constantly try to make the best use of everyone’s time and attention. The ultimate goal, however, is to get a strong sense of what initiatives and projects are departments working on and how we, as a company are moving towards our goals. 

One of my favorite ways to define this focus after we prioritize a project is via kick-off meetings. Kick-off meetings serve as a big magnetic pinboard for ideas. Big, small, and sometimes crazy, all thoughts are welcome since to a great extent, we are our own client. Once these are all laid out, we can make better decisions as to who can rock which role and then establish a timeline for its completion. 

At the same time it's important to remember that changes in direction can and do happen and new tasks might jump into anyone’s workload. Experiencing burnout, losing motivation and enthusiasm is damaging to both a team and a project. 

Luckily, the tech industry has paved the way to empower employees through thick and thin, which leads me to...

Lesson #6: There’s more to company culture than donuts

When I graduated college, I hoped I’d never work in a cubicle. Reduced spaces made me feel distracted and anxious. When I worked in advertising, our office had been designed to give everyone enough space to work without feeling confined. “Woohoo,” I thought, “no cubicles!” All the spaces worked great for individual and collaborative tasks (plus we’d get donuts once a week). 

I thought I’d hit the office culture lottery. Life was comfortable, but I also didn’t know any better. 

Since recruiting and keeping the best talent is a priority in Silicon Valley, startups have been at the forefront of a work culture revolution. Making sure that the team has the necessary tools and environment to work not only comfortably but happily drives performance up and employee churn down. In a competitive place for companies like San Francisco, those are two things that can help a company succeed

At HelloSign, work culture is as important as the product we all work to improve. It’s a reflection of the work ethic we share as a team, along with more specific practices that allow us to work and feel great. 

Our beloved Team Ops department tackles a lengthy and sometimes hectic list of tasks that allow our office to run like a second home. Our workspaces are comfortable and arranged for collaboration while more secluded rooms exist for meetings, calls, and other noise sensitive tasks. Our kitchen is always fully stocked with snacks and drinks, an inventory that keeps growing as our team increase in size. 

And just like home, we all typically sit together at lunch time and enjoy good food and conversation.

Lesson #7: Startups love your brain

One of my favorite aspects of having this culture is that it is built by honest feedback. As new team members join and add to our work culture with their experiences and suggestions, Team Ops is always improving processes and practices so they reflect the needs of a growing organization without compromising our values. 

As an employee, I value these efforts not only for what they are, but for how they’re trying to improve work life. Fifty years ago, the standard office was a place where employees could obtain merely an income. 

Now, many companies invest in empowering career growth and strengthening team relations that foster innovation.


Working at a startup is a great opportunity to experience company models that have driven great products to success. If you enjoy the fast pace environment of an agency, then a startup will offer a very similar rhythm. You will also encounter the opportunity to re-work projects that have been through a cycle of implementation and are ready to be re-evaluated and improved. 

Acknowledging design as problem-solving rather than just crafting communication is the first step in determining where you want to take your career. As appreciation for design keeps growing, more opportunities arise for creatives to work and make a difference in a variety of industries. Your design dream job can certainly now lie in places you’ve never thought to look before and you might just end up helping build the next big thing. 

For more insight into HelloSign's design, you can check out our latest project, "The Daily Scroll". If you're interested in joining the HelloSign team, we'd love to have you. Learn more here.

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