Finding Quality Remote Work

For those of you just starting the process of going nomad, know that having remote work in which you take joy is vital. Many have written about the particular vagaries of remote work, with isolation and the resulting paranoia being just two challenges. I’d like to focus more on the initial hunt for remote work and finding the perfect fit to ensure longevity and stability so that you can enjoy a balanced, more full life as a nomad. Here we go!

My remote job search was guided by a few principles developed from past experience. For me to be happy with a role I knew I needed to find a company that met the following:

1. The product drastically improves quality of life and is accessible.
2. The company is innovating and leading in an overlooked space.
3. The company’s business model is easy to understand and sustainable.
4. Remote employees exist at all levels and across all orgs.
5. The company culture actively encourages a work/life balance.

These principles were important in finding a company that fits our lifestyle, our family, and my professional aspirations. Insisting on all of them may be difficult but it’s worth it and trust me, these companies do exist. The big “But!” is that this will no doubt extend your job search.

Here’s why delaying employment in favor of company fit and innovation is so important. A company that doesn’t make a meaningful impact to the lives of its customers, or is accessible only to a select few, will likely have high rates of attrition and/or an inequitable compensation model to drive leadership retention. Dunder Mifflin’s low turnover seems to be the exception here.

A company with a simple and sustainable business model is nimble, enabling even large orgs to align quickly to execute on a vision. Complementing this with a remote workforce can be an inexpensive option that turbo charges a business if that model is fully leveraged and embraced.

The essence of a remote strategy is companies can attract top talent outside their immediate vicinity, often at a lower cost, while providing employees location flexibility and a salary that’s often higher than their local job market. The secret ingredient is of course TRUST. How a company deploys this strategy is usually a good indicator for the level of trust and understanding they have of the remote model. Do remote employees exist at all levels or only in one org at lower levels? Do on-site employees work from home as needed, or is there a hard line between office employees and remotes? I’ve found that if remote workers are subtly treated as a separate workforce, the company usually isn’t fully invested in remote work. When that’s the case, paranoia is justified. They may not trust that you’re getting your work done, they may not go out of their way to make you feel like a valued part of the team, and ultimately it may be hard for you to grow in the kind of stifled, anxious environment to which these factors lead.

Company culture is not ping pong tables or company Uber accounts. It’s what employees say in private Slack channels, at the dinner table with their family, and the internal dialogue they have as they evaluate their professional career. If employees actually love working for the company (as opposed to mostly loving what the company does, or love the paycheck), you’ll probably love it too, which leads to longevity and career growth.

Leaders in great companies build diverse teams with skills that complement each other in order to deliver on the impossible. Building that dream team requires hiring people with deep experience to offer, often at different stages in their life. Some may be willing to prioritize work above everything else (E.g. My 10 years at Amazon), but most discover along the way that they can do more with less. A great company culture acknowledges this by encouraging personal development outside of work, celebrating family life, monitoring hours for signs of burnout or skill gaps, and recognizes employees who maintain balance while delivering on company goals.

Here are a few red flags to look out for in your search: an “Everything is Awesome!” mentality about the product or service, unethical marketing or reporting practices, lack of diversity and experience at senior levels, conflating trendy office perks with work/life balance, and remote employees existing in one org. I’ve experienced all of these and it never ends well.

So, how long did it take for me to find my ideal fit? 3 months. I searched jobs boards and reached out to companies directly, applied for approximately 60 positions at 42 companies while being extremely selective, interviewed with 12 of them, and ultimately accepted an offer from Willow Pump in June of 2019.

Willow checked all the boxes and turned out to be everything I expected and more. Not only are they first in their market, but they are one of the most well-funded femtech startups in the world. Willow makes the first silent, wireless breast pump that fits in a bra (#2 and #3 – innovating and leading in an overlooked space, simply & sustainable business model).

I joined the Customer Care team to focus on optimizing systems that enable the team to scale while identifying self-service solutions that ultimately eliminate contacts and reduce overhead. My role is remote, and so are many others within the company. Willow doesn’t actively sell itself as a remote friendly place, but we should. There are remotes in every team and at every level, which has attracted experienced and diverse team members.

Every team is stacked with talented and passionate people who are eager to improve the pump and the lives of moms. For my Amazon peeps, these guys are Mom Obsessed! It’s even in their lexicon – Mom needs this, Mom said this, Mom is having trouble with that. It’s not “Customers” or even mom”s”, but the singular Mom to whom we’re hyper-focused on bringing joy. I love that!

While everyone at Willow has a title, few actually have it in their sig blocks or Slack profile. Ideas and challenges are accepted at every level with genuine interest in improving our service and product for mom. We also don’t have an org chart, which sometimes causes confusion around who to connect with on an idea or who to loop in on change controls, but all of this makes for a flat org structure and breeds strong cross-functional teamwork.

Lastly, I’ve found the team dynamic to be incredibly positive. My manager and others always assume good intentions which drives trust throughout the company. This approach is particularly important with remote teams where negativity can prompt paranoia and kill productivity. This element is so simple, yet possibly the most overlooked solution to many workplace and productivity issues.

If you’re on the hunt for a remote position, consider taking a week or two to really think about what you need in return from that company to truly be happy. Your job search will be more targeted. You’ll be genuine and more confident in your interviews, and with a little patience hopefully land your dream job and realize the full benefits of a remote position. Best of luck, you got this!