My Hope for the Future of Work

Jomayra Herrera
Dec 2, 2019 · 11 min read
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A lot has been written about the future of work. Every time I check twitter, there’s a new take on what it means, what hot company just raised in this space, and where someone thinks the puck is going. The reality is that if you ask 10 different people what the future of work means, you will probably get 10 different answers. And this all makes sense — everyone has a different experience and understanding of what work means to them.

When I was growing up, work was something you did to put food on the table and keep a roof over your head. Work was my parents taking the night shift and sometimes working multiple jobs at once because they wanted a better life for me and my sister. Work was me juggling 2–3 jobs at a time while I was in college in order to cover my expenses (yes, even Stanford students have to work). Work was both a necessity and a privilege — a source of dignity and stress.

For a little bit of background on me, I come from pretty humble beginnings and was the first in my family to go to a 4-year college. Access to education and, as a result, meaningful work has always been something I’ve cared deeply about. So much so, that I went to graduate school for education (this was not a fun conversation to have with my parents). I then started my career at an early-stage startup that developed software to help teachers with their professional development and had the great fortune to spend the last 3 years investing at Emerson Collective, where I spent a lot of my time focused on companies sitting at the intersection of education and employment.

Over the course of the last few years, I’ve had some time to think about what I hope the future of work looks like for the vast majority of people and wanted to share them here.

Before I jump in, here are a few stats that ground my thinking:

Here are 8 ways I hope the future of work evolves

1. People will have the data and tools to take charge of the direction of their career

It turns out that while we’re pretty good at predicting what roles or skills are going to be automated, we’re really bad at figuring out what roles will exist in the future (who knew we would need social media strategists 10 years ago?).

We know the pace at which you’re going to have to retrain and likely switch jobs is only going to increase in the future. And yet, many of us do not have the resources to navigate the transitions. Your options? You can engage a recruiter (expensive), take one of these fun quizzes (not very helpful), or leverage your state’s workforce development website (here is Florida’s — it told me I should be a babysitter!).

None of these are particularly helpful. Unfortunately, our best “real time” labor market information still relies on the scraping of job postings and other lagging indicators. As a result, we don’t have a good sense of where we should focus our efforts in terms of skill-building and career progression (and this doesn’t even account for your preferences and passion). Labor market data providers like Burning glass and EMSI that power a lot of tools with their APIs are continuously improving but there is still a lot of work left to be done.

I hope with the increasing amount of data being created and the pace at which people are switching careers continues to accelerate, there will be more solutions that help people to navigate and make better decisions related to their careers.

2. There will be new innovative and accessible education pathways that will more strongly link work and learning

We started with MOOCs (massive online open courses — think edX and Coursera), which helped to increase access to content but not necessarily opportunity as the completion rates of most courses is <10%. We then moved onto the age of the bootcamp where if you could afford to shell out $15K and not work for 3 months, you could become a software engineer.

We’re now in what I would describe as Bootcamp 2.0 — where we have options that offer new and innovative financing mechanisms (e.g. ISAs), recognize that it might take longer than 3 months to learn a new trade, incorporate work-based learning into the curriculum, and have options that expand outside software engineering and into fields like sales and design. A few that fall into this camp include SV Academy, Flockyjay, Holberton, Kenzie Academy, and Lambda School, among many others.

The number of students that leverage these alternative pathways is still pretty small compared to traditional universities. For example, only ~23K students will graduate from coding bootcamps this year compared to the ~3M bachelors and associates degrees that will be awarded. That said, the number continues to grow every year and in many cases are supplements to a traditional degree.

I expect that traditional universities will continue to build new and innovative ways to access their offerings and become more relevant to the current labor market, especially given that over 40% of college graduates are underemployed after they graduate. I also believe there is a lot more opportunity to build alternative pathways that fall outside of technical skills (e.g. sales, marketing, and creative fields) and also embrace that there is a rise of hybrid roles for which no training programs currently exist but some estimates suggest could represent almost 12% of current job openings.

3. Employers will invest in their employees to make sure they can bring their best self to work

For example, in 2018, just 4% of employers surveyed offered benefits focused on reducing student debt — that number doubled to 8% in the 2019 survey. Companies surveyed increased benefits they offer in categories like wellness, career development, and flexible working.

With a tight labor market, employers are increasingly searching for ways to retain and grow their talent. For instance, the majority of large employers view addressing the skills gap within their workforce as a top priority. This creates an incredible opportunity for companies like Guild Education* to help enable employers like Walmart, Disney, and Lowes offer education as a benefit to their workers.

I expect this trend will continue with increased investment in areas like education, financial wellness, and emotional well-being.

4. There will be more opportunities to monetize what we’re passionate about

Interestingly, being self-employed is associated both with higher overall life evaluation and with more negative, daily emotions such as stress and worry.

I’m excited about the companies that are arising that not only help people take employment in their own hands but also help them make a living off of what they are actually passionate about. For example, Patreon, Gumroad, Teachable, OutSchool, Substack, and Skillshare, among many others provide a platform to help creators monetize off of the skills and abilities that make them unique. They also offer flexible working options, which is an attribute that workers increasingly value.

Self employment is certainly not for everyone, but I do believe that we will continue to see the rise of these platforms, especially in verticalized spaces (e.g. teaching, writing, etc.).

5. Employers will value your skills more than your degree

Companies like Pymetrics, Triplebyte, and other talent assessments have helped to enable employers to more accurately measure skills and attributes that are actually predictive of whether someone will succeed in a role. Over 80% of companies now use a form of pre-employment assessment. Armed with this kind of data, HR professionals can make fairer decisions on how they think about hiring. Moreover, talent marketplaces like Handshake have played an important role to help increase access to job opportunities for job seekers, regardless of what school they went to.

With the rise of alternative credentials, a consistent difficulty in filling open roles, and more assessment tools than ever, I expect the role of the degree and pedigree to matter less in hiring and what you can actually do start to matter more.

6. Workers, especially in non-traditional settings, will have access to a financial ecosystem that helps them thrive

There is a rise of companies that help employees who don’t have access to traditional benefits, such as Decent Health, Catch, and Icon. Banks that are made specifically for the solo-entrepreneur in mind. And, there are income optimization companies focused on serving the new type of worker like Steady.

I still believe there is a lot left to be done in tools that actually help you figure out how to increase your income. A lot has been built to figure out what you should do with the cash you already have, but, for the vast majority of people, the problem isn’t figuring out what to do with your cash, it’s actually figuring out how to get more of it. I still believe there is a role to play in leveraging and combining data to help users figure out the best path to actually growing the amount of income they are generating every month.

7. We will recognize the future of work is intimately linked with the future of care

Companies like Wonderschool, Weecare, and Myvillage are attempting to address the challenges of affordability and supply, but there is still a massive amount of unmet demand when it comes to childcare. As a result, I expect there will be an increase in employers playing a more active role in helping their employees with childcare, whether it be through providing more flexible work options or actually offering childcare as a benefit. I also hope there will be new innovative companies that help to bend the cost curve on childcare options.

Moreover, many working adults not only have their children to consider but also their aging loved ones. So many act as unpaid caregivers, which has both economic and emotional implications. Companies like Mon Ami* and Honor do incredible work to help assist with elder care and there is still a lot of work left to be done to continue to make care more affordable and accessible.

8. We will live in a world where your safety net includes your community

The vast majority of people don’t have that safety net and, as a result, don’t have the luxury to take risks that may put them in a much better position as it relates to their career. It’s also really, really hard to transition jobs, especially if it’s in a field that you’re not familiar with. Companies like Career Karma help to create digital peer circles for people who are trying to navigate the next step in their careers (they are starting off with people who are interested in starting at a coding bootcamp). These circles help to connect you with folks who have a similar experience, can offer support and accountability, and are a resource for you as you go through a complex journey. I wrote about many other companies focused on building communities in this post.

There continues to be so much opportunity for companies that not only help you strengthen your existing relationships but also help you build net-new ones that you can lean on, especially as you navigate complex journeys like a career transition.

So where do we go from here:

But I felt compelled to lay this out because over the holidays I kept thinking about something someone I deeply respect told me before I left my last role. It was along the lines of:

“My only wish for you is that you remember why you started in this career. It was never about getting into the hottest company. It was always about putting capital to work to move the needle in the issues you care deeply about.”

I strongly believe there are massive, category-defining companies waiting to be built that will usher in a new era of work defined by fulfilling and meaningful work, passion, and community. I can’t wait to see them.

Building anything that falls in the categories above or want to work at companies like this? Email me at — would love to chat!

  • Cowboy Portfolio Company
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Startup Grind

Stories, tips, and learnings from and for startups around…

Jomayra Herrera

Written by

Investor at Cowboy Ventures. Writing at!

Startup Grind

Stories, tips, and learnings from and for startups around the world. Welcoming submissions re: startup education, tech trends, product, design, hiring, growth, investing, and more. Interested in submitting? Visit our submission form here:

Jomayra Herrera

Written by

Investor at Cowboy Ventures. Writing at!

Startup Grind

Stories, tips, and learnings from and for startups around the world. Welcoming submissions re: startup education, tech trends, product, design, hiring, growth, investing, and more. Interested in submitting? Visit our submission form here:

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