In Part I of this series, I shared my vision for an Empowered Economy — an economy where career-related autonomy and security are reconciled and workers are able to thrive.

In Part II, my plan was to discuss the new “career stack” that is evolving to enable a more empowering career journey. Over the past few months, many of you have asked when I would release Part II and, sadly, I haven’t quite figured out how to VC full-time and write. But 2021 is a new year so here it is!

The Career Stack for the Empowered Economy

In this article, I will highlight some of the key insights, but you can always find the full deck here (deck allows you to click on company logos).

Before I dive in, I think it’s important I share the lens through which I view how this landscape should evolve. I believe the most important part of privilege is not that you are always safe or wealthy — it means that you often have the benefit of making decisions with an emphasis on maximizing upside as opposed to minimizing the downside. And when I imagine the new career stack for an empowered economy it gets closer to ensuring that each individual can start to reorient their thinking to focus on the upside of their decisions. With that, let’s dig in.

Framework for the Career Stack

In order to start exploring the career stack, I broke down a career journey into:

  • Phases of your career: the important parts of your career journey, which, in a time of increasing reshifting of careers, acts as a cycle as opposed to a static timeline.
  • Enablers for mobility: the components of your life that enable career and economic mobility.

Exploration: Identifying A Career Path

The process of identifying the right career path and choosing an employer is daunting. It presumes an understanding of labor market trends, viable and growing career paths, what it takes to get into and succeed in that career, and insider information on specific employers. With an increasing amount of the workforce reskilling and shifting employers, the need for more effective exploration solutions is increasingly needed. The more that we are able to provide potential workers with support as they explore potential career paths, the more they can avoid potential pitfalls and actually focus on doing what it takes to achieve their goals. A few interesting areas of opportunity below.

  • Glassdoor 2.0: With the nature of work rapidly changing (e.g. remote work, increased interest in flexibility and diversity, etc.), there is an opportunity to recreate an employer-branding solution that is more relevant to candidate interests and accrues more value to workers.
  • Exploration solutions for reskillers: Historically, career exploration solutions have targeted students or knowledge workers who are upskilling. With the rapid increase in reskillers, there is an opportunity for new exploration solutions to specifically serve this population. Career Karma is attempting to do this by starting with finding the right training option for you as a reskiller.
  • Better predictive career data: Career data is largely based on lagging indicators like scraping job posting data. Unlocking additional and more predictive data on future careers can create a layer for new career exploration applications to be built on top of.

Placement: Finding And Getting The Job

While companies like Indeed and Monster currently have market dominance in job search, companies that offer more curated offerings (e.g. Incredible Health and Handshake), on-ramps into careers (e.g. apprenticeships), and the ability to employ yourself are starting to create new opportunities for finding and getting access to jobs. That said, the process of democratizing access to finding work still has a lot of room for improvement. A few ideas below.

  • Apprenticeships beyond software engineering: Apprenticeships create a great opportunity to learn and earn at the same time. Most opportunities have largely existed in software engineering, but there is an opportunity to expand into other supply-constrained verticals like healthcare and manufacturing, where jobs also can provide access to a living wage.
  • Verticalized platforms that go beyond job postings: Incredible Health has done a great job of providing value to nurses by offering curated opportunities, creating a location to host their professional identity, and offering community. This model can expand to other verticals that allow candidates to generate value beyond just job postings.
  • Enhanced support to set users up for success on self-employment platforms: Most workers that leverage platforms for self-employment did not intend to run their own business, which means in order to succeed they need support beyond the platform infrastructure. They need help in marketing themselves and operations in order to generate meaningful income for themselves. Stream has done an interesting job of this by taking a more hands-on approach to onboarding and training their creators.

Application: Thriving On the Job

I split this portion into “with an employer” or “self-employed” because the tools needed to grow and thrive on the job in these two scenarios differ.

With an employer

In Part I of this series, I described “corporate entrepreneurism”, which was a state in which there was increased internal mobility and redeployment supplemented with corporate-provided upskilling to enable these transitions. In a world in which the need for labor market skills is changing so rapidly, companies will have to learn to adjust and leverage the existing talent they already have in their companies. This not only helps to reduce the volatility within the company, but it also creates a safety net for employers that may be at risk of getting laid off. Going back to my original lens, this allows workers to worry less about the downside and instead optimize for the upside of their decisions. That said, this is area is far from mature — below are some ideas for improvements:

  • Automated Internal Mobility: Internal mobility solutions have historically required a huge amount of organizational behavior change. As data around skills and preferences become more readily available, the opportunity to create less consultative and more automated internal mobility solutions for employers increases. It’s been exciting to see new companies like Anthill, FutureFit, and Flux address this.
  • Employee advocacy: With the decrease in unions and an increase in remote work, employees’ ability to self-organize and advocate for changes in the workplace has taken a hit. Solutions to help preempt, identity, and solve employee grievances are necessary for creating more empowered workplaces.


This is the part of the career stack that is in need of the most progress. The support and safety net for “non-traditional” workers is effectively non-existent. If we hope to provide our workforce with the flexibility they desire (and the related benefits that accrue to consumers through these platforms), we have to create an equivalent vibrant ecosystem to support them. Portable benefits providers and financial services companies that are catering to this population are certainly starting but there is much needed regulatory support and additional solutions to help realize the potential of self-employment.

  • Improved regulation to support and provide financial security to “non-traditional workers”: Not all solutions can be driven by new companies (though there are incredible companies doing work in this space). In order to unlock meaningful support for all types of workers, there is a need for better protections for non-traditional workers like portable benefits and more affordable health insurance options.
  • Solutions to optimize and stabilize income: One of the most pressing challenges of “non-traditional” workers is income volatility. Solutions that can help smooth out income and also optimize how workers spend their time/labor can help to enable new types of work to more sustainably scale.

Learning: What You Need To Learn to Grow In Your Career

Education is where I started my career and what sparked my passion for economic mobility solutions. There have been meaningful improvements in the education sector, especially for adult learners, over the past decade but there is space to build better infrastructure to deliver online learning and new solutions in verticals that have yet to be “disrupted”.

  • Training solutions in supply-constrained verticals like healthcare and manufacturing: Training solutions in fields like software engineering, data analytics, and design is largely saturated. There is an opportunity to target fields that expect an increase in demand and offer jobs with a living wage.
  • Better infrastructure for online learning: Online instruction could be 100x better than it currently is. Using zoom for learning loses the best of in-person teaching (e.g. small group collaboration) and doesn’t leverage the benefits technology can offer (e.g. using facial recognition data to predict confusion or engagement) During COVID, new solutions like Engageli have arisen but they are still early.
  • Better assessments for hiring: Assessment for software engineering exists, which helped to enable the acceptance of hiring software engineers without traditional credentials. As we start to create better assessments for other fields, that increases the acceptance of alternative credentials and enables the broader alternative training industry to grow.

Professional Identity: Who You are and Who You Know

LinkedIn was founded over 18 years ago and now has over 700 million users all across the world. It has become the de-facto place where you go to host your professional identity and curate your network. But, if you talk to 10 of its users, I’m willing to bet at least 8 of them will tell you that it’s the product they use because their network is there but it is far from ideal. With a new and younger generation, an increasing “non-traditional” workforce, and vertical markets that have industry-specific needs, there is an opportunity to build a new place to host your professional identity.

  • Verticalized networks that deliver industry-specific value: Incredible Health targets healthcare workers and Bravado focuses on sales professionals. Each offers users to create a digital identity that specifically addresses the nuances of their particular industry. This model can extend to other verticals where certifications and forms of networking are nuanced and can’t be accurately captured via LinkedIn.
  • LinkedIn 2.0: LinkedIn is incredibly difficult to disrupt given its network effects. But with a younger generation of workers that is increasingly not on LinkedIn and new types of workers (e.g. freelancers) that aren’t adequately served by the static timeline model of LinkedIn, there is a massive opportunity to create a new professional network. Contra (Cowboy portfolio company) is starting to build towards this vision with a focus on independent workers.

Community: The People Who Keep You Going

Community is an increasingly important asset in your personal and professional journey. We’ve seen a rise of new community-oriented companies over the past few years, which I’ve written about previously here. Just like we have gyms for our physical wellness and therapist for our mental wellness, I believe there will be a new space for our career wellness — this will be a space that is rooted in a community of like-minded peers. But in order to grow to become a meaningful business, there is a lot to be built beyond the community.

  • Expanding beyond community to deliver additional and measurable value to members: As companies where community is the product continue to be built, there will be an increasing need to find ways to deliver differentiated and additional value and that members can measure and are willing to pay for. Career Karma has done this by leveraging the power of the community for information and accountability for reskillers but also expanding to provide personalized guidance on training pathways and offering a digital portfolio for users.

It’s Time to Build a More Equitable Future

The opportunity to support workers who are searching and applying for, currently working, and/or in the process of pivoting to a new career is massive. It is hard to understate the tectonic shifts that are happening in the workforce and that has only been accelerated by COVID. If you are building towards a future that helps to empower workers, regardless of their zip code, background, race, and/or gender, please reach out to me at

Originally published at

Partner at Reach Capital. Cowboy Ventures and Emerson Collective alum. Writing at!