Pathway Ventures: Investing in the Human Side of the Future of Work

Pathway Ventures
5 min readOct 5, 2020


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1.1 Billion workers globally are expected to have their jobs impacted by automation.

54% of all workers will need reskilling. 52% of workers will soon participate in the gig economy.

Even before a pandemic rattled the globe, the pathways by which workers were navigating the economy were evolving dramatically. And then COVID-19 displaced 50 million people from the workforce in the US alone and massively accelerated the trends shaping the Future of Work.

Amidst the economic upheaval of 2020, we believe there is more opportunity than ever to support early-stage founders who are creating new models of economic mobility.

For that reason, we’re thrilled to announce the launch of Pathway Ventures, a pre-seed and seed stage venture fund investing in the human side of the Future of Work. We’re looking to back the next generation of founders that are driving economic mobility through innovative new models of earning, learning, and community building.

If you’re building something in this space, we want to hear from you!

Who are we?

Both of us have built our careers as Edtech and Future of Work “enthusiasts” (some would use the alternative term: “nerds”).

We’ve built innovative startups that have helped tens of thousands of people transform their education and career pathways, and between the two of us, have been functional leaders across product, marketing, operations, and partnerships. We’ve also been on the investing side of the table before, having funded edtech companies from pre-seed to private equity.

But throughout all our work, what kept putting our respective paths on a never-ending collision course with each other was our shared passion for building the ecosystem itself: often devoting our nights and weekends to working with early-stage founders and sharing our advice, resources, and investor connections to propel their teams and the sector to the next level.

Why are we building this now?

As COVID-19 has cemented one of the largest ever shocks to the economy and accelerated disruption in the workforce, we have been energized by the number of investors who have added Future of Work as a category on their websites or their Twitter bios. But when we’ve dug deeper into these emergent “Future of Work” investors, we’ve been disappointed that, to many, this category seems to be primarily defined by enterprise productivity SaaS platforms and low code/no code tools (for those that even have a definition).

Given the incredible trajectory of trends around the skills gap, career transitions, the gig economy, and remote work, we believe there is a significant gap in the market to invest in the human side of the Future of Work.

For us, this thesis is defined as investing in startups that are creating new models of economic mobility and fundamentally impacting a worker’s livelihood in the economy.

Finally, the more we have supported early-stage founders, the more we have realized that they value the support of other entrepreneurs. The two of us are incredibly excited to launch Pathway Ventures as current operators in the sector. We believe strongly that this operator-investor structure will give us a unique lens to identify promising startups, a unique ability to support founders, and quite frankly, will be a true embodiment of the Future of Work itself.

What are we excited about investing in?

In the coming months, we are excited to share more about each of the categories that we have strong theses in, but for now, we’ll just share a taste of some of the categories we are thinking about:

Workforce Retraining

The skills gap continues to widen as employers increase the digitization and automation of the workforce. Traditional education models have proven ineffective in having the agility to meet evolving employer needs, leaving significant room for new models to support workers in gaining skills that lead directly to job outcomes.

Some areas we’re excited about:

  • Middle Skills Pathways — enabling non-degree learning tracks with clear job outcomes in formats that are specifically built for working adults
  • Work-Based Learning — providing practical workforce skills through apprenticeships and other learning experiences that reduce friction for both job seekers and employers
  • Specialized Job Platforms — facilitating job outcomes for specific industries or groups that will enable rapid growth and agility in aligning to labor market needs

Startups we admire in this category: NextStep, Springboard, WhiteHat, Riipen, Shift

Career Support & Community

The average person is now expected to have 15+ jobs over the course of their career. There is a significant need for lifelong support in navigating career pathways and finding community that is unbundled from a single workplace.

Some areas we’re excited about:

  • Career Navigation — supporting people in discovering in-demand career and learning paths and understanding where their skills and interests are most aligned
  • Professional Coaching — providing employer-agnostic career guidance and resources to achieve professional goals, both in transition and within job experiences
  • Unbundled Communities — unbundling professional networks from school and work by facilitating new models of collaboration and connection

Startups we admire in this category: FutureFit AI, Career Karma, Pathrise, On Deck, Chief

Flexible Work

Traditional 9-to-5 jobs with one full time employer are increasingly becoming a concept of the past, leaving room for new innovative platforms to earn income, but also exposing pain points of a more flexible work structure where there is still opportunity to create supportive infrastructure.

Some areas we’re excited about:

  • Creator Economy — enabling individuals to monetize their skills more directly with technology platforms that reduce intermediaries
  • On-Demand Staffing — creating a just-in-time approach to matching the supply and demand of talent for responsibilities that go beyond traditional gig platforms
  • Independent Worker Support — providing the portable benefits and infrastructure that will empower the increasing number of independent workers at all skill levels

Startups we admire in this category: Outschool, Torch, NurseDash, Catch, Steady

Distributed Workforce

The pandemic has accelerated adoption of remote work, but the overall geography gap has also continued to widen as economic clustering drives a locational mismatch between the supply and demand of labor. Models that support remote and hybrid workers will continue to gain traction, but there will also be opportunity for relocation and the emergence of new geographic hubs.

Some areas we’re excited about:

  • Remote Staffing & Tools — enabling workers to more easily access remote work opportunities and empowering them to succeed through remote-first tools
  • New Geographic Hubs — fueling talent pipelines, employment, and economic growth in regions outside of traditional economic hubs
  • Relocation Models — facilitating the relocation of individuals to increase labor market fluidity in gaining access to new employment opportunities

Startups we admire in this category: Tango, Bitwise, Kenzie Academy, Placement, Outtalent

Building something in these spaces? Let’s chat!