Investing in the “Future of Work”

Allison Baum
Apr 10 · 8 min read

The What, Why, and How of Technology’s Transformation of the Workplace

I grew up watching my parents’ jobs slowly get replaced by technology. This had a huge impact on me and my family — financially and emotionally. As my parents now approach retirement age, it is still a critical topic. When I started working on Wall Street during the Financial Crisis, I saw the pattern repeat, this time for me and my colleagues, as once-lucrative trading jobs were easily replaced by algorithms to save on the bottom line. It was alarming to see the career I had only just started suddenly cease to exist.

Since that time, every step in my career has been driven by a relentless pursuit of understanding how business is changing so that I can anticipate, adapt, and benefit from the changing nature of work instead of being blindsided by it. For me, the mission of venture capital is to not only see the trends impacting the future but to actually play a role in how they take shape. That is why I am focused on finding, investing in, and collaborating with entrepreneurs building the technology that will create the future of work.

What do you mean by the “future of work”?

Simply put, the future of work is everything related to how jobs get done. This includes who does them, what they involve, when, where, how and why they get done.

More specifically, there are four core technology categories that will determine how jobs get done in the future. This is where I am searching, learning, investing, and building:

  • Automation services (applied AI/ML, SaaS, workflow management)
  • Human capital services (HR tech, training, education)
  • Digital and physical infrastructure (cloud architecture, financial services, team communication tools)
  • Security and identity management (authorization, cybersecurity)

That said, the funny thing about the future is that we don’t know what it will look like — so it’s important to define the space expansively enough to leave room for reinvention that we can’t yet imagine.

Why is “the future of work” so important, anyway?

We’re not making any more money than we were thirty years ago

Beginning in 1980, the introduction of the computer led to a decoupling of wages and productivity, converting careers into jobs and jobs into part-time jobs, making it harder and harder to earn the lifelong security that “a good job” once promised. From 2000–2014 productivity increased by 80 percent, while wages increased a mere 1.2 percent.

This means that when companies make more goods for less time and money (aka productivity), shareholders benefit but employees do not. Today, nearly 5 million people are working part-time because they can’t get full-time work, and even among people with full-time jobs, 30 percent have been forced to take on extra jobs to cover their costs.

We are not saving money… like, at all

The whittling away of the middle class is unfortunately a long-term trend. Sixty-nine percent of Americans ages 18–64 have less than $1,000 saved. By the government’s own estimates, retirement welfare benefits like Social Security lack adequate funding beyond 2035, meaning many Americans will not have the financial cushion to retire at the same age as previous generations. This combination of longer careers and an accelerating rate of change in technology means that the half-life of jobs will only get shorter and shorter. Some estimates predict artificial intelligence will automate up to 47 percent of US jobs in the next ten to twenty years, forcing us all to adapt faster and more proactively than ever before.

Also, work is literally killing us

When work sucks, we suffer. The average American spends 90,000 hours at work over the course of their lifetimes — the only activity we do more is sleep. Given the amount of time spent on work, it has a big impact on our state of being. Unfortunately, over eighty percent of workers are so unhappy at their jobs that the dissatisfaction spills over into their personal relationships. Therefore, over 70% of all workers are actively seeking new jobs. Just as physical labor had an impact on our physical health, knowledge work is impacting our mental health. The American death rate from drugs, alcohol, and mental disorders has nearly tripled since 1980.

Clearly, the ways we built value in the past are no longer working for us today — and certainly won’t work in the future. Technology’s disruption of jobs is creating irreparable tears in the fabric of our society. As both individuals and as a society, navigating the future of work will rank among the greatest challenges of our lifetimes.

How does the future of work look, exactly? Introducing the 3 D’s.


As a case study, let’s think about my mother’s cousin, Bobby, a long-haul truck driver from Nebraska. Truck driver is in the top three most common jobs in nearly every state in America. Today, a long-haul truck driver in America can support a family on a median income around $42,000, above the national average in spite of the fact that 94% of truck drivers do not have college degrees. There is currently a shortage of ~50,000 drivers, a number only expected to triple within the next ten years as older drivers retire.


Let’s fast forward: The year is 2032.

1) The future of work is DIGITAL (not physical)

All predictable, repetitive tasks are automated. Human work focuses on non-repetitive tasks only, such as strategy, monitoring, training machines/each other, community management, complex sales, and creativity/innovation. This has created fundamental challenges in terms of reskilling, training, talent management, and mental health. Additionally, the continued exponential proliferation of digital data has led to a boom in cloud infrastructure, data warehousing, and analysis needs.


Spending many hours alone on the road, Bobby had chronic back problems, drank a lot, and was also a chain smoker. He passed away several years ago, but his son Timmy is now a driver for XTruck, a self-driving truck company. Unlike his father, who had to pay significant fees to train and get his Commercial Driver’s License, Timmy got his ADL (Automated Driving License) through an ISA (income share agreement) training provider, which provided training and certification free of charge for a portion of his salary for his first three years. He is only actively driving for 10% of his time in the truck, which includes taking over driving in difficult situations like unsafe weather conditions, loading, unloading, parking, last mile driving, interacting with other employees. The rest of the time, the truck is driving itself and Timmy can be working on something else.


2) The future of work is DISTRIBUTED (not centralized)

Extremely high-value jobs are primarily creative and strategic, requiring the collaboration of multiple parties in different locations. Lower value jobs, still lacking wage growth, cannot sustain families. Most individuals have multiple jobs at once, and do not sit in an office (aka the flipped workplace). All jobs are rapidly evolving, so it is normal to change jobs relatively frequently, as well as multiple times over a lifetime. Most of these jobs are in the form of sole proprietorships and small businesses. Tools for small business operations, collaboration infrastructure for distributed teams, resource allocation and talent acquisition are critical needs.


Because he is doing less but theoretically more valuable work, Timmy earns about the same as his father did (~$42,000 per year), which is not enough, so he has three other jobs that he does while he’s on the road. He has a small online business selling photographs from his travels, he sells his personal location data to advertisers for a daily fee, and he also does customer support for an online trucking therapy network for those who feel isolated from their lifestyle and need support from the road.


3) The future of work is DATA-DRIVEN

All jobs are fully quantifiable and trackable, so time and resource allocation decisions at both the company and individual level are quantitatively driven. Compensation is meritocratic and outcome-focused, emphasizing measurable results instead of number of hours worked. Data is basically infinite, so the ability to navigate and harness its power into relevant insights is the only way to gain a competitive edge.


Instead of being paid by the mile, Timmy’s compensation is based on productivity, not presence — his pay is determined by a complex algorithm of miles driven, hours logged, accuracy, and customer reviews. His routes are determined by the company’s self-driving software, which integrates weather and GPS with real-time data about the cargo load and the destination facilities to determine where and how he arrives. For his other jobs, he uses a personal algorithm to determine which of the four are more lucrative, and he adjusts his own time accordingly. His biggest challenge is not “How do I know what’s working?” but more “I have so much information, how do I weigh data from which source, and once I know what it means, what should I do about it?”


Final words

No matter how we imagine the future, it is impossible to deny that we are living in unprecedented times. We can let technology determine the future for us, or we can reimagine it ourselves.

I’m excited by the seemingly endless possibilities ahead of us. We are equipped with the most powerful tools that have existed in human history. Now, it’s up to us to do our jobs in a way that works for us — not the other way around. If you’re up for the challenge, let’s talk!

Trinity Ventures

A collection of posts from the Trinity Ventures partnership and portfolio. Learn about the firm at www.trinityventures.com.

Thanks to Melissa Sobel.

Allison Baum

Written by

Venture investor in the future of work @trinityventures

Trinity Ventures

A collection of posts from the Trinity Ventures partnership and portfolio. Learn about the firm at www.trinityventures.com.