Fueling rocket ships and thinking about the stars

Photo by LinaVeresk, via Twenty20.

I’m so happy and humbled to have joined the incredible team at Lightspeed, where I have strong mentors to learn from as well as a substantial platform. I first started making angel investments and advising companies after leaving Slack, without planning to invest professionally. I even turned down conversations with firms that reached out. Like a lot of former founders, I’ve had some very poor interactions with VCs that colored my impression of the industry as a whole.

But over the course of the next year I discovered that I really loved helping founders grow their businesses, hire teams, find product/market fit, and learn to scale themselves as leaders. And becoming a venture capitalist myself, especially at a top tier firm like Lightspeed, felt like the best way to continue the mission I took on when I left Slack:

In part I left because I want to bring that standard of respect and inclusion into more of Silicon Valley, and because I want to find that level of intense challenge again: How do you scale from 500,000 to 5+ million DAU in two years while growing revenue, driving activation, and building a diverse, empathetic team?

What better way to bring a high performance and inclusive growth mindset into more of the tech industry than by investing in the next generation of founders? It also meant a lot to me that I wouldn’t be the first or only female partner at Lightspeed. You don’t change the industry by hiring just one woman; you change the industry by hiring many of us.

While much of what I’ve learned building teams and products is applicable to the challenges that all venture-backed companies face, the day-to-day work of venture investing couldn’t be more different. Growth teams measure their feedback cycles in days; product teams measure them in weeks. Venture feedback cycles are years long. And rather than making thousands of data-driven decisions with clear and immediate customer feedback, VCs place a small number of big bets.

I learned that getting comfortable with placing big bets seems to be about two things: finding incredible founders and developing a thesis about the future of a few spaces. One of the reasons I chose Lightspeed was the chance to invest in both consumer and enterprise companies — an opportunity that makes good use of my misfit, ambidextrous skill set.

What follows are the themes in which I’ll be actively investing for the next few years, across both early and growth stages. If you’re a founder building a company in the following spaces, I’d love to meet you.

The (Continued) Consumerization of the Enterprise + AI/ML Helpers

At Slack I observed a generational divide in how engaged people were with our product. User research showed higher levels of engagement, better retention, and higher propensity to pay among Millennials than in older cohorts. It’s not that younger people intuitively understand technology better but they are accustomed to learning new technology on their own. They expect to be able to figure out software and implement themselves — exactly the modality provided by self-service enterprise software.

What’s often misunderstood is that the oldest Millennials are now almost 40 years old. This helps explain why we are “suddenly” seeing preferences for intuitive software show up in the enterprise. Existing verticals like messaging and scheduling are being revamped, as are software packages for specific market segments like design, customer service, and back office processes. There’s room for more areas of knowledge work to improve including anything from task management, documentation, RFP generation, content development and testing, lead qualification/targeting, and market research.

A second inflection point is possible as these newly consumerized sectors are combined with machine learning and artificial intelligence. ML & AI-enhanced business tools will replace rote cognitive and non-cognitive tasks within existing workflows, like note-taking, deal research, and follow-up communication. Machines will make people smarter and these services will improve business outcomes in their verticals by giving knowledge workers insight into their best leads, consistent patterns of won or lost deals, an edge in written and visual communication, and give human beings more time to spend on hard to automate areas like face-to-face communication and relationship building.

As the specialization of knowledge work increases competition for talent (and Millennials openly share details of their salaries and benefits with their friends) white collar workers expect the companies they work for to provide more engagement and growth opportunities. Companies of all sizes are expected to provide services to their employees that formerly only large enterprises could afford, like coaching and fertility benefits. As this trend continues, we’ll see services arise to help SMBs provide parental and paid leave, mentorship, social events, opportunities for new skill training, access to state-of-the-art tools, and connections to expert communities.

Data Wells, AI/ML, and Automation in Pink & Blue Collar Industries

Work continues to move to mobile devices as blue collar (manufacturing, construction, field work) and pink collar jobs (customer service, nursing, education) come online in ways that mirror and improve upon existing solutions for knowledge workers. This is largely driven by the same generational trends that are changing white collar enterprise software.

Hourly retail and restaurant workers are starting to adopt enterprise messaging apps and in the near-future they’ll begin to be evaluated and find new jobs using similar apps. Flexible work options that are already widely available (like Uber, Lyft, Instacart) will force other sectors to offer flexible labor options in order to compete. Services will emerge that match workers with flexible jobs and tasks — baristas, sous chefs, clerks, nurses, nannies, and customer service agents will go where the pay is best and the timing fits their schedule. Employers will need services that source appropriate candidates and match them with tasks, integrate with and provision enterprise software on temporary workers’ personal devices, and develop algorithms to deploy new workforces at scale.

A third class of worker is emerging somewhere between 1099 and W2 employment; benefit structures to serve employees and employers like family and sick leave, retirement accounts, training, and insurance will need to be figured out.

Flexible work in these sectors has cross-generational impact. While task and hourly work has always been an entryway to the workforce, it will increasingly be how people end their careers. Not only are Boomers living longer than previous cohorts, the 2009 recession wiped out a huge amount of Boomers’ home equity and retirement accounts at a point when it was too late for most of them to fully recover. Many Boomers will be unable or unwilling to fully retire and need ways to generate income and spend their time.

Not only will companies specifically market to this demographic but the influx of Boomers back into the workforce will expand the talent pool to include former professionals. Boomers will want platforms to share their expertise, find relevant & age-appropriate work, update accreditation, and increase technical fluency or learn new skills. Employers will need services to recruit semi-retired or retired professionals, match experienced workers with apprentice programs or roles, accommodate these workers in their businesses, and provide benefits that fit their phase of life.

Most workflows are still trapped in manual and paper processes, and data that should be easily accessible — is my supply chain connected to a supplier that’s been compromised? — can take weeks of manual work to uncover.

Workflows will continue to be digitized. It’s not just workflows that are locked up: a lot of actionable data is simply trapped on paper. More industries will need to solve the paper problem by digitizing and indexing existing paper records in a manner that meets compliance and regulatory needs as well as enables AI/ML-based insights. The legal industry is a natural start but manufacturing, agriculture, pharma, medical, and traditional retail and CPG companies will need vertical-specific solutions.

Internet Native Social Networks & VR/AR as the New Self

Communities and modalities of self-expression shift as generational norms change. People who grew up in the 1980s and 90s wanted to capture fleeting moments: Gen-Xers sat next to the radio waiting for a favorite song to play so they could tape it. There are only dozens of photographs and very little video of Gen-Xers (today, ages 39–58) and first-wave Millennials (today, ages 25–38) as children. It makes sense that these cohorts created companies like Instagram and Youtube — they grew up wanting to save moments. Conversely, second-wave Millennials (today, ages 13–24) were photographed and videoed endlessly growing up; their parents made them email accounts and bought them domain names before they could even legally consent to being online.

This generation values live or fleeting experiences. Video is demonstrably important here, along with the rise of streaming social experiences as well as AR features and apps. Social networks where people have a multiplicity of identities or temporary, easy-to-discard accounts will emerge and look more like a series of smaller walled gardens than one massive network. And as this generation enters the workforce, their experience finding jobs will mirror the flexibility of these social networks as many of them become members of verticalized workforces deployed via mobile apps.

It will become commonplace to attend large-scale events like sporting championships and music festivals remotely as drones, 360º camera-enabled robots, and light body cams proliferate. What we consider “an event” may also change. Lighter VR hardware and better AR experiences will allow anyone to be on the field during the World Cup or front row at Coachella.

With the advancement of VR/AR, computer vision, and AI/ML video and audio manipulation technologies, we’ll also be able to experience being different people — not just having a different viewing position. Playing Rock Band was an early, low-res approximation of being a rockstar, but one in which people were still somewhat limited by their own skill level.

In the future, consumers will adopt experiences in which they’re able to feel like they’re not just viewers but primary actors. Games, music, sports, and even what we think of as film or TV will allow people to have first-person agency. These new experiences will likely first be offered in custom-built physical retail locations first before migrating into the living rooms and bedrooms of consumers.

Do we see the same future?

If you’re a founder just starting out, or if you’re ready to take on a growth investment, I’d love to meet you. How can I help?

Advisor & angel investor. Former VC at Lightspeed, former Head of Growth at Slack. Happy to help.