The JAMStack & the startups building it

A special edition with Technically's Justin Gage for this week's JAMStack Conference

As an angel investor in Webflow and now full-time investor in companies like WorkOS, TakeShape, GitDuck and other great dev tools, I get asked a lot about what’s to come for software development and the future of work for individual builders and contributors.

This week marks an important milestone for the JAMStack community, it’s the first virtual conference hosted by my friends at Netlify including founder & CEO Matt Biilmann, the up-and-coming media mogul and everyone’s favorite developer evangelist Cassidy Williams and the broader JAMStack community that’s revolutionizing the developer experience with better performance, lower cost and greater scalability.

If you haven’t already, subscribe to Justin’s newsletter Technically, it’s personally my favorite tech newsletter for technical, non-technical, and triple threats across a number of industries :)

The JAMStack and the startups building it

As the line between frontend and backend has blurred over the past few years (thanks React), the JAMStack has emerged as a new paradigm for building sites and apps. The stack itself is generally easy to understand, but the ecosystem – tools, plugins, and APIs – isn’t. We’re going to walk through what the JAMStack is, how to categorize tooling, and why modular use case specific APIs are going to continue to grow in popularity.

Javascript, API, and Markup

The JAMStack is an architectural pattern (sort of) for building apps that moves away from the traditional web server model and focuses on serving static files from “the edge” (data centers physically close to your computer). JAM stands for Javascript, API, and Markup:

  • Javascript: all code is in JS, for both frontend interactivity and API requests and handling

  • API: instead of a monolithic web server, all backend functionality (authentication, users, etc.) is served via APIs

  • Markup: your whole site is just a bunch of HTML files served statically

This is like, very different from what most larger apps look like. If you’re accessing a web app like Twitter in your browser, there’s probably a ton of server side logic dictating what you see, how you log in, and everything else that’s custom about your experience. In a JAMStack app, all of that logic would be encapsulated in simple APIs.

These ideas have been around for a while, but the JAMStack concept is definitely having a moment over the past couple of years:

jamstack google trends

There’s even a JAMStack conference that started in 2018, started by a group of repeat founders from early JAMStack companies (Contentful, Gatsby, etc.) that have continued investing in the ecosystem.

The past few years have been a perfect storm for the kind of apps we’re talking about. Javascript is now the most popular programming language in the world, used by 70% of devs last year and likely more in 2020. GraphQL is used by almost 40% of JS devs, and even Apollo by 25%. Hosting has gotten laughably cheap, and services like Netlify give you automatic deploys, a global CDN, and authentication for free.

As with everything in web development, JAMStack apps vs. traditional web apps isn’t entirely black and white. Even if you hide complex server logic behind easy to use APIs, JAMStack apps need to have a backend somewhere; and caching and serving files from a CDN isn’t exactly a new idea.

jamstack tweet

Think of JAMStack less as an architecture and more as a philosophy for where application logic should sit and what best practices for serving sites should be. In that vein, keep an eye out for Redwood.js – they’re taking aim at a full framework for JAMStack apps complete with an actual backend.

The JAMStack Ecosystem

The easiest way to understand all of the available tooling out there is to break it down by JAM – Javascript, API, and Markup.

1. J is for Javascript

It’s a meme that Javascript is the worst, and some teams have been focusing on improving ergonomics by building on top of it. The best known example is Typescript – it’s basically strongly typed Javascript. The ability to define static types means you’ll be able to catch errors before your code runs. Static typing is standard in languages like Java and C++, and Python added pseudo-support last year. Another example of a related JS add-on: Purescript.

2. A is for API

Even if your backend is nice and clean and obscured behind a simple API, application logic has to live somewhere. The serverless ecosystem has been growing pretty quickly: all major cloud providers offer the ability to run functions without setting up a server, like Lambda on AWS. Over the past few years though, hosting providers like Netlify and Vercel have started to support serverless functions as add-ons. They’re both just white-labeling other cloud providers for now, but that could change in the future. AWS’s Amplify is lurking (along with ages old Firebase), too.

Another important area of the ecosystem is CMS providers. If you’re running a blog or publication, you’d traditionally need to use a Content Management System like Wordpress or Drupal – deployed on a server – to write and manage your content. For JAMStack apps (or regular apps too, really), newer providers like Contentful and Storyblok expose content through REST or GraphQL APIs so you don’t need to manage any servers yourself. There are a lot of headless CMS solutions out there.

3. M is for Markup

This is where things get interesting. Probably the biggest story in frontend over the past few years has been the meteoric rise of client side rendering via ReactVue, and Angular. Building componentized pages that interact well with your data model is now more of a science than an art. Alongside these kinds of libraries, a new suite of static site generators like HugoJekyllGatsby, and Next.js are making it simpler to go from content to built page.

The last missing piece here is hosting and deployment. Like Firebase did for mobile apps, companies like Netlify offer platforms that simplify a lot of the annoying parts of building JAMStack apps, like a global CDN, automatic deploys, identity and login, and serverless functions. More about them in the next section.

Two types of tools: point and platform

As with pretty much all developer tools, the JAMStack landscape can be split into two basic approaches: do a really good job at one task, or offer a full platform for accomplishing an entire workflow.

→ Point solutions

Most of the tools we covered across the J,A, and M try to be useful for one particular task: Contentful for CMS, Lambda for Serverless, or Hugo for static site generation. You can’t realistically finish an entire project without using multiple of these, and they don’t necessarily integrate well out of the box.

→ Platforms

Companies like Netlify and Vercel, formally known as Zeit, are trying to build full platforms for building JAMStack apps – they take care of almost everything, from deploy to functions to CMS. Individually, each piece that they offer isn’t going to be the best on the market, or even close to that; but the power of features integrated together can sometimes outweigh shortcomings of individual products (just ask Microsoft). This is part of why Netlify is trying to own the content and narrative around JAMStack sites.

For an exhaustive list of JAMStack related tools, check out the awesome-jamstack repo on Github.

The Future: Use Case Specific APIs

Earlier, we looked at tools like Contentful; they provide a fully managed CMS that gets exposed via an API. CMS is just one well scoped use case – writing and managing content. But the Contentful model is getting a lot more popular as a broader category: SaaS tools that take care of a full piece of a workflow with a very use case specific series of APIs. Here are a few examples of more established ones:

  • Algolia – search as a service via configurable APIs

  • Auth0 – identity and authentication as a service via API

  • Optimizely – APIs for feature flagging and experimentation

  • Shopify Plus – headless e-commerce, like Contentful

  • Sendgrid – send emails to your users via API

  • Stripe – IDK if you’ve heard of them, they’re hiring

These tools have 2 equally important parts:

  1. A series of APIs to integrate directly into your app

  2. A frontend / admin panel for visibility and management

Take a look at Algolia, for example. You push data, configure indices, and call search all via a client library like Javascript. Once you have the Algolia APIs working in your app, you can use their dashboards to get analytics and see how users are interacting with what you’ve built.

These services have nothing to with each other in terms of what they actually help developers do, but they all rely on the same approach of providing value through a narrowly scoped set of APIs (and they’re API first, even if there are frontends) that solve a particular functional use case.

One way of looking at these third party APIs is as a natural progression from JAMStack’s core tenet: couching complexity behind well designed APIs that make actual deployment easy. The next logical step is outsourcing those APIs.

jamstack diagram

I think this is going to become an increasingly common piece of how developers automate parts of their work. A few newer services I’m keeping an eye on:

  • Memberstack – APIs for building and managing memberships

  • Getform – APIs for building forms into your site with “no backend”

  • Sendbird – APIs for chat and messaging in your app

  • Snipcart – API for adding a shopping cart to your site

Some of these services are more infrastructure-y (think Plaid, Algolia) while some are more functional (Memberstack, Sendbird). The common thread is that they need to solve some non-trivial problem (if it’s too easy to build yourself, you will) while still giving developers the flexibility they’d expect from something more custom.

Thanks to Justin Gage and Bucky Moore for some good ideas. If you liked or hated this, share it on TwitterReddit, or HackerNews.

Why I built Silicon Valley in Figma

How a workplace product became a viral social network overnight

As work and life have converged, we continue to see new virtual experiences for nearly every major life event and daily activity.

New startups are being formed with no physical office space. Zillow, a publicly traded company, announced a fully remote policy for its 5,000+ employees until the end of 2020. The new playbook for people & culture is currently being written for a new way of worklife: more flexibility, fewer meetings and an optional office in the future with new safe, socially-distant features.

For the first time in its 45-year run, the late night show that unites America, declared from Tom Hanks’ kitchen, “Live from Zoom, it’s Saturday Night Live!” Bar mitzvahs and baby showers now take place on screens and first dates once scheduled at a local bar are audio streamed on Clubhouse, complete with a remote bartender and an audience. 

While sheltered in place, I’ve thought a lot about our quirky culture in Silicon Valley and why the media, #techtwitter and invite-only, private beta, and ‘skip the line’ tools and apps all fail to paint an accurate picture of the open, thoughtful and inclusive nature of daily life in Silicon Valley. Our daily serendipitous interactions are far better than our public-facing personas.

As a long-time gamer, elder egirl and frequently labeled tech bro, I thought what if we created the Sims or Animal Crossing, but for the people of Silicon Valley?

This thought kicked off what would become Stay at Home Valleya spatial interface and digital recreation of the Bay Area tech ecosystem that anyone could access and collectively build.

A single Figma file shared with a simple link: no wait list, invite code, or moderator.

Bringing the Serendipity and Energy of The Bay Area Online

Before moving to San Francisco, I lived in a number of places starting in the suburbs of Ohio then Sydney, Hong Kong with a number of month long stints other places in between. Since then, I’ve fallen in love with Mexico City, “split my time” with Los Angeles and frequently have the same thought: there’s no place quite like Silicon Valley.

As we translate our in-person interactions into online equivalents, it’s hard not to miss the electricity of the city: driven individuals and teams, the eagerness to pay it forward, and the unbridled enthusiasm that we lovingly call founder craziness. I’ve described Silicon Valley as a place where a cold email and a coffee can change your life.

Paul Graham’s ode to great cities succinctly captures how our environment can shape us:

“Great cities attract ambitious people. You can sense it when you walk around one. In a hundred subtle ways, the city sends you a message: you could do more; you should try harder.”

As someone who has personally experienced the magic of running into someone at Bluebottle or catching up while waiting for an Uber, I wanted to build an online equivalent that captured the serendipitous moments that make Silicon Valley great.

I wanted to create a safe space where anyone could share company updates, meet someone new, or build something from scratch.

I worked with designer, Fiona Carty, a Boba Guys-alum who I hired two days after the company let go of 400 people and shut 17 locations in a single day.

Fiona contacted me via Instagram DMs and I was blown away by her ability to build authentic communities through technology that's traditionally used for work: Figma, Notion, and Airtable.

We built Stay at Home Valley in Figma late one evening. We started with a few key buildings and tech influencers. Shortly after, we shared a link to the public Figma file to the #DesignTwitter community and launched it on Product Hunt

How the Tech Community Responded

Stay at Home Valley saw 15,000 visits in less than 24 hours. In total, the map has over 200 startup offices and points of interest including Dropbox, Instagram, Webflow, and the Salesforce Tower. It also saw coverage in Fast Company, Business Insider and New York Times tech, memes, internet culture writer Taylor Lorenz tweeted about it (twice!)

Visitors to our virtual world built their startup, added their office dog, and re-opened their favorite places like Boba Guys, Mission Cliffs and nostalgic points of interest.

For two weeks, we pushed Figma’s 50 editor maximum per file limit, which we candidly called “Dreamforce-level traffic” in and out of the city.

While many online communities and digital gathering can be difficult to moderate with harassment, spam, and the new threat of Zoombombing, we saw zero malicious postings or spam. If anything, this was an early signal that it is in fact “time to build.”

Founders, designers, individuals with no design experience collaborated to host COVID-19 relief events, celebrate new rounds of funding and build a better city altogether with more housing and free, safe transportation.

Here are some of the landmarks and moments recreated in Stay at Home Valley:

  • Residents of Stay at Home Valley re-opened The Wing, which laid off hundreds of its staff including friends in SF, and invited Audrey Gelman to join a charity event to support The Wing Relief Fund.

  • Spotify CEO can be spotted near the Spotify SF office for a charity event supporting Spotify's COVID-19 Music Relief page dollar-for-dollar up to a total Spotify contribution of $10 million.

  • Flexport was added to the map as the company focuses their efforts on COVID-19 relief; they’ve delivered 62 million pieces of personal protective equipment. They’re also recruiting in Stay at Home Valley, a sign near their HQ reveals that they're hiring infrastructure engineers. 

  • Notion announced a $50M funding round at $2B valuation – Index Ventures' Sarah Cannon was digitally added leaving the office while Cristina Cordova is seen joining Stripe as their Head of Platform & Partnerships. You'll find shoes outside the office, a nod to Notion's no shoes culture. 

  • Stripe announced its latest round $600M round with board member and avid sailor Diane Green outside sailing in Stripe's moat protected by unicorns. 

  • Adam Noffsinger, a product designer at Cruise, added autonomous vehicles throughout the city to provide a safe form of transportation for the citizens of Stay at Home Valley during shelter in place. 

  • Celebrity CEOs were added including Naval Ravikant in the clouds, Tobi Lütke playing Starcraft, and Ivan Zhao celebrating Notion’s $2B valuation. 

  • The community "re-opened" their favorite local businesses: Boba Guys re-opened across the city, local climbing gyms invited people back, and trendy date spots like Dumpling Time came back to life. 

  • Inside jokes are hidden throughout the city. Near the headquarters of Square and Twitter, you’ll find a secret tunnel for Jack Dorsey to travel between meetings. 

  • Beyond the Bay Area, new cities like Seattle, Los Angeles, Salt Lake City, Lisbon and more emerge with major points of interest and a growing startup scene. In the spirit of distributed work, “Remote Land” was added, where the fully remote team at Doist sits. 

  • There was a romantic engagement announcement near Dropbox's office. 

  • AWS, Google Cloud, Azure and Riot Games hover symbolically in the sky.

In between historic buildings, interesting startups, and city landmarks, Stay at Home Valley gave people a fun way to recapture some of the magic of The Bay Area and beyond.  

With an extended period of time at home, my hope is we’ll continue to see the builders that will thrive in the new world think of creative ways to bridge the gap between real life and the virtual world.

If you’re building something new, either a startup or a fun creative project, say “hi” on Twitter.  

The 6 builders who will thrive in the new world

Designers who can Code, Career jumpers, Ambitious advisors

As the global pandemic leaves us frozen in place, it’s impossible to imagine a future that resembles the past. There will be no return to normalcy. Instead, we’ll need to create a new reality that’s resilient, anti-fragile and grounded in flexible, empathetic values as we re-enter the physical world with a new perspective. 

COVID-19 has underscored the importance of individual contribution — to flatten the curve, to navigate the new normal and to build the future. The need to build infrastructure, institutions, products, processes and ultimately new possibilities for both work and life.

Who are the creators, founders, and forgers who will build the new world?

With the proliferation of open-source, no-code/creators tools and new professional networks, the builders who will thrive in the new world will not only ‘think different’, but look and build different.

The 6 types of builders who will thrive in the new world: 

  • The Designers who Code

  • The Career Jumpers 

  • The Ambitious Advisors 

  • The Creative Hackers 

  • The Industry Academics

  • The Community Builders

The Designers Who Code

When we combine technical excellence with opinionated design, we arrive at the designers who can code. Shipping an MVP and iterating based on user feedback is the default for startups; committing to a creative vision and marrying art with technical acumen and user-informed, but not dictated, features has created multiple $2B+ category leading companies: Figma, Notion to name a few. 

In circumventing the debate of whether design-led companies can achieve both creative and technical excellence or whether designers should code , we can observe the transformative tools that are built when they can code. 

A design-led founder to the core, Ivan Zhao is building Notion for a “post-file, post-MS Office world”. They’ve adopted a design process that’s quick and iterative by hiring designers who can code: “All designers at Notion can [code]...we love solving problems holistically.” In building tools for thought, Notion is helping people craft conceptual frameworks for life and work, solve harder problems collaboratively, and hack on ideas without writing code. 

Informal polling suggests that the majority of designers push or write code at least sometimes. We’ll increasingly see technical designers found companies that bring design-thinking to new products; Rahul Vohra’s experience as a game designer informed the game-like experience of Superhuman

Technical designers bring aesthetics to computing and create products that draw people in and keep them engaged in a thoughtful and inherently more intuitive way.  

The Career Jumpers

The best builders rarely stay in their lane. Instead, they find new opportunities to cross-pollinate their learning across different problems, roles, and industries. I call this triple threat mentality, it’s balancing multiple careers or creative projects that reflect multi-dimensional skills, interests and values.

The career jumpers collect and synthesize the expertise and skills they’ve gained across sectors into new insights, moving from law to biometrics or publishing to technology. Or Tech Twitter’s favorite: tech journalism to venture capital. 

This week, Josh Constine announced he will be leaving TechCrunch to join SignalFire as Principal and Head of Content. He’ll be in good company as fellow journalists turned venture capitalists include: Kim-Mai Cutler, Alexia Bonatsos, Katherine Boyle

For readers outside of the Silicon Valley tech bubble, Peloton’s Robin Arzon, a head instructor who brings unapologetic swagger to her guided rides, continues to be my go-to example for the determined career jumper. She’s Peloton’s VP of Fitness Programming, an Adidas brand ambassador, and the author of Shut Up and Run.

She began her career as a lawyer and spent seven years as a corporate litigator. She opted out of the partner track at her law firm and went all-in on a career in fitness. Her contributions to the Peloton brand are invaluable; the company’s S-1 filing reveals how crucial instructors have been in building Peloton into a fitness juggernaut with over 1.4 million members: 

If we are unable to attract and retain high-quality fitness instructors, we may not be able to generate interesting and attractive content for our classes.

On a platform where riders get attached to their favorite instructors, Arzon’s unlikely career jump from law to fitness and her six year tenure at Peloton has no doubt had an impact on the company’s $8.1 Billion valuation.

Likewise, after finishing her Law and Business degree, Margaret Zhang saw opportunity beyond a traditional path. She dove deep into digital media in 2009 when she started her blog, now with over a million followers. Since then, she’s worked in the fashion industry as a multi-hyphenate: filmmaker, photographer, consultant, and writer.

She co-founded BACKGROUND, a global consultancy with a focus on connecting Western and Chinese for luxury and lifestyle brands. She’s worked with companies like Chanel, Gucci, and Louis Vuitton. Cultural builders like Zhang –– crafting content, capturing snapshots, filming stories –– have the world’s ear and frequently use their platforms to creatively bring attention to issues like sustainability and environmentalism.

Another class of career jumpers includes the hourly hustlers: often gig workers who channel their tenacity and grit into quickly earning lucrative skills online and finding new ways to make money. For instance, this includes Uber drivers turned no-code website developers. These experience meaningful upward mobility that comes from being entirely self-taught. 

@HarryStebbings recent tweet

The career jumpers are skilled in the art of the pivot and make strong founders because they’re flexible and adapt quickly to new challenges. It’s easy to confuse their next move with starting from scratch. In reality, they’re simply plotting a continuation, treating their careers as a jungle gym rather than a ladder. They blend together the expertise and skills they garner along the way to craft innovative products and businesses.

The Ambitious Advisors  

Advisors, agencies and freelance executives have a unique upper-hand: access. 

In creating a personal service offering and working across a number of companies, they have a front-row seat to the problems faced inside companies and an iterative playbook for ways to solve them. What’s different from the ambitious advisors from career consultants at major firms is their operating experience inside tech companies and their ability to smoothly transition between full time roles + advising on evenings and weekends to full-time advising, and in some building a venture scale software company using services to bootstrap their way to product market fit. 

Before founding the Internet Archive and Alexa, Brewster Kahle worked at Thinking Machines which built and sold software. However, the company also provided consulting services that allowed them to work with publishing giants, like the Wall Street Journal and Encyclopedia Britannica. Kahle shared his experience in Founders at Work:

We started what I think became the first web studio, or web services business. We worked with big players, whether they were newspapers or magazines, that wanted to publish on the Net. This allowed us to work with big boys very early on.

We continue to see ambitious people in tech consulting and advising companies. Prior to co-founding Oxide Computer Company, Jess Frazelle consulted on technical specialties like containers and Linux architecture. A sought after designer, Pablo Stanley, has a full time role as a Design Lead at InVision, uses Superpeer to make extra money by offering 1:1 advice calls for a flat fee for his followers and designer friends, and recently started Blush to bring illustrations to everyone. 

In the case of emerging tech sectors like JamStack, we see a large percentage of founders come from an agency background where building web projects for clients leads to a unique insight on ways to improve the software development process for others. Stackbit and TakeShape are two recent venture-backed examples.  

The Creative Hackers 

The creative hackers win friends, influence people, and break the internet. They find ways to bring products and experiences to life without writing code. Instead, they dream up big projects and forge partnerships to bring them to fruition or build with flexible no-code tools. 

In the midst of the current pandemic, creative hackers are finding ways to bypass social isolation and bring people together online. 

Marco Marandiz, the co-founder and Head of Marketing at Elliot, launched Virtual Mall, a collaborative spreadsheet for people to interact with their favorite brands. 

Ani Acopian, Suzy Shinn, and @Scott Buscemi teamed up with an unlikely partner to create scrubhub.tv, a parody hand washing video site, to raise money for non-profit organizations helping people affected by COVID-19. Those showing resilience and creativity in tough times are the makers we’ll continue to see break new ground.

I recently took a shot at creative hacking by building Stay at Home Valley in Figma, an interactive space where anyone can build, celebrate good news and make new friends.

In less than 12 hours, 

  • 200 startup offices and points of interest: Dropbox, Instagram, Webflow, Salesforce Tower

  • The community "re-opened" their favorite local businesses: Boba Guys re-opened across the city, local climbing gyms and favorite trendy date spots 

  • Notion announced $50M round at $2B valuation from Index Ventures' Sarah Cannon seen leaving the office, Cristina Cordova joined from Stripe as Head of Platform & Partnership. You'll find shoes outside the office, a nod to Notion's no shoes allowed culture. 

In the case of Stay at Home Valley, we didn’t quite break the Internet although we saw Dreamforce-level traffic for two straight weeks in a single Figma file.

The Industry Academics

Academia is losing its luster as a career track. Tenure is increasingly difficult to obtain, particularly for women who opt for marriage and kids. Subject matter experts passionate about their expertise are corralled into administrative duties that distract from making breakthroughs in their field. Those who stay often cite the same challenges: meagre pay, time consuming grant applications, and institutional politics.

Academics are finding new homes. Companies like DeepMind and OpenAI recruit research scientists with PhDs to solve complex challenges in artificial intelligence. We also see academics infiltrating marketing and growth teams at companies like Airbnb and Slack as data scientists or venture capital firms as research fellows or scientists-in-residence. Academics are in a unique position to merge their deep expertise with industry experience to become innovative founders. 

Others in higher learning are taking their teaching experience and leveraging it into ideas for startups. Melanie Perkins, the founder and CEO of Canva, created the design platform after combining the lessons from two phases in her career: teaching students how to use Adobe design tools and starting Fusion Books, a company that published yearbooks online. 

Teaching design at The University of Western Australia helped her realize that photoshop was arduous to learn and prohibitively expensive, while starting her company was an education in the power of low-code tools and how to run a business. Perkins' following act, Canva, was most recently valued at $3.2 Billion and allows millions of people to design simply and inexpensively.

The Community Builders

We need innovative products and services to shift the world towards progress. We also need movements. The Community Builders build platforms that help other companies start their own businesses.  

Tobias Lütke has built Shopify into a business that supports over 1 Million online storefronts. They’ve experienced rapid growth by empowering small and large business owners; Lütke revealed in 2019 that Shopify passed the $1 Billion dollar revenue mark with the highest growth rate of any SaaS company ever. Shopify isn’t only a platform for sellers, it’s also a platform for tech builders. Gorgias, a help desk for e-commerce stores, is the first customer service app built for Shopify and a venture-backed startup. 

The community builders frequently angel invest in the next generation of companies in their category and bring a high level of transparency to educate founders and support individual creators. 

Ankur Nagpal, the Founder and CEO of Teachable, is an active angel investor who shares metrics, open-sources investor updates and continues to mentor Teachable employees even after they’ve moved onto their next thing. 

Teachable’s entrepreneurial culture has already led to Sid Yadav and Andrew Guttormsen creating Circle, a community platform for creators. 

Matt Biilmann, the co-founder and CEO of Netlify, is another example of an active community builder who has invested in a number of developer tools including social network for software engineers Dev.to, CodeSandbox, headless CMS TakeShape

Community builders are natural company builders. They value thoughtful curation and quality; they eschew the attitude of growth at all costs. As founders, they’re natural evangelists who invest in user education and steadily increase revenue.

A preview of what’s to come

I started a modern VC fund to reimagine work alongside thoughtful founders building new opportunities for creators, designers, developers, and individuals who use technology to launch a new business or be better at work.

The vision for WLV was developed alongside my early angel investments in Webflow, Dev.to, LunchClub, Girlboss and others. I’ve learned from community builders and invested in them from the very beginning.   

What I love most about WLV is our community of designers, developers and amazing authentic creators like serial creative founder Sophia Amoruso, Instagram poet Rupi Kaur, streetwear founder Bobby Hundreds, law student turned influencer and creative director Margaret Zhang, and my investors who have built the world’s greatest platforms that started as entertainment and creative outlets and scaled into platforms for new classes of work like Spotify, Twitch, Zoom.

We ‘think different’ and ‘look different’ by design.

Last week, we released our new brand and we’ll continue to share fund updates on Twitter, interview creators on Instagram and as always, I’d love to hear your thoughts and comments on this post. Say 👋 on Twitter

@WorkLifeVC on Instagram

How Megan Rapinoe and re—inc are challenging the status quo in the time of COVID-19

My exclusive interview on building a remote startup, angel investing and political activism when sports and entertainment are at a collective stand still

For the first time in modern history, most of the world is at a collective stand still. 

Many industries like professional sports and entertainment are on pause until further notice. The Hollywood Reporter estimates the film industry alone has already seen a loss north of $7 billion, and the industry is bracing to take a total of $20 billion off the books.

In this extended period of uncertainty, Megan Rapinoe and the US Women’s Soccer team are not slowing down. In fact, they’re operating with the same speed and intensity that they bring to the field as venture-backed founders, philanthropists and angel investors.

I call this triple threat mentality: founders, creators, and talented individuals balancing multiple careers or creative projects that reflect their multi-dimensional set of skills, interests and values.

For Megan Rapinoe and the founding team at re—inc, they’re leading the charge during COVID-19 and taking action in three key ways:

  • Scaling a venture backed startup, that’s been fully remote from the beginning.

    They use Slack, Zoom and other tools that have been recently pulled into mainstream culture. For the first time in history, Saturday Night Live started this week with Kate McKinnon saying: "And live from Zoom..."

    To say that we’ve entered a new world for work would be understatement. Work and life have converged in ways that no one could have predicted.

  • Angel investing and spearheading philanthropic initiatives to build the next generation of companies challenging the status quo and support non-profit relief efforts for athletes, creators and individuals directly affected by COVID-19.

  • Driving political discussion online to educate the American people.

    Megan Rapinoe’s live discussion with US Representative Alexandria Ocasio-Cortez served as the first mainstream break down of the $2-trillion economic stimulus package passed in March and she continues to be a strong voice for the American people on navigating uncertain times ahead.

On Worklife Live, I sat down with Jessica Tillyer, re—inc’s Co-Founder and Chief Brand and Experience Officer, and Jenny Wang, re—inc’s Co-Founder, for a conversation on navigating remote work and building a values-aligned company that’s challenging the status quo and breaking down stereotypes on what’s possible for triple threats in every industry.

We’ve turned this exclusive interview into an actionable guide for early stage founders and anyone pursuing new creative projects.

You’ll learn how to:

  • Build a community that becomes a movement

  • Adopt the mindset of an athlete: focus, determination, coachability

  • How to leverage your personal brand, company resources and investor network for good


Build a community that becomes a movement

The celebrity-led startup isn’t new. Movie stars, athletes, and influencers alike have made forays into business ventures ranging from wine to make-up palettes. Yet, re—inc and its famous founders have done something decidedly different with their own venture-backed startup. Their clothing is gender neutral and they’ve eschewed cookie-cutter classification by producing everything from artwork to experiences, they aren’t another celebrity selling branded merchandise. In a crowded world of consumer products, where everyone is looking to differentiate, re—inc has created a movement that extends far beyond sports fans into a multi-dimensional battle cry for individual purpose and power.

Every aspect of the model challenges the status quo: values-first, not celebrity-first

This isn’t coincidence –– it’s by design. re—inc knew the values they wanted their brand to embody before they’d even dreamt up the product or the name “re—inc”:

We started from a place of brand and business before we even figured out what the product was, which meant when we were from the very beginning, writing what our purpose statement was and what our values were.” –– Jessica Tillyer

The Founding Team at re—inc developed a brand that centered around “equity, creativity, art, and originality” that arose out of virtual white boarding sessions on Zoom. How did they get there? Rather than joining the ranks of just-another-celebrity-lifestyle-brand, they thought deeply about the core values and purpose of their company and what they wanted to accomplish, They reflected on personally formative experiences that could inform what their brand could represent. A few concrete ideas emerged:

  • Why just resist when you can reimagine?

  • Reimagine the status quo.

  • We're not interested in regular.

These statements and questions inform how re—inc approaches everything they do –– whether it’s bringing underrepresented collaborators to the table or dropping a WFH Capsule Collection as an opportunity to re-invent work culture and create a movement for a more inclusive and worklife moving forward.

Every action impacts your reputation and ability to connect with your community and hire top talent

Your brand isn’t your logo. It’s easy to think of your brand as a checklist that includes creative assets like “watermark”, “brand colors”, and “typography”. These are certainly a part of a brand, but they’re not the only considerations. They also shouldn’t be your starting point. Instead, consider this:

A brand is really just a feeling or emotion and the impact it has on you.” –– Jessica Tillyer

Startups typically view “brand” as a big company concept that becomes a priority once you’ve scaled your marketing team. But today, every move a founder makes publicly contributes to the perception of the company and its ability to connect with customers and hire top talent.

A few questions to ask:

  • Are you listening to your customers?

  • Are you watching the macro-environment and ways to support the community around you?

  • Are you operating with the speed required to deliver noticeably better customer experience?

  • Are you investing in brand identity and creatively expressing your values?

By closely considering these questions, you can develop your brand as a feeling and cultivate a community that scales into a movement and not just a look or marketing tactic.

Brand starts with founders and scales with the company across design, development, customer support, and everyone else whose work impacts the customer experience.

Examine if your values are internally and externally consistent

To build a values-aligned company, what a company says externally has to be consistent with the experience and values for employees internally. People are increasingly allergic to marketing and choose products and services with honest, transparent, and consistent values.

At re—inc, values are the foundation of what they share with the world and how the company runs, including who they choose to work with:

We're so careful with all of the partners that we work with. We created this company to create a new pie, and we feel very strongly in equity and distributing that pie. For example, when we look at photographers, we want to make sure that the crew that we work with are representational of the future that we're trying to create.” –– Jessica Tillyer

"When we raised our first round of funding, we took the same approach. Our lead investor is an incredible woman who was a D1 National Champion in women’s soccer at Stanford, and is today a brilliant investor at one of the best Sand Hill firms and known advocate on sports for social change and impact." –– Jenny Wang

Cultivating a community isn’t just important to attract early users. It’s also crucial for recruiting and retaining talented team members to help drive your company vision forward. When a company’s internal culture fails to deliver what it represents externally, you’ll see dissatisfied employees move on and take their negative experiences with them. By creating a culture that’s internally and externally consistent, you can build a single cohesive story that scales into a supportive movement that impacts future companies across different industries.

Adopt the Mindset of Winning Athletes

Re-Inc has been intentional on creating a new category that’s different from other celebrity-founded startups. The company is grounded in modern values and delivers the same work-ethic Megan Rapinoe, Tobin Heath, Meghan Klingenberg, and Christen Press bring to the field to score goals and win championships:

I've come to realize, it's all about precision and incredible gut instincts and being able to trust those. If you are the best soccer player in the world, your sense of precision and instinct is probably better than any of the rest of us.” –– Jessica Tillyer

A company’s identity evolves over time and require founders to be agile, collaborative, and forward-thinking in the same way that they view the evolution of their product.

In the case of re—inc, the team has been fully remote from day one and continue to be ahead of the curve with gender neutral and work from home ready capsule wardrobes.

Be coachable and receptive to feedback

Starting a company is a team sport. Founders need to trust designers to create a visual identity and design a product that’s intuitive, engineers to efficiently build a stable platform and customer support to be on the front lines to solve time critical concerns, especially during moments of crisis like we see today.

In tough times, the re—inc’s Founders know to adapt and drive towards the same goal: 

If you have been an athlete your entire life, you're used to being coached constantly and you're really, really open to feedback and coaching. That's something I've really learned from our founders. So often in the workplace, we're taught to protect ourselves from coaching or feedback and say, ‘Hey I'd love some feedback,’ but that's not always true. Something that I've just really, really loved is our company is so open to coaching and feedback. [We] allow ourselves to be very vulnerable in that way and know that we all have each other's best intentions [at heart].” –– Jessica Tillyer

For early stage founders, especially first time founders, seek out coaches that can give you honest feedback on personal strengths and ways you can augment the team’s ability through angel investors, advisors and new hires.

In Re-Inc’s case, they sought out Jessica Tillyer for her background developing new brands for Fortune 100 companies and entrepreneurs, including a client list that includes Eileen Fisher, American Express, and IBM. Tillyer initially joined Re-Inc as a consultant and an advisor, but went on to join their team full time as a Co-Founder and their Chief Brand and Experience Officer.

To find a good coach, start by asking questions:

  • Does the current team have the bandwidth, experience, credibility to deliver what’s expected at this time?

  • Are there ways that the team move faster or more efficiently alongside trusted peers or companies with similar values or strategic alignment?

  • Can the team leverage angel investors or advisors with a specific skillset to keep the team lean and highly efficient?

These honest questions help founders develop a coachable mindset that’s centered on building a top-performing team.

Hone your instincts for quick decisions

Early stage company building requires rapid iteration and in recent weekly constant and thoughtful reforecasting, especially when it comes to internal culture and team planning. In the world today, companies have to balance speed and iteration on the product side with a thoughtful and strategic approach to how they engage with individuals on social media, acquire and engage individual customers and onboard and offboard individual employees.

Founders today still have to make fast, short-term decisions, however each decision must be calculated and collectively striving towards the same long-term goal.

The Founders of re—inc have this ability in spades:

The forward mentality is very much an attacker one, but also a try and fail fast one, which I think re—inc has. We've been able to iterate very quickly [and] try and test out new things. We haven't shied away from new maneuvers or new ways of connecting with people.” –– Jenny Wang

Leverage Your Company’s Visibility for Good

Building a community or audience comes with an opportunity to do good, whether that’s partnering with organizations to support a worthy cause or driving important conversations forward. Find the right causes and conversations by digging into your company’s core values and carving out a space where you can pay it forward in a way that feels natural.

re—inc founders like Megan Rapinoe have used their social platforms to be vocal about issues like migrant justice and equal pay. Most recently, Rapinoe recently sat down with US Representative Alexandria Ocasio-Cortez for a discussion on the stimulus package. Founder activism naturally translated into their company being focused on causes of its own. For Re-Inc, that was giving back in a way that was tied to artistic expression:

We have always been committed to progress in art. That is fundamental to our purpose. We believe to create progress, you also need art and creativity as inspiration.” –– Jessica Tillyer

re—inc hosts art auctions with every new collection they release. Their last one included a piece created by Tobin Heath. They gave 17% of the proceeds to Alternate Roots, a Southern USA based arts service organization that supports the creation and presentation of original art, and an additional 17% to the National Domestic Workers Alliance, an advocacy organization promoting the rights of domestic workers. 

Give what you can

In the early days of a startup, charitable giving and partnering with nonprofits can feel like a large monetary and time expense for a small and scrappy team. However, leveraging your network of founders, investors and community for good doesn’t need to become an exorbitant expense to your team –– instead, give what you can.

For re—inc, that was a recent donation to Inner City Arts, an LA-based organization:

We had a conversation and realized we wanted to do something that wasn't related to our products at all. So we gave $10,000, which was a small donation, but from our perspective as a tiny little startup, it was what we could give and feel really good about”. –– Jessica Tillyer

Consider creative and lean ways your company might be able to help values-aligned organizations or create your own dedicated charitable contribution arm

  • Set aside team time for virtual volunteering: 9 places to virtually volunteer

  • Give employees monthly spend to support local restaurants and cafes

  • Use your product for good: female founded, low-alcohol apéritif company Haus launched The Restaurant Project to co-create custom apéritifs with popular restaurants across America.

  • Offer your software for free to non-profits and COVID-19 critical projects

Put people before profits

In moments like this, of course there's going to be paralysis from a business perspective. You're going to feel a sense of paralysis. From a personal perspective, it's emotionally really difficult. But I think as leaders, our responsibility is to drive forward. Not drive forward to make sales or anything like that, but to drive forward, to give people inspiration and to help people get through this moment.” –– Jessica Tillyer

With the US Women’s Soccer Season cancelled, the player founders are at re—inc are finding creative ways to connect with their fans and supporters using the power of social media:

“When all of this happened and all of a sudden [Megan Rapinoe] was at home, we realized there was this huge opportunity to bring that conversation even closer to our community through Instagram Live. So we started doing these Reset the Table conversations on Live. [Megan Rapinoe] was hosting them and they've been going really great.” –– Jessica Tillyer

At Worklife, we believe work is increasingly multi-dimensional and startups can learn from triple threats from every industry: founders, creators, and individuals balancing multiple careers or creative projects.

WorkLife is a way of life.

re—inc embodies this in entirety:

Our CEO Christen Press [is]...having the absolute highlight of her career. She is outperforming on the field and doing better than ever. Almost every day before she goes into the field, she's Slacking with me until the very last minute. We're working out the final details.” –– Jessica Tillyer

Intersections are where the magic happens and the best platforms have all started with a small number of users and scaled into cultural movements that reimagine both work and life. The best consumer platforms started as entertainment and scaled into new classes of work: streamers on Twitch, influencers on Instagram and retailers on Shopify. And we see today, the best workplace products can scale into mainstream consumer adoption: Zoom is 2020’s hottest yoga studio.

Watch my conversation with Jessica Tillyer and Jenny Wang on Worklife Live for additional insights on how to start building a community today and the tools re—inc is using to stay connected and productive as a remote team.

As always, I’d love to get your thoughts and feedback on Twitter.

Why "Crossing the Chasm" doesn't work for workplace products

How to build a balanced self-serve and enterprise-grade platform with multiple reinforcements

After Michael Grinich left Nylas to work on a new company, he interviewed dozens of cloud companies and consistently heard three things when companies moved from a self-serve product & go-to-market strategy to a hybrid model of self-serve + scalable enterprise:  

  1. Startups wait too long to talk to enterprise companies: founders viewed GTM as a binary decision to start either self-serve vs. top-down sales. Most start with a self-serve strategy that’s most compatible with engineering, product and design founders, especially ones coming from a high growth consumer company 

  1. Product & Engineering teams inaccurately forecasted the time and budget required to build enterprise-required features ie: SSO/SAML, audit logs, etc. 

  1. GTM teams required a significant shift in company strategy and team priorities: pricing, positioning, packaging, sales collateral and an appropriate team structure that meets both self-serve and enterprise customer demands

While consumer companies “cross the chasm” by scaling from early adopters into mass market adoption with essentially the same product, enterprise founders have to take a more strategic approach and continuously ship new enterprise-grade features in parallel as they continue to iterate on the core self-serve product. 

Enterprise startups don’t cross the chasm, they bridge the chasm with a balanced self-serve and enterprise-grade platform with multiple reinforcements.

Startups entering a large market with little competition have the ability to stay self-serve for as long as possible, but for most enterprise founders the ability to build enterprise features while still shipping new, innovative self-serve features will be their greatest competitive advantage. 

A Product Manager at Slack told Grinich: "I would guess we've spent $30M building enterprise features...and we're probably only halfway done."

While this interview was conducted nearly a decade into Slack’s journey and shortly after the launch of Microsoft Teams, it serves as a both a positive reinforcement that the bottom-up playbook is a strong launchpad for startups and a reminder that self-serve is a starting point and not an end point. Self-serve leaves whitespace for new entrants and market incumbents to fast follow with an unfair distribution advantage. 

Eventually Slack moved upmarket, built their Enterprise Grid, and won over large corporations after nearly a decade of attracting startups and small businesses while incrementally scaling into larger companies. Slack serves as a good reminder that the move into enterprise brings unpredicted costs, structural and cultural changes to the team and often times wages war with a large challenger, in Slack’s case Microsoft.

For most early stage companies who solve a known problem for a specific buyer with a single product, a self-serve motion needs to be met with an expansion strategy into new use cases, products or verticals. Companies working towards venture-scale growth have to move upmarket and sell to enterprise customers who provide repeatable annual recurring revenue, are less likely to churn, and historically, endure in times of economic downturn.

Despite the potential upside, many self-serve businesses hesitate to transition from self-service to enterprise-grade SaaS. Why? There’s a chasm between points A and B, as pointed out by Geoffrey A. Moore in his bestselling book Crossing the Chasm: Marketing and Selling High-Tech Products to Mainstream Customers

While Moore is right about the problem, he’s wrong about the solution: the gap between self-serve and enterprise sales can’t be crossed, it needs to be bridged.

There’s a common misconception that enterprise companies are either self-serve or bottom-up. This fallacy creates a fairly large psychological hurdle for early stage companies who view the decision as a binary outcome with immediate impact on engineering, product, and design teams and noticeable changes to company culture as the team begins to hire for marketing, sales and customer success. 

This is where Moore’s framework for Crossing the Chasm is easily misinterpreted by enterprise companies. Enterprise startups don’t cross the chasm, they bridge them by building a balanced self-serve and enterprise-grade platform with multiple reinforcements.

Grinich, now the Founder and CEO of WorkOS, has spent nearly a decade in the cloud, including working at Dropbox. He’s developed deep insights on how companies can win enterprise customers by bridging the Enterprise Chasm: 

In B2B cloud SaaS apps, there's something called the Enterprise Chasm that separates small early adopter users from large enterprise companies. Bridging this really efficiently and quickly is the most important key to winning a product category across the whole market.

At SaaS School, an invite-only program for entrepreneurs to learn from leading experts at the fastest growing software companies, Grinich provides an insider look on what it takes to cross the Enterprise Chasm. He emphasizes that Founders don’t need to make an either-or decision –– startups can and should offer self-serve and enterprise options in tandem.

Grinich provides answers to three key questions that startups have before embarking on the quest to win their first enterprise sale:

  • What makes it difficult to cross the Enterprise Chasm?

  • Is bridging the Enterprise Chasm worth it?

  • How can my company make our app-enterprise ready?


What makes it difficult to cross the Enterprise Chasm?

The self-serve SaaS model begins with bottom-up evangelism from early users and scales into highly efficient and low-effort revenue growth, combined with low operating costs, that allow companies to hire fewer and more senior people. Countless seed stage and Series A startups have adopted this model and found early success with relative ease. Unfortunately, adopting a model for enterprise sales isn’t as simple or straightforward.

Bridging the chasm from self-service to enterprise customers is challenging from multiple perspectives.

From a leadership and management perspective, it's a big challenge to hold these two states in your mind and motivate the team with both. It's not easy –– there's technical challenges, there's organizational challenges, there's motivation challenges. Figuring out what to do is challenging and figuring out what the first steps are is really challenging. It can feel overwhelming...that's one reason why companies don't proactively do this and would rather go back to the safe place, which is building for themselves or building things for their friends, even to the detriment of the longer term business.

To ready founders for the challenges that lie ahead, Grinich points to the common hurdles startups can anticipate as they go down the path toward the enterprise market.

Enterprise features are complicated. Because there are so many details involved with building enterprise features, there’s a larger opportunity for bugs to crop up during the process.

Developing complicated features takes a long time and requires a meaningful investment. If you want to gear up, make sure you’re ready to dedicate the time and money required. Building enterprise features is a marathon, not a sprint.

Engineers don’t always like building enterprise features. In many cases, companies are dealing with legacy technology and coding enterprise features isn’t fun for engineers. On top of this, these features aren’t visible to end-users; they’re only visible to IT managers.

Enterprise requirements generally aren’t shiny or fancy features. Instead, they’re low-level integrations or security features. Engineers rarely get recognition or promotion for them, which means they’re not jumping up and down to work on them.

Feature prioritization is hard. Figuring out the importance of different enterprise features can be daunting. It requires in-depth customer research with enterprise ITs to collect requirements and feedback to figure out which features get prioritized over others. 

Grinich notes companies should prioritize features based on the needs of future potential customers –– not just early-adopters:

It's not based on who your current customers are, your current early adopters, but who you're going towards. You might not be talking to the right people... and build the wrong stuff for a long time. It's hard to develop confidence around knowing what to build when you're going [to the enterprise] market.

The most significant difference between self-serve and enterprise-grade platforms is that the user is no longer the buyer. Your buyer is now somebody at an executive level that has different needs, priorities, and expectations. This adds a layer of complexity to the process.

Splitting focus is necessary. There’s a false dichotomy between self-serve and enterprise-grade SaaS. Not only can you have both, but it’s preferred.

If you don't build for enterprise, a competitor will come in, take that market, and make it nearly impossible to win it back. On the other hand, if you don’t keep building end-user features, a new startup can pull users away with shiny new features. Splitting focus, while difficult, is essential.

Is bridging the Enterprise Chasm worth it?

Transitioning from self-serve to enterprise is a daunting and challenging process. It requires time, money, and for companies to make a cultural shift. Is it worth bridging the chasm? In short: yes. 

Bridging the Enterprise Chasm, comes with key benefits:

  • Increased product defensibility. Introducing enterprise features means increasing product differentiation, which will help you build a moat around your business. 

  • Decreased customer churn. Enterprise deals bring stability, predictable sales motions, and a significantly lower churn rate. That means customers stick around longer so the growth compounds over time.

  • Expanded market size (TAM). If you’re selling mostly to SMBs, at some point, you’ll run out of customers. Getting your foot in the door of enterprise SaaS will open up room for growth.

  • Accelerated revenue growth. Bridging the Enterprise Chasm will help you increase revenue and sit behind the steering wheel instead of being dependent on venture capital.

Unfortunately, the risk of not bridging the chasm isn’t simply inertia; it’s an eventual downward spiral. Not going upmarket (or waiting too long) leaves your startup vulnerable to your competitors. While you’re preparing for a seamless shift, challengers may enter the market and offer features that the lucrative enterprise segment finds appealing, after you’ve done the work of building an innovative product and educating the entire market. 

If you don't go up market to the larger segment, you can have the instance where a competitor is able to come in and capture those lucrative enterprise deals where you've done all the work to warm up the whole market.”

Formulating a strategy to cross the Enterprise Chasm opens up new opportunities while simultaneously defending your position against newcomers.

How to make your app enterprise-ready

Every transition needs adjustments and companies need to evolve holistically to cross the Enterprise Chasm. To successfully make the leap from A to B, companies need to be ready for some go-to-market changes related to the product, positioning, packaging, pricing, security, compliance, and many other aspects of their business. However, Grinich recommends that founders focus on one area first –– product:

You already have demand from people who are in enterprise environments that you can capture. And product changes are sort of the most universal...they're the same things across multiple product domains. Product wise, the requirements are relatively similar [for enterprise customers].

Even though every business is unique, there are three commonalities across industries that enterprise IT managers want from a product: 

Visibility. Knowing what’s happening is one of the biggest concerns for enterprise IT managers. The easiest way you can address this need is to build an audit trail

This is an activity stream that shows what’s happening in the application, and almost every enterprise SaaS product has this feature. When implementing this, make sure that the audit logs match standard schema, they’re searchable/filterable by IT admins, and they’re exportable in different formats (like CSV, Splunk, S3 buckets). 

Control. Enterprise IT managers want to be in control and choose what can and can’t happen in the tool. The first thing to do is to allow users “Single-Sign-On” via their identity provider (e.g. Okta, G Suite, ADFS Microsoft, One Login, Ping, Gluu, WS02, Shibboleth, KeyCloak). 

This is required to enforce their IT security policy, so if you want to play with the big companies (or nowadays even mid-market), you have to provide this feature.

Trust. Enterprise customers expect guarantees. To seal the deal, they want a partner they can trust –– from reliable customer service and secure data management, to a commitment to quality of services (SLA).The first step is building your Security Policy document

Aside from this, some of the surveys that customers might ask you to fill in during a vendor security assessment include things like the Consensus Assessments Initiative Questionnaire (CAIQ), Critical Security Controls, Standardized Information Gathering Questionnaire and the most common in the Silicon Valley - the Vendor Security Alliance Questionnaire (VSAQ). 

Aside from the technical nuts and bolts of the processes and procedures to create trust with enterprise customers, Grinich summarizes how startups should approach this process:

What you're doing here is codifying your security practice and your security positions in a way that you can communicate it to them...This is not actually a product or technical thing. It's expressing what you do operationally inside the company to show that you're trustworthy.

Leveraging WorkOS to cross the Enterprise Chasm

Grinich highlights specifics on building visibility, control, and trust into your company’s products to win enterprise customers, but emphasizes these are only the first steps of many:

This is not an overnight process. It takes time, so be patient. You need a balance between talking to your really excited early adopters and getting a lot of feedback from them and trying to close them, but not reading too much into them and understanding there's a bigger, brighter world out there.

Though preliminary, these first steps can be enough to garner several million dollars in enterprise ARR. Grinich recommends startups think early about bridging the Enterprise Chasm to unlock new opportunities and create a safety net:

Getting a handful of enterprise deals can be enough to boost your revenue and push you into the next series B...If you don't think this applies to you and you're thinking, ‘Oh, we'll just do self-serve forever,’ I would really start questioning that and really think about the opportunity.

Transitioning from a self-serve business to a balanced self-serve and enterprise-grade platform takes time and energy. Grinich’s company, WorkOS, is a developer API that helps products become enterprise-ready. This lets startups sell up-market and unlock revenue from large customers. Their SAML/SSO integration is completely free but still in private beta. (Let me know if you’d like an invite and I can connect you with the Founder).


Watch Grinich’s full SaaS School talk for additional insights on why Box beat Dropbox in the game of enterprise and how the role of Product Manager needs to be adapted for bridging the Enterprise Chasm.

As always, I’d love to get your thoughts and feedback on Twitter.

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