Reflections on SaaS & Careers in Tech from Andrew Bartholomew, Yale College ’09, Strategic Vice President at SquareSpace

After Andrew Bartholomew’s visit to Yale SOM, we got a chance to ask a few questions. Andrew’s work at Squarespace gives him a great perspective on the SaaS (Software as a Service) business model, and his success illuminates the importance of “integrative thinking.” In addition, we got to ask his advice on tech careers and benefited from his insider knowledge on the future of Squarespace.

Yale PoE: Why are so many businesses moving to an SaaS model? What are the challenges and benefits to this type of business model?

AB: SaaS is everywhere now—there are many large SaaS-first companies (Squarespace or Slack, for instance), and others that have evolved into SaaS (such as Adobe’s Creative Cloud, or Microsoft's Office 365). The advantages are significant:

• Simpler go-to-market. Companies don't have to do on-site visits and install servers or software. Ideally they just point potential customers to a website and let them sign up.
• Lower customer acquisition costs. The result of this simpler go-to-market is, generally, lower customer acquisition costs. This means companies can scale up faster once they find product-market fit.
• Practically infinite scale. A growing customer base can piggyback on the up-front investment in application development and infrastructure.

There are some tradeoffs though:

• Longer payback periods. You front load the platform development and customer acquisition cost, but because SaaS is paid for with a subscription you make the money back in small increments over time. This means that scaling SaaS companies can be extremely cash intensive.
• Constant proof. This is the flip side of simpler go-to-market and lower customer acquisition costs. Because the barrier to trying a competitor is often quite low, you as a company have to constantly deliver value to customers.

At this point, many companies have proven out the durability of the SaaS model and customers are increasingly familiar with it. The result has been an explosion of SaaS investment and growth in recent years and it's exciting to be a part of that.

Yale PoE: In an industry where people change companies often, you’ve stayed with Squarespace and risen quickly. How did you decide to invest your career heavily in this company?

AB: It feels more like the company chose me than the other way around. I joined Squarespace almost six years ago when I decided to skip law school and instead build deeper technical skills. I’d been doing technical work at the New York District Attorney’s Office and the idea of being surrounded by engineers who were much more skilled than me sounded fun and low-risk compared to student loan debt—but I can't claim I had any broader plan. Since then the company has grown from 60 employees to over 700, and every day I’m grateful for the skill and thoughtfulness of the people I get to work with.

I think staying at Squarespace comes down to the fact that I’m so motivated to learn new things. The pace of the company’s growth has allowed me to take on what feels like entirely new work each year. That diversity has kept me constantly engaged, excited, anxious, and curious.

Yale PoE: While on campus, you mentioned that you are constantly in “learning mode.” Where do you go to learn new things?

AB: The place I start is by asking the question, “What kind of thinking do you want to be good at?” For me the answer is integrative thinking: building a model of different points of view to find an optimal path through. This type of thinking is different from deep excellence in a single craft, or the discovery of truly new knowledge. It rewards a working knowledge of many different mental models.

So my approach to learning is purposefully scattered. I try to read things that have only tenuous connections to my work or current interests. My learning ecosystem:

• Twitter and Feedly: Lots of reporters, economists, academics, and writers. I scroll through once in the morning and once at night looking for things to save to Pocket and read on the subway.
• Pocket: I’m an obsessive user. (The recommendations are now surprisingly good, too—in addition to saving things from Twitter I consume a lot of the recommended articles.)
• Books: Completely scattered and often based on recommendations from my author/editor wife. A box of books arrived today at my desk that includes a book about octopuses, photography assignments, and a graphic novel.
• Podcasts: My least diverse medium. Exponent, Longform, Rationally Speaking, Ezra Klein, How I Built This, FiveThirtyEight, HBS Cold Call.
• Work: I cast as wide a net as possible internally, staying in regular touch with people all over the organization so I can keep a roughly complete picture in my head. I also never shy away from taking on a new responsibility because doing is the best way to learn.
• Travel: I love going to a new place, walking through the streets with my camera and simply observing. The contrasts with home reveal all the hidden assumptions I hadn’t considered before.

Yale PoE: What advice would you give to MBA students who are interested in pursuing careers in marketing or product management?

AB: Giving broad advice is something I shy away from because my experience is still, in the grand scheme of things, quite narrow. I’ll just note a couple of behaviors that I’ve seen be consistently valued:

1. Ask questions. It took me a while to figure out that none of us really knows what we are doing. We all have different experiences and skill sets but figuring out how the whole thing fits together will always be a process of exploration and experimentation. Naive questions are often the most valuable in these circumstances because they often force us to examine our fundamental assumptions. (There’s also lots of evidence that great managers set themselves apart by asking more and better questions.)
2. Do the work. It’s amazing how big a differentiator this can be. It’s tempting to let a project slide, to put off something that seems small, or to focus only on the fun parts of the job. But reliably delivering what you promised is a highly underrated talent, rarer than you’d think, and something managers deeply depend on.
3. Try something new. Don’t spend too much time worrying if what you’re doing today has some clear path to what you want to be doing in 10 years. Instead look at each day as a learning opportunity and build the story based on the things you see in the rear view mirror.

Yale PoE: What are some exciting things that Squarespace has in the works?

AB: There’s a lot of product innovation happening (including new tools for online merchants), but I think the project that gets me most excited is internationalization. Squarespace has been available only in English for the first 14 years of its history; that’s about to change. There’s so much we’ll only be able to learn by doing. Learning about new customers, new competitive dynamics, and new go-to-market options makes our international push both very exciting and, honestly, a little scary. That’s exactly the right balance to keep me engaged and motivated.