Datadog’s Alex Rosemblat on the Importance of Really Knowing Your Customers

Editor’s Note: This is the second half of a two-part interview featuring Alex Rosemblat. In the first installment, Rosemblat provides in-depth insight into how Datadog transforms non-technical sales hires into “almost engineers.”

Early Career War Stories

Sometimes, the “hard way” is the best way to learn a lesson. Take it from Alex Rosemblat, VP of Marketing for Datadog, a monitoring service that aggregates data from disparate sources to provide Dev and Ops teams with a unified view of large-scale application infrastructure typically running on a public cloud. Long before Rosemblat joined Datadog, he and a classmate at MIT’s Sloan School of Management partnered to create their first software product. Though the product solved a legitimate problem they each had encountered in their respective careers, it wasn’t proving viable in the market. Something was missing. “In our previous companies, both my co-founder and I had struggled to
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When bootstrapping a SaaS product, what should you be aware of?

Just a few observations from bootstrapped SaaS companies I’ve had some involvement with:
  • It probably will take 3–4 years longer to get to $10m ARR or so. I don’t fully have the data to support it, but usually, bootstrapped startups take longer. Atlassian and Qualtrics took longer to get to $10m ARR. But after that, they grow just as quickly.
  • You or your co-founder will freak out about how expensive (and for the best ones, highly compensated) sales people are. Once you have a few reps that are doing a good job closing, you may get mad / frustrated that they are making far more than anyone else in the company. Even if you don’t get mad, one of your co-founders might. Bootstrapped SaaS companies seem to have trouble making the transition to the fact that your best sales reps should be making real money.
  • You may have a harder Continue reading "When bootstrapping a SaaS product, what should you be aware of?"

Start with the Premise that Everything is Noise

We each know that focus is the most effective way to work, but hearing the mantra to focus doesn’t help narrow our scope. What’s the best way to focus? Start with the premise that everything is noise and then work to find the exceptionally valuable or important things for each day and for each project. That’s the thesis of a book called Essentialism. Defaulting to the idea that everything as noise simplifies decision-making about time allocation. In many areas of our life, we classify noise unconsciously. Archiving email spam, filtering out irrelevant boarding announcements at airports, and driving by habit. How can we replicate the same idea at work? By asking, is this noise? Is this among my top 3 priorities? Will this effort be exceptionally valuable? I remember walking through an exhibition at the SF Moma that showcased the design work of Dieter Rams. The SK-4 phonograph player above Continue reading "Start with the Premise that Everything is Noise"

The Official SaaStr Podcast #019: David Cancel, CEO @ Drift Hires People, Not Skills


Welcome to Episode 19! Following our meeting at SaaStr Annual 2016, I am thrilled to welcome David Cancel. Now David really is a serial entrepreneur, having founded 5 companies, with the last, Performable, being acquired by HubSpot, resulting in his taking up the position as Chief Product Officer at HubSpot. Now David is the CEO @ Drift. Drift allows you to talk to your website visitors and customers in real time. David is a master when it comes to hiring, company culture creation and maintenance, and team building, and we dig into all that in today’s episode, as well as:david_cancel

Why David’s golden rule to recruiting is hiring people, not skills. Why is cultural fit so important for future employees? How can you test for it in an interview? Can you hire a team of all A-team players without having insane competition and friction? What does David mean when he Continue reading "The Official SaaStr Podcast #019: David Cancel, CEO @ Drift Hires People, Not Skills"

How hard is to build SaaS from zero to $100k MRR without investors?

I think my learning is three-fold. First, it depends on the team. Most of the SaaS unicorns have been built on at least some venture capital … but a number haven’t. Atlassian ($5b market cap), Qualtrics (private unicorn), etc. have gotten there without it. The real question is How Lean Can You Be. Second, most bootstrapped SaaS companies grow slower in the earlier days without capital to boost them to Initial Traction and Scale. Atlassian and Qualtrics took an extra 3–4 years to get to Initial Traction and Scale vs. some of their peers. But … Third, once any SaaS company hits $8-$10m in ARR … they all grow at the same rate. So if you can suck it up, and somehow, with a super-lean team, get to $10m ARR … then that’s another great way to get there. Especially in a less competitive space, where a little extra time Continue reading "How hard is to build SaaS from zero to $100k MRR without investors?"

Who are the natural strategic acquirers for the typical SaaS product? How many viable acquirors are there?

There are more potential acquirers than you think … but the odds are far lower that an “obvious” candidate will ever buy you than you think. Let’s break this apart. First, the “obvious” guys. That Salesforce, Google, Facebook, whomever will buy you. Well, here’s what I learned on both sides of those sorts of deals (as a VP at an acquirer and CEO/founder of 3x acquiree) … the “list” is both obvious … and odd. What I mean is yes, there are always 2–3 companies a BigCompany really truly 100.0000% wants to buy. Instagram, then Snapchat, then WhatsApp were clearly on Mark Zuckerberg’s Must Buy list. He got 2/3 of them. But … beyond that, there are 1000 other applications that it would make 100% logical sense to acquire to an outsider. That any given acquirer isn’t remotely interested in buying. And … the priority list changes. Sometimes annually.
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What Everyone Should Know Before Starting a SaaS Company

Recently we did a great AMA-style “Quora Session”.  You can see the whole list of questions and answers here.

One fundamental question asked was What Everyone Should Know Before Starting a SaaS Company.  I think we’ve hit the core things on SaaStr over the years, and we’ve added more structure on the SaaStr Academy … but this was a good chance to pull together perhaps the 5 most key things to know IMHO/IME.

The top 5, with links to the related posts:

Apartments are the hot new tech sector

apartments in china Welcome to the land technology forgot. High-end leases negotiated and signed via fax. Millions of dollars in apartment inventory tracked on whiteboards with dry-erase markers. Client histories recorded in longhand in legal notebooks and stashed in manila folders. Multi-family real estate (i.e. apartment buildings) is one the fastest-growing sectors in the country right now. Read More

At what point in time did you know EchoSign was going to be huge and what signaled that?

Unfortunately I didn’t really understand how big the market would be until after the acquisition had closed. We’d crossed $1m MRR / $12m ARR during the deal and after that, after our acquisition … revenue accelerated. There were many reasons for it, but one was market pull. Not much else changed — same team, same product, for most part, same customer acquisition channels. I just didn’t really see it, not really, until I wasn’t running it anymore. View original question on quora