Career Update: I Joined RudderStack as Director of Customer Success

We’ll start with the big news: after several years of consulting, I joined a San Francisco-based startup called RudderStack1. I’m incredibly excited about the product and team, but more on that later.

The consultancy, Yield Group, is still trucking, helping mid-market companies achieve data-driven growth. I’m also an active part of the team running OffSite, an ad tech product that we launched out of the consultancy.

I’ll share details on RudderStack later in the post, but first, a quick look back.

A quick look back

Almost a decade ago, I wrote about my first major career change2 , moving from the world of creative marketing agencies to the world of early-stage software startups and investing.

Re-reading that post gives me pause as I consider the seeds God was planting as far as my future career journey. I certainly had high hopes as a hungry professional in my early 20s, but would never have imagined the experiences that were to going be logged in my personal history.

The quote about procrastination from that post also makes me smile, because the words were as true for my transition to RudderStack as they were for my transition to a software accelerator program all those years ago:

The work you do while you procrastinate is probably the work you should be doing for the rest of your life.

–Jessica Hische

When work doesn’t feel like work

At Yield Group, I did many things, including strategic advising, training and execution. My specialty and passion, though, was marrying strategy with the technical plumbing that enables data-driven growth.

Leaning on my learnings and mistakes from scaling my own company, I had the opportunity to architect and implement several “customer data tech stacks” for a variety of different business models.

As I reflect on those projects, the moments where I had a direct hand in seeing the marriage of strategy and technology drive stepwise gains for a business were the times when work didn’t feel like work.

Enter RudderStack

Part of my core thesis when architecting a customer data stack is that the foundation is always comprehensive collection at the data layer. Anyone close to data-related  work knows that accomplishing comprehensive, clean data collection is no small feat (and even then you need to route the data).

There are multiple tools out there that help with this process, but as I helped Yield clients shop for and stand up solutions from various vendors, I began to see a giant hole in the market. Long story short, the pricing models and feature sets for available options had major problems. Either the unit economics of the pricing model only worked for specific business models (high-value B2B), the cost and feature set were built for large enterprise, or the infrastructure simply wasn’t robust enough for scale.

An entrepreneur at heart, I first considered building an alternative, but then found a company attempting to fill the hole with a new product. After some digging, I attempted to buy the company along with my business partners and signed a term sheet, but in diligence the product itself turned out to have serious technical problems.

Shortly after the deal fell through, we found a post on Hacker News3 about a new project called “Rudder” (now RudderStack), an open-source alternative to the major player in the market (which I had used extensively, often with great frustration).

I immediately reached out to the RudderStack team to learn more. Our initial call led to additional calls, product feedback and eventually a few implementations that I led for Yield Group clients.

Then, about two months ago, the RudderStack team called me and asked me to join the crew.

Leaving the consultancy wasn’t easy. Together with an incredibly sharp business partner and close friend, I’d built a great team, a great set of clients and was working on several high-impact projects. My ability to continue running OffSite was also a major requirement.

In my bones, though, I couldn’t resist the entrepreneurial call to have skin in the game with a product I believed in due to first-hand experience (more on this below).

Fortunately, the team at Yield Group was as excited as I was about the opportunity—we all wanted RudderStack to exist and become a major force in the world even before I was asked to join the team. Also, amazingly, right before founding RudderStack, the CEO ran and sold an ad tech startup and was excited about supporting my involvement in OffSite.

So, after careful consideration (infused with excitement), I said yes.

The decision wasn’t limited to my passion for the product, though. As with many major decisions in my life, I apply a sort of “investment thesis” to vet opportunities on variables beyond individual personal impact, though that is important as well.

My career “investment thesis” for joining RudderStack

Here’s a quick overview of the high-level framework I used to evaluate the opportunity at RudderStack.

First, the market, product and team (or, “would I invest my own money in this company?”)

While impact on my personal career is important, a great job on rocket ship that never makes it off the launch pad isn’t attractive. With as objective a perspective as possible, I tried to put on my investor hat and honestly answer the question, “would I invest in this startup with my own money?”

Here’s a quick overview of my vetting process:

Giant and growing market?

RudderStack operates in the data space, which itself is a massive market and can be defined in a number of ways. Even if you narrow the scope and look at a specific slice of the market, customer data platforms, the total opportunity is currently estimated at $2.5 billion and expected to grow at over 30% to $10.5 billion in 20254.

Needless to say, there is a significant market opportunity here.

Good market timing?

Market timing is a key ingredient to success for many companies, but the concept gets far less airtime than market size, product strategy and go-to-market strategy (I’ll write more on this in the future).

Even in a massive market, timing can present unique challenges. For example, being too early is expensive if you have to create awareness for a new technology or category. Being early can also set you up for disruption if you become too big to make quick changes as the dust settles on how customers want to buy and implement the technology.

RudderStack’s primary competitor has spent a significant amount of money establishing the category and technology. My personal estimate is that they have low single-digit penetration and the first real alternatives are entering the space. At the same time, the outdated technology of slow-moving enterprise incumbents is ripe for disruption.

So, not only is this a great market, it seems like the timing is lining up to be favorable.

Product-first go-to-market strategy

When I first met with the primary investor and CEO a year ago, I was immediately impressed with their product-first go-to-market strategy.

Instead of starting with marketing, they spent the first year building an incredibly high-quality product as open source. Community feedback accelerated feature development and adoption. At the same time, they proved out actual demand from companies who wanted to buy the product. Said another way, the foundation is a solid one, poised and ready for scale.

For what it’s worth, I think the open-source approach has incredible potential and the market timing there is probably favorable as well, especially considering several recent acquisitions of open source companies5

A-player leadership team, personally and professionally?

I spent a good bit of time researching and talking with the leadership team with the goal of understanding their goals, fundamental beliefs about markets and businesses and personal priorities.

Having now worked with each of them, I can say with confidence that the leadership team are all A players.

The right investors

Last, but not least, I spent time on several extended calls with the primary investor. I know from experience that great products with great teams can be hindered by investors with differing motives (which isn’t always transparent during diligence, unfortunately).

RudderStack’s investors have proven track records and balance valuable strategic insight and support with the freedom leadership teams need to solve problems on the ground.

Second, my role

If the company passes the sniff test as far as market, product and team, I consider the role, which is an investment in my personal career.

I’m a very content person (not naturally, but by the grace of God), so I don’t need titles or money to be happy, but I have an extreme hunger to solve hard problems and have the freedom to build strategies, teams and process to form the solutions. Ideally, I can execute alongside people who are smarter and more experienced than me.

Here’s what excited me about joining RudderStack:

  • A seat at the strategic table (ability to give input on company and product)
  • A chance to develop a muscle that I haven’t officially flexed yet (customer success)
  • A company culture with bias towards velocity and execution (RudderStack thinks hard, then executes hard and fast)
  • A company with no egos on the leadership team
  • A really cool product that I love nerding out on and using
  • An opportunity to develop connections with A players and talented investors

Off to see the wizard

Being a part of an incredible company and team is a true privilege. I’ll keep you posted as the journey unfolds.

1. You can learn about RudderStack on our website.2. You can read about my entrance into the world of software and startups in this post from 2012.3. You can read the original thread on Hacker News here.4. You can read about the growing CDP market on Business Insider.5. You can read about the acquisitions of RedHat on Wired.

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