Jim is the definition of a veteran. He’s been instrumental in category defining tech companies, starting with Apple in the 90s, Kodak, Yahoo, New Relic and lastly as the CMO of Stripe. In between, he also found the energy to start several companies (with two exits), and advise dozens of startup founders on go-to-market.
1. Since you started your career at Apple, how have you seen marketing and go to market strategies evolve? What changes have you found most impactful, and how have these changes affected your approach to marketing?
In those days Apple’s B2B go to market was a 100% sales-led motion, through both direct sales and an extensive set of distributors and resellers. The most profound change since then has been the rise of bottoms-up, buyer-led sales motions - both through self-serve and open source adoption. Sales-led still plays a role, in particular with larger customers, but companies who ignore the bottoms-up motion do so at their peril. At both New Relic and Stripe, a meaningful number of large customer accounts started with self-serve.
2. Actually I have always wondered if ‘go to market’ had really evolved in the past two decades, or if we’re just renaming concepts that existed: ‘growth’, ‘product-led’, ‘sales-led’, etc.
Consumer go to market has been “product-led” for a very long time - and has evolved in different ways with the rise of social media, influencers, and mobile as a storefront in your pocket. We could do an entire piece just on those dynamics. In the B2B space, however, I’d argue that many of these concepts are new as vendors have scrambled to provide consumer-quality interfaces and buying experiences as more and more buyers are driving the evaluation and purchase process. The internet was also still in its early days two decades ago, and the idea of growth techniques was very much in its infancy then.
3. Could you share some anecdotes about building your own company in the early days and transitioning to a SVP role in a larger corporation like New Relic? What were some challenges you faced, and how did you overcome them?
We started Opsmatic to address a serious pain point we’d all faced - software configuration issues taking down our production infrastructure. Over 40% of outages across the industry were caused by this, and observability tools at the time were only focused on metrics and logs, not the configuration state of your hosts. At the core of our solution was a software agent on each host that ran with root access, so we had to establish trust and credibility with our potential customers. We were fortunate to have a strong product-market fit, but more importantly a network of colleagues that helped us land well-known companies early in our life (Uber, Slack, Twitch to name a few) that gave us credibility by association. To this day, my best practice for any company is to prominently display key customer logos above the fold on the home page to establish immediate credibility.
All this led to the sale of Opsmatic to New Relic, and I have to say they did a masterful job throughout the process, so it went quite smoothly for our team. Obviously we were now in a bigger company, but our core team remained small and focused as we scaled the infrastructure observability business at New Relic. One challenge I faced immediately was that various product teams had approached PLG in very different ways, so we had to establish some standard patterns for bottoms-up adoption and then work across the organization to ensure the customer experience was consistent. Thankfully, the resulting conversion numbers did the selling, so we made rapid progress!
4. I’ve seen you’ve advised and built companies from scratch and also have been a leader in later stage brand names, such as Kodak, Yahoo, Stripe. Can you talk about your experience with pricing for early stage companies versus late stage companies? How do you approach pricing strategies differently for these two stages?
The primary difference has been experimentation velocity. At earlier-stage companies, we’ve had less existing customers and revenue that would be impacted by pricing and packaging model changes, so have more rapidly tried different approaches. At the later stage brands, we more typically would do limited A/B testing with a small sample to avoid the risk of negative impact on our customers or our business, but in general I’d say we didn’t iterate as much - with the exception of new product launches where we’d engage customers early and often to get qualitative feedback on the model and price points. A common approach across both company stages has been a strong focus on understanding where the value really lies for the customer, and tying the pricing model directly to that.
5. You describe yourself as a ‘data-obsessed’ leader. That might be controversial but sometimes I think early stage founders obsess too much about data, while their data set is too small: it can be about figuring out pricing, or cost of acquisition for instance. In that case they might draw questionable conclusions from a few data points, while the informed founders’ intuition might be more impactful. Is it something you’ve witnessed as well?
Every whiteboard in every office space I’ve ever been in has had the phrase “if you can’t measure it, don’t ship it!”. I’ve found data cuts through opinions like a knife, even when it’s a smallish data set, and leads to faster and better decision-making. Of course intuition and “gut” are also key, but I try to balance that with the data (or seek qualitative feedback when the data set is small). It’s the rare founder that nails this with gut alone in my experience.
6. What I’ve observed is that companies don’t iterate that much on pricing, regardless of the stage. Do you share this observation? Why is that?
In my experience, the primary issue has been the state of the billing system.
It’s often home-grown or built using a legacy provider, which leads to a lack of flexibility and inability to easily experiment.
These days, it’s critical to have tooling that allows for a wide range of billing units, pricing, and packaging. The other issue is that many leaders do not view pricing and packaging as a strategic lever, which is a shame given how central it is in the decision process for a customer.
For example, with analytics tools, most customers want visibility across their entire team - so a seat-based pricing model will be too costly and can literally sink the deal.
7. I’m super curious about your role as VP Community as Yahoo. Monetizing communities is always tricky. Communities get that whoever creates and animates a group needs to somehow ‘make a living’, but it’s often a delicate motion to implement. Can you talk about your thought process around monetizing communities at Yahoo? Is there a parallel with open source communities?
At Yahoo, the Community business included Yahoo Answers, Yahoo Groups, and Flickr. These were largely consumer experiences with an advertising revenue model. Users contributed to further their online reputation, support others in their sub-community, and occasionally to drive their own business (in the form of stock photos for sale on Flickr or a Yahoo Group set up to serve small business customers.) We explored a number of approaches to monetization, including deep category sponsorships in Answers (like the Tax category during tax season) and an “order prints” button on Flickr enabled through a partnership. The advertising-aligned models were the most effective given Yahoo’s strong focus on an ad model.
There were a few parallels to open source communities - namely people actively contributing to help others and frequent in-person meetups to share best practices (this was well before Covid.)
8. For SaaS founders and executives, what reading recommendations would you have for the early days and the later stages of a company's development when it comes to go to market strategies?
First, there are two foundational books: Crossing the Chasm and Positioning, The Battle for Your Mind. These are required reading for anyone building and launching a company (and for those running later-stage companies where competition is fierce and the field is noisy.) I’m also a huge fan of Elad Gil’s High Growth Handbook (for any stage) and the newly-released Scaling People by Claire Hughes Johnson, who hired me at Stripe and is an exceptional company builder. The latter book is not GTM-specific, but has essential lessons and practical tools for leading people, which is the hardest part of company building and scaling. There are many other great books out there, but I have to admit that these days I spend more time reading blogs and other online posts by a wide range of leaders. One of the most thought-provoking is Stratechery by Ben Thompson, which examines companies, their business models, and broader ecosystems - good inspiration when pondering your own business strategy and economic model.
9. What's the most surprising thing that has happened to you in the tech industry throughout your career?
I’d have to say that there have been several instances where leaders took big chances on me to take on new initiatives where I had no prior experience. For example, at New Relic, after a year leading product, CEO Lew Cirne asked me to lead the Commercial Sales team, a then 200-person global team responsible for about half of the business. I was fortunate that he believed in me, had the support of great leaders in that team, and the funding to build out a growth team to optimize that business. tl;dr it went well!
10. Lastly, this is *really* my favorite question ever: what was your dream career when you were a kid, and how did you end up in the tech industry?
I dreamed of becoming an astronaut, so I could go into outer space and explore the far reaches of the galaxy. The enormity of the universe still amazes me to this day, and I’m hopeful that some day I’ll be able to buy a ticket to at least our outer atmosphere! In university, I studied photography and graphic design, and became fascinated with the then quickly-evolving publishing technology space, which led to joining a startup in Boston (Lightspeed) that was in its very early days. A partnership with Apple followed, which eventually led me to Silicon Valley to join Apple and I’ve been here ever since.