What’s next

Last week, I left Automattic and the WordPress VIP team. You can read more about that move on LinkedIn.

The reactions, comments, and messages in response to my post have been humbling, as they were internally when I announced my departure.

When I write words like “it’s been an honor and a privilege,” I mean them. It has been an honor to work with some of the smartest and kindest people I’ve ever met, and it has been a privilege to walk into some of the biggest media companies, government organizations, and B2B marketing organizations on the planet to talk about open source technology and hand out stickers.

What came before

I wrote briefly in my LinkedIn post about the work I’ve done for the past seven years, and I’ll elaborate on that in more detail here.

Last time I switched jobs, Automattic was the first place I applied, and I knew it was where I wanted to work. I wanted to go to the best possible company for remote work, and I happened to have a strong background in working with publishers and their technology. The WordPress VIP team was a natural fit.

A few months after applying, I did a three phone interviews during our family vacation week at the beach in the Outer Banks. During the first call, Nick (now the CEO, then the team lead) asked if I knew that “Enterprise Growth Engineer” was a sales role… “Yeeeeeeeeessssssss,” I replied, “product management is a lot like sales. Gotta convince stakeholders to invest time and effort in an idea. Gotta present evidence, track progress, diligently report on analytics, inform strategic decisions…”

Nick might’ve chuckled, I don’t remember, but he coached me to just be myself on the next call, which would be with a technical salesperson, but to think a little harder about how to talk about my sales “experience” when I talked with the hiring manager on the final call. It worked. I did a trial, fielded an offer, and then onboarded at the end of November 2017.

The team was amazing, and I started learning immediately. Onboarding at Automattic in those days required a rotation doing support on WordPress.com via tickets and live chat. I spent three weeks helping customers move buttons on their websites, renew plans, get refunds, or troubleshoot DNS issues with their shiny new domain. That might not sound like enterprise-grade labor, but it provided the perfect introduction to the internal tools I would use for seven years, and just as important, the culture and approach to getting information inside Automattic.

When you show up in a Slack channel with hundreds of people in it to ask a question about a tricky domain issue, you had best come with a well-formulated sentence that got to the point, was aimed at the right people, and proved that you had already looked in all the right places to find an answer without bothering anyone in a Slack channel with hundreds of people in it.

You would know you had done a good job of the above if someone engaged you to help investigate further. You would know you needed to look harder in the docs and tooling first if someone answered “Where have you looked so far…” because reader, that meant you had not looked hard enough, or at best, some documentation needed updating, and that could be your job, too.

When I started, the hiring manager told me it would take six months to close my first deal, because this was a complicated place, product, and sale, and it would take that long just to understand the business.

I closed my first deal after five months and three weeks, right on schedule, with a small California weekly that still runs on WordPress VIP today.

Over the next year, I would close deals with much larger publishers, always deploying my newsroom and corporate media experience — ideally in the form of empathy and familiarity with their problems — to help convince news organizations that they no longer needed to build their own content management systems, and their businesses (and communities) would be better served by spending all that time and money on journalism, or at least on new products features for journalists and their audiences to use.

I was right.

Later in 2019, after Salesforce invested in Automattic, I moved to a role handling Technology Partnerships, with a mandate to fill in the gaps between the open source WordPress ecosystem and our competition in the Digital Experience Platform category. My task was to find partners who could provide our customers and prospects with everything a CMS doesn’t do on its own. Personalization, Analytics, A/B Testing, and enterprise-grade Video, Digital Asset Management, and Authentication, among other categories.

Working in partnerships was fun, even at the height of the pandemic in 2020 and 2021. The best people who work in partnerships are naturally curious, eager to learn about each other’s business, customers, value drivers, integration points, and lives. I had great conversations with people from other companies every day.

We built out a cozy enterprise ecosystem with the best partners we could muster, came up with creative ways to measure revenue and impact across our companies, and helped each other close deals whenever we could.

The Salesforce investment in Automattic was always an open door to build an integration, and in 2021 and 2022, I navigated the Salesforce partnership process, community, and marketplace to develop, launch, and market a Marketing Cloud integration engineered and supported by one of our Agency Partners. I did demos and discovery with dozens of customers and prospects in 2022, wearing all sorts of hats: product, solutions, sales, partnerships, bizdev, marketing, and more.

Attending Dreamforce and HubSpot’s Inbound conference within a few weeks of each other in the fall of 2022 opened my eyes to something critical: Tracking attribution and referral sources in an open-source ecosystem with an open platform where customers could deploy any code they wanted? It was difficult. Especially when compared to the closed-source walled garden partner ecosystems at Salesforce and HubSpot.

In 2023, I took the sabbatical I earned after five years at Automattic, and came back ready to move into Customer Success, where I led the development, launch, and delivery of a new Architectural Consulting offering on our Professional Services team. Architectural Consulting is where we answered the biggest questions served up by our biggest customers. How to set up a network of sites the right way the first time — or the second time, after a migration — or how to build better standards and processes for running an internal open source approach with contributors from a variety of teams, to name some common examples.

What I had learned working in sales and partnerships (and for years in product and related roles at Gannett, GateHouse Media, Publish2, and other places) was that I was great at talking with customers. If customers talked with me, they were more likely to stay customers, and to become bigger customers. (Increased retention and GRR, if I can layer in some more jargon here.)

What now

• I’m finishing this post on the second business day since I left Automattic. I’m kicking off a more formal job search shortly, starting with the Never Search Alone methodology, book, and community.
• I’m learning. Listening to podcasts (more on that shortly), reading about how other companies work, leaning into GenAI tools for more than research and writing help, and planning to catch up with old friends and colleagues.
• I guess I’m supposed to be taking a break. I’m not sure I can do that right now, but when I step back from the computer, I have plans to clean up my office, rearrange some furniture, maybe paint a wall, maybe not. I’m not making too many rules for myself right now, but of course I’m working in some mindfulness and some exercise, but like I said, this is day two. Ask me in three weeks how my habit-building is going.

What’s next?

That’s a good question.

It’s going to be a minute before I have my mission statement sharpened, but today it looks something like this:

I am seeking a role in B2B Partnerships or another GTM position in a sustainability technology company, or otherwise, in a similar role where I can contribute to sustainability efforts in a technology company.

More to come.