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When I was laid off from FullStory in early February 2023, I told myself that I was going to take at least a few weeks to just relax. It’s so rare in our adult lives that we get a chance to take an extended period of personal time.

It turns out I’m terrible at that. The Monday after being let go, I reached out to a ton of people and booked my calendar solid.

I didn’t want to sit and relax. I wanted to use this time to have as many conversations as I could and to meditate on my future career paths. What do I really want out of the rest of my life?

By the numbers, I connected with six people over Zoom (some a few different times), six I met for lunch or coffee, three different phone calls, one really great email exchange, and three Slack conversations. That’s a total of nineteen different people who helped me brainstorm my next adventure. It was a mix of friends, colleagues, mentors, institutional investors, and entrepreneurs.

This was a new experience for me— connecting with so many different people to talk about careers. It was extremely valuable. If you take one thing from this article, I hope it’s this: lean on your network before making big decisions. It feels like a superpower that allowed me to 19x my brainpower.

After a lot of thought, I’m joining Vantage as Director of Community this week. It’s a cool company with smart people, a great product, and I’ll get to continue making interesting FinOps content (basically turning the thing I’ve been doing for fun in my free time into a full-time job). Not to mention, it’s based in New York City, and I’m personally excited to be back in an office working with people again.

But that’s not what this article is about. Here, I want to share my own thinking and decision-making process, as a FinOps Practitioner evaluating next career moves. Hopefully this can help anyone else who might find themselves in a similar place.

Different Paths

I’ve been working in “FinOps” since the early days: starting partially in ~2016 and moving into a cloud cost-dedicated role when I joined Datadog in 2018.

I’ve also been active in the FinOps Foundation community since its early days — as a FinOps Foundation member for over four years and the host of the monthly NYC FinOps meetup since launching it in August 2020. I joined the FinOps Foundation Ambassador program when it launched, became a FinOps Certified Practitioner, and presented at the first FinOps X conference. I also publish a variety of FinOps content (and more!) right here on this website.

My work experience, as well as my activities in the community, has opened up a ton of doors, and given me the freedom of choice for my next career path¹. As I see them, my choices are as follows:

• Join a late-stage startup as a FinOps practitioner (same as I’ve been doing so far)
• Join a large enterprise company²
• Go it alone (either consulting or an independent “thought leader”)
• Join a vendor

It’s a lot of options, all very different from one another. Here’s how I approached things.

Starting at the end

I’m not immune to analysis paralysis³. I needed some way to narrow down my options. I was able to do this by starting at the end: where do I want my career to have taken me in 20 years?

I don’t know exactly what it looks like, but there are a few specific things I know I want. First is to both have and foster a strong network, and to be the type of person that can connect people in my network together in useful ways.

I’ve also always been interested in startups and venture capital. Early in my career, I realized that I didn’t really have the itch to be a founder myself⁴, but I want to be in and around that world. So the second thing I want for my future self is to continue to operate in that world. Maybe as an advisor, a board member, or angel investor. Or maybe that means partnering with VC firms to help their portfolio companies.

If I want to be truly valuable in this space (or any space), the best way to stand out is to find and build “specific knowledge.” I want my skillset to be so unique and valuable that when certain professional situations arise, I’m the best person to help.

So, all that gives me a fairly clear picture of what I want to be doing with my time, given the choice. It’s not really clear how I make money from that in twenty-years time, but those sort of details can be worked out later.

I have my lodestar for career-based decision-making.

Late-stage startup (same old same old)

The first option, and direction with the clearest path, is to join a company that’s in a similar size and shape as Datadog and FullStory were when I joined. This would be a Series D private company, somewhere between 500 and 1,000 employees, with either no or very nascent FinOps practices.

This is the clearest path because I’ve done this before (and written about it in detail). When I left Datadog for FullStory, this was the path that I was following.

I think I’m ready for something new. I already have experience at a company this size. If I’m serious about gaining specific knowledge, I need to branch out into different areas.

Large Enterprise

There are a ton of large enterprise companies that are in the process of building and advancing their FinOps practices. My experience at Datadog and FullStory would apply neatly into an organization like this.

Not only that, but these “big league” companies pay really well for senior positions.

These types of roles don’t provide a direct path to my 20-year vision, but they don’t really hurt it, either. I had a few interviews⁵ that really made me stop and seriously consider this option.

But, just like joining a late-stage startup, I don’t think this path really benefits me in gaining specific knowledge — it’s just more of the same work but at a different scale.

But after talking to some of these companies, it was much harder saying “no” to this path than I expected.

Go it alone

Another option that I considered was to build something myself. As I see it, there are two main ways to do this:

1. Advising/consulting
2. Education/thought-leader

The thing that really appeals to me about building something myself is that there’s no ceiling on how big it can get. The sky is the limit, as far as I’m willing and able to push.

Being an independent consultant or advisor in the FinOps space is an idea that I’ve been chewing on for many years. I think I have the experience to attract interesting clients, and the ability to craft a compelling offering and deliver on those promises.

When you’re an independent consultant, however, the majority of your time is spend finding and fostering leads, and building those inbound sales funnels. And that work just isn’t that interesting to me. Plus, I like the stability of a regular paycheck, and nice company-provided health insurance⁶.

Another option for going it alone would be to lean into the FinOps Education work I’ve already been doing a bit here on my blog. I love this type of work, which is why it’s what I’ve been doing in my free time.

I have a ton of ideas for creating in this space. Things like an email newsletter, more blog content, and video content. Maybe even building something akin to A Cloud Guru, but for the FinOps space. I’ve spoken to several vendors who are hungry to sponsor independently-created FinOps content, or launch affiliate programs.

But if I built this myself, I have no idea how long it would take to start bringing in the income that I want (if ever). Plus, that’s a lot of work to do all myself, without any external support. And, like consulting, there’s a lack of provided healthcare coverage.

The independent education/thought-leader path is really appealing to me. But in the end, the cons outweigh the pros for me. I really enjoy being a part of a larger team, working with others towards a larger goal, and collaborating on priorities and project outcomes.

A solo project might eventually get there, but the type of work it would take initially isn’t the type of work (or type of risk) I want to take right now.

FinOps Vendor

And finally, we have the option to join a FinOps vendor operating in the space. You know, the people selling pickaxes during the gold rush.

There’s been an explosion of new businesses and SaaS tools focusing on cloud spend in the past several years. The problem space is so large that there’s room for a ton of different philosophies and approaches.

I believe we’re still in the Opening stage of the Consolidation Curve. As a FinOps Practitioner, it’s been exciting to watch from the sidelines (as a potential user of these tools).

But before companies decide to use a third-party tool, there’s typically a build vs buy analysis, about whether to spend the money on a tool or spend the money on developing a solution in-house. Thus far, all the companies I’ve worked for have landed squarely in the “build” camp.

As a result, I hadn’t been following the vendor space very closely. When I took some time over the past couple of weeks to really explore the space in more depth, I was very impressed.

But what value can I, as a FinOps Practitioner, bring to a vendor? And more importantly, what value do I want to bring to a vendor? As I see it, there are a few options.

Sales Support

Vendors in the FinOps space need experienced and knowledgable FinOps Practitioners to help close deals and support existing customers. Sometimes the role may focus on one of these areas, and sometimes it’ll hop back and forth between them.

Cloud billing is so complicated that it’s hard to build a plug-and-play solution that’s going to work out-of-the-box for every customer’s situation. Prospective customers often need a very hands-on POC (proof of concept) in order to actually make the sale. This often takes the form of the FinOps Vendor doing most (or all) of the work to set up the tool and deliver value directly to the customer in the form of 1) actionable data and 2) a new ongoing process using this new tool.

FinOps Practitioners can enter this concierge service period both setting up the tool, and being a knowledgable point-of-contact for the prospective client, helping increase confidence in the tool. Thus, vendors need sales-side FinOps Practitioners who are at least as smart as their prospective clients, if not smarter.

As for me? I’m happy to jump into this role as needed, but I don’t think I want this as my main role. It gives me too many flashbacks to the many years I spent in retail, and I worked hard to get out of the boots-on-the-ground sales side of a business. Personality-wise, it’s just not for me.

Product

Product Management is a field that has always interested me. And being a part of the product team at a fast-moving startup is one of the most exciting places to be.

Product management is where you really feel like an entrepreneur. It’s a cycle of talking to customers, designing a new product/feature, releasing the product/feature, rinse and repeat.

A Product Management team is often threefold: a Product Manager, a Designer, and a Developer. Having an experienced FinOps Practitioner as part of this team will only make the group stronger, but you’ll need a FinOps Practitioner who can step into one of these three roles, rather than joining in addition.

A FinOps Practitioner in addition really only serves the role of another customer for the Product Management team to interview. One of many.

I’m familiar with this FinOps Practitioner-as-customer role because it’s the role I served at Datadog while the company built its Cloud Cost Management product.

But Product Management has always fascinated me. I’ve always attempted to watch closely from an outsider perspective. I’ve read a few Product Management books, and gotten a much better understanding of the Product Management process.

But, if I were to step into a wholly Product Management role myself, I feel I would need a good amount of mentorship in order to really succeed in the position. My skills and confidence as a PM are definitely not at the hit-the-ground-running level. Which is exactly what most startups need.

So while I’m interested in continuing building out my skills in this area, pursuing a dedicated Product Management role is not the right move for me at this time.

Marketing/Community leadership

Helping a company with its community and community management isn’t a role I really knew existed a year ago. But, as I’ve continued to publish FinOps content on my website and host the NYC FinOps Meetup, it’s a role that more and more companies have seen as a valuable fit for me.

I’ve been reading a lot about Developer Relations (DevRel), and how companies can use evangelism to support the business. Marketing to developers is unique because it can’t in any way be marketing. Because of this, most FinOps vendors aren’t interested in technical writing explaining why their particular tool/solution is the best. Instead, they want their name associated with independent, valuable, content that serves the community⁷.

It’s this role, which I had never really considered before, that caught my attention the most. Creating this type of content is fun for me — it’s what I choose to do in my free time. Choosing a role where that was my day-to-day sounds amazing.

The more I learned about this field, the more I realized it was a great fit for me, and uniquely suited for my professional experience. My years in journalism, and my English degree, would be put to good use.

Additionally, stepping back and examining my bigger picture, this type of role is a direct path to my 20-year vision. I have experience working at a late-stage startup, but no experience yet working at a small early-stage startup. If my end goal is to work closely with startups, my next step should be with a smaller company.

Decision criteria

The first big decision I made was between continuing on as a FinOps Practitioner or going in a different direction. And I realized that I’m ready for a change. I’ve been in the day-to-day weeds of being a FinOps Practitioner for over half a decade now. If I took another role as a FinOps Practitioner it’d just be more of the same, the only differences being the people I’m working with and the maturity level.

One thing I’ve done, in my free time throughout my career in FinOps, is create content. It’s always brought me joy to write blog posts, present at conferences, host the NYC FinOps Meetup, and more broadly meet other FinOps Practitioners. I needed to find a way to do this sort of thing full-time.

With those realizations, joining a FinOps vendor seemed like an obvious choice. I met with a ton of vendors after I let FullStory, and learned that there’s a ton of interesting stuff happening in the vendor space.

The required parameters were:

• It had to be a great product
• There had to be a great team
• Alignment on goals

Optional, but also taken into account:

• Solid investors (for the external validations)
• Located in New York City

There were a few companies that met all three required parameters. Others that had most of the optional ones, too. But Vantage was a perfect fit.

My role at Vantage

The really cool thing about joining Vantage is that I get to largely continue doing what I’m doing. I want to continue to share knowledge about the FinOps space, in an unbiased and transparent way. Tools are just one aspect of a FinOps role, and I plan to continue talking about the whole shebang.

At the same time, I’m looking forward to growing the community at Vantage. This means a ton of new content and events. I’ll be hanging out in the Vantage Community Slack, if you want to join me. If you’re in New York, feel free to reach out and say hello. And if you made it to the end of this post, you’ll probably enjoy my (not-at-all-about-FinOps) monthly newsletter. So sign up.