Progressing Your Career In Operations: Q&A With Lindsay Crittendon

AdaptivOps recently sat down with Lindsay Crittendon, Former Senior Director of Strategy and Operations at Headspace, to discuss her experiences and how Ops professionals can advance their careers.

At AdaptivOps, we have had the pleasure of speaking with Lindsay Crittendon on multiple occasions, spanning a wide range of topics relevant to Operations professionals. In our most recent interview, we asked Lindsay to expand on her career trajectory and what advice she could offer other people in the world of Ops looking to progress and advance in their careers.

Can you tell us a little bit about your career prior to working at Headspace?

15 years before starting at Headspace, I was working in Market Research and Consumer Insights, a very niche part of the world of R&D. I took this route because I wanted to learn as much as possible about how to use business data and challenge myself to think creatively on a daily basis. Looking back, I really appreciate all of that experience because it helped me learn how to ask the right questions. I believe that the best Ops people don’t just deliver an important piece of data; they ask questions, discover why that piece of data matters, and figure out how it can be used with a certain intention.

Over the years, I worked in various departments, including sales and marketing, but consistently found myself pulled into the realm of Operations. This piecemeal introduction to Ops actually served me well because I think that the best Ops people can see both the forest and the trees. They can keep one eye on the big picture while also getting into the details and understanding how to operate the machinery of the business.

Thus, I found that, if I wanted to make the biggest impact in my organization, I couldn’t just stay in a singular role; I needed to be cross-functional. Somewhat ironically, if you have the motive or drive to make an impact outside of your group or department, you are far more likely to end up in an Operations role.

You’ve been in the Ops game for about 7 years now — how has it changed over that time?

When I first started in Operations, it was even more ill-defined than it is now. There were essentially two types of Ops roles; you had the Systems & Data persona who didn’t really have a say in strategic decisions and wasn’t meant to speak up much, and you had the persona of someone who was given an Operations title because the company just didn’t know what to do with them. They needed someone who could fulfill a “catch-all” role and take on a wide range of projects and responsibilities within the organization.

Fast forward to today, and the biggest change is identifying what “Operations” can mean and the importance of defining it. I’ve seen much greater intention when defining operational roles in recent years. For example, a company might assign a title like “Revenue Operations,” which speaks to the multi-dimensional aspects of Ops, as opposed to a title like “Sales Operations,” which is only tied to a single department.

In short, there is a greater definition of the role of an Operations Director and Operations in general. This has allowed for Ops-minded professionals to actually have room for career growth, as well as greater definitions regarding their roles within companies.

What skills should operations professionals be honing in order to gain an advantage in their careers? What are companies looking for?

When someone is first getting started in Ops, there is a lot of power in being a generalist. One of the best ways to do this in a credible way is to work in a number of different disciplines. I believe that for Ops professionals to be really good, they should have a cross-functional and multi-disciplinary background. Why? Because most Operations roles require you to put yourself in the shoes of the people with whom you’re working.

So first, start out broad and absorb as much information from the people around you. And second, really work to understand and experience different disciplines that are touched and affected by Operations. This way, when it comes time for you to be the glue that holds the company together, you can be the glue with a much greater sense of credibility.

This isn’t to say that being a generalist will make your career easier. In fact, it could make it harder early on. Many hiring managers will want specialists with a lot of experience in one specific area, as opposed to someone who has some experience across a broad range of disciplines. But over the long term, I honestly think that being a generalist will help you become a better Ops professional and advance your career.

Why do you think operations is a somewhat “unsung” role within an organization? How can we as a community advocate for that to change?

Many Ops professionals don’t like to talk about themselves. It can feel safe (in the moment) to focus the conversation on specific issues or other departments, but this only contributes to the lack of understanding surrounding Operations. Instead, Ops professionals should work to explain exactly what they are doing within the organization.

For example, working on roadmaps (both within the Ops department and for the entire organization) can continuously provide insight into what an Ops person does. An Ops professional doesn’t just sit in the back of the room and answer difficult questions from time to time. Ideally, an Ops professional is a strategic guide and partner who helps people within the organization get through some of their toughest moments. But if an Ops professional doesn’t talk about what they do, stakeholders won’t always see them as a strategic guide or partner. Consequently, Operations people have to take a page from marketing teams and learn to talk about themselves and what they are doing more often.

As an added bonus, this strategy can help energize employees because it alerts them to the fact that management is aware of day-to-day issues and is actively working to solve them. If your company is not running well operationally, the people who feel it the most — aside from your customers — are your employees. They see the problems, they want to raise their hands and do something about it, but that’s not their job.

However, if you have Ops professionals within your company, it can be their job. So if Ops is actively working to improve the company operationally, it builds credibility and trust with your employees. The employees can feel that their employer is investing in making their jobs better and easier.

In Ops we tend to be a “catch-all,” which can lead to burnout. How do you prevent overextending yourself when your skills are in high demand?

This is actually something that I have struggled with a lot. It is also why I have worked very hard to define what Operations does and define the responsibilities given to my team. In doing so, it can help prevent a business from using Ops as a “catch-all” department.

So, what are we accountable for and what are our roadmaps? Once you answer these questions, make sure that these roles are over-communicated. This way, when someone comes to you with an unrelated problem to solve, you can appropriately remind them of your duties as an Ops professional within the company.

This isn’t to say that you can’t solve their problem, but you can show them how it fits into your roadmap and timeline. It’s not always easy to say “no,” but if you have conviction in your roadmap and remit, you can easily look at different requests and identify which ones fit within your responsibilities and which ones do not.

Thank you for taking the time to speak with us today. For everyone who wants to find out more about you online, where can they go to look?

Thank you for having me! It’s always great to connect with the community. And while I’m not really active on Twitter anymore, people can always connect with me through LinkedIn!

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