What is a Freelance UXR/UX Strategist/CPO?

Moderated by Martha Malloy, Guest Speaker on How to Freelance
This is an abridgment; view the full video presentation here.

Martha’s offering as a freelancer or independent consultant is unique as it includes UX research, UX strategy, and working as a fractional chief product officer.

What Have You Learned about Freelancing?

I have had a very meandering, or what I call a passionate, curiosity throughout my career. 2016 was a pivotal year where I transitioned from advertising and marketing into tech and found my love in UX design and research and even fractional product leadership as a Fractional CPO. Over time, I have realized that I have accumulated a unique skillset with my background in design, research, and product management. I can continually repackage myself in this quest to work less and have continued to evolve my career, a journey that has been really exciting. 

The first lesson I’ll share about this freelance journey is the impact of prioritizing my overall well-being and mental health. This was the main motivation as to why I left a “really good on paper” full-time role at Loopio where I was Director of Design and Research. I had been intrigued by the idea of a four-day workweek for many years. I interviewed for a number of companies and even tried to convince management at Loopio to change their policy. But that did not work out. In the end, I decided to design my own work life and stepped away from Loopio in November 2021 to go full-time at consulting.

Since then, I have discovered how to be compensated well working just four days a week. Monday through Thursday I work with clients and then use Fridays for networking and business events. With this schedule, I am able to prioritize my well-being and mental health and have the freedom to design my life in a way that I wouldn’t be able to in a full-time role.

In the beginning, I wasn’t sure if I could really commit to being an independent practitioner. I was exploring full-time role opportunities, and in some cases, interviewing on the side, and then also doing consulting work while looking for new business. From my perspective, however, going this route can be self-sabotaging. If you’re going to commit to freelancing, it’s important to stay as focused as possible, because if your focus is split in different directions, you’re not giving it the fair chance that it deserves. 

Another lesson I learned is how much I personally hate self-promotion on social media; it has always felt contrived and uncomfortable. Where I thrive the best is in networking situations: virtual or in-person events, networking breakfasts, or even one-on-ones where I can really chase after referral opportunities. This is in contrast to a woman I know who puts a lot of time into her social presence and being seen and respected in that way. That suits her really well.

So, the message here is there are different ways to market yourself. Find what feels right to you. Having that continuous “heads up” mentality is crucial to not falling into the trap of working constantly on your consulting, hoping that if you send out a few messages you will magically drum up new business. It’s something you have to invest time into continually.

What is a Freelance UXR/UX Strategist?

There are a couple of ways to look at this. Often, it seems that strategists work more on the agency side in higher-paying strategist roles. An interesting place to look up is The Moment which is an innovation and service design company. They have innovation strategists or, another term which is used, innovation designers. A company I worked for called Normative has a lot of different roles for strategists and hires contractors that are strategists.

But if you are thinking about finding a contract that a company is looking for, they generally have pretty traditional delineations. Are you a product designer, a UX researcher, or a service designer? If you’re trying to sell your services, I think referring to yourself as a strategist is a wonderful way to communicate that you have business acumen, as well as go beyond classic UX research and design into the planning, designing, executing, and sharing of insights.

If you say you’re a strategist that usually means that you can handle more ambiguous and complex problems and synthesize them into something that a UX researcher could use to conduct a study.

How Do You Balance Multiple Freelance Clients and Projects?

You need to know how comfortable you are with context-switching in order to decide how many projects you can realistically balance. I’ve definitely seen the advantage of working Monday to Thursday with a single agency client where I’m an embedded team member. In this way, I turn things on Monday and turn them off Thursday. Be careful not to overload yourself, especially at the beginning as you’re strengthening your freelance muscle. I admit I sometimes go over hours because my personality is to put in the time and work until the deliverables are up to my personal standards of quality.  

It’s important when thinking about how to value and price your services to make sure that you consider how you work and about the hours that you’re going to put in. Don’t forget to include the initial upfront discussion to get the actual contract to the final line and try to make that into a more fixed project fee pricing rather than just counting the hours.

In terms of Fridays for me, I have a sticky note reminder to constantly grow my pipeline or remember who I need to follow up with. It’s important to keep myself organized with the tasks that I need to stay on top of – not only the immediate needs of the projects that I’m on but also thinking through business development. This leads me to follow up more than I’d like to in order to push something over the line. It takes hustle and work to confirm or finalize contracts and figure out how to balance it all, but it’s worth it.

What is the Best Way to Find Freelance Work?

I usually only approach people when I know I can provide value to them. It’s not an “ask, ask, ask” situation because they’re people with whom I’ve built a good enough relationship, where I have the gut feeling that they want to help me if they can. It doesn’t feel like I’m promoting myself in this way – I’m just talking with a friend.

I’ve always had that practice my entire career with job searching. I think often people are too quiet when they’re looking for a job and they’re not telling enough people around them what they’re passionate about, what they’re interested in, or what kind of work or client they want to work with. 

I have found that even some of the most random conversations I’ve had have actually turned into business opportunities. That’s literally how I have my product discovery training engagement. A childhood friend and I were chatting and he thought of a CTO at an investor relations software platform company and said, “You two need to meet,” And that was it. Those organic connections are really important.

What is a Fractional Chief Product Officer?

I noticed a lot of startup companies invest in engineering at first because a founder has an idea and can’t turn that idea into reality unless you have engineers. That’s kind of a basic need from a software company’s perspective. They tend to over-index on engineers early on, and then focus on design and product management and other positions that fall behind that. They typically don’t have the budget to hire a full-time Chief Product Officer. What you’ll see at first is that they hire junior design product management people onto their teams, and then there’s this gap in terms of experience and knowledge and best practices when it comes to product management, design, and research.

I do everything from establishing a discovery practice to helping clients with product vision, strategic initiatives, and product pillars to having the research they’re doing bridge into building a road map for the team. Right now, this is anchored in research, but my responsibilities have broadened into product and strategy as well as optimizing the dynamics between engineering, design, and product management.

I’m kind of making it up as I go along because this is the first time I’ve been a fractional CPO.  It’s another stretch opportunity where I’m going to just figure this out. I’ve found a couple of other fractional CPOs who are willing to share their experience including what they charge for their services. I did my homework first before I came back to the founder and negotiated what this role could look like and what kind of budget they had for me to join the team. 

As a Fractional CPO, Do You Spend More Time on People or Process?

This situation is a little bit unique. I was fortunate because I’d worked with Quill initially for six weeks doing product team training. It wasn’t specific to discovery and we had actually received a grant here in Ontario. The founder applied for it and was able to cover a large part of my fees. So, I got to know the team on a coach level which was helpful to assess their skill sets and tool gaps. They were able to make a lot of progress in the time that I worked with them. This then allowed me to have this follow-up conversation with the founder which led to this opportunity of becoming a Fractional CPO. 

In my work now, sometimes I’m there more from a mentorship standpoint making sure that I work closely with the head of project management and design manager. The design manager is fairly early in her career and at times, I need to provide hands-on design guidance. On the other hand, with the product manager, who is in a more intermediate stage, I tend to back off depending on where she has the least amount of expertise which is generally around research. So that’s where I focus most of my time with her, whether that means directing her towards resources, articles, videos, or books, or working together through a challenge she is facing.

How Can I Find Clients that Need Fractional CPOs?

One of the things I have been trying to practice is that every time someone gets in touch with me, whether in business or volunteer interactions, I will ask if they know of any founders or companies that might be looking to hire someone with my variety of skill sets. I will also ask if they would be comfortable providing an intro or sending me their LinkedIn profile. Think about the people around you, those you already know, those who care about you, and ask them to be your “ears to the ground.” An interesting technique I learned from another freelancer recently, was to ask the founder that I worked with at Quill as a fractional CPO if she would post a LinkedIn testimonial about her experience working with me. That was very effective in getting a number of people to reach out to me to learn more about my services. Do not be afraid to ask for help from those people who want you to succeed and are willing to advocate for you.

What is Your Biggest Fear About Freelancing?

I’m married to someone who’s very sales-oriented and one thing that he’s encouraged me to think about is to look at the long game, and the long game could be like a year’s time frame. So if you’re doing a business plan development, think about what is the minimum amount of income that you can make in a year and still be okay; whatever that “okay” threshold is personally for you. Then instead of thinking about needing back-to-back work, think about how many projects you need to bring in this much money, and how much you would need to bill to achieve that.  

This kind of thinking helps because it’s hard to have work that perfectly lines up and I don’t know if that’s the right problem to solve or the best problem to solve versus if what you’re trying to accomplish is to reach a certain annual income. You might be able to make twice as much at a certain contract versus another. You might have more flexibility there that would alleviate some of the pressure of the back-to-back alignment of projects.

People that I have spoken to that are innovation strategists, for example, don’t have consistent business. But when they do have contracts come in, they’re big. So they actually live a lifestyle where they work a fraction of the year on projects and they have idle time to do other things. There are other things you can do like create passive income, like creating a course or some kind of content that people would actually pay for. Use your time wisely when you’re not being paid by a company to find other ways of making an income. Be creative, adaptable, and flexible. If you want to lower that stress level, I would encourage that sort of creative thinking.

How Can I Protect Myself Financially?

Payment terms are very important for a freelancer. The way I approach this is 50% of my project fees are due upon the start date and 50% is due at the end. That payment term depends on the company and I try to negotiate that to be as short as possible: usually 15 or 30 days. In this way, I cut the risk in half.

If you think somebody has the ability to pay the 50% upfront and you don’t get into any conflict or disputes, and everything goes well, that person will also honor that commitment for the last 50%. It’s always a risk. But if you are seeing signs and feeling concerned about the dependability of the client you’re working with, you might want to up that percentage and get more than 50% or even consider asking for all of it upfront. Use your instincts. If you’re feeling some distrust, don’t ignore those feelings and protect yourself in your contract and payment terms. 

Martha Malloy is a fractional product leader, strategist, UX research and product discovery coach with over 15 years of experience in technology and digital marketing spanning diverse industries (automotive, healthcare, education, travel, hospitality, retail, CPG, and financial services).  She has built brand, product, and service experiences for global enterprise companies (BMW, Spotify, Red Bull, Diageo, RBC) and tech startups (Loopio, Q4, Willful, Quill). She currently helps startups and scale-ups unlock new growth opportunities using modern product discovery and lean research practices. Martha empowers product teams to continuously capture powerful customer insights, proactively evaluate risks and test their assumptions through rapid experimentation. Find Martha at www.marthamalloy.com.

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