Warm Intro #03: Kevin Twohy and the Rise of the Fractional Leader and Connector

For the past few years, a growing trend in the market is that more and more seasoned leaders have been opting for “fractional work” instead of jumping into their next full-time role. 

“Fractional work” is both a post-COVID buzzword, and also a real, long-term market shift in how people engage with companies. It’s a mode of working for a company on a part-time or interim basis, often in a leadership capacity, supporting a wide range of activities. The benefits on both sides are clear: companies get the expertise of longtime leaders in their field at a lower cost than hiring them full-time, while the fractional person gets to take on a variety of projects simultaneously with greater control over their time.  

We could talk about why fractional work is on the rise, and we have our own observations and theories (more on that in a future post). But what’s particularly interesting to us, is that it has yielded a rise in a new wave of leaders who are helping companies recruit – who aren’t recruiters. Many people are now contracting for a company as interim leaders, while helping to recruit the team that will carry on the work when they leave. It makes perfect sense: they’re domain experts who have built teams across their career, and now they can do that for more than one company at a time.

We’re excited to see how this new mode of work is transforming how companies operate. We spoke to Kevin Twohy, an independent design leader and Liftoff community member who has been working in this model for over 10 years (before it was even called “fractional”). Kevin is known as one of the best 0-to-1 designers by scores of companies, including Mirror, the New York Times, Everlane, Mill, Daily Harvest and dozens of other venture-backed startups. He’s also helped many companies hire their first designers and teams, who help carry on the work when he leaves. As a result, Kevin has become known as a mega-connector, someone who can help companies find everyone from designers and copywriters to engineers and 3D animators. After connecting hundreds of people to opportunities, he’s now offering “teambuilding” as its own offering in his consulting menu.

He shared his insights about fractional work and how helping companies build teams has become a large part of his day-to-day work. He also shared great advice for people interested in pursuing this way of working.

(Plus: after Kevin’s interview, we share some of the latest searches on Liftoff, exclusive to our community.)

— Eleanor

Q: You are an incredible connector. How did this come about?

Every little interaction I have — whether it's an inbound inquiry for a project or just someone that I meet — is just a way for me to give a little bit of help to someone and create a positive loop. 

It's definitely something that has happened organically. My work is independent design work, and I’m often one of my clients’ first designers. So I see a lot of teams, and I bump into a bunch of really interesting people on those teams. Every project is an opportunity to uncover someone great. 

I started to realize that connecting people is just a way to be helpful to people – both the asker and the recipient. I think this is one of the very few things in life that is a win all around. When someone comes to me and says, “I need this type of person” and I know someone who fits it who wants that same thing – it’s a win-win-win. I can connect them, and I get the benefit of having helped them both out. This is the nerdiest thing ever, but it's like an exothermic reaction. It creates more energy than was put in. And I just love that.

Q: In the last few years there’s been a trend in people taking on “fractional roles” or “fractional work.” How did you get into this?

I just started to realize that most pre-product-market-fit companies would rather have a ⅓-time designer for 18 months to give them more longevity and oxygen, than a full-time designer for 6 months. 

So that was my insight that led me to start splitting my time between companies. My entry into it was not because I had an inherent desire to be fractional.

Q: What’s interesting is that fractional leaders are not just helping to execute, but also helping to build teams and recruit people to the company. You clearly do this for the companies you work with. Do you consider yourself a recruiter?

That's definitely what I do. I don't really use the term “recruiting” when talking to clients, but it's not because there's anything I don't like about it. 

Instead, I like the word that Liftoff uses — connector. To me, the thing about the framing of "recruiting" is that it is its own end. You do the recruiting activities, to recruit. For me, recruiting is a means to an end, and the end is building new products. You need people to do it and you need to be able to find those people. But I wouldn't call myself a recruiter mainly for that reason – because it's not the hat I put on when I get to work. It's just something that falls out of it. 

When I’m doing 0-to-1 product design at companies, they often need some help building their design org through hiring. Because I’m embedded with the people and the company, I bring a perspective to hiring that very few recruiters can. The design world has its own unique ways of hiring — we have portfolios, and a lot of it is very visual. I am able to look at a portfolio and get really clear with the client on the constellation of skills we need, and can screen out the vast majority of candidates just through that. But also, because I’m embedded with the company, I have a great sense of culture fit and chemistry, and can help find someone who will be an amazing fit. 

Q: How many people do you estimate you have hired or placed over the course of your career?

I’ve probably placed dozens of full-time hires, and probably in the hundreds for contractors. Sometimes it's folks that I know are great, and sometimes it's folks I discover. I'm constantly reviewing portfolios. I put them in my list and the next week someone asks and I can make a connection.

I recently mentioned on Twitter a big creative database that I maintain, with tags for different areas of expertise. I've been adding to it for the last 10 years, and then in recent years, I started to invest a lot more into it. It's essentially filled with the set of people that form the ensemble that you need to build an early stage consumer company from scratch and launch it: designers, engineers, art direction, animation, and 3D, in various proportions. I have a part-time assistant who helps with tagging and maintenance of it.

I love getting an email from a stranger saying, I don't know you and I don't know how this happened, but someone reached out to me on your recommendation and I got the job. It's a beautiful thing.

I'm now piloting a light-touch design advisory that's separate from my hands-on consulting work, because I can only do one or two projects a year. In this lighter-touch model, I meet with companies once a month, and one of the things I decided to include as part of it, is access to this full database along with help using it.

Q: How would you advise people who want to get into doing this hybrid "contracting while helping to hire or connect" mode themselves? 

Start doing and getting great at your domain expertise. The ability to help people hire and build their teams, ideally will come naturally as you network in your domain.

If you're interested in making connections and hiring, maybe you can charge straight at that and be a recruiter. But if you’re interested in doing a hybrid thing where you’re contracting in your domain and helping to hire, my best advice would be to focus on your domain expertise first. Because if you contract for companies as a founding engineer, you’ll end up connecting people to engineers as a natural by-product of that work. Connecting people also expands your network, and having more people in the world who know exactly what you do generates more opportunities for you. It becomes a true flywheel, that benefits everyone.

Q: Where do you think this fractional trend is headed? Do you think more people will be doing this in the future? 

I think fractional work will become more popular, and that more people will be doing it in the future. 

It all starts with fractional work becoming more visible, because people are influenced by precedents. You could think of fractional working as sort of “advanced” freelance. Based on the number of emails and comments I get from people interested in this type of work, anecdotally I know “supply” side of people is there.

On the “demand” or company side, I think it just makes intuitive sense. Companies that hire freelancers already understand that units of work do not perfectly correlate to 40 hours / week. Especially for startups, hiring outcomes are incredibly binary — it either works or it doesn’t work, and if it doesn’t work, all of that time and effort was being spent in the wrong direction. So wouldn’t you rather spend your precious time and resources on getting a small amount of expertise from the most experienced people that you can? It’s just another way to think about it: hiring very experienced fractional employees can help me head in the right direction, so all of the other money that I’m spending is actually moving us toward the right goal.

And the person is not just helping to build the right product — but also build the right team.

Thanks so much, Kevin, for sharing your insights and experiences with us!

If you have more thoughts on this topic, or ideas for future posts, please send them our way.

EXCLUSIVELY FOR THE LIFTOFF COMMUNITY

The team at Medbill AI is looking for a Founding Designer
Medbill is a Seed stage startup founded by Oscar Health veterans building an AI-powered app that helps consumers navigate one of the most confusing, painful parts of the healthcare system — their medical bills and healthcare plans. They're seeking a designer with 4-7 years of experience in both early stage 0-to-1 environments and beyond, to lead design of their consumer-facing app, as well as internal customer support tools and touchpoints around the app. The role must be in EST time zone. They're happy to offer $10,000 for helping them to find a fit. Feel free to suggest great people or re-share here.

The team at Atticus is looking for a Director / Head of Growth Marketing
Atticus is the leading platform connecting people with disabilities to government benefits. They also help victims of accidents and violence get compensation from insurance. So far, they've gotten thousands of people access to over $2B in life-changing aid. They are a Series B company backed by Forerunner and GV, and are already profitable. They're looking for a Head of Growth marketing who has overseen a growth program at a startup, ideally in a business with a complex funnel or set of product offerings. The role is ideally based in NY or LA, but can be remote. They're happy to offer $10,000 for helping them to find a fit. Feel free to suggest great people or re-share here.

The team at Dot Product is looking for a Founding Designer
Dot Product is building "AI Coworkers" for Operations teams, called "Operators". They are a Seed stage company backed by Index Ventures and Lachy Groom. By empowering companies with Operators, they're lowering the barriers for creating and growing businesses. Their first product is a Voice Agent Operator that augments Customer Support teams. They are excited to be hiring for a full-stack product designer with at least 4+ yrs of experience, to join as their Founding Designer and lead design. The role must be based in SF. They're happy to offer $8,000 for helping them to find a fit. Feel free to suggest great people or re-share here.

The team at Slingshot AI is looking for a Founding Designer
Slingshot AI recently raised a Series A from a16z, Felicis and Menlo Ventures. They are an AI-powered mental health app that provides support to anyone in crisis, at any time. They are seeking a full-stack product designer with 5+ years of experience, ideally with experience in daily use mobile apps. It's a great opportunity to work with a very strong technical team that also values the magic and joy of design. The role must be based in EST or UK time, and is ideally based in NYC. They're happy to offer $8,000 for helping them to find a fit. Feel free to suggest great people or re-share here.

Interested in creating a search? Sign up for our waitlist here:

Liftoff connects you to incredible opportunities and talent, through people you trust. Learn more.