The Fractional Frontier: Gabrielle Tenaglia on Letting Go of Relics

For some, ‘freelancing’ has become a loaded word. In the past, it’s been associated with insecurity - but in a climate of rampant redundancies and restructuring, ‘insecurity’ feels more universal than ever before. In that context, it’s perhaps time to look afresh at ways of working which challenge traditional models. 

Partners in Crime’s ‘syndicate’ approach - one of fractional employment in which individuals dedicate only parts of their total working time to single employers - isn’t a new invention, but it is newly relevant. As the company says of the creatives, strategists, and talent that make up its syndicate: “some may call them freelancers, but to us they’re Partners in Crime”. 

For clients, the streamlined approach means that costs are lower, and the creative is powered by staff which are hand-picked and bespoke to them. But there are benefits for those staff, too. 

Gabrielle Tenaglia is a consultant, advisor, and fractional CMO who helps clients solve big, complicated problems. For instance, she’s the fractional head of marketing at Lettuce Financial Labs - an automated tax and accounting product for solopreneurs, contractors, and freelancers that’s designed to help them unlock the value inside their businesses. To get a sense of how she views the current landscape of fractional employment - and how those fractional employees can get the most out of their roles and careers - LBB caught up with Gabrielle… 

LBB> Gabrielle, why was a fractional employment model something that first appealed to you? 

Gabrielle> I’ve been fractional on four occasions in my career. Each time I’ve worked as a fractional employee, there has been a different reason behind it.  

The first time, it was because I wanted to be an Outward Bound instructor, working out of a town called Ely in Northern Minnesota in the summers. I knew at the time that there was no full-time job that would give me that kind of flexibility, so I decided to start freelancing. 

Other times it has been about flexibility, or needing change from the job I’d been doing. When I’d just had kids, I wanted more flexibility than a regular job might allow. I’ve realised that working this way gives you the ability to try things out before you commit to them. 

LBB> Do you think that’s how employers see it, too? 

Gabrielle> Most people who are part of my team today work fractionally, and our product was built by a 100% fractional team. I do think there is a benefit in getting to work with someone before there’s an obligation for a full-time commitment, and also to let them try working with you. If we do want to then have a conversation about working full-time, it will be a decision for both parties to align on. 

LBB> Perhaps that’s a more realistic model for the world of work as it exists today. We’re no longer in an era where people work at companies for 20+ years - that idea feels like a relic. 

Gabrielle> It is a relic! And it’s not coming back. Let’s be honest about it, because we’re moving so fast in the other direction.

We are always going to have a proportion of our staff working fractionally at Lettuce for a few of reasons: 

First, we make a product that serves this audience and want to ensure we’re in touch with what people who work in this way are thinking, feeling, and doing. We want to be empathetic to their challenges. And second, there’s such rich expertise you can tap into when working with fractional folks who are specialists in the things they do and have deep experience in solving problems for clients. If organisations aren’t taking advantage of that expertise they’re missing out.

Finally, working fractionally is about results, not process. Cindy Gallop said this recently in a panel we were on together. It’s such an important part of our culture, and one of the huge benefits of working with fractionals. They are focused on delivering the results. It’s what drives their businesses.

LBB> Have you seen attitudes towards fractional employment change throughout your career? 

Gabrielle> People are more open to it, for sure. Coming from the ad agency world, it’s always been normal to see agencies scale up and down for pitches or after big wins. But I think there are other kinds of companies that are becoming more open to fractional employment. 

In every discipline, there are now deep specialities. Marketing, for instance, is fifteen different jobs. Fractional employment is a model that lends itself to taking advantage of specialties and having people come in with the ability to execute on very specific goals. 

LBB> If you could change one thing about how the industry operates that would support fractional working, what would it be and why? 

Gabrielle> When you’re a fractional employee, you’re effectively running your own business. We are in a time of huge transition, as people are trying to make this model work. So when you are employing fractionals in your business, you’ll do better if you help people make this transition and learn how to manage their own small businesses.

In so many ways, the infrastructure of our economy needs to catch up to how people work in the modern world - but in the meantime folks need help with tax returns, managing their accounting, and the sort of admin that you need to run a successful business. 

The truth is that almost everything you’ve learned as a W2 employee about how to manage your taxes and accounting is wrong. As a result, so many folks end up overpaying their taxes by a huge amount - which can be a factor in someone deciding whether fractional employment is even a viable path for them, and that is such a shame. There will be many people who don’t even realise they can afford to be fractional employees. That’s a missed opportunity for everyone.

LBB> Do you think that fractional employment works best for people who have already established themselves within the industry, or does it work for everyone? 

Gabrielle> I do see it across the board. When I think about the early stages of my own career, I learned everything I know from sitting next to my boss and listening to feedback he was giving both me and others. I accept that’s much harder to do when you’re working fractionally, and you have no choice but to be more intentional and purposeful in seeking out development opportunities, mentorship, and community. 

However, let’s be real - when companies say that they’re asking people to come back to the office to improve learning and mentorship, they rarely have any dedicated plans for employee development or mentorship. All they’re actually hoping is that the blunt proximity of being near other people is going to be enough to improve employee learning. I’m not sure that’s as effective as deciding to be intentional whilst you work remotely. 

LBB> If you could give one piece of advice to someone who’s starting out in a fractional role for the first time, what would it be and why? 

Gabrielle> I always give the same advice: Tell yourself that you are doing a great job. There’s no-one who is going to pat you on the back and tell you that - you have to do it for yourself, because you need the encouragement to keep going. 

This is hard, but it is also fulfilling. It gives you more control over your life. It lets you make choices about what's right for you, how you work, and how you want to balance the role of work in your life. 

LBB> Is it a lonely way to work? 

Gabrielle> It doesn’t need to be. I’m pretty intentional about making sure I have a community. I’m part of several groups where we turn to each other for advice. Another piece of advice I give folks is to make sure you are getting out and meeting people. I'm very intentional about making sure I have some in-person connection every week, be it with an old colleague, a current client, or someone in my network who is also fractional, and who maybe I could partner with to do some work. It’s so important to make sure you get that sense of connection and partnership. 

LBB> So perhaps there’s a certain type of person for whom fractional employment is never going to work. Maybe if you’re not someone who self-motivates, or has that innate level of intentionality and purpose? 

Gabrielle> I’m not sure I’d agree. Looking back on my own career, I can recall plenty of times - both in full-time and fractional roles - where I was not being intentional, not planning, or not thinking seriously about the kind of career I wanted to pursue in the long-term. I was just doing what the next expected thing was. 

I’m not saying I have huge regrets over that, but those were moments of missed opportunity because it was so easy to fall into the trap of not looking beyond the short-term. I think it’s easy for anyone to do that, no matter what kind of personality type you are. Working fractionally puts those longer-term questions under more of a microscope and invites you to answer them, thinking more as someone who’s running their own business. That’s a very useful thing, and anyone can benefit no matter who you are. 

LBB> That’s a really interesting perspective. Zooming out, it feels like this whole conversation is part of a wider discussion about a ‘new way of working’ that’s been bubbling away since the pandemic. What’s your take on that? 

Gabrielle> I think we’re only at the beginning of this shift. We’re not going to go back to the old world - there really is a new way of working. I think we need to keep talking about this, because organisations and people alike have to adapt. As they do, we’ll see new opportunities for personal and business growth for everyone.