Scalewise’s 5 Steps: How to make a success of a portfolio career


From getting up to speed quickly with the right clients to communicating clear expectations to founders, follow these five steps to make a success of interim and fractional leadership.
Swapping the monotony of a sole employer for the dynamism of multiple scale-ups? Trading the relentless pressure of a full-time role for the flexibility to work under your own steam? Shifting your energy from internal politics to areas where you make a difference? Be it in search of a new lifestyle or a new challenge, there are many reasons for making the transition to a portfolio career as an interim or fractional leader, but once you have, how do you make a success of it? Follow these five steps.
1. Get the right client match
It’s not just about finding clients, but the right clients. The ones that suit your working preferences, skillset and experience. The ones that fit into your work-life balance. The ones where there’s instant cultural chemistry from the off.
“It’s really important that you get the right client as you need to make an impact in a very short space of time,” says Margo Hayward, a recent convert to a portfolio career after 21 years in tech sales. “You need to get up to speed really quickly, so both parties need to have a number of discussions to make sure you’re the right fit.”
For Nora Khalili, who went out on her own fractional journey in January 2020, that involved some soul searching. “Is this the right skill-match? Do you get along? You need to check if there is a comms style match and culture match with the founder. That they are in the mindset to accept your advice. There’s nothing worse than coming in where a person thinks they want help, but actually wants to be told what they’re already thinking”.
2. Get up to speed quickly
The dynamism of a portfolio career is one of its main selling points. For example, you could be spending six months building the sales function at a tech scale-up and then spend the next three months advising on lead generation for a FinTech unicorn. However, that dynamism means you need to act fast.
“Getting up to speed was one of my biggest challenges,” says Margo Hayward. “I couldn’t have imagined how fast they expected me to do it. I had six days to learn the business, the proposition, the entire team and come up with a plan in order to fix it.”
“You don’t have a long honeymoon grace period,” agrees Nora Khalili. “You need to think about who has the answers you need and how to get that info quickly. For example, talk to someone on the tech team, the people in product and get the founder’s perspective. Be strategic with your time with them. Talk to customers, speak directly to them, shadow interactions with them – do they agree with your hypotheses? It’s intense, but remember as you’re not a full-time employee, you don’t need to do lots of onboarding or build a relationship with everyone. Just get straight into the meat of it.”
3. Define clear expectations
Timelines and expectations go hand-in-hand. No one can be expected to turn around a sinking sales pipeline in one quarter, for example, so from the outset, you need to be upfront about what’s achievable, according to Margo Hayward. “You need to be clear on setting expectations as early as you can. What can you do and what can’t you do? When you define what isn’t your remit and what is, it is much easier to be successful.”
For Sophie Carter, an experienced interim leader and Chief Fractional Officer at Scalewise, “it’s very important to define the scope and follow a process. The problem or solution might be obvious, but making that change happen can be challenging. You need to be realistic about what you can achieve.”
4. Focus the founder’s attention
Working with scaling companies, it’s likely that you’ll be hired by the CEO-Founder and it’s crucial to keep their eyes on the prize. “Communication is key,” says Nora Khalili. “How much does the founder want to know? What is too much information for them? That often depends on their working style: some founders prefer granular detail, others top-level. However, all founders have shifting priorities, so you need to keep their focus on what needs to happen if you’re going to achieve the desired outcome. You need to upward-manage your client in that way.”
Margo Hayward agrees that you need to “have your plan and communicate it clearly and regularly to founders,” while Sophie Carter believes that it’s important to work out why the founder has hired you in the first place. “Do they want to pass on a problem or work together to solve it? If they just want to hand it over and hold you accountable, then the relationship won’t work. You need the founder on board to drive that change.”
5. Test your hypothesis
Most interim or fractional leaders have worked as either CROs, CMOs or VP of Sales or Customer Success. They are seasoned problem-solvers, but that experience can come at a cost. “Given our level of experience, it’s tempting to quickly have a hypothesis of what the fix should be,” advises Nora Khalili, “but don’t let your own experience cloud what’s currently happening at this company at this moment. Have conversations with other people in the company. Take the time to test your hypothesis and learn.”
According to Sophie Carter, you also “need to understand the nuance of each company’s culture before you can solve the problem. Learn, absorb, dig in and analyse.”
Next steps? Speak to Scalewise
It’s easier to make a successful transition with the support of a team. At Scalewise, we help you with all of the above. We match you with the right clients and organise chemistry calls to ensure a personality match between you and the founder. We help you set the scope, define clear expectations and communicate regularly. We provide tips for upward-managing clients and an external sounding board for your hypotheses.
What’s more, as we handle the client contracts and invoices, you can focus exclusively on the job at hand. Get in touch to find out more. 

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