How Connectd Is Powering the Shift to Fractional Leadership

In this episode of the Revenue Revolution Podcast, Mick Gosset speaks with James Matthews, Chief Commercial Officer at Connectd. They explore how fractional leadership is reshaping startups and scale-ups, why demand is shifting toward commercial and go-to-market roles, and how founders and operators can succeed in the future of fractional work.

This conversation covers the realities of hiring and operating with fractional leaders, common red flags on both sides, and how AI and remote work are accelerating long-term changes in how companies build teams.

How James Matthews built a global commercial career

James Matthews has spent close to 20 years working in sales and commercial leadership. He began his career in currency broking before moving into data and information sales at Informa, where he gained experience selling complex solutions into enterprise environments.

He later moved internationally, setting up sales teams in New York and São Paulo. This gave him firsthand exposure to scaling go-to-market teams across different regions, cultures, and buyer profiles. He then joined a startup called Agflow in Geneva, an experience he describes as challenging but formative.

Although that business did not succeed, James emphasises how much he learned about early-stage growth, risk, and execution. Those lessons directly informed how he approaches startups today. Around five years ago, he joined Connectd in London as one of the early team members and has since seen the company scale to around 130 people. He now serves as an exec director and also works in board advisory, non-exec, and fractional roles.

What Connectd does and how its marketplace works

Connectd is a marketplace that connects startups and scale-ups with fractional talent. At Connectd, fractional work includes board advisors, non-executive directors, and part-time functional leaders across areas like sales, marketing, finance, and operations.

The company’s mission is to help businesses and individuals transition into and succeed in the future of fractional work. For startups, this means accessing senior expertise without committing to full-time hires too early. For individuals, it means repositioning experience into flexible, outcome-driven roles.

Connectd operates a reverse recruitment model where monetisation primarily comes from the candidate side. James explains that the platform offers training, mentorship, and structured pathways for professionals looking to move into fractional work, including a guaranteed first role. Sales cycles on this side are relatively short, with an average order value of around £2,500.

On the startup side of the marketplace, Connectd currently offers access for free. James explains that this decision improves the quality of businesses and roles, creating better matches and long-term outcomes across the platform.

Why fractional work is accelerating after COVID and AI adoption

James explains that fractional work historically carried a stigma. Many organisations measured value by hours worked rather than by outcomes, judgement, and experience.

That mindset has shifted significantly since COVID, alongside the rapid adoption of AI across workflows. As tools automate more execution, startups increasingly value access to experienced leaders who can make better decisions, faster. Fractional leadership fits this need because it prioritises impact over presence.

"One of the things that held fractional work back was… stigma… it’s all about the hours that you put in, rather than the knowledge you have."

James sees this as a structural change rather than a trend. Startups and scale-ups are no longer just open to fractional leaders. They are actively seeking them out as a way to stay lean, flexible, and competitive in a faster-moving market.

How incentives and equity should work for fractional leaders

A frequent concern from commercial leaders is how compensation works in fractional roles. James is clear that fractional sales and commercial leadership should still include skin in the game.

That might mean commission, equity, or performance-based incentives, even if the structure looks different from full-time employment. In his view, alignment around outcomes matters more than the exact mechanics of the deal.

He also points out that expectations around tenure have changed. In many startups, staying more than two years now counts as a long-term commitment. Fractional roles often start small and expand over time as trust builds and the business grows.

James highlights why fractional sales and marketing leadership is so popular on Connectd. Instead of hiring junior talent without process, startups can bring in experienced leaders to define ICP, build a sales motion, implement tooling, and create repeatability. As traction grows, these roles can increase in scope or convert into longer-term engagements, often with equity still playing a role in early-stage risk-sharing.

What startups look for in strong fractional leaders

According to James, startups evaluate fractional candidates on two levels. First, can the person solve the functional problem the business has right now. Second, can they do that effectively in a fractional capacity.

That second question is often overlooked. Working one day or one and a half days per week requires strong prioritisation, communication, and influence. Managing teams, driving change, and delivering outcomes without daily presence is a distinct skill.

He explains that startups are often cautious when candidates have never worked fractionally before. The same applies to board advisory and non-exec roles, where understanding governance, board dynamics, and risk management is critical. Without prior experience, founders can struggle to trust that a candidate will add the right kind of value.

Why go-to-market advisory is now in highest demand

James describes a clear shift in startup priorities over the last five years. Earlier, product and engineering dominated decision-making, with most energy focused on building features and improving the product itself.

His earlier message to founders was to ship faster, get the product into customers’ hands, and learn through feedback. Product improvement depends on commercial exposure. Today, he sees that pendulum swing further toward commercialisation.

Startups are now more focused on proving traction, refining go-to-market strategy, and generating revenue efficiently. As a result, go-to-market advisory boards are currently the most in-demand advisory roles on Connectd. Product, tech, and operational advisory boards remain important, and fractional CFOs continue to be a core part of the fractional ecosystem.

Why RevOps is emerging as a key fractional function

Mick shares that he is seeing increased demand for fractional RevOps roles, especially as AI reduces friction in product development. When teams can ship faster, commercial systems often become the bottleneck.

That bottleneck shows up in handoffs, automation, forecasting, and revenue visibility. Fractional RevOps leaders can address these gaps without building large internal teams too early.

James agrees and adds that RevOps includes many specialist skills. Fractional and project-based RevOps work allows startups to solve specific problems quickly, rather than relying on rigid structures that may not fit their stage.

How to position a strong fractional profile

James explains that Connectd invests heavily in helping professionals reposition themselves for fractional work. A strong fractional profile looks different from a traditional CV.

Traditional CVs are backward-looking and focus on roles held, targets hit, or teams managed. While those details can matter, especially in regulated roles, they are not enough for fractional positioning.

James recommends forward-looking positioning that clearly states the outcomes you help deliver. Founders should be able to read a profile and immediately understand what problems you solve, in which context, and for what types of businesses. When that clarity is missing, it becomes difficult to match candidates effectively. In his experience, this is usually a positioning issue rather than a capability issue.

Red flags fractionals should watch for in startups

James stresses that early-stage startups are often messy by nature. Processes are immature, and founders are under pressure. That said, there are clear red flags fractionals should not ignore.

A major warning sign is misaligned scope. If a startup expects full-time impact from a half-day-per-week role, and is unwilling to discuss adjustments, problems will follow. He also advises looking closely at how founders treat their teams and whether trust and respect are visible across the organisation.

"If people are trying to bring you on board… for half a day per week, and are asking way too much of you… that is a huge red flag."

James suggests speaking with others who work in or around the business whenever possible. This provides context that a single founder conversation cannot. He also notes that fractionals need to be comfortable operating in imperfect environments, sharing an example of Connectd once using Airtable as a CRM in its early days.

Why ego is one of the biggest threats to scale

When discussing founder challenges, James identifies ego as one of the most destructive forces in startups and scale-ups. This applies not just to founders, but to anyone who becomes defensive or resistant to feedback.

Startups face constant problems and rapid change. When people hide mistakes or avoid difficult conversations, issues compound quickly. James argues that listening is one of the most important leadership skills, especially at the top.

He credits Connectd’s founder, Roy, for being willing to listen and accept uncomfortable feedback. His view is that founders need regular, honest input about what is not working. Progress depends on acknowledging imperfections and acting on them, not protecting ego.

How James approaches forecasting in a remote-first world

James answers a listener question about managing sales cycles and forecasting in remote environments. His approach is to avoid relying on a single forecasting method.

Instead, he recommends triangulating forecasts using multiple inputs. These include CRM data and rep commits, pipeline analysis to detect sudden drift, simple macro indicators like headcount and seasonality, and external performance trends tied to pipeline size.

He reframes forecasting as a learning mechanism rather than a prediction tool. Forecasts will always be wrong. The value lies in analysing the miss, whether that is underperformance or overperformance, to understand what really happened in deals and behaviours.

"Forecasting is most useful as an education tool anyway… you do it so you can get it wrong."

The question James leaves for the next guest

Before wrapping up, James leaves a question for the next guest on the podcast, aiming to encourage honesty and reflection.

What is the biggest mistake you have made in your sales career?

Final takeaway

Fractional leadership is becoming a core part of how modern startups scale. Platforms like Connectd reflect a broader shift toward flexible, outcome-driven work supported by experienced operators.

For founders, success depends on clarity, openness to feedback, and realistic expectations. For fractional leaders, it requires strong positioning, comfort with ambiguity, and the ability to create impact without full-time presence. Together, these dynamics define the future of work.