Advice from SaaS Leaders: Building Winning Teams as a Start-Up

The path to success as a start-up can be both exhilarating and daunting for founders. As these companies chart their course towards growth, one of the most critical decisions they face is building the right team. As technology leadership and GTM recruitment specialists, Oakstone gathered insights from seasoned tech leaders on what they think start ups should prioritise when making hires and expanding their teams. 

Nick Bareham, Fractional CRO and Sales Leader, highlights the dynamic nature of roles within start-ups and emphasises the importance of hiring adaptable collaborators. "You need people who are ultimately team players who will roll up their sleeves, get the job done, whatever that might be, day to day, and love that challenge."

He continues, "If I'm trying to hire for an earlier stage business, I'm really looking for character traits rather than a perfect match in terms of actual skills, experience."

Nick's thoughts on hiring adaptable leadership are shared by Martin Moran, Advisor at One Peak Partners. "I think it's really important to look at where the start up is now. A lot of work I do these days is around building leadership teams. Leadership teams have to have a combination of skills, characters and attributes. So, it is really important to consider the broader team rather than an individual hire."

Moran continues, "I have a philosophy that the number one team in any organisation is the leadership team. It comes before their functional expertise. So, in hiring those key roles, organisations should always consider what they are looking for as a team. Let's say you're hiring a CRO. How does that CRO complement the skills of the CMO and complement the skills of the CEO, and how are they going to work together, and how are they going to be a cohesive team that's going to drive the company forward?"

Creating a cohesive and collaborative leadership team is essential for several reasons, particularly when it comes to the future planning of building a great go-to-market (GTM) team. 

Perry Gale, Fractional CRO and previous VP of Sales at Cyara, supports Moran's advice on hiring leaders as a team. "One of the big problems for start-ups is they need to put people in the processes together." Perry continues, "Start-ups are in a particularly vulnerable position because they have to grow up rapidly, and they have to rapidly find the people, the processes, and the technology that's going to help them to grow up. They come with great enthusiasm, often great products, and sometimes not much experience."

How do you create a collaborative leadership and GTM team as a start-up? 

Perry Gale, "The first important step is to identify who your leaders will be early and take the advice of people who know, like Oakstone. One of the things about Oakstone is that they have worked with many of the candidates for many, many years. They know them intimately."

Martin Moran, "The advantage of having one trusted recruitment partner is you can sit down and discuss that broader context. It's not just 'here's a JD, go and fill this JD." It's a "here's a profile of the individual one, here's a profile of the company's culture, here are the key individuals, the key roles we already have." You can discuss how that fits in and what I'm looking for beyond the skills of a CMO, a CRO, or a CEO."

Beyond the benefits of having one trusted provider, Nick Bareham points out the common start-up pain point of having to 'sell' opportunities to prospective candidates due to being unknown, "If we have obvious candidates in our networks, most hiring managers tend to go there first. Beyond that, you have to sell yourself as the hiring manager. You also need to sell the organisation and the journey they're on and, therefore, the opportunity for the candidate. Now, if that can come from a longstanding name in the industry like Oakstone, it has a degree of third-party validation. And that's, I think, one of the key reasons that we would use a firm like Oakstone."