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  • You can do it! A guide to breaking into rollups

You can do it! A guide to breaking into rollups

Inside: rollup starter team / nailing interviews / building public profile

Why rollups?

We’re halfway through Q4, and many of our readers start pondering what’s next career-wise. Another year at a consulting firm? At an investment bank? At a so-so investor or a recruitment firm? 

Of course not. Join a rollup – or build one. 

Achieve greatness and build generational wealth. 

Here’s how. 

Before we begin – kudos to our partners Camino Search for sponsoring this article. Once you’re ready to make the move, make you sure first ping Harry Hewson or Nathan Placks!

Getting started

What does a newly created rollup look like? PE-backed platforms tend to have the following structure:

  1. CEO – usually someone with the domain expertise. Think Scott Saclad @ Everfield. Must haves are credibility vis a vis sellers, an eye for talent & IR nous

  2. Head of M&A – a jack of all trades in the beginning (insofar as acquisitions are concerned). Over time will oversee a team that includes: a dedicated origination person; a post-merger integration analyst; and a couple of execution people

  3. Finance Director – typically assisted by an outsourced bookkeeping team, but pretty hands-on nevertheless

  4. CTO or a Tech Advisor (can be outsourced to begin with)

Controversially, I don’t think that hiring a COO or a CPO from the outset is necessary. I’m not saying that firm-wide processes or operational excellence aren’t important. More often than not, what this really means is people buying subpar businesses, gutting them to the core – and then parachuting someone from HQ to do a “turnaround”. My takeaway? Don’t buy declining businesses and treat people like adults, and you won’t need this massive overhead. 

I would argue that the single most important USP of a new rollup is its differentiated investment thesis, supported by a robust origination playbook. In other words: a) buying quality businesses cheaply, b) in bilateral processes, and c) at scale. You don’t need a professional degree for this. 

My story

I’d wanted to become a dealmaker ever since I was shown a snippet of “Boiler Room” in an Organizational Management class (the Ben Affleck speech…I know ). Aged 22 I decamped to London – from Latvia to pursue a business school degree. Levered to the tilt. In retrospect, the ensuing decade-plus feels like a dull continuum of deciphering seniors’ pathetic scribbles, pleading with analysts to do another all nighter, and “collecting buy-ins” for promotions. I ended up not loving investment banking – but not knowing what to do either. My overtures to super funded / hyped scaleups were for the most part unsuccessful.

And then two years ago, I stumbled upon rollups. 


Pavel introduced me to the founder of a small company called Threecolts, which was then just a few months old. The founder, Yoda, was looking for a Head of M&A. When I told him I wanted to be the CFO, he just shrugged and asked me to write down the job spec. In the ensuing 18 months, we 10X the revenue, raised $100M+ in funding and created a ton of shareholder value – even as the ecommerce rollup industry gradually imploded. 

Tip #1: Do your research

Good news first: the rollup industry is flourishing! Flush with cash but starved of large cap deal flow, PE firms keep setting up new platforms. New verticals are emerging too. Youtube channels. Airbnb listings. Hubspot and Atlassian consultancies. The VC to PE deal flow is picking up as well

Read industry blogs, come to Rollupeurope networking events, build relationships within the ecosystem and figure out where the capital is flowing. It doesn’t have to be SaaS or even tech: think Teamshares and corner shops

Tip #2: Leverage your strengths  

I don’t think I would’ve landed the CFO gig in a bigger, more established rollup because it’s more competitive and the recruiters are not incentivised to take risks. I went in brandishing my key strength (i.e. M&A experience) and over time, learnt the ropes. 

The reason we see so many former recruiters and software salespeople in M&A origination roles is because these two jobs require being client friendly 100% of the time. You come in knowing how to generate leads. Over time, you learn how to execute deals. 

Tip #3: Put in effort

In the 4 years I’ve been doing Tech M&A, I must have interviewed +/- 300 people. Over 90% of these interviews were write-offs: demotivated people seeking a way out but not necessarily a way in. I introduced case studies as a filter and even then, most hand-ins were generic and hastily put together. 

Why bother in the first place?  

By now there’s enough publicly available content to evaluate just about any type of tech and non-tech business. You can even generate decent starter pipelines using a combination of ChatGPT, scraper tools and common sense. 


  • In 2024, ditch your boring job and join a rollup (or create one)! We show you how

  • The industry is growing, with new verticals emerging all the time. It’s a matter of maximising opportunity while minimizing competition

  • You don’t need software experience, or even a degree to land at a job at a new rollup. What you do need is a short “time to value”, such as ability to generate deal pipeline

  • When choosing where to apply, do your research, leverage your strengths and put in effort. You’re going to succeed!