Colleague Spotlight: Alex Winter

| By:
Gregg Lalle

Meet Alex Winter, Director of Expansion Sales in EMEA. I’m personally so happy to have watched Alex grow in his career during his tenure at ConnectWise and look forward to a bright future with him supporting the EMEA region. I asked Alex to share his career journey at ConnectWise and what working here means for him. 

Getting started at ConnectWise 

What did you do before joining ConnectWise?   
Prior to joining ConnectWise, I studied business management at Newcastle University. Like most young people, I didn’t have a definitive career plan, but I managed to land a graduate placement with a large automotive manufacturer in London. After a few years of learning the ropes, I was looking for a new challenge. Frankly, I had very little understanding of software sales or ConnectWise back then. However, after meeting Sam Callaghan, our VP of EMEA Sales, I quickly became aware there was a whole new world to immerse myself in.

Being a ConnectWise colleague 

What different roles have you had with the company?   
I’ve been very fortunate during my time at ConnectWise to hold a number of different roles within the sales team. I initially joined as a Territory Business Development Rep for business continuity and disaster recovery (BCDR) products, looking after North of England, Scotland, Ireland, and South Africa. I had a diverse portfolio, but being a native Geordie, I was positioned well to serve the region.

After around 12 months, I moved into a BCDR team lead position, supporting the management team in hiring and training the newer team members. Another nine months later, I progressed into Regional Sales Manager for the territory, where I finished third globally in my rookie season.

Following just over 18 months as a Regional Sales Manager, I took my first step into sales leadership. During my time, I’ve been responsible for both acquisition and partner sales, supporting service providers across the entire ConnectWise portfolio.

My most recent role as Director of Expansion Sales now means I’m solely focused on leading the team to help partners overcome systemic industry challenges, such as resourcing, cybersecurity, and best-in-class performance.

What do you enjoy about working at ConnectWise?   
Firstly, working at ConnectWise is incredibly rewarding. We help the small- and medium-sized business (SMB) and managed service provider (MSP) communities achieve their vision of success. Even though some of the challenges that we’d tackled in the past still exist, our partners’ needs have evolved today. We are laser-focused on being a better business and creating an equal environment where new and existing colleagues can grow their careers.

Secondly, the constant state of learning. Due to the fast-paced nature of technology and the MSP space, every day presents an opportunity to grow both personally and professionally. I’ve been fortunate enough to hold a few roles here, so I’m constantly being challenged. It’s rewarding to work with other smart and driven team members. With the creation and acquisition of new solutions, you’ll never hear me say I’m bored from a solution perspective.

Last, but not least, colleagues and culture. We spend so much time at work, and when you couple that with the emotional rollercoaster that is sales, it becomes important to surround yourself with people who are equally as passionate. Our team is driven by the success of partners, the company, and their roles, whilst having a good time. I’d say we have that in spades at ConnectWise.

What’s something about your job that makes you feel accomplished?   

What we’ve achieved here in the EMEA office. I was the 15th or 16th hire in the London office, which we quickly outgrew, and we’re outgrowing our current space of 100 people. It’s rewarding to help many colleagues become exceptional sales reps after they’ve joined ConnectWise and to see the number of partners we’ve helped along the way.

And now for some fun!  

If you can have any superpower for 24 hours, what would it be and why?   

To have the willpower to avoid crisps and dips. They are my nemesis, and I’d love to be able to say no. I could really do with this as an everlasting superpower.

What’s your go-to karaoke song?   

Toby Saysell and I did a pretty sweet rendition of “Bohemian Rhapsody” at the sales kick-off in front of around 200 colleagues.

What’s one bucket list item you’re looking forward to?   

I have yet to put a bucket list together at the ripe old age of 31, but skiing in Colorado and travelling to South America are up there.