Unprecedented with Derry Holt

Published 10th December 2021

A background into you and your business?

I'm Derry, the Founder & CEO of OneUp Sales. We're a B2B software company that provides a sales motivation & management platform to the recruitment industry. We started in 2015, and now have a team of 14 staff with 150-ish clients, and still growing!  

My personal background is development (video games specifically) so this is very much a "first-time founder" gig for me. As for the business, it's been much the same focus since 2015 with a few speed bumps and roller coasters along the way.

Define leadership and what being a leader means to you.

Tough question. Most would say leadership is about vision and aligning your team with that vision. It's a good short statement, but maybe a bit unclear without the context of what "vision" means. I'd say it's "being able to inspire & guide a group of people towards a goal". From arranging a night at the cinema with a few friends to carrying out a mission in the military to achieving self-defined success in business, that definition applies to them all.

As for being a leader, to me, it means taking ultimate responsibility (extreme ownership) for everything and everyone you "lead" over. That means being resilient enough to weather the rough times, having the flexibility to adapt to a changing situation, being "human" to those you interact with, communicating well, and plenty more. Being a responsible leader requires all of those things.

What were the 3 biggest (or best) decisions you made in 2020?

The world was still full of uncertainty at the back end of 2020 but the business couldn't sit and wait for it to blow over. 

The first was the decision to bring everyone back from furlough in September. We didn't lose anyone voluntarily during COVID and part of it is that we didn't want to leave people sitting at home doing nothing for too long when you consider how much some companies used furlough for.

The second was to get back to a bit of selling myself! We didn't have much choice when we had no sales team and about 30 interested companies getting in touch in Q3. I took them all on and closed a good number. It'd been a long time since I'd sold within the company so it was good to get my face back in the furnace. This led to decision 3...

Hiring a new VP Sales in December 2020. We could have shied away from hiring an executive and held out longer, but we pressed on. We've enjoyed great growth in 2021 as a result and I'm glad we didn't sit on our hands.

What remains your 3 biggest challenges?

Finding great people. We have many great people, but finding more of them is always a patience game. The job market is white-hot right now for candidates so it's competitive as all hell. Maybe Challenge 1.5 would be "standing out" with Challenge 1 being the finding great people part.

Challenge number 2 would be building an amazing remote culture. We're bridged nicely by physical meetups every 6 weeks but I'm still thinking about how we make remote working truly work for us. The team enjoys the flexibility and everyone is amazing, but it could be better. 

Challenge 3 is settling on a future direction for the company. We reshaped our vision recently into "Make sales teams amazing", now it's putting that into action. It can take many forms and I think we're about there but it's a big call that will affect the business forever.

Looking back to March 2020. If you could change one decision that you made, what would it be? 

I probably wouldn't have slammed my foot on the brakes as hard. We really went full turtle mode: furloughed everyone (except my co-founder, our Head of Customer Success, and I), cut our salaries down to nothing etc. The positive to that is we came out of COVID with a good bank balance and so could afford to rehire staff we lost at the start of COVID, the bad being that we lost 6 months of potentially valuable development progress.

Advice to the leaders of tomorrow?

Simplify, simplify, simplify. Flashy is cool but sometimes complicated. If you feel a bit lost in how to "properly" run an organisation, check out the Entrepreneurial Operating System or something along those lines. 

If you have enjoyed this blog and would like to learn more about Derry and his company, you can visit the OneUp sales website here.

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