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Interview with Salesloft's Ollie Sharpe

10 min read

Ollie Sharpe is VP of Revenue for hugely successful sales engagement platform SalesLoft, and the head of what he describes as the best sales enablement team in the world right now.

Across this SaaS Expert Interview, we talkedthe importance of team wellbeing (inside and outside a pandemic) and great team culture, how external expertise can help your team, and how to make the best use of your time as a salesperson today.

As part of our whitepaper case study on how SaaS companies have adapted to remote work, we interviewed a number of experts, below are Ollie's key insights: 

How Ollie Has Adapted To Remote Sales Leadership

There have been some tools that it has become impossible to live without. For Ollie these have been things like a solid sales engagement tool, using a video card to explain products remotely, and remote communication tools. He also notes that data has been key to remote sales, platforms like Doku, Cognizant, and Sales Navigator.

Making sure that you're using time right in the day is really important when working remotely. Ollie shared that he has now put his calendar into half hour slots, and tries to stick to that for tasks and calls.

Understanding how people are feeling is essential. It is very important to keep a pulse on the mental wellbeing of your team. How you do this needs to be defined by sales leaders depending on your specific team.

How Lockdown Impacted Salesloft’s Sales Culture

Ollie notes that SalesLoft had already done a lot of work on their sales culture, so it was a case of tweaking it. If companies went into lockdown and remote working without this culture already in place it would be very hard to build from scratch remotely.

When working from home, it’s hard to draw defined start and end times to your day. Sales leaders have had the challenge of ensuring that people stop working when they are supposed to. They are now having to think “how do I check people aren't working past 5pm?”. It’s important to remove the culture of just checking emails at 7pm as a standard thing - people need a defined end to the work day.

How Ollie Has Built A Positive Culture Remotely 

Ollie has focused on building a culture where everyone's close, they have fun, and they have a laugh together, but they also work hard together. His leadership is focused on the happiness of employees, whereby one of the core values is team over self.

At SalesLoft, they start meetings with personal and professional highlights of the last two weeks and Ollie notes that even something as small as that makes a difference. It’s great to get people talking about what’s on their mind and what’s going on so they can open up and really say how they feel. The more open we can be as leaders, the more open you’ll find your team.

Having a network of people, and encouraging mentorship is really important. People need to rely on each other in these times, so being able to call others with questions and get some advice can be amazing. Encouraging this kind of culture is key.

How Salesloft Have Adapted To A Remote Onboarding Process

Sales leaders are in the position where they’re interviewing people they’ve never met and may never meet face to face. This can feel strange and takes some adjusting to.

When working remotely, we have to make more effort with communication during the onboarding process. You can't just go, “let's grab a coffee and let me learn from you” in the same way, so sales leaders have to encourage their team to reach out to the new people and put time aside to have a half hour chat with them.

This interview was conducted as part of our whitepaper study on remote work in the SaaS world. Get your free copy here.

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