By Jonathan Costet

Zero to Won: Work-Life Balance in Sales with Ollie Sharpe (Salesloft)

Zero to Won: Work-Life Balance in Sales with Ollie Sharpe (Salesloft) In this episode, we catch up with Ollie Sharpe (VP Revenue EMEA at Salesloft) to discuss how supporting work-life balance...

Zero to Won: Work-Life Balance in Sales with Ollie Sharpe (Salesloft)

In this episode, we catch up with Ollie Sharpe (VP Revenue EMEA at Salesloft) to discuss how supporting work-life balance and hiring for culture adds can drive team performance. Before joining Salesloft, Ollie spent 10 years at LinkedIn. He's spoken a lot about the mental side of the sales game and brings his learnings to sales leaders looking to build high-performing teams in the competitive world of sales.


  • Hiring for culture-add: 0:50 - 6:20
  • Driving performance by encouraging work-life balance: 06:20 - 10:25
  • Managing stress in sales teams: 10:25 - 13:25
  • Winning - and failing - as a team: 13:25 - 19:44

3 Key Takeaways

#1 Ditching cookie-cutter recruitment

A lot of managers make the mistake of hiring people that are too similar. Ollie is no exception: he's made that mistake in the past, and knows first-hands the limits of not having a diverse team with diverse thoughts. This time around, he's hired for culture fit - with people in the org trained to hire on culture - while also making sure each team member brings their own superpower to the team. Going past the cookie-cutter approach doesn't just happen: with each new hire, you need to ask yourself "what does this person bring to the team that no one else brings?"

#2 Reducing stress in sales

Understanding the parts of the role - like Q4 - that are stressful allows you to make sure you're creating the right type of environment where people can perform at their best. Your culture can be engineered to help achieve that: whether it's making sure that team members are making time for important things in their lives, articulating the company's higher goal, creating an honest culture so that team members can openly share the difficulties they face, or owning targets together with leadership and building a plan to achieve that goal together. And it comes down to leadership to set the tone for the rest of the team to follow by being open about their own struggles.

#3 Playing as a team

Sales is a team sport. Being able to learn from others strengths to improve in areas where you might have weaknesses is a huge advantage - and most teams do practice this. However, sales remains a competitive space. And that competition can be turned internally, with sales reps feeling like they are competing against one another in the same team. The mindset that Ollie tries to instil in his team is that "We compete as a team and our success comes to the team or failure comes to the team. Unless you're a one-person company or the only person doing something, anything else is a team sport."

Full transcript of our chat with Ollie Sharpe:

You joined SalesLoft quite recently.  Could you tell us a little bit about what makes the sales culture there unique?

Ollie Sharpe:

There's a lot that makes it unique.  One thing just to understand is that I left LinkedIn after 10 years which is a company that really has a fantastic set culture within the company.  So, one of the things that was very important to me in my next move was finding a company which prides itself on its culture.  I remember deciding for myself that I needed to join a company they're proud of or a culture that I can help to build and luckily with SalesLoft I came across a company that's very proud of its culture and won a number of awards for it. 

And what it normally comes down to is, a company that has core values that aren't just written on the wall and nobody actually lives by, that shows. And LinkedIn is a company that actually live by their culture and values.  At SalesLoft, as well, we live by our core values such as glass half full and putting the customer first.  And when decisions are made around core values, it means that the culture, the consistency of the culture, and after meeting everybody, how welcome I was made to feel when I joined the company was unbelievable, and I can safely say I've landed on my feet at a company with a fantastic culture that I can replicate over here in the UK and EMEA.

In terms of what that culture looks like in the sales team's day to day at SalesLoft, what are some of the elements where you really see it shine?

Ollie Sharpe:

It's hard to be specific with that because, really what it is is, in order to be a process, we have processes that are purely for a culture interview.  So, we have a panel of people internally that have been trained on how to interview around culture.  So, we have consistency across teams which we know they are a culture fit/culture add, I think that's very important thing to think about: not just culture fit, which you don't want everybody to be exactly the same, but culture add, at the same time.

At the moment we've gone through this difficult process of moving some accounts over to EMEA even though they were brought on in the US, and it's just great to see our team working as one team to make sure that we're putting the customer first in our decisions of how we manage things and how we do the hand-over process.  So, everyone is the same in regards to, or similar, in regards to the ways that we are goal driven.  But, also, we are more of a collaborative team culture than other cultures as I've seen them in the past.  And it is hard to answer because it's just a general feel of everybody within the organization.  I set out to build a team that fits with our culture, but also everybody brings along their own superpower. 

So, everybody is different.  Even when we go out socializing, you can see the differences between us, but we all have one common image which is just the way that we fit into our culture.

On that notion that you're bringing of culture add, I was curious if that was done quite organically and just based on the candidates that you're meeting and thinking already, "This will be a nice addition to the team's culture," or do you have some specific values or attributes that you're actively seeking out and thinking, "Right, to really balance the team I need to find someone who's superpower would be this…"

Ollie Sharpe:

Yeah.  I think it was done on purpose. I think that one of my learnings from when I started as a lead was, I didn't do that.  I made a mistake.  I went for a cookie-cutter approach that my team was very similar to each other, and that doesn't add the benefits of having a diverse team with diverse thoughts from different people and ideas.  So, I learned the hard way, and I made a specific effort at this time when I was looking at, if I had four people for two roles, I made sure they would fit in, would fit with the culture.  But then I'd think, "What does this person bring to the team or culture that no one else brings that we don't have in anybody else?"  And that's what made, I think, my recruitment this time.  So enjoyable to do, and when you look at the team, how they interact with each other and when one of them realizes that so-and-so over in the other room any special power is doing X, Y, and Z that they're going to and it just makes us stronger.  But we still have the commonality of our core values that we all are aligned with at the same time.

That's something that you've spoken on quite a bit, actually, is that the mental side of the game and how sales is obviously about performance and about driving revenue.  But the conditions for success are played out almost on a psychological level for each member of the team.  I'm wondering, "How do you create a sales culture that supports that?"

Ollie Sharpe:

I think that, when it comes to the mental side a bit, there's part of the role that are parts of sales that if we understand we can help the levels of stress we go through.  Like Q4 and things, when things get tough, how we react to those, and it's becoming resilient, and there's a great book by Dr. Steve Bull who is a sports psychologist.  He's worked with Great British Olympic teams, and he's put together a mental toughness model which actually looks at the four types of things that are happening in any work environment, actually more prone in the sales environment, that help us cope with those.  Like this turnaround toughness.  When things go bad for us, how do we react to that?  So, understanding how we can cope with them ourselves is important but also building culture within an organization that helps people.  People talk about job being engaged but also not let the stress get to them because, let's be honest, there's more and more things in life that are not jobs.  I probably got too stressed hitting target until about four or five years ago when my wife was diagnosed with cancer, unfortunately, but my boss at the time, she's all right now, but my boss at the time was very supportive in getting me to think about that my wife is the most important thing, and once I looked after her, then my family is the next most important thing, and the next thing is myself, making sure that I'm in the right mindset.  And if I ticked all of those boxes, then I could actually do some work, or can do some.

So, in building that culture within an organization, which I thought was five areas and which is about making sure it's inclusive and people can belong to it and they belong, creating an open and honest culture where people can talk about their issues. It's not a problem to turn up one day and have other things on your mind and we all have our own stresses, and the worst thing you can do is keep it inside.  Creating a good work life balance within an organization so that people can go do the things that they enjoy and that comes very much down to that performance pyramid where they talk about making sure that you put all your rituals in place around your spiritual and emotional, mental, and physical, so your body and your mind performs at their best. 

Also, people understanding what's important.  Like I said, about my experience.  And, also, having a purpose. Company sales teams are not just coming in and doing their day-to-day chores everyday but having a purpose that's leading to a bigger purpose, whether for the company or the world around us, makes a big difference about how motivated we are but also how happy we are in our roles.  So, that to me, is more around the culture, but then I think leadership has a role to play in this because we can build a culture and we can ruin a culture.  And, to me, it's all about me being human, approachable, and leading by example, and that's what we should think of as leaders to make sure we're building the right cultures to reduce the levels of stress and anxiety within our teams, but also people perform best when they're at their happiest, and that's when they've got a good culture around them with a purpose they believe in.  And that's what I believe in.

That's a really powerful story, Olie.  Thanks for sharing.  And it touches onto one of the things that I know counts very much for you is, the whole mental health aspect that's often overlooked in the workplace and especially when it comes to sales.  What are some concrete steps that teams who are looking into that could implement based on stuff that you may have done yourself at SalesLoft or at LinkedIn?

Ollie Sharpe:

First of all, for individuals to understand the areas of our role that will stress us out, which is that mental toughness model that I spoke about, that's a good start.  But when it comes to the culture side, one of the key reasons, I believe, or two key reasons is, people put too much pressure on themselves and people put too much pressure on each other - as in leadership - sometimes.  So, it's making sure that we have it. Sales should be a partnership between a leader and a salesperson to achieve that common goal of their target.  And, a lot of the time, a leader will only get involved when someone hasn't met their target or to celebrate somebody hitting their target.  And that, to me, is wrong.  It should be the partnership at the beginning of building that plan and how they are going to achieve that goal together.  And that reduces stress level because it's on both of their shoulders.  I decided to take somebody on that worked with and to employ them and work with them to help them achieve their target.  If we don't hit it, it's our problem.  It's not their problem.

So, if then they're not right for the role, then we've got to work at what role would be right for them and how we can improve them or develop them.  That's one thing, but also, people that don't feel that they can be open about their issues at home or outside of work or they're even less stress levels within work, that's the biggest thing to me so I try to create an open environment where in a team meeting we'll make you have check-ins where we're talking about the highlight from the last two weeks.  And it comes in to the leaders showing that they are human, talking about the stresses that they have, what matters to them, and showing that they're not the be all and end all to being at work and don't think humans were designed to just constantly think about work. And it's easy to do especially in Q4 in sales to put all your time into work and not take the time out that you are exercising your body and your mind and to doing the things that you want to do.  So, making sure that every, you're open and honest, have a good work life balance, and making sure that everyone can be open about their issues and stresses that they have.

And throughout our conversations, you've drawn a lot of comparisons between the world of sales and the world of sports.  And, obviously, sales is a bit particular in that, depending how you view it, it can be either a team sport or it can be an individual sport.  How do you make sure that the culture you're putting in place in your team is encouraging the right behavior, and what are some of the levers you can play around with to change it?

Ollie Sharpe:

I, 100%, believe that sales is a team sport. I think that, unless you're a one-person company or the only person doing something, anything else is a team sport, because whether you're a team as in 11 people on a pitch, you're a team as one person, running around a track you have people behind you, and you learn from other people.  Those people help you to be your best.  So, we try to have a very collaborative work environment that's even taking another salesperson on a meeting with you for you to learn how they've done something is making you better at your job.  So, it's very much around the team environment that we try to build it, whether it's me or somebody else helping out.  And if you think of all the best sports in the world or the best tennis players, most people have a weakness and most people have a strength.  But if you can learn from the others that have the strength where you have a weakness, it will make a big difference to you. 

I came from a background…  I did two years of door-to-door sales and I went into recruitment.  And recruitment is very much competitive space even within a company.  So, you're competing with the person next to you, and that's where I'm trying to make sure I'm on the other end of the scale that we compete as a team and our success comes to the team or failure comes to the team.  And that's what I'm trying to drive.

How does video fits into your sales strategy and your process at SalesLoft?

Ollie Sharpe:

We all know that people in sales, face-to-face meetings, have more chance of closing, and technology and video conferences mean that if you can't be right in front of somebody, you can still have that common connection, that personalized approach that increases the ratios of getting things closed.  I think that a lot of people are talking at the moment around sales all about trust.  Trust is easier to build when you're looking somebody in the eye even if it is to go over video.  We use video end-to-end when our product integrates with video within an email so we can send videos in emails, and they get a higher open rate and reply rate.  But, then, also when we do meetings, we also use video conferencing.  I've done it for years and, I think, if you can't be with somebody face to face in person, then doing a video conference makes a massive difference from doing it over the phone. I mean the first level is email.  Next level is on the phone.  Next level is video conferencing.  Next level is actually face to face.

In your opinion, what are some of the tips that get shared today that you think are just misguided about how salespeople should be approaching their jobs?

Ollie Sharpe:

I think it's more around leadership and style of people because I, being measured on KPI's that are meaningless.  What's happened in sales, the bar has been raised because the response rates, of course, it's not like it used to be.  Sales used to be, people had less calls whereas now you have PPI calling you every two minutes.  So, what has happened is that the bar has been raised so that there's two ways you can think about that.  Do we actually just make more outbound activities and hope that from the 100 calls we used to do where we get talking to 10 people, if we do 200, we get talking to 10 people. 

Or, do we, which reduces the quality of the actual message, or do we actually increase the quality of the message and make it more personalized, make it more specific, but reduce from 100 down to 50?  And that is the common problem that people are coming across at the moment, and it's the awareness or not being aware of the tools out in the market to help with that and just thinking, "Well, let's just work as we've always done but double the outbound activities," is not the answer.  People and just not aware of the technology that is out there at the moment that is trying to work on all the ways to mend things.

Check out the full video on Youtube. For more Zero to Won, visit

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