Finding A Sales Mentor With Scott Leese

by James Ker-Reid - July 14, 2020

Sales for Startups Founder and CEO, James Ker-Reid, talks to Scott Leese, an all-rounded, top sales leader, sales mentor, author & entrepreneur. 

We hear from Scott about his approach towards ensuring his multiple streams of income, including some advice about being offered equity and share options when joining a company….

  • Thanks for joining us today, please tell us more about yourself Scott

Thanks for having me! I run a few different businesses right now – my own consulting firm, Scott Leese Consulting which includes advising early-stage startups and founders where I specialise in the £0-£25m stages to help build up a sustainable and scalable sales organisation. Also run which is a micro sales conference which we host in Costa Rica a few times a year – and I co-host the surf and sales podcast with my buddy Richard Harris. A few years ago, I wrote a book called ‘Addicted to the Process’ about transactional sales. I’ve been in the SaaS game for almost 20 years now – a 6-time Head of Sales, had a few mediocre to decent exits under my belt, building and scaling sales teams most of my professional life. 

  • Take me back to that moment when you first got started in sales – what did that look like, what was your role?

This is quite a long complicated story actually….I played 2 sports in college, tennis and soccer and ended up playing some soccer beyond that when I went to grad school. After this, I was 23 years old and not really had a job before and I wasn’t get paid to play or coach sports at this point. I actually ended up getting really sick and was in the hospital for the majority of a 4-year period, fought for my life at some points, ended up with 9 major surgeries, 4 major abdominal surgeries, 2 life-saving surgeries and got hooked on pain medicine through that process – it took me a while to get better from that so I was 27 years old when I got my first sales job – quite late to the party.

I got into sales because it was the only thing I could think of to make up for the lost time. My sense of urgency was heightened, and I knew was it was like to have nothing, I felt like I understood the competitiveness of sales – that was the athlete in me speaking. That was why it was a real strategic decision on my part to go into sales; work hard, get paid well….don’t perform well, get cut. I understood that dynamic and expectation. All this was about 16 years ago when I first started in sales. 

  • Since you first started, what do you think has changed over the last 16 years in sales?

The obvious answer that comes to mind is technology all around us to support our selling efforts. When I first started I didn’t use a CRM, I didn’t have a headset, I had a handheld wired phone scrunched between my neck and shoulder. There were none of these tools like CRM, enablement, drift marketing, video prospecting  – none of that existed.

Fundamentally, I think Sales has become much more about the buyer and the buyer’s journey which is a good thing. If you look back to the 80s with the whole wall street, boiler room – I think that’s died off or at least close to it. We’re focussed where we should be, which is on the customers, what problems they have and how we can solve these problems for them. Those are the two biggest shifts that have come to mind – technology and our approach.

  • Something that I noticed you’ve mentioned before is equity and share options – what’s your advice on this, particularly maybe at this time of COVID 19, for salespeople joining companies or employees that have been offered this?

A lot to unpack here. My best piece of advice would be to read up and study and understand what equity means; the implication as far as taxes are concerned, how long it would take for you to realise some of this income, how much you’ll have to pay out in order to exercise those options, what’s a fair stake depending on your role and what stage the company’s at, etc etc.

The education piece is something I’m passionate about as a sales mentor because most people don’t know anything – I know VPs of Sales that don’t really understand how the equity process works. So the biggest piece of advice is to educate yourself on this stuff. I’m a big proponent of going into early-stage companies and that’s for a number of reasons, you drink from a fire hose at the beginning, wearing several different hats all at once and there’s a challenge in that and an honour in building something from scratch and betting on yourself and couple of other people rather than a huge company that’s been around forever.

You really can feel the impact that each particular person can have – if you’re making a big impact, you deserve a stake in that company – that stake will obviously differ depending on the level you’re at and what you can offer. I’ve spent my career working in the early stage and placing these bets on myself and on some of these companies.

You’re most likely not going to get filthy rich, unless you’re a founder, or of course, you could get really really lucky running a department of one of these unicorn companies. You can get nice liquidity events that could help you with certain purchases etc, but we do need to dispel the myth of someone going to an early-stage company as a 25 year old sales rep and making a million dollars in equity sales – that’s not how it works. I’m passionate about trying to give people the reality of this situation 

  • Any particular information sources that you would recommend that people can go to in order to learn more themselves about this?

Not necessarily that I can think off of the top of my head and this is one of the challenges. I’m sure there’s stuff out there, but what’s the go-to resource? I don’t know! And I’ve been in this game for quite some time.

Recently we did a podcast with Richard Harris and Colin Cadmus – previously VP of Sales of Aircall in the US – and we talked about this for over an hour and we had tonnes of great feedback, so in a few weeks we’ll be doing a webinar along with Sam Jacobs, Founder of Revenue Collective, to talk about equity and unpacking what it means, all the implications of it and more. We see a gap in the market and we are going to try and fill it. 

  • Building from that – another thing you’re passionate about is people creating secondary and tertiary sources of income. Any advice to those out there who perhaps have their own consultancy or business income who are looking to find other sources of income?

I think in the modern world it’s incredibly difficult to get by just on one particular job. I remember when I first got started in sales, I thought making 6 figures would be the end all and be all and once I got there I would never have to worry about money again.

Well, this changes when you have a wife, 2 kids, mortgage etc and before you know it, it’s expensive. I think everybody should try and diversify their portfolio to speak. How to get started?

Figure out what you’re good at and what you can teach people and then lean into that. If you’re a business owner it makes total sense to start a consulting business and give advice about that. A long time ago I started buying cheap real estate properties, renting those out and getting income from those.

One of the reasons I wrote my book was to get royalty cheques each month – it’s not outrageous amounts of money, but anything you can do that adds $500 a month or more to your bank account, it adds up!

There’s a famous quote saying the average millionaire has 7 different streams of income. I heard that years ago from a sales mentor and my mind was blown, finding out these millionaires aren’t just millionaires because they are really good at their sales jobs – of course not, they are doing way more. They’ve got their regular gig and maybe monetise some content etc.

An easy way to add supplementary income is to add affiliate partnerships and relationships – we are probably both very familiar with all the sales technology available out there, so if we love a product and can evangelise it, we can get paid for that and requires very little effort. I want people to think more along those lines – I’m always thinking about how to make more money, a few hundred dollars here, a thousand there – it can add up. If you think that way long enough, some good ideas start to come up and you can have conversations with people who have this already figured out. 

  • What are your thoughts on ‘mastering’ your primary income and having a waterfall effect on your secondary incomes (a Grant Cardone concept), compared to trying several different methods of different incomes and seeing which one works best?

The concept isn’t to have 7 full-time jobs, that’s just not sustainable. The concept is to have 7 different streams funnelling into your bank account with 5 or 6 of them being almost no effort – that’s the goal. It doesn’t have to be purely passive, but little amounts of effort.

I don’t follow the sales mentor Grant Cardone so I haven’t heard that myself, but I understand the theory of the waterfall concept and I do think that people, especially younger people, they’ve heard all the advice about side hustles from their sales mentor, but they forget where it comes from – you better be really really good at your first or main job – that’s where it flows from. Once I got really good at sales and managing teams, I was in the mindset of knowing what I’m doing and feeling comfortable and thinking what I could do to start generating different incomes.

For me, I saved up $50K and decided to put it down on a property, after working out the maths and working out I’d make $500 a month from that money I’ve already made – generating monthly income and also long term equity increase too. And I would repeat this process. But this all stems from being really good at your core job. 

  • For those that are wanting to get started and maybe go into that secondary flow of income – any pieces of advice you would give those people?

I think the best things you can do is network your way into knowledge. When I was getting started there wasn’t the same sense of community…you and I would never have met or be having this conversation through our contacts.

The world is shrinking right now and you have communities, such as LinkedIn, that are full of people who have been there and done that and who are bigger, better, faster, stronger than you. A lot of people are willing to share content and information for free all day every day and especially right now. There are events happening every day right now, even through COVID, you’re almost able to get your own PhD in sales with all the content out there that you can access and speak to the right sales mentor.

So what I would do if I were just getting started is to start building relationships with folks like you and me, and just reach out, try to interact and engage with their content and develop a relationship. If you develop a relationship enough, it becomes much easier to ask someone for their time in order to ask a few questions. There’s plenty of people out there who will do this happily and for free – find a sales mentor or two. And it’s always worth having a few sales mentors rather than just one – one person’s advice might not ring true to yourself, but others might. 

On another note, one of the easiest ways to differentiate yourself out there these days is to actually do what you said you’re going to do. I attach the note at the end of all my messages that says ‘let me know if I can ever be of any help to you’ and I mean it. I respond to every email I get of someone asking me for help, I respond to every LinkedIn message, I respond to all my comments on posts I make, I give out my mobile number all the time, I respond to every text – I’m very accessible and that builds up a level of trust and authenticity.

That’s the type of sales mentor or person you want in your network – it doesn’t do me any good if someone offers their help and then never interacts with me or responds to me again. But then you push those people to the side of your network, move on and keep reaching out until you find the right people to help you grow and enrich your life.

  • If anyone wants to find you and what you’re up to where should they go?

Linkedin for sure is the easiest. My websites and – you can find my book ‘Addicted to the Process’ on Amazon and my podcast ‘Surf and Sales’ is on all the usual providers out there. I encourage anyone who wants to reach out to me to have a chat and I appreciate the time today James to connect with your audience. 

Great to connect with Scott today, thanks! 

We want to thank Scott for today’s interview, a really good conversation with a sales mentor that I hope everyone reading can take something from.

That is all from us at Sales for Startups today, be sure to tune in soon for more interviews with CEOs and Founders of some great companies that are shedding some light on the current issues we are facing. If you’d like to be interviewed please comment below or feel free to connect with me on LinkedIn or submit a request on our website.

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