On thing that I’ve realised throughout this series is that intensely personal interviews make for the most compelling reading. Therefore I’m grateful for how blunt and honest Howard Paine is in this interview.

Having been a top performer for fast growing tech companies in Appdynamics, Permutive and now ZScaler, this is a insight into the psychology of a hugely valuable modern salesperson.

You can read Howard’s full biography here

Jamie: What have you enjoyed the most about moving into sales?

Howard: I think the stuff which goes along with performance which is very obvious, compensation. That’s very satisfying during the stage in my life, where I was married two years before I got out of the army, and being able to provide properly for the family. Equally, I haven’t had to give up on what I enjoyed at the military, where you can be a performing member of a team and have the satisfaction of everyone sharing in the highs of the team effort. It’s the best of the individual recognition and team merits, especially for me – I’ve worked for a start-up which was bought by Cisco, and now for a new start-up which is again in hyper-growth. Everyone’s in it together, big highs, low lows, a lot of stuff that I’ve found very exciting and interesting.

Jamie: Did you choose those companies in part because they are high growth start-ups. Was that something you were looking for?

Howard: 

Yes, absolutely. I think those kinds of companies attract the best kind of people. I believe that you are a product of the 10 people you spend most of your time with. These companies seem to be full of strong people – they take all the best people because they are growing quickly enough to pay them.

They have that momentum about them, which is very captivating, very interesting, and that’s why I read the Glassdoor review for my first company. It sounded a bit quite intense, and people most likely got quite scared of it, and I was like, “Well, it can’t be worse than the military.” I was interested. The interviews that she had were meticulous. They break you down, try and challenge you, quite intense, but it got my attention, and I kind of dreaded them and being made to feel like an idiot, but I always went back, because it was interesting.

Jamie: Would you say then that a harder interview process in a job is a positive for you?

Howard: It depends what you’re looking for. I think for salespeople, yes.

I think if you’re not comfortable sitting in an uncomfortable conversation and holding your own or if your aim is to avoid conflict, then I’d say going to sales might not be your thing.

Jamie: What have you found the worst thing about being in sales thus far?

Howard: Most of my family do vocational things because they believe in them, and they care. It really matters what we’re putting out to the world because my parents are teachers, my sister’s a doctor. I served in the army, and then my other brother made a fortune in sales. I do that now, and I sometimes think if I stopped selling software tomorrow, does it matter? Am I moving things along in a way that really matters to me?

What I try to tell myself is that you have more to give back and look after your family, and it also gives you other opportunities to influence stuff. In fact, the first two bosses I’ve worked for in sales were both great, and ultimately both did really cool stuff for charity. They used their resources to do some pretty cool stuff, so I think that’s the thing I’ve had the most success with.

Jamie: Do you have recommendations on what you can do to increase the conviction and purpose of what you’re selling, even if it isn’t your vocation?

Howard: Yes, pick something that chimes with you. I know even though it sounds quite basic,

I generally think you should sell the best product, to avoid selling people down the river – like you’re trying to convince them of a false argument. I find that impossible to do. I find it very hard to sell without integrity, which is a lot bigger of a motivation for me than just a pay check. I chose companies that I generally believe had a differentiating, beneficial impact on the companies they worked with; had great reviews, and had great feedback from what they had done.

They have sold what that they actually believed in their mission statement, even if it was just improving external teams’ performance.

In my new company, we help publishers who generate all this content, and the people helping them stay afloat without external funding and without external interference. I think that’s a pretty good cause. It’s not serving our fellow man, but it’s a good thing that you can feel good about. I’d recommend that no-one work for companies that sell something where you don’t actually believe in it. I think it will shine through, and if it doesn’t, that shows something about you.

Jamie: Would you describe the products that you sell as complex?

Howard: Yes, I would. I guess my description complex would be that there’s a lot of people involved, and a lot of moving parts. They have an education element; some reframing is needed. There is a lot of stuff that needs doing with a lot of people, and it all needs to be coordinated to make something happen. I would recommend that you learn how to sell complex products. If they need to hire people, and you can make a complex sale, they’re going to be hiring the best people available regardless of cost.

Jamie: What skills and attributes have you noticed in the people who can do a good job of complex sales versus those who don’t do as well?

Howard:

I’d say the key ones are really simple. It’s doing them really well consistently over a long period; that’s tough.

I think there’s a lot of EQ, emotional intelligence in that understanding of who you’re dealing with. A lot of curiosity is needed. The ability to ask good questions and figure out what is actually happening inside their head instead of assuming anything is key. You’ll come across so many different scenarios, and different people, that the best way to do is to assume you don’t know much – people who keep doing those things are consistently great.

Jamie: Has being from a military background helped you move into sales?

Howard: Yes. I feel quite comfortable speaking to senior decision-makers or people who you perceive as a senior, like CEOs, without any fear. You don’t feel that same kind of connection. If you ask why people would not get into sales, often the reason is that people listen to the negative stigma; its long hours of hard work and asking uncomfortable questions and being in uncomfortable situations and that puts a lot of people off. That people would consider travelling two to three days a week to Germany and sleeping in a hotel bed as tough is a bit crazy. It’s all relative, I think. There are a lot of military characteristics and attitudes that suit sales really well.

Jamie: Would you recommend that a salesperson do something that’s a bit more difficult, to give you perspective?

Howard: I can only really answer for me. Yes, absolutely, I would. I think it’s interesting that if you look at it, salespeople live a pretty great life, with big highs. There is more pressure and job uncertainty than other jobs, but it’s pretty good overall. When I left the army,

 I stepped back and realized, “Actually, no one’s going to die.” Nothing terrible is really going to happen; the worst-case scenario is that you lose your job and find another one. I think keeping that emotional distance from the outcome of sales is fantastic. The more you act as if you don’t care, as if you’re not emotionally connected, the better your calls will be.

Jamie: How often do you remind yourself that ‘no one’s going to die?’

Howard: I remind myself of that during the trickier times, and I think that’s what really matters to me. I’ve seen people have really good careers and their motivation keeps decreasing since they stay in the same situation. If you’ve got something in mind that means a lot to you, be it financial freedom, family, or whatever, then it is all much better.

None of those things should be entirely dependent on my job. If you think any of those things would go away or stop existing if you get something wrong at work, then you have to ask yourself some questions anyway, but none of those things tend to happen. The things that I care most about wouldn’t change if I got fired tomorrow. I’d just find another game to play.

That’s not to say that I’m completely ice cold and I tell my boss what I think every time. It just means that it helps put my perspective on it. You need to have that kind of relativity to what rest of the world looks like.

Jamie: What elements of culture make a sales team really perform and stay in an organization?

Howard: I’ve worked with two very different teams. I say the first one was unexcused elitists and had a bit of a personality cult going on. It was all about high standards. I mean radical feedback, really open, but at the same time, I think it wasn’t as balanced as it should normally be, and they had a really high turnover rate.

They were good to people and treated people fairly, but equally, I didn’t think they really cared. I didn’t want to play there.

I think when you don’t get too caught up in that game, and you do realize that actually, there is a team element to it. For me, it is great news if someone goes really well. I’m competitive with my colleagues, but actually, it’s all good for us. It’s all about going in the same direction.

I think the company should have a unified purpose which people can believe in. I think sales dominates the culture of a growth company like that. I think not to let that happen is really important because they tend to be extroverts anyway; tend to be very loud and curious, and tend to have the biggest immediate impact on performance. I think it actually makes a company centred around these salespeople. I don’t think it always works.

I’d recommend it to anyone in any career that you make a choice based on three things. For me, in sales, it was people, product, and market. I do it in that order. If you work with really good people, then, that is the single most important aspect. If you’ve got a great product, you have to believe it actually works, and I hate to be selling the third-best solution in the market without a good price. I think it kind of feeds back because the best market will attract the best people to the best opportunities, and that’s where it’s fun. You’re passionate about whatever it is if you have those three things.

Jamie: What are the biggest pieces of advice you’d give to aspiring salespeople?

Howard: The other one is, be really, really honest with yourself about what you want to do. What is important to you? What does a good job look like? Everyone would like a job that pays well.

I’d say choose the challenges you want, not the good bits you want. Choose which difficulties you put out with –  the pressure, the big highs, the low lows, the travel, or the uncomfortable conversations. These are all things that you will do because you’re excited about the outcome. If you’re just choosing it based on all the good bits, I see a lot of people not having a good time.

Jamie: If you had your sales career again, what would you do differently?

Howard: I speak fluent German. They interviewed for a sales role and said, “Because you’re coming out the army, you don’t have the experience. We thought we’d start you in an upsell role.” The reason was that they didn’t have any Customer Success Manager in Germany. My advice to myself would be: “Back yourself, you can do well without having experience there,” but I didn’t know any better, and I was worried about finding a job, which you need to have to sign off from the military. You have to give two years’ notice, and then you have to find a job while you’re still there, so it’s quite a lot of pressure. I think I would have been a little further ahead if I just said, “No, that’s your job on your advertisement, and I am good enough for that one.” At the time, I just felt like I needed to get started. I like the company. It didn’t do any long-term damage, but that’s how it started.

Jamie: I was wondering if you could tell me about a specific sale that you didn’t make, but it taught you something really valuable?

Howard: I spoke about not being too emotionally attached to the outcome and making pragmatic logic-driven decisions, not emotional ones. I spent six months dealing with a French publisher because I wanted it to work. I was emotionally connected to the outcome because it would’ve been really exciting. Everything, all the flags, all the logical thinking, all the process told me that this was a waste of my time, but I went along with it, and it’s cost me a lot of time and effort. Having an honest discussion with them, and with myself, would have saved me months of effort and stress. Maybe, if we’d all been honest and just had that frank discussion, it could have all been avoided.

Jamie: Could you tell me about a time you’ve made a sale, shows off the skills and knowledge you’ve gained so far?

Howard: My first end-to-end sales call was one which had been salty before but ended up pulling through. There

were few reasons for that; it was a difficult one in terms of complexity, but I approached it as, “This is going to be my gold standard,” when I was going to do everything exactly as it should be, whether I felt it was worth the effort on some points or not. It took a lot of feedback sessions with leadership in our company. I wasn’t entirely sure in the outcome but trusted the process, trusted in the team, and it went awesomely. We did all the right things the right times. There wasn’t any magical knowledge, or that I suddenly got lucky, but I followed the process and just stuck with it in a logical manner, and got advice when I needed it. It was as good of a high as you can get.

Jamie: What was that moment like when you realized that it was going to work?

Howard: It’s awesome. I think the nicest thing was how excited everyone was for me. We had a long list of messages coming in. We got a lot of people who are generally excited for you, who work with you on it and so invested in it as well. That’s a nice thing about sales, you are accountable – for the bad things because you’re in the point position, but for the good things, it’s your name on the account. For better or for worse, it’s great.

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