Sales Is Not What You Think: Interview with Kelly Hackmann

Gabriel Glasser
Nov 6 · 6 min read

This week I interviewed Kelly Hackman about his experience in a sales role. Kelly is a Praxis alumni. After finishing his apprenticeship at PandaDoc in San Francisco, he was offered a full time position and worked there for 2 years.

Kelly is my cousin, and is the reason I came to know about, and ultimately apply for, the Praxis program. He now lives in Washington and is in the process of opening a restaurant. Kelly is an insightful and all around interesting person, so interviewing him was easy and enjoyable. I hope you enjoy the interview, and can learn something about sales from Kelly’s perspective.

What made you want to go into sales?

To understand how sales could be a helpful profession, as opposed to how I had always seen it in movies and TV. I wanted to learn it as a prescriptive profession, rather than just as getting commission. I had heard Isaac and TK talking about it on their podcast, and then I read books by Zig Ziglar and others, and I thought, “I have this entirely wrong”. I felt like I owed it to myself to go get it right, in the trenches by doing it myself.

Did it come natural to you, or was it hard to learn?

Everyday is different, it depends on how you’re feeling that day, at least for me. I don’t think it came naturally, but at that point in my life I was writing a lot, and I think when you write more you become a better speaker (your vocabulary and timing), so I think that helped. A lot of modern sales is just emailing, so writing helped a lot with that. I had been in the practice of communicating effectively, so I wouldn’t say it came natural to me.

What are some of the major skills you need to succeed in sales?

Verbal and written communication, as well as time and task management. Giving every prospect your full attention in that moment, and being completely repetitive, disciplined and diligent about communicating.

What was your first week like at PandaDoc?

It was information overload. It’s called on-boarding. The first week is learning everything you can about the product or service. A lot of new information, but it was exciting because it was coinciding with moving to a new city.

What did your role look like in terms of day-to-day activities?

The first six months it varied a little bit, but a lot of it was just constant customer contact or prospect contact. A great way a lot of companies on-board, or I think should on-board, is by just doing customer service starting out. You answer support tickets. I don’t think most companies do that, but at PandaDoc that’s how I started. I was working the online ChatBot. I routed customers to every department of the company depending on what they were coming for. That was a good way to learn the company. But sometimes the on-boarding can be a lot.

Did you ever have to meet people in person and “wine and dine” them?

That was later on when I was an account manager, and I was building relationships.

What is that like? Are you trying to persuade them in person, or are they existing customers?

Usually they were existing customers that happened to be in town. It was more just friendly — going out to lunch to get to know each other better. But it could be an entirely different situation where you’re going to conferences and meeting with clients at the conferences.

What’s the hardest part about sales?

The discipline. Some people get burnt out pretty quickly, especially in outgoing sales, because you get a lot of rejection. You need the discipline to not let that get you down. You need to have a conviction that the product or service will help people — that will help you cope with all the rejection. And you need to be organized while you push forward.

What’s the most rewarding part about sales?

Every sales person is a little different. For me, it was knowing that I had helped a company, by persuading them that we could help them. The sense of making things go better for other people. And the commissions aren’t bad either.

What were the hard skills you needed to learn for your sales role at PandaDoc?

PandaDoc is an SAS (software-as-service) company, and a lot of the other stuff we were using were other SAS products. It’s like a little ecosystem of software that you become familiar with. The most important were Google Calendar and Gmail, as well as Salesforce, which took a bit of leanring for me. I was learning Salesforce to do back-end stuff, however, which a lot of sales people don’t have to do.

Is Salesforce a program for keeping all of your prospects straight?

Yea, it’s like a 21st century Rolodex, that can do some really powerful data analysis about your clients and future clients. It helps you save a lot of time. You can also wire things through it. You’re using other apps within Salesforce, so it’s really the one website you have to go to.

How is sales important to the overall success of a business?

Sales creates incoming revenue. Nowadays the line between sales and marketing is getting pretty blurry, but sales and marketing are the face of the company. They set the expectations that everything else follows. The sales team is not an island unto itself, and neither are the account managers, customer success managers or support people. Sales people just sell the product, but what they’re also doing is setting up an entire row of actions after that.

While the sales person goes onto the next client, others have to actually provide the service to the customer, and that’s what the company really is. Sales people just get clients in with expectations. So sales people have to be accurate about what their promises are, and they have to have a good understanding of the product or service they’re selling. A rookie sales person might say anything, not knowing fully if it’s true, just to please the prospect.

So would you say a big part of succeeding in sales is understanding the product or service well?

Generally, the sales people are not going to know the product as well as the implementation people or the support people, who know it like the back of their hand. It’s a fine line. Sales people might not know the technical details but they know what it’s supposed to be used for.

But sales people are also giving feedback to the entire company on what they should be doing. If they’re not making sales, and it’s because the customer says the product does’t do “x”, and the company doesn’t change to make it do “x”, than everyone fails.

Do sales people have to understand the experience of the customer more than any other department?

It’s them, and account management. Account managers are having meetings with existing customer all the time who are using the product, so that’s where most of the feedback for the development team and the engineers comes from. Sales people just give feedback on what’s not getting people in the door.

Does sales work closely with the marketing team?

Sales leadership does, but the average sales person at the average company doesn’t. The marketing team is usually seen as the enablers of the sales team. They make marketing collateral, case studies, or what’s called “battle cards”, which is a way to gauge your companies’ stats against competitors. Marketing is responsible for making a lot of that stuff, in addition to advertising and getting the companies’ presence out there.

Is there anything interesting about sales that you think most people don’t know?

The big mouth, flashy salesman that you see in movies — they don’t last long on the actual sales floor. It’s the people who are really humble, task oriented and disciplined that succeed. It’s not who you think. Sales teams are different at every company based on the culture there, but that was my experience at PandaDoc.

Gabriel Glasser

Written by

Innovator interested in finding more beautiful and meaningful ways of approaching life. Moth after the flame of meaning and depth of experience.

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