What I’ve Learned From Selling Software with No Experience

In October 2014, I applied for a sales role with Shopify Plus, the enterprise division of Shopify. I knew this was a different type of company because in the job posting it said the position required “0 years of experience”. ZERO YEARS! I was just finishing university when I applied and as a student looking for their first full time gig, the role at Shopify Plus sounded like a dream come true. Finally, a job where I could escape the paradox of needing to have experience to get a job, but needing a job to get the experience. (P.S. we’re hiring — but only apply if you have no experience)

Although, I never considered myself to have a sales personality, I decided to give it a shot.

The hiring process was tough, but I made it. I finished school in April and started on my journey in sales full-time in May.

So after my first eight months as a professional salesperson I’d like to share with you the misconceptions I had coming into this career, those I discovered are inaccurate, as well as some techniques I’ve learned building an outbound sales process.

For reference here is how our team works:

  • Shopify Plus is an enterprise SaaS ecommerce platform
  • Our average selling price (ASP) is north of $10K in Annual Recurring Revenue (ARR)
  • Our sales cycles range between a couple of days to a couple of months
  • Our customers range from companies with $1M in revenue to the Fortune 50
  • Our entire model is inside sales

My job is pure outbound. I don’t get leads or any kind from the company. I source my own leads, make initial contact, and manage the entire sales cycle from start to finish.

The Waterloo Sales Lab in Jan 2015

Part 1: Misconceptions of How to Succeed in Sales:

When I started I had some ideas on how sales would work. But I found out that a lot of the traditional wisdom I had heard just wasn’t accurate.

If you have a good relationship with your prospect, they will buy your product.

Traditional Wisdom: Building rapport with a prospect is important, since no one wants to buy something from someone that they don’t trust. By having a good relationship, a sales rep can candidly communicate with the lead, get their true opinion on the product, and even influence their decision.

What I found: While the above may be true, I found it’s only a small segment of what gets a deal done. What’s more important than the relationship is providing value to your prospect. Value can mean many things; in this context, it’s simply about making the prospect feel important, clearly understanding their problem, and then creating a tailored and educational experience that ties in the product. This will lead to a sale more than being a sweet talker. Relationship plays a part, but no one is going to buy your product just because they like you.

You need to have a strong value proposition in your first contact with your prospect

Traditional Wisdom: Salespeople have to have a well defined value proposition and ROI statement (e.g purchase our product and your revenue will increase by 500%!!, etc.), when they first approach their prospects.

What I Found: This approach actually has a very low success rate. People don’t buy features, they buy solutions. The problem with up-front, ROI approach is that you don’t have any idea on how their business operates, so how can you be sure your product is viable solution? A better method is to approach a cold prospect with high-level, industry advice. The main goal of initial contact is to have a conversation, that’s it. The advice you provide should be new and unique information so it has the greatest impact and establishes you as a domain expert. Ideally, the prospect can use this information to look good in front of their bosses. The goal for the sales rep during this call is to discover how the prospect does business, uncover any obvious pain, and push the conversation in a direction where the product could add value.

The Waterloo office in June 2015, minus 3 members

Number of closed deals is the only thing that matters

Traditional Wisdom: Sales reps are only as good as how many deals they have closed.

What I Found: The greatest challenge for me was that I wanted to see results from my efforts quickly. Yet, when you start a career in sales it can often take months to see impact, in terms of closed deals. It took me about 4 months to start seeing consistent results, so when I first started I had to reframe my expectations and focus on short term metrics like # of people reached, # of conversations, # of deals created rather than deals won. So when starting a new sales position start with goals which are more immediate and help you feel like you are making progress.

Present the competitors as inferior

Traditional Wisdom: I expected that in a sales role I would need to have an arsenal of information to showcase how other product were inferior to mine. What’s better than crushing your competitors right?

What I Found: A good sales rep doesn’t talk about the weaknesses of its competitors (even when asked), but instead focuses on the strengths of their own product. At Shopify Plus, we call this “staying classy”.

Despite my misconceptions I found that sales was both challenging and exciting. The variety of my daily interactions was immense and I got to experiment a lot with the best ways to get prospects engaged and move deals forward. In the next section I’ll share some of the things which have worked for me as I have built my process.

Oct 2015

Part 2: Strategies and techniques used in building an outbound sales process:

Breakdown the process into small parts, and optimize the bottlenecks

The greatest challenge when starting anything from scratch is learning where to focus and what to prioritize. In the beginning, I tried to do everything and then quickly realized there wasn’t enough hours in a day. So I wrote down all the things I would need to get done to be successful.

The list looked like this:

  1. Prospecting
  2. Outreach
  • Emails
  • Calls
  • LinkedIn

3. Quality of Conversation

  • Demos
  • Selling Techniques

4. Nurturing Deals

5. Expertise in the product

6. Expertise in the industry

With my list in hand I started to focus on each individual part, putting careful attention to identifying bottlenecks in my process. Then I broke each step into even smaller segments. As an example, prospecting broke down into the following sub-steps:

  • Finding a company
  • Finding a relevant contact
  • Finding their email
  • Finding their phone number
  • Finding where they’re located (for timezone)

The advantage to this process driven analysis is that I could now do research and reading on a very specific topic, learning as much as I could on how to make that step move fast. My research led me to form repeatable and efficient process flows for each step. Once I optimized one part, I moved on to other parts that weren’t as efficient. This allowed me to prioritize and really focus on gradually creating an complete and efficient process.

Track everything to build your machine

The head of Shopify Plus has a saying, “Your opinion is interesting, but not relevant. Show me your data.” So in order to see if my experiments are working I need to track lots of metrics. We have software that holds some of this data, but it’s often high level so I decided to do it manually. The metrics I track daily are:


  • number of prospects
  • number of qualified opportunities
  • number of qualified deals


  • number of total emails
  • number of new companies reached
  • number of new contacts reached
  • number of replies from first email (in cadence)
  • number of replies from second email
  • number of replied from third email


  • number of calls/ voice mails


  • number of conversations from first email
  • number of conversations from second email
  • number of conversation from third email
  • number of conversations from calls

demos/ sales qualified calls:

  • number of demos or sales qualified calls

number of deals created:

  • number of deals created from cold calls
  • number of deals created from current email cadence
  • number of deals created from old email cadence
  • total number of deals created


  • number of contracts created
  • number of contracts signed

lost deals:

  • number of deals dropped

Knowing your metrics provides visibility on your efforts, and it’s really neat to see how you could consistently reach out to a certain number of companies and it will result in about the same number of deals created each week. I also track these metrics so I learn what my sales efficiency stats are, like:

  • # of outreach to connect
  • # of outreach to deal
  • # of outreach to win
  • close rate

Once things start to work efficiently, the aim is to optimize so you’re able to do more with less.

Learn fast by working on more deals

Marc Andreessen wrote about a study correlating age and outstanding achievement in creative individuals, and it is very applicable to sales. The best way to learn quickly is focus on quantity rather than quality. After each completed process, you should gain feedback and incorporate it into the next one. It’s all about the data! This is better than focusing on perfecting one single deal. Andreessen worded it as “maximizing your at bats”.

In sales, this means the simplest way to be successful is to be working on more deals. Each one will be different, but have enough similarity that you’ll have the ability to learn and continuously improve your technique. With this in mind, the main goal is to optimize for number of deals.

I still have a ton to learn, and everyday I’m crazy scared — scared that people won’t reply to me, scared of rejection, scared of deals falling through. But being uncomfortable everyday like this has helped me learn fast and evolve.

In eight months I’ve had the opportunity to talk to hundreds of companies doing really cool things and sold hundreds of thousands of dollars in software, which is crazy! I’m looking forward to evolving and learning even more in the next year.

If you found this insightful, let’s connect on Twitter. I’d love to know why, and hear your story. Thanks to Loren Padelford for his feedback, and Jevin Sidhu for the final edit.