How A Top Enterprise Sales Rep at Shopify Uses Account-Based Selling - - Relationship Intelligence for Sales

How A Top Enterprise Sales Rep at Shopify Uses Account-Based Selling

By Jaxson Khan in Sales

If you’re in e-commerce or pretty much have any idea of what’s happening in tech, there’s no way that you could miss Shopify. In a few short years, they’ve become the leading multi-channel cloud platform for commerce. The company is valued at over $12 billion and Google was even angling to acquire it.

One of the fastest growing segments of the commerce giant’s business is Shopify Plus, a premium offering for high-growth enterprise companies. We last talked about Shopify Plus when we interviewed Hana Abaza.

Which brings us to Chris Grouchy, a top outbound enterprise sales rep in the fastest growing part of one of the fastest growing companies in the world. Chris has aced his quota quarter after quarter so we wanted to ask him some questions about how he sells.

Interview with Chris Grouchy on Account-Based Selling

Nudge: What does Shopify do differently?

CG: Shopify is a commerce platform that lets businesses sell to where their customers are today and tomorrow. Over 500,000 entrepreneurs trust Shopify. Shopify Plus is a commerce operating system that powers high-volume merchants that want to grow bigger, faster.

With tech becoming such a big part of budget decisions, it’s hard not to think about your tools constantly. Tech can be an enabler or a detractor. Failing to get it right will spell problems for your business. Just look at the iconic Toys R Us, which recently filed for bankruptcy.

Choosing tech shouldn’t get in the way of actually building your business. At Shopify Plus, we let businesses focus on their core competencies (marketing and product) by stripping away complexity and unnecessary IT headaches. I think that’s how the top brands will win long-term.

Nudge: Why Shopify for you?

CG: My parents are small business entrepreneurs. My childhood home doubled as an office for my parents. I loved the chaos and learned to love helping them (though I was probably in the way most of the time). So, I’ve been living with entrepreneurs my whole life and am incredibly appreciative of the challenges that they face.

We live in an ever-changing world – you don’t necessarily have to be part of an organization for 30 years. In fact, you probably shouldn’t. I recently read that most Canadians have less than $10,000 saved up, and most Canadians carry large sums of debt. I don’t think this is what freedom looks like. So is just working a 9-5 job good for people?

I think one of the reasons that more people are turning to technology like Shopify is to become entrepreneurs and to diversify their sources of wealth. Shopify provides freedom. Freedom of time and money. That is a good thing for society.

Coming out of school, I only saw one company in the entire world that was providing that kind of freedom to people –– and that was Shopify.

Our CEO, Tobi Lütke, recently said at our annual conference “Shopify will always take the path that leads to more entrepreneurs”. I couldn’t have said it better. It will help a lot of people, empower them, and lead to more money and help people it. And I am fundamentally aligned with that mission.

Nudge: So, why not just go start your own business?

CG: Shopify Plus is an experiment that began about three years ago. What if we could take the Shopify offering upmarket and provide the white glove support that enterprise businesses have come to expect from their technology vendors? Can we still offer those customers the best merchant experience? And so the Shopify Plus adventure began.

In true Shopify fashion, Shopify Plus took a contrarian approach to hiring. The early team wanted people fresh out of school who were curious, willing to learn, and were determined to see this rocketship succeed. And while we’ve grown, the sales operating philosophy remains the same. We take sales reps and let them manage the entire sales cycle. From start to close, you have full autonomy over your deals.

Contrast the full-stack sales rep model with the BDR/AE approach where if you’re lucky you will spend 18-24 months as a new grad doing the BDR work but never closing deals. Then you get promoted to AE and finally get to close. While this works for most SaaS organizations, I’m pretty impatient and wanted to be able to do every sales activity on day one.

That’s ultimately one of the big reasons why I decided to join Shopify Plus. I could learn to sell on the steepest learning curve and be part of this mission to make commerce better for everyone.

Nudge: That’s awesome. And what’s your background? Where did you come from? What’s your story?

CG:   I studied at Queen’s University and graduated with a Bachelor of Commerce degree. Nearly all my friends took consulting and banking jobs. Going through school, I thought those were the only two options. But still… as someone who eventually wanted to build a business, I didn’t think those would actually be great options. So for a while, I felt stuck. I loved business but felt that consulting and banking just wouldn’t make me a better entrepreneur.

I thought a lot about the day-to-day that I’d need to master in order to build a company. It wasn’t about building slide decks and living in Excel spreadsheets. It was about engaging with real people and customer with real problems, and learning how to communicate with them and provide value.

I grew up in Brighton, Ontario. It’s a small, close-knit place of about 12,000 people. Big news: a few months ago we finally got a Tim Hortons which, as you know, in Canada puts us on the map.

When I was finishing up high school, I ended up winning a national scholarship and also served as a student trustee on the school board.

More recently, I was also lucky enough to be named a Venture for Canada Fellow, which is the national youth startup fellowship that pairs you with a company and a cohort of other aspiring entrepreneurs for two years.

And that all helped set me on the path that I’m on now.

Nudge: Alright. So how do you sell, Chris?

CG: I definitely believe in account-based selling, so I’ll outline how I set up my approach, what I do day-to-day, and how to track results.

First off – people buy emotionally.

They buy based off of relationships. Nobody likes to talk to a sales rep because buyers are coming on average with something like 57% of their buying decision already in their mind. You need to create the best customer experience and help them navigate their organization and problem in the right way to get the best buyer journey properly.

All my interactions are outbound and cold. Instead of jumping in totally cold to that call or email, I conduct extensive lead research to see if it’s even the right person, time and offer.

I try to answer a couple of key questions:

  • Who is the right decision maker?
  • What is the main pain point?
  • Do I have a hypothesis that could explain why they are experiencing that problem?

To proactively understand company priorities, I seek out insights.

I get company insights from for news and social mentions of a company. That comes right in my inbox. With those insights in hand, I can curate an email to that decision maker by personalizing it to their own priorities.

Next, I have a cadence.  I am crazy persistent in between calls, emails, and InMails until I get a definite no. Usually, about 8-12 touches on key accounts.

Typically, I set a task inside of my CRM (we use HubSpot) and that’ll prompt me to re-engage.

Nudge: Does your sales approach ever change?

CG: Yes. While consistency and good process lead to repeatable revenue, sales is a dynamic sport. So how do we factor in the dynamism of sales into our selling processes?

I really like the doctrine of wartime sales vs. peacetime sales. I adapted this mental model from Andreessen Horowitz’s co-founder Ben Horowitz’s Wartime and Peacetime CEO philosophy, which he explains throughout his epic book The Hard Thing About Hard Things.

In sales, it’s either peacetime or wartime. Always one exists, but never both simultaneously.

In peacetime, you focus on new opportunities and filling the top of the funnel. This means prospecting new key accounts, having qualification calls, creating new deals, and mapping out the needs of those key accounts. An indicator that it’s peacetime is that your fellow reps are taking it easy and probably scheduling vacations.

In wartime, you’re focusing on getting those deals through the funnel. It’s crunch time. You have a number to hit and the countdown is on. Hit it by any means necessary.

Fundamentally, it is tough to do both at the same time. In sales, there’s a very high cognitive switching cost between wartime and peacetime activities. I think that focusing on one thing is a good management system for most people.

When he was building PayPal, Peter Thiel was notorious about his employees only focusing on one thing. This allowed them to be more effective, develop extreme focus, and contribute something of depth to the organization.

I structure my quarter around war and peacetime. Day to day, my activities differ based on whether it is ‘war’ or ‘peace’.

Nudge: Well that’s cool. And kind of scary. Can you go deeper on how you structure that?

CG: It’s a simple system, which is why I like it so much.

Peacetime — Beginning and middle of a new quarter.

Wartime — Quarter-end, Q4, and year-end.

By definition, you spend much more time as a sales rep in peacetime.

You could map your days like this:

  • Mon-Wed: Prospecting and Outreach
  • Thurs-Friday: Booked Meetings and Deal Strategy

Peacetime activities consist of:

  • Morning research and prospecting
  • Sending emails, InMails, and scheduling calls in the afternoon
  • Book customer meetings for first and second discovery calls
  • Never been a great multi-tasker, so I silo my days out

Wartime days are very focussed and should be like the following:

  • Mon-Wed: Demos and Contract Negotiations
  • Thurs-Friday: Object handling (last minute) and Deal Closing

Nudge: So how do you close deals?

CG:  Closing becomes more challenging as you go upmarket. For smaller customers, you’re usually interacting with the person who will be signing the contract on day one. So there’s velocity to the sales process. Big deals mean bigger teams, and that’s a political landscape that makes ABS critical to getting it done.

Therefore, on large deals, we need to consider these three teams, the language you use with them, and the insights that you draw and use them to communicate. You need to create champions that will push your message further when you are not around.

We will interface with marketing, IT, and the executive team.

  • Marketing and sales are revenue centers.
  • We target them in an e-commerce business first. They are measured based on growth metrics. Cost isn’t much of an issue here because they are focused on delivering new revenue growth. Strongest case when we get to C-Suite level to back me up.
  • IT is a cost center. Their objective is to cut costs.
  • They may complain about spending and even justify their existence if your technology can do what they do better. So we have to create the best ROI scenario that is echoed by marketing and sales that this is the best allocation of funding.
  • Executives care about ROI –– revenues and costs come to play here. Ideally, you want to check the IT boxes and have a champion from marketing and sales championing the initiative to the executive team.

The triangle of account-based selling that we focus on looks like this:

  • I use Nudge to track my relationship strength with those people. And then I can determine if I have a weak or strong relationship.
  • If I go through the deal process and find that it is stronger, now I can take those insights back and have more candid/direct conversations with them.
  • If you have a weak relationship –– start building rapport! If you have a stronger relationship, start having direct conversations. If they’re being more open with you, leverage additional information to help them make a buying decision.

Nudge: What’s in your sales stack?


Nudge: I want to push you on this –– have you reflected on what are the differences between you and the rest of your team in terms of your approach?

CG: I focus on the quality of contact. I am very focussed on reaching out to the RIGHT person. It’s not about making 100 generic dials per day. You want to come up with a hypothesis that grabs the attention of your prospect.

So I do rigorous preparation before a sales call:

  1. Understanding what the contact cares about.
  2. Coming with insights and questions that help you uncover information.
  3. Framing questions with a hypothesis “I noticed X which is likely contributing to Y, how are you handling that today?”

Look, the sales reps at your competitors are focused on checking boxes for your prospect. So how can you be different? Show them what boxes they haven’t considered. That’s how you build trust as a consultative sales rep.

So to get those insights, I spend at least 20% of my time on research.

Without plugging you guys too hard… before, I would sometimes spend 1:1 amount of time preparing – 30 minutes of research for one 30 minute time. I can often cut that time in half because I have the insights that Nudge provides me, all in one window.

Nudge: Well as team member… I’m very glad to hear that. So with your approach, what’s harder? What’s easier? And what is still missing in how you do account-based selling?

CG: The key theme is time savings by not doing office/administrative work – recording notes, entering information, data entry, manually adding information on prospects. Reducing the number of tabs. I’ve made solid improvements here and am eager for more.

Nudge: So Chris, do you think account-based selling is the future? And if they want to, how can new BDRs/SDRs adopt this approach from the start?

CG: Start by seeing what the rest of your sales team is doing. Shadow calls. And identify their collective bad habits. Learn from others, but don’t fall in the trap.

Automate administrative work.

Figure out the best lead sources – for you. What are the ones that no one else is prioritizing? This is my secret recipe – so go find your own.

Nudge: Thanks for sharing your toolkit earlier. Do you have any specific knowledge resources to recommend on account-based selling?

CG: Everyone should read Influence by Robert Cialdini. The power to persuade leads to the impact that an individual will have in life. Anybody from the top sales reps to folks like Warren Buffett and Charlie Munger have used these tools. And the audience doesn’t even know it.

The world runs on different cognitive biases. You’ll be far better off knowing them.

Nudge: And I know you’re an avid reader. What book are you on right now?

CG: At any point in time I’m working on a bunch of books. Right now:

Benjamin Franklin: An American Life by Walter Isaacson and Principles: Life and Work by Ray Dalio (life changing)

Thanks, Chris!

Jaxson Khan
Sr. Marketing Manager
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