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Welcome to The Merchant Life, for retailers and retail enthusiasts wanting the insider perspective of all things retail.

Now let’s talk shop.

In this week’s newsletter we focus on B2B sales.

To be more specific, we want to take a closer look at selling tech solutions to retailers; whether it be selling e-commerce to small businesses, learning about how retailers feel about tech salespeople or understanding that customers may not really know what they need in a tech solution – we got that covered and more.

Raj Dhiman, our resident sales expert, takes over for this edition of the newsletter and minces no words with his sales hot take.

Homer Simpson Animation GIF by FOX TV
Let’s go!

The Future Depends on B2B

I’m proud to be in sales.

high five tina fey GIF by Ray William Johnson
No shame in my game.

I especially love being in tech sales, having sold loyalty, e-commerce and developed partnerships for small and medium-sized businesses (SMB) for the last 8 years.

One guiding principle that helped me throughout my B2B career – businesses are experts in their space. The baker starts a bakery because of their passion for food, airlines are experts in putting planes in the sky, grocers are experts in getting fresh food into the hands of customers, doctors help heal the sick, and so on.

What I’m saying is:

It’s the job of B2B salespeople to help these businesses focus on their craft by providing our solutions.

I would argue that, indirectly, B2B sales will power the future of retail.

If retailers had the capability to build their own chatbots, livestreaming platforms and data analytics tools, then there would be no need for innovative tech companies to provide solutions.

According to a database on

  • There are 134 privately owned retail SaaS companies.
  • Their combined revenue is $641.2 M.
  • They serve about 7K customers and employ over 10K people.

Combine these stats with those companies that are publicly traded, the retail tech space is a beast.

We also have to acknowledge that the B2B sales space is changing.

In 2015, Forrester forecasted that 1 million B2B salespeople would be out of work due to self serve e-commerce.1 Salesforce in their 3rd State of Sales report noted that 57% of reps were going to miss quota in 2019.

Further, buying decisions require more interactions to be reached and the number of stakeholders involved is increasing.

The B2B sales space is not only changing but is GROWING.

Why do we care?

As the sales space grows and salespeople are onboarded, the concern is that there are many salespeople who don’t have a clue.

They are unaware of how their templated messages are being perceived. Instead of selling the value of a meeting, B2B companies enable reps to offer gift cards to prospects as an ‘incentive’ to book a call. Sales managers are well versed in generating reports in a CRM but are they just as versed in their coaching skills?

Messages like this (and Liza receives about 30 a week) quite clearly show that the salesperson has no clue what we do, our business, and has never bothered to do their research.

Don’t get me started.

Mind you, this is not to say that there are not awesome sales pros out there doing great things.

The lousy ones make the job more challenging for the good ones.

Selling Shopify to SMBs in Canada

In 2016, I was a sales manager at Rogers Communications, a Canadian telco, leading a team of inside sales reps. At the time, Rogers got into a short lived partnership with Shopify to sell the e-commerce platform via outbound cold calling.

My team of four was given the nod (alongside two other teams) to blaze the trail and make the sale. I was fortunate to be given a chance to build up my own sales methodology and playbook vs. what was already being used.

We had great ideas and were able to set a ton of meetings with excited prospects. Within 90 days of hitting the phones, our pipeline was building rapidly and we felt great about our progress. However, getting deals over the finish line proved to be difficult and lengthened the sales cycle.

In speaking with our SVP about my team’s challenges, he said:

“In asking business owners to sign up, we are asking them to make a fundamental change in the way they do business.”

I had a flashback at that moment…

When I was learning my sales fundamentals, my manager described the two key reasons why customers will not buy from you.

  1. They don’t trust you.
  2. Your solution is perceived as being too complicated.

The key word is perceived.

If the solution feels like too much work to implement, it becomes very easy for a customer to say no.

We had to simplify how we presented the product.

Our team was successful in closing more Shopify deals and at a higher price point when we focused our conversations on what will change in the way they do business and how to navigate that change when launching an online store.

You Make It Sound So Easy
It’s what we do!

For example, a small candle maker was concerned about getting access to real time shipping rates. They were accustomed to lugging all their packages to the post office to ship their orders, no knowing the price of shipping. We showed the customer, via screen share, how shipping rates within Shopify were not only comparable vs. their current method but they didn’t have to leave the platform to plan their deliveries.

video game store owner loved the idea of launching an online store, but their main concern was getting their staff trained on a new platform. We presented the product to staff with a focus on the ease of use and worked with them to introduce the new process, eliminating the stress of onboarding a new program.

A couple who owned a furniture store loved the concept of online shopping but hesitated to pull the trigger until we provided use cases of similar stores and competitors who were using the e-commerce platform.

In retrospect, I think about how simple this is.

At the time, it seemed like an earth-shattering discovery.

What Retailers Told Us

We spoke to two of our retail friends, Taylor Littlejohn of Knixwear and Veronika Saxena, formerly of Walmart Canada. We asked them questions about how salespeople approach them, their internal processes for buying technology, and feedback for sales teams when making their pitch.

Here are the highlights of the discussion:

Q: What are your thoughts on cold calling/outreach from salespeople?

Taylor: I find myself being overwhelmed with messages on LinkedIn or email and I know it’s a SaaS thing. If I’m not in the mindset of buying software, these messages end up being more of an annoyance.

Veronika: Cold outreach is helpful if you can get ahead of the customers needs. Most times, the messaging comes across as being driven to make quota as opposed to helping me solve a problem.

Q: What is the process like internally when you want to go purchase a tech solution?

Taylor: For us, we identified that we can’t live in Excel anymore because we were growing so fast. But, we wanted to find something that can add value but be as close to what we are doing right now because a big overhaul won’t work; we’re strapped for time as it is. We start doing our homework by looking online and asking others in the industry about what they are using.

Veronika: Sometimes whether we know it or not, we need a vendor to help us validate or pressure test what problem we are trying to solve and then give us the understanding of how their solution can help us as oppose to us looking at it as “tech for the sake of tech”.

Q: Can you describe some of the experiences you have had with companies when you are in the buying cycle?

Taylor: Bigger software companies don’t always value the brand names they are talking to, if we are not a big logo then it feels like we’re getting snubbed. We had this experience quite a few times. So, we had better luck by connecting with other people in our industry and understanding what they were using.

Veronika: Big tech vendors, who have been around for a while, tended to view us as a number, much like how I might have felt in University, except this time I’m a number with money. In some instances, I felt like I was dealing with someone who just wants to hit a quota. You can easily end up getting oversold, and that can create a lot of spend and rework later down the road. 

Q: Where exactly can (or can you provide examples where) salespeople add value when making a purchasing decision?

Taylor: One company offered to do a demo account for us using our data. This helped us so much because we could see our data in the new environment. Providing the experience of being IN the software was great; almost like attending an open house!

Veronika: In bigger companies we like to think we know what problem we are trying to solve and how to solve it, but we need help. This is where we want to have a meaningful interaction with a tech provider. Do they have a point of view? Have they done their homework to understand our business? Can they show us use cases of other businesses like ours and what they are doing to help them?

Q: Any other advice that you can give the sales teams/leaders that might be reading this?

Taylor: Tech providers need to be more aware of what’s happening in the space they are selling into. Even if you know only 25% of what you should know, it can be very helpful. Also, be more human and personable in your interactions. I know SaaS techniques must work because there’s a bible out there devoted to this stuff, but being personable can help you stand out.

Veronika: Know the industry, do the due diligence to know your customers, know that you’re not just selling your solution you are selling your brand.

RSG Insights – Top Ten of the Playbook

Based on my sales experience, what I’ve learned and still continue to do to this day, here are my TOP 10 TIPS in selling to retailers today:

Salespeople can be super, if they just keep it real.

Like Mario.

He’s Super.

Super B2B 64. Pulled from Twitter.