• Revenue Operations Sales Execution

Building a Remote Structure for the Future of Sales

Daniella Bellaire

Daniella Bellaire
Head of Sales, Shopify Retail

Building a Remote Structure for the Future of Sales

When COVID hit, it became very clear that the days of “the office” would change forever and in-person sales would no longer be the standard. For some, this revelation came with a fair amount of trepidation, while others saw it as an opportunity to evolve. 

At Shopify, we witnessed the tremendous impact the quarantine had on our customer base, which caused many of our merchants to remarkably reinvent themselves and adapt. So, we decided to get ahead of the curve and adapt with them. This meant adopting a digital-by-default mentality across our global organization. 

This timely shift affects departments in different ways, and developing a remote sales team in particular has been a learning curve—one that requires constant communication and transparency, as I explain on The Forecast:


Developing a remote sales structure is a constant work in progress, but certain activities are showing early signs of success. Here’s what my team at Shopify has learned on the journey to becoming a digital-by-design company.

Social interactions need to be reinvented

While we had about 3,000 employees that were working from home before the quarantine, we also had team members that really thrived in the office setting -- it was where they made their friends and had their daily social interactions. We quickly realized that we would need to recreate that human element to support our staff in the new digital environment. 

The need for connectivity between our team members caused us to be more intentional and proactive about our rituals and communication, to ensure their well-being and continued development.

We quickly spun up a task force around social activities, as a result and invited sales reps and leaders to own it. On a regular cadence, they formulate what kind of social interactions and remote opportunities for engagement we want to do as a team and then go about organizing them. Over the summer, they hosted fun remote activities, like baking challenges, remote cocktail making classes, shared embarrassing childhood photos, and prompted team members to chat on Slack socially. These engaging and meaningful interactions continue to strengthen relationships within our teams.  

Leadership development is more important than ever

Remote or not, if you’re in a high growth sales environment, salespeople need to be constant learners. That continued learning is imperative to success, especially now that the market is changing. 

As sellers, we have to be agile in our positioning and how we go to market because the landscape may change drastically. That’s why leaders must continue to develop adaptable, antifragile, and resilient sellers. 

In our sales organization at Shopify Retail we strive to hire lifelong learners who invest in themselves to improve their craft every day of every week. Because ultimately, if you don't invest in your own development, the business will outgrow you -- because we're growing that quickly.

In that same vein, we believe that leaders should empower their reps to make quick decisions. This not only aids in the development of the rep, but also helps the business scale faster. When reps can make those in-the-moment decisions, they can seize opportunities with prospects, allowing them to scale the business faster. 

Businesses should become more customer-centric

Scaling is certainly important to the business, but leaders can’t be so focused on the speed of scaling that they lose track of doing what’s right for the customer. 

In our sales organization at Shopify Retaily, our mission is to make commerce better for everyone. We believe that scaling is a byproduct of putting merchants and their needs  first. We make sure not to dilute the quality of customer success in order to hit those numbers. We would rather scale a little bit slower than we could have, but do so the right way for our merchants ensuring their success and ultimately ours as they are retained. 

Data plays a critical part in our customer-focused mentality. We monitor sales calls and prospect sentiment, ranking calls and tracking how they perform at each stage of the sales process. 

We then share this data with the team through custom dashboards and scorecards. That way, they can see what’s working and repeat it. They can identify problem areas and adjust, which makes for more successful sales processes. As a byproduct, the reps’ data-driven decision-making skills are sharpened daily, bringing us back to the importance of leadership development and continued learning. 

The future of sales

The future of remote sales is bright and full of opportunities for those who rise to the challenge. I’m encouraged that we’ll continue to see leaders emerge from a wide variety of experiences and diverse backgrounds. I love that we’re bringing up the next generation of sales talent and leadership, and that they’ll help us build a brighter future and make sales more inclusive for everyone.  

About the author: 

Daniella Bellaire is the head of sales for Shopify Retail, a platform that offers ecommerce and point-of-sale features for business owners.

Interested in more episodes of The Forecast?

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