Leading with Innovation: Digital and Retail Pioneer Tara Conway Shares Her Vision for the Future of Big-Box Retail

Kimberley Carrera: What initially drew you to the retail industry, and what keeps you passionate about working in this field?

Tara Conway: I began my journey in retail at the age of 12, working at my mom’s General Store. Our family was deeply involved in serving customers and creating merchandising plans. The General Store was more than a business; it was a community hub. 

From the start, I’ve been driven by a focus on customer experience and a curiosity for impactful change. The beauty of joining retail during the digital era was that everything was unknown, which made "test and learn" my go-to strategy. 

My passion for retail persists because the industry is constantly evolving, presenting new challenges and opportunities.

Kimberley Carrera: How would you define digital transformation in the retail space, and why is it critical for both traditional big-box retailers and eCommerce D2C brands?

Tara Conway: Digital transformation was once all we talked about in retail, but with the accumulation of technical debt and an overwhelming array of options, its definition has evolved. Transformation means different things depending on the stage and priorities of each brand or retailer. 

For some, integrating live chat or producing video content, though not novel concepts, can still be transformative. The critical factor is that retailers and brands must invest in changes that drive efficiencies. 

Many are perpetually playing catch-up, and without proactive steps, they risk continuing to fall behind, both their competitors and their customer expectations.

Kimberley Carrera: What emerging technologies do you believe are having the most significant impact on the retail industry today, and how are they changing the landscape?

Tara Conway: Absolutely, AI will play a pivotal role, and it will be fascinating to observe how retailers and brands handle the associated biases, ethical concerns, and cultural implications. 

However, the true focus should be on data mining and management. While AI is important, data itself is the critical asset that should be recognized on the balance sheet as the ultimate differentiator. 

We can’t ignore the impact of mobile devices, and though some experiences have been created and customized for customers, optimizing the use of these devices in stores will be crucial. The key for retailers will be the need to overcome various barriers and friction points to find the right balance between technology and human interactions. 

This evolution is similar to the early 2010s when chatbots were first introduced; despite initial challenges, and many brands choosing to go back to human managed chat, today, most customer interactions are managed by bots or conversational AI.

Kimberley Carrera: What disruptive innovations are currently challenging the traditional retail model, and how can both big-box retailers and D2C brands adapt to these changes?

Tara Conway: Culture, organizational structure, skillsets will be increasingly challenging as we continue to see mass layoffs in the tech sector but yet a push for digital transformation – HR and leadership teams will need to rethink and rebuild their teams in ways that can support the foundational retail know-who as well as the digital and tech savviness necessary to drive innovation. 

Social commerce will transform the world of marketing, targeting, and customer/brand engagement.  Though emerging in Canada, in some parts of the world can make up over 40% of ecommerce and with the continued growth of newcomers to Canada, the customers who are comfortable and expect this option is growing.

Kimberley Carrera: Can you elaborate on the importance of an omnichannel strategy for retailers? How can big-box retailers and D2C brands effectively integrate their online and offline channels?

Tara Conway: Omnichannel is the ultimate form of flexibility and adaptability to your environment, but only if you build it in a way that you can flex with demand, both customer and business demands. 

As a concept and retail strategy, it was created in the early to mid 2010’s to capture the need to bridge the growing divide between ecommerce and bricks and mortar. Retailers began to embrace the role that digital could play in influencing traffic and experiences in-stores and developed strategies on how to optimize it.

For years retailers have been trying to be channel agnostic and to create strategies that cross all channels, the same way that a customer would; however, this has been flawed in the actual design. It was always built through the lens of the customers on the front end, however, the backend to support its growth and evolution has remained siloed.  To truly become omnichannel, build your plans both on the front end for your customers but as well on the back end for your employees and with the technology.

Kimberley Carrera: How are AI-driven personalization strategies transforming the retail experience? Can you share examples of retailers who are excelling in this area either in North America or Globally?

Tara Conway: Personalization has been around for over a decade, but initially, it was more about general customer segmentation rather than true individualization which has often led to disappointment with customers and with the metrics. 

What we see now is many retailers winning with chatbots and AI integration to help guide customers through the experience to a qualified Rep, and winning is defined both by customer satisfaction but also in higher quality experiences by allowing the tool to work through the administrative elements. 

Companies utilizing AI for order management and inventory flow across all channels are particularly ahead, especially given the lessons learned from the pandemic about preparedness. While difficult to see as a customer, the fact that we see less out of stocks, and don’t hear about high inventory positions is an indicator that some retailers have found success.  

Retailers that I think are doing great things are Zenni, an online business for glasses – the only place I shop for my fashion accessories. They have a virtual try-on tool that allows me to try on all of their glasses to see how they will look on my face, and have recently launched shoppable videos for customer interactions that display on their site so I learn as I shop both from their experts and the customers watching along.

And, as a new HelloFresh customer, I’m impressed with how quickly my experiences are changing and becoming more tailored to my preferences – they’ve now become my go to for recipe ideas, even if I’m not receiving a box that week because it knows my preferences, protein, veg etc. and what meal types I’ve set – it’s quick and easy to find a new idea, without the searching and browsing of before.

Kimberley Carrera: What role does customer data play in effective personalization, and how can retailers ensure they are using this data responsibly and ethically?

Tara Conway: During my time at ToysRUs, we leveraged the data from our registry program, it was incredible to be able to use the behaviour of the majority to target the next phase of pregnancy and purchasing needs, and now this is at a much grander scale with the amount of information people are willing to share but comes at a cost. 

Customer expectations have never been higher, while they are willing to share their data, especially with brands that they trust they expect that the experience we give them is tailored, is specific and should continue to get better - not meeting those expectations can be just as bad for a brand as not doing personalization at all. 

Data will be the differentiator for retailers, in a world of first-party data, faltering loyalty programs, need for AI innovation – without data retailers will struggle to keep up and differentiate themselves against their competitors. 

But the challenge we face right now is the overwhelming amount of data, getting to a point of capturing the right data to support a decision or program is the task retailers need to take on, this paired with the transparency to the customer will be key.  

A secondary, but more important element for retailers will be security, how/what/where is my data being used and why – if customers trust you enough to share their data we must all ensure we treat it with respect in our choices of how we use it.

Kimberley Carrera: Which retailers do you think are leading the way in personalization? What specific initiatives or technologies have they implemented that set them apart?

Tara Conway: While not traditional retailers, I think that banks and insurance providers have been doing amazing things with digital experiences, tailoring the messages and offers based on all that they know about you and what services can actually be a complement. 

Because of the trust they already have with their clients and because of the incredibly stringent compliance/security standards they work within they have been creating initiatives that are hyper-tailored and are delivering on engagement and results.

Challenges and Solutions

Kimberley Carrera: What are the main challenges retailers face when integrating AI into their personalization strategies, and how can they overcome these obstacles?

Tara Conway: 

Where to start is always the challenge, many retailers know the vast opportunities that exist, but truly struggle with the decision of where to begin. The amount of data, the touchpoints, and all the indicators across channels creates mass volumes of data which makes it difficult to get to real time actions that make sense to the customer. The second challenge beyond the data is the technology, and integration between systems. Many retailers are on legacy systems, so bridging the two for efficiency and optimization can become a difficult financial hurdle to overcome.

Lastly, a challenge that has plagued many for years is resistance to change. From ecommerce, mobile commerce, to social commerce – there have always been those that have been uncomfortable or unwilling to embrace which has been a downfall for many. If retailers don’t recognize it and create a culture that becomes more accepting of risk-taking, of embracing the unknown, and celebrating versions of failure.

The best way to overcome this is to shift to a progress over perfection mentality, start small, learn and let your successes compound. Use your success from early wins to create new processes and onboard those who are resistant to accepting this, let them be part of the strategy, the execution and celebration of wins. 

I would also find the right partner, this is a new space for many, and similar to the buy vs. build debate, this is the time not to try to go it alone or to build a team internally – there are experts in the field who have done the testing and learning – leverage them and allow your team to grow alongside them.

Kimberley Carrera: How should retailers measure the success of their AI-driven personalization efforts? What key performance indicators (KPIs) are most indicative of positive outcomes?

Tara Conway: In AI-driven programs, you would use all the same metrics, such as engagement, conversion, and revenue – business measurements don’t change however, it's crucial to define a measurement or benchmark for accuracy and build processes that integrate human intelligence into the AI workflow, balancing efficiency with the knowledge and experience of your teams. 

Returning to solid A/B testing is vital, especially as your AI programs gather data and experience from customer engagement and running campaigns and programs in parallel with both traditional and AI processes will help establish benchmarks, build trust, and enhance learning within your teams. 

Finally, establish transparency by informing your customers about why and how you are leveraging their data to improve their experience. Trust will go a long way if you are upfront with your customers from the beginning.

Kimberley Carrera: Looking ahead, what trends do you foresee dominating the retail industry in the next 5 years? How should both traditional retailers and D2C brands prepare for these changes to stay ahead of the curve?

Tara Conway: Commerce will be woven into our everyday life, from our social communities, where we consume content, and lines will be blurred so drastically that we will become less aware that we are “shopping” with brands, but instead living our lives with the convenience of brands integrating with our experiences.

Convenience and high expectations of customers will continue to dominate retail, those that can create it, whether the traditional convenience elements of speed or cost, will be the ones that are able to continue to bring their customers back. 

Whether it be a one-stop shop convenience element like Staples with Telco, ServiceNow and Amazon Returns, or those that are integrating other complementary services into their footprint, allowing customers to almost multi-task while they shop.

Brands and retailers need to push beyond the traditional definition of retail, get beyond the definition they have always had of themselves and what they “want” customers to think of them and find and understand customer behaviour and how they can integrate into that.

Kimberley Carrera: What advice would you give to aspiring marketers looking to make their mark in the retail sector?

Tara Conway: Listen, listen and listen some more – digital has created the landscape where you can listen and learn more from your customers than ever before.

Be willing to take risks, say yes to the unknown and push boundaries. Those who dare to move away from the status quo and traditional models will be the pioneers of the new evolution in retail, redefining the industry for both themselves and their customers.

Kimberley Carrera: Tara, what is one platform you can't live without?

Tara Conway: As a retailer, GMB is the one that I think can give you so much insight into the stores, customers, reviews, etc – it’s often the front door to all of your customers now with mobile devices and local search. But personally I’m having a ton of fun with Perplexity AI, it’s ChatGPT but with the references so you can validate the information and its sources.