CART INSIDERS — Edition #2 Recap: Leading Insights on How to Maximize Your Holiday Season

Leading insights, holiday season.

Greg Zakowicz

Greg Zakowicz

Director of Content

Reading Time: 6 minutes

On September 24, Omnisend went live with the second edition of Cart Insider’s E-Summit. This time around, it was a one-day digital summit focused on tips and best practices to get your store ready for the holiday season. The event featured professionals from all walks of the ecommerce industry, including CEOs, CMOs, Content Managers, and Co-founders.

Speakers included those from the brands ONE Championship, Brummell Co., and Hydrojug, as well as industry experts from ShipBob, Justuno, Future Commerce, Gorgias, Smile, Shopify Plus, Hawke Media, and Aftership—who all shared actionable insights on different aspects of holiday ecommerce preparation.

Whether you missed it or want to relive the event, here are some of our favorite takeaways from the day.

Session 1: Weight Loss and Ecommerce: Lessons Learned from Losing 143lb

Speaker: Phillip Jackson, Co-Founder, Future Commerce

Phillip Jackson’s opening keynote walked us through his weight loss journey and what he learned from it. Phillip shared how he attributed his results to setting the right goals and making better choices and how he applied those lessons to his career. He shared how and why anyone can do so much more than they ever imagined, both in business and in their personal life.

Key Takeaways:

  • Set attainable goals which will result in better actions and results
  • How setting goals that are not attainable can have bad results
  • Invest in creating virtuous cycles for yourself so you can make better choices
  • Understand why you’re setting specific goals and how they impact the bigger picture

Session 2: Q4: How to Get Creative On-Site

Speaker: Mat Bingham, Director of Agency Partnerships, Justuno

Mat Bingham shared great tips on how to get creative on-site and how to stay ahead of the competition before, during, and after the holidays. Mat touched on the importance of bringing cohesion to your brand by preparing early for your holiday strategy, not only on your website but also through email, paid ads, SMS, and other marketing channels.

Key Takeaways:

  • Organic lead capture has a higher intent to engage with your brand—show them a different ad then you would someone visiting your site through a paid lead capture
  • Stand out with SMS campaigns—this is a great tool to use alongside your email campaigns
  • Increase average order value by including product recommendations in your campaigns
  • Use a countdown timer with promotions to create a sense of urgency with shoppers

Session 3: Check Your List Twice: Prepping Your Lifecycle Marketing for the Holidays

Speaker: Cheri Selva, VP of Lifecycle Marketing, Hawke Media

Next up, Cheri Selva sat down with us to talk through your holiday promotional calendar, testing strategies, and how to extend your planning after the holidays. Cheri touched on the importance of early preparation and possible shipping delays due to the increase in holiday online shopping.

Key Takeaways:

  • How to use engaged segments, not batch-and-blast, for testing
  • Have a strategy for each of your segments
  • Compile your data and look for trends. This is something you can use in Q1 and beyond.
  • Use abandoned cart notifications and offers
  • This year, with stores closing or limiting capacity due to Covid, more businesses will rely on email and SMS to get in front of their customers

Session 4: Steal the Season — Leveraging Technology to Create the Ideal Omnichannel Holiday Experience

Speakers: Brian Peters, Strategic Partnerships, Shopify Plus

Gabe Macaluso, Director of Customer Success, Omnisend

Debbie Soon, VP and Head of Consumer Products, ONE Championship

Omnisend, Shopify Plus, and ONE Championship came together to discuss the importance of utilizing multiple channels in your holiday campaigns. Debbie Soon, VP and Head of Consumer Products at ONE Championship, joined us in this open discussion to talk through their success in using multiple channels and how creating a great user experience is critical for their success.

Key Takeaways:

  • Marketing at people vs. marketing with people—email has to be valuable for the consumer you’re marketing to. They have to feel like they are a part of something more than just a sale and feel like they are a part of a community.
  • Collecting data is the best way to learn how to re-target customers
  • Get a fresh set of eyes on your website to see what else you could be doing
  • Understand what your consumers are actually doing on your website to better understand their journey and how you can better serve them

Session 5: Black Friday Customer Service Redlines Checklist: 5 Tips to Survive The Madness

Speakers: Billy McClennan, Strategic Partnerships, Gorgias

Hayden Wadsworth, CEO & Co-Founder, Hydrojug

In this session, Billy McClennan of Gorgias was joined by Hayden Wadsworth, CEO of HydroJug, to talk about what they are seeing from a brand side as it relates to holiday prep. Billy and Hayden discussed customer support’s importance during the year’s busiest time and ways to provide a great experience for your customers.

Key Takeaways:

  • Because there will be a surge in ecommerce, you want to make sure your team forecasts how many customer support tickets you can expect
  • Customer experience is dependant on the level of customer support your brand provides
  • Standing out from your competitors starts with customer experience. Don’t overlook how you interact and treat your customers.

Session 6: Using BFCM to Turn Bargain Hunters Into Devoted Customers

Speaker: Tim Peckover, Content Manager,

Tim Peckover joined us to discuss how to turn holiday bargain hunters into repeat customers. Each holiday season is filled with first-time customers. Being able to convert these purchasers into year-round customers is instrumental for growth—but that can be challenging due to the steep discounts offered during the holidays. Tim shared insights and tips for increasing customer retention from seasonal shoppers.

Key Takeaways:

  • Retention model—acquire, engage, retain, and make those customers a part of your brand’s community
  • When it comes to engagement, make sure you’re creating an experience for your customers before, during, after their purchase. Doing this will keep customers engaged and more likely to turn to repeat customers.
  • Build a brand community. Customers should feel like they are a part of your brand story.
  • Utilize loyalty programs. If designed right, they can help build a community and keep engagement high.
  • Your brand story is important to share—have a voice and remind customers why they’re a part of your brand’s story.

Session 7: Creating The Best Post Purchase Experience For Your Customers As We Head Into The Busiest Time of the Year

Speaker: Joe Wyatt, Head of Partnerships North America, Aftership

Aftership’s Joe Wyatt joined us to talk about the importance of the post-purchase customer journey. It’s just as important to make sure your customers receive a positive experience after placing their order than before. As consumers anticipate their deliveries, this is a great way to engage with your customers as they’re looking for updates and waiting for their packages.

Key Takeaways:

  • Customer buying journey—we spend a lot of time and money building out the customer journey, but we often look past the post-purchase experience.
  • Well-done shipping notifications can build brand loyalty and engagement throughout the entire purchase journey
  • Letting customers know how and where to reach you with info on packages creates a good experience from start to finish

Session 8: How To Launch, Sell, and Fulfill 15K Pairs of Socks 1-Day Before Thanksgiving

Speakers: Casey Armstrong, CMO, ShipBob

Steve Staffan, Founder and CEO, Brummell Co.

The day’s final session was a fireside chat with Casey Armstrong, CMO at ShipBob, and Steve Staffan, CEO of Brummell Co. Steve shares how he founded Brummel Co., a men’s clothing company, while knowing very little about ecommerce and possessing a finance background. Steve discusses how he grew his brand as a bootstrapped company, and why connecting with your customers is critical for success.

Key Takeaways:

  • Offer individual discounts to your loyal customers and personalize your touchpoints
  • Understand the importance of building your brand and connecting with customers as much as possible
  • Data is huge for insights and visibility into your customers—this will show you how to serve them better and keep them engaged with your brand

That’s A Wrap!

Our second edition of Cart Insiders did not disappoint! We had a full day of content with presenters who shared helpful tips and real-life experiences and lessons learned. Our speakers delivered insights from every stage of the user experience and shared valuable takeaways you can implement immediately. As the day progressed, several themes began to emerge: the importance of creating a brand community, focusing on post-holiday marketing, and the need to personalize the user experience. Recognizing these themes, understanding how they impact your business, and how to apply the lessons learned from other companies are what events like this are all about.

We’re glad you joined us, and we look forward to bringing you the third edition of Cart Insiders—stay tuned. If there are topics you’d like to see covered or companies you’d like to hear from, please let us know!

This article originally appeared by our friends at Omnisend.

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