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Article 10 min read

Q&A with Chatdesk: How to make the holiday season a CX success

Chatdesk co-founders Aneto Okonkwo and Andrew Olaleye share how to prepare your customer support team for a successful holiday season.

By Sarah Olson, Senior Associate, Content Marketing, @seolson5

Last updated December 3, 2020

Like everything else in 2020, the holiday season is looking a little different this year.

That’s why we got together with Chatdesk co-founders Aneto Okonkwo and Andrew Olaleye to talk about how good CX (and a little planning) can help keep the holidays merry and bright.

Read on for the full conversation, and if you like what you learn, join our Startup Central Slack Community for more conversations like this.

Top 3 highlights:

Click to jump to the section you’re interested in, or view the full transcript below.

  1. Talk to your team about holiday protocols.

    Make sure marketing, fulfillment, and customer service agree on realistic expectations for the holiday season, and have a plan for how to handle “moments of truth” such as late deliveries.

  2. Lean on AI-powered tools to help keep up with increased demand.

    While some customers may be cutting back on holiday spending, e-commerce sales are up 32 percent this year. Chatbots can help you answer all the routine holiday questions with less effort.

  3. Empower your team to connect with customers on a personal level.

    This has been an incredibly difficult year, and many people won’t be able to see their families for the holidays. Show empathy for customers who may be feeling a little lonely.

Full Q&A with Chatdesk

Greg (Zendesk): To start off, could you tell us a bit about yourself, home-town, and position in the company?

Aneto (Chatdesk): I’m the co-founder & CEO of Chatdesk. Companies use our software to increase customer happiness, grow sales, and scale on demand. I’m based in Brooklyn, New York! 🗽

I previously worked at Google for 7+ years as a Product Manager. My most recent projects at Google included Voice Search and the Google Assistant.

In my spare time I enjoy watching European Soccer, especially Arsenal FC.

Andrew (Chatdesk): Happy Thursday, everyone! I’m a co-founder of Chatdesk. Prior to starting Chatdesk with Aneto, I was a Manager at McKinsey & Company, where I led projects around call center operations and customer experience design across Retail and Financial Services. I’m originally from Atlanta!

I’ve lived and worked across North America, Europe, and Sub-Saharan Africa, with 10+ years experience within operations, strategy, and finance.

In my spare time I enjoy studying consumer behavior from around the world (have visited 60 countries across 6 continents). In addition, I love supporting Kentucky Basketball, UGA Football and Chelsea FC!

Greg (Zendesk): What was your first job? How/why did it lead to CX or your interest to dive deep into numbers?

Aneto (Chatdesk): My first as a teenager was as a Summer camp counselor at the Chicago Park District. My first major experience with CX was at Google when we launched a new payment system and staffed a customer service team in India. We also built automated self service tools to enable customers to check their balance and block their cards via text message.

Andrew (Chatdesk): My first job was working as a server / host at the World famous Waffle House. This was my first dive into customer service—taking orders, cleaning tables, and making sure customers were happy. I learned how to listen to people, show empathy / patience, and make some amazing hash browns (Scattered, Chunked, and Diced)! 🙌🏽

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Greg (Zendesk): As we approach the holiday season, which stakeholders within your company should CX leaders meet with to plan (if any)?

Aneto (Chatdesk):

  • Marketing: Confirm what promotions and marketing activities will be running during the holidays. Anticipate the types of questions customers will have and align on the messaging for responses.
  • Fulfillment: For e-commerce businesses, the holidays often cause a spike in order status requests right before the holidays and then a spike in returns right after. Discuss potential approaches to create self service FAQs, tools and forms to make it easy for customers to help themselves or give your team the needed information easily.
  • Your team: Confirm the staffing schedules for your team so that you have enough team members to handle the increase in volume. Ensure that everyone has sufficient training and updated information. I’ve also seen some companies plan some fun activities to celebrate and reward the team after since some of them might not be able to take vacation during the actual holidays.

Greg (Zendesk): What types of holiday changes in the CX process have you seen brands make?

Andrew (Chatdesk): Great question, Greg! Many best-in-class companies we work with focus their CX changes on educating new customers and limiting contacts. Here are a few examples:

  • Creating specific holiday support landing pages with commonly asked questions
  • Updating macros with personalized responses for typical holiday season questions
  • Adding self-service options and automation to handle Order Status and Returns / Exchange requests. Many of the brands we work with use tools like Loop Returns, Happy Returns, Returnly, Return Magic and others

Greg (Zendesk): Any creative approaches you’ve seen to drive awareness and customer loyalty?

Aneto (Chatdesk): Loyal customers sometimes miss out on the holiday promotions because they miss the specific time period when deals are available. This causes disappointment and further increases in ticket volume with complaints or requests for price adjustments.

To address this, one of our customers designed a promotion specifically for existing customers which was sent out prior to the broader campaign. This helped to build loyalty and also reduce ticket volume.

Greg (Zendesk): What should the staffing plan look like? Hire temps? Bring in the team members from other functions?

Andrew (Chatdesk): First off, I encourage each company to analyze last year’s holiday volume and / or Q3 2020 to understand how your volume might spike.

Once you have a sense of the additional staff you need to handle the increased volume, identify staffing options that provide the following:

  • 🚀 Low cost and fast ramp up: On average, it can take up to 6 weeks and cost $7,000-$15,000 to just train and onboard 3 additional support agents.
  • 📈 On-demand pricing: Given the increase of pre-sale questions from customers during after-hours, you want a staffing option that extends your service hours, without being too expensive.
  • 💌 Personalized support: There is a huge emphasis this year on customers demanding more personalized support. Brands who can hire support agents who truly represent their brand will provide a better customer experience and drive more sales.

To learn more about how we’re helping companies launch on-demand support for the holidays with US-based superfans, check out or feel free to reach out to me directly.

Greg (Zendesk): Given the increase in volume, how should brands handle customer “moments of truth” such as late deliveries and returns?

Aneto (Chatdesk): There’s no easy answer to this one. The key is to prepare and align with your leadership on what types of policy exceptions and appeasements you will be able to offer for different scenarios.

Even if there’s no budget for appeasements, we have seen companies achieve high CSAT and NPS during the holidays with the following approaches:

  • Share proactive updates. If there’s a delay, don’t wait for customers to reach out
  • Apologize profusely and show empathy in your language.
  • Give customers alternatives. Examples we’ve seen include shipping out an alternate product, discounts on a future order, etc. Customers won’t always take the offer, but they typically appreciate the gesture.

Greg (Zendesk): How should you measure success during the holidays? What are the key team metrics (e.g., response time, conversion) that should you monitor during this time?

Andrew (Chatdesk): Key success metrics should center around sales, customer happiness, and efficiency. Here are three metrics that most of our customers are tracking:

  • 📊 Utilization Rate: Ratio of time your agents are handling tickets by total time worked. Industry Average is 60-70%
  • 🌟 CSAT / NPS (Net Promoter Score): How satisfied are customers with their experience and are they willing to recommend your services to others. You can enable Zendesk Satisfaction Ratings if you don’t have this setup already
  • ✉️ Response time: Time taken (in seconds) by the agent to respond to a customer’s message
  • 🛒 Conversion rate: Percentage of visitors (online/social) who purchase something on your site. Industry average is 1-2%

Greg (Zendesk): What machine learning and artificial intelligence tools can companies use to manage costs and increase efficiency?

Aneto (Chatdesk): There are a lot of great tools out there. Here are few that companies can roll out quickly in time for the holidays:

  • Zendesk Answer Bot is a great option for teams to help deflect repetitive tickets from email and chat.
  • Zendesk Guide has a feature called Content Cues which will provide automated suggestions for new articles in your Help Center.
  • The Chatdesk Teams solution that Andrew mentioned earlier is also a great add on to Zendesk to help solve repetitive tickets and increase conversion by 10%+ on Facebook and Instagram with additional personalization. You can be up and running in a few days with a free pilot for the holidays and no dev work or pre-work is needed.

Greg (Zendesk): What are some risks of rolling out new tools or processes so close to the holidays?

Andrew (Chatdesk): Key risks we see include potential errors and decreased customer satisfaction scores and sales. Unfortunately, some companies are not able to fully test the new tool or process in time to ensure the entire team (especially temporary workers) can comfortably utilize them.

📅 We recommend that companies launch new tools and processes at least 3 weeks before the holiday period begins.

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Greg (Zendesk): What do you expect to be different this holiday season because of COVID-19?

Aneto (Chatdesk): To be honest, like everything else in 2020 it’s a bit difficult to predict! Here are some things we know for sure:

  • 💵 Some customers may reduce their discretionary spending or skip holiday shopping altogether due to the ongoing uncertainty from layoffs and furloughs.
  • 💻 Nonetheless, there will be more online shopping overall because people are less likely to go to stores to avoid the crowds. US E-commerce sales are up over 32% this year.

  • 📦 There will be more shipping delays because the postal services and shipping carriers are already overloaded.
  • 🙂 Customers are looking for more personal connection with brands. Because of COVID, some people might be lonely because they can’t travel to see their friends and family. This is an opportunity for brands to show extra warmth and build loyalty with their customers by offering that extra personalization.

Greg (Zendesk): What best practices have you seen for “post-mortems” and reporting on the results from the holidays?

Andrew (Chatdesk): This is a great point! Since purchase intent for most customers remains high directly post-Holiday into January, companies should brainstorm how to capitalize. Here are two areas:

  • People and process: Identify leaders throughout your company to summarize key metrics for their team during the holidays and action items.
  • Tools: Leverage tools to quickly understand patterns / insights that your leadership team can act on. Chatdesk’s free customer insights dashboard is an easy way for companies to automatically tag conversations for every channel you interact with your customer on. To launch in minutes set up a free account at

Greg (Zendesk): Do you have a mentor, or mentor others shaping your success? What is your personal leadership style or approach to coaching?

Aneto (Chatdesk): For me, being a leader is about being a servant to your team members to help them achieve their goals and full potential. My personal leadership style comes from some books that are required reading for new managers on our team including High Output Management and The First 90 Days.

Greg (Zendesk): Got any book or podcast suggestions for me?

Andrew (Chatdesk): Two of my favorite podcasts include Timesuck and Jalen & Jacoby. Check them out! 🗞️🏀


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