Community Round Tables are a great way to gather and exchange ideas. In case you missed our first one back in the fall, we wanted to make sure you had access to read through all the content again outside of just Slack.

If you’re new to Support Driven, we have a Slack community of 8K+ members who care about customer support.

Our hope for Community Round Tables is that they not only educate you but help you network and build relationships.

So whether you’ve already started planning for the 2021 holiday season or not, please enjoy Support Driven’s Getting Ready for the Holidays Community Round Table. (Thanks to Assembled for suggesting this Community Round Table topic!)


Give us an idea of your work responsibilities and a short description to help us understand what your company does/who your company serves. Cake or pie? If you could be anywhere in the world right now, where would you be?

Kat, Head of Operations at Passport Shipping

I run Operations at Passport Shipping. Passport is the international shipping carrier of choice for modern DTC brands. We offer best in class parcel logistics, duty and tax calculator for DDP (a duties prepaid shipping option), branded tracking page, and high-touch customer support. We’re a seed series startup on the cusp of an A, and I’ve spent the last 2.5 years building up our Customer Support and Brand Success teams from a team of me (!) to teams of 7 and 3 respectively, going from supporting zero → 150+ brands and from pre-revenue to $MM ARR.


Our support structure is interesting, while we are a B2B company, we also do B2C support for the end customers of the brands we serve. Therefore support + success work SO closely together and even within our support team, we have a bifurcation of “partner support” agents who answer shipment related questions for our brands vs. their end customers. Oh….can I deviate and say ice cream? It goes well with either cake OR pie.

Sean, Manager of Customer Care at

I am Manager of Customer Care at Kindred. Kindred’s solutions combine AI with advanced robotics and a full suite of integration and support services to ensure optimum performance over the long term. I manage two support teams, a team of onsite field techs, and a team of remote product support techs. We provide Robots as a Service to retailers across the US. Pie and somewhere much warmer than where I am today.

Talal, Customer Love Team Manager at Looker

I manage a support team across Zurich, Tokyo, and California. My work can involve anything from scheduling and figuring out resources, to jumping in on customer calls and helping plan the future of the Department of Customer Love (the support org where he works).


I work at Looker, a data analytics platform that aims to allow companies of all sizes better understand, model, and govern tons and tons of data. I, unfortunately, do not like sweets, but I would love to be in Taiwan right now. I hear things are quite excellent, COVID-wise, and it’s somewhere I’ve never been.

Craig, Senior Lead of Plus Technical Suppor at Shopify

As the Senior Lead of Plus Technical Support for Shopify Plus, I am in charge of the strategy for supporting our merchants through their technical issues with the Shopify platform. Shopify is an e-commerce platform for merchants to sell their products. We serve merchants ranging from small mom-and-pop shops, to large multi-national name brands. Pie 100% – Specifically a strawberry rhubarb custard pie. As it gets colder here in Canada, I would say something like Jamaica!


When do you start holiday planning? What does your holiday planning process look like? What tools are involved with your holiday planning?


We start in the late summer, as  Black Friday/Cyber Monday (BFCM) is one of our biggest sales periods and we need to be prepped early and our merchants also start early, for example, preparing inventory, new products, sales codes, as well as  website layouts/themes.


For support specifically we plan for extra staffing, on-call programs, and escalation flows in both directions: That means both if engineering discovers a problem using their tooling, as well as if support becomes aware of an issue through a customer contact.


We also create backups in case of any outage in our main communication tools. So for example, if our video conference tool goes down or Slack does, where do we go from there.


We usually start planning at the end of October. We start by making sure everyone gets in their preferences on PTO. Then we look at data for previous years using Looker and build our own projections. We then use Assembled to look at the forecast there and compare the two.


We then move on to several rounds of adding events that customers might tell us or things that pop up and fine-tune that plan. We build in some contingencies, and we always have someone staffed for urgent issues. A lot of our customers work on holidays, so we need to be there for them.


I work at a shipping company, not just a shipping company, but an international shipping company (as you can imagine, COVID has really thrown us for a loop both in terms of increase in volume for certain products and a DEFINITE increase in tickets due to delays). So when we talk about holiday planning, it’s not just staffing up for support, but also understanding what our holiday shipping cutoffs are going to be (e.g., when we need shipments by to guarantee holiday delivery), any historical holiday delays for our largest countries, and making sure that we run an educational campaign through my success team to make sure that the brands that ship with us understand all of the above. All of this is to say that holiday season planning is on my mind mid to late Q3 when we gear up for Q4 planning.


Our customers do up to 50% of their business in the 6 weeks starting Nov 1st, so most of the year is prep work. Q3 is almost all dedicated to beginning the prep work for the peak season, Q4 is surviving it, R1 is a post mortem and planning on the previous successes/failures, then Q2 is a chance to test before the prep starts to begin again.


“Our big struggle is actually trying to combat the burnout caused by COVID spikes prior to the holidays, rather than making sure that we are staffed up enough for holidays.” -Kat


What do you look at when forecasting for expected volume and staffing levels for the holidays?


We look at historical data, and we have a ton of that, being a data company and all. Then we look at any events our customers are holding and have potentially given us a heads-up about. We also try to match our our sales pipeline and how that has grown (in 2020) and what it might mean for our support volume.


Take the number of tickets in Q3 2019 and compare to Q3 2020. Based on the increase in ticket #’s. I then take Q4 ticket #’s and break the tickets down by day and hour. I take the number of hours spent in Q4 2019 and increase by the percentage of ticket increase, then based on the pattern of times/days of the ticket assign out the hours. I use a Google Docs sheet for this.


(2020 has been) a bit anomalous given the current rush to e-commerce because of COVID. But our main data point was identifying the usual % increase in load and applying it to our new normal.


As a relatively young company, we’re really just figuring out forecasting and staffing appropriately. What I will say is that COVID was actually a huge stress test for us – our tickets spiked between 300-400% depending on the week from our previous holiday season for 4 consecutive months from April-July. So even if holiday spikes do occur because of higher volume and delays (which we know they will), our team has the bandwidth and capacity to handle it…because nothing can be as bad as what felt like every Australian customer asking about why their shipments were taking 2+ months to deliver.


In terms of staffing, our big struggle is actually trying to combat the burnout caused by COVID spikes prior to the holidays, rather than making sure that we are staffed up enough for holidays. We look at our historical ticket to shipment ratios from our holiday season and extrapolate that across the percentage of growth we’ve experienced in shipments from the last year, and even then – the tickets are significantly less than peak COVID when shipments just weren’t moving out of the US.


We also have a great Tier 1 ticketing team (a homegrown team of 3 in Egypt) that is really able to churn through most of the WISMO (where is my order) tickets that we receive. Growing out our own team remotely in a foreign country where none of us had real ties is a whole other experience in itself.


“Understand where you want your CX to be and what it will take to maintain that.” -Craig


What tips do you have for making the case to leadership to increase staffing?


Easier when you know your key KPIs: Response, Resolution and Average Handle time. Take the increase in tickets, and show how those will impact each of the above, and then explain why having additional resources will help.


Start with what you want to deliver and then Data, data, data. Understand where you want your CX to be and what it will take to maintain that. Focus on: Response times, and support scope. What can our support team do and not do and what is needed to achieve that?


We spent a LOT of time building out an outsourced “experiment” that is working so far – basically building out a support team of our own in Egypt. Each agent is college-educated, and we pay a fair salary on Egypt standards (less than 30% of what we’d pay an entry-level agent in SF) – so for Tier 1 staffing, justification is pretty straightforward.


While we are able to staff up pretty easily, the unit economics are still crucial to justification (my CEO is all about the unit economics). As a B2B company, these are answers to questions like what is the cost per ticket, how many shipments per new brand we onboard (and with that tickets per shipment), how many tickets can an agent handle per day effectively, how can we show that while we’re increasing deflection and self-service, but justifying that because of growth – we just need more based on capacity.


Also, on the flip side – what is the financial detriment to the company if these tickets are not answered within a certain SLA – is it a factor that will cause your customers to churn or not return? This is a less straightforward case, but an important one to keep in mind — marketing spends so much money to acquire a customer and they’re thought of as revenue drivers but support and success (if not directly handling renewals / upsells) are thought of as cost centers even though retention is cheaper and SO important.


Depending on the complexity of the product, starting early will be key. Investing in support sometimes falls down on the priority list, but we take a different approach at Looker. We do have a product that is more complex than your typical software, but the philosophy stands. Caring about customers means having to invest in support. For a SaaS company, keeping customers happy is essential, and support is often a great way of doing that. In short, please invest in support. You’ll see it down the line.


“Our team operates as a single unit. To keep that effective and grow it, you’ll need to spend the time and money to connect people.” -Talal


What tips do you have for scaling training?


It might seem SO simple – but documentation is KEY and re-visiting the training every so often. As a smaller startup, up until early 2020, there was almost no documentation or super scattered documentation as we all relied on tribal knowledge. We were justifying not building out central documentation, which is super tedious, because we were “working too fast to document” and “everyone knew what they were doing”. What we have now is definitely not perfect and will be continuously improved, but we were able to see how effective true documentation was just from the difference in ramp up time for our new hires.


It’s also important to not just have support documentation – but really having the support team understand how the product works and documenting nuances as well. Support is the eyes and ears – I like to call them the canary in the coal mine – they’re the first line of defense to realize something is wrong, and in order to recognize that, they need to really understand the product.


-Standardize training and consolidate it.
-Tribal knowledge is great, but you need to collect it in a single, searchable, repository.
-Mentorship and keeping people connected in some form is key. It might be more of a Looker thing, but our team operates as a single unit. To keep that effective and grow it, you’ll need to spend the time and money to connect people.

How do you manage schedules on holidays like Thanksgiving, Christmas, and New Years? How do you manage the schedule so it’s fair to the team?


Our schedule spans 4 different timezones, and it has regional owners. It gets tricky, but we try to have other regions carry holidays that they don’t generally celebrate.


We ask for everyone’s time preferences on shifts, and we try to rotate people and have them try different shifts to keep things balanced.


We also work closely with other regions to use the global presence and relieve some of the pain points a region is going through. We stack up the beginning or end of a region’s shift, for example, to help another region out.


We have a booking time frame that opens in the summer that allow people to book time off on a first come first serve basis for holidays. We make sure we have enough staff in place and then open up as many slots to accommodate as much of vacation as the business can allow.


Christmas and New Years most of the facilities we support close, so for those we run on an on-call only basis. For other holidays we ask our employees to volunteer to work. As my employees are hourly and mostly young this is a pretty easy sell, because they earn 1.5x pay while working holidays.


“If you take care of your people, they will take care of the SLA for you.” -Sean


How do you balance the need for people to take a fair break or take time off with meeting your SLA’s? 


For the first piece – we were met with major burnout and my head of support and I have worked really hard to destigmatize the importance of taking mental health days on our team. It starts from leadership – so I push my Head of Support (and me!) Yas to take mental health days as well. For a while, we were also having each teammate take a half-day every other Friday or picking a random day each month to take off to reset. An important piece to making this successful is making sure there is an explicit team agreement that in order for this to happen, every member of the team will have to take on a little extra work on some days in exchange for these days. If someone feels like they are pulling extra work for someone else to take time off, but it’s not reciprocated, it can breed resentment.


Less from the people side, creating realistic SLAs and moving towards continuous improvement in our OKRs / not setting unrealistic expectations is also a huge factor – knowing the size your team is at now.  Asking the questions – why are our SLAs set where they are? Do we value speed vs quality? What type of questions are truly urgent and time-sensitive?


If you take care of your people, they will take care of the SLA for you. We do have a block of time each year (Nov 1-Dec 15) where we don’t allow for vacation requests.


SLAs are extremely important, but so is time off. The main thing we do here is hand over anything that needs attention to other team members. That way, the customer always has our attention, and our teams can take their well-earned time off and disconnect.


Being realistic with the load we expect. So that means on statutory holidays we know the load will be lower, so open more spots. We also make sure there is always lead coverage to support the team and it isn’t seen as leads get time off and ICs do not.

What do you do if the incoming volume is more than your team is able to handle and adding more staff isn’t an option?  


In the past, we’ve mass answered tickets (are they all asking generally the same question? How can we get ahead of it?) and we’ve also pulled in members from other teams – notably our success team is also all trained up on support & investigation.


Our first holiday season, I created a basic Macro template doc and we round robined through everyone (CEO included)


We usually call on our functions in the team that are not actively supporting customers. We have other functions in the team that manage our tooling or education programs, for instance, and they used to be on the front lines of support. When situations like this happen, we send out an ask, and they come to our rescue. It all goes back to growing the entire team as a unit and making sure people empathize with customers and each other.


Self-serve and preparedness are so vital in these situations. Update your KB, all your internal documentation etc. to make sure all repeatable tickets can be immediately resolved/deflected. You need to reduce the load through removing the “easy” stuff while still providing the value your team/company provides. The key is not to reduce quality, but to improve the execution/offering, so your team can act more efficiently.

We hope you’ve enjoyed our first Community Round Table. Please stick around for more in the future!

If you’re not already part of the Support Driven Slack community, join here.

Subscribe to get our weekly newsletter straight to your inbox.

%d bloggers like this: