Your sales kickoff is one of the few times your whole sales team is in the same place, which makes it all the more important for you to get your SKO swag right. After all, these are the items that your reps will bring home, wear on customer calls and meetings, and take on work trips.
That’s why, instead of automatically going for the same polos you ordered last year, it’s time that you think about what your sales team would like to use. Is it a quarter-zip, a tumbler, a backpack? Or all of the above?
In this guide, we put together five sales kickoff swag kit ideas for SKO 2027 so you can give your sales team swag that they will definitely use.
What makes good sales kickoff swag?
Before we delve into the swag ideas for your SKO swag kits, it’s first best to discuss the things you need to look for in your SKO swag.
Your sales reps can wear it in front of a customer
Apparel is usually one of the first things that a customer will see when they meet with your sales rep. So, you can opt for polos or quarter-zips as they can be worn by your reps during meetings. Just make sure to keep your logo small and choose colors that can be easily paired with jeans or slacks.
Your reps recognize the brand
Sales teams tend to notice labels, as they’re the ones who bring in the revenue for your company. Peter Millar, Vuori, TravisMathew, and Stanley are some of the brands that are suitable for sales kickoff. You don’t need to spend on a recognizable brand for every SKO swag item, though. One strong hero swag can be enough to make your whole SKO swag kit feel more premium.
Your reps will actually use it
ASI’s 2026 Ad Impressions Study found that 78% of US consumers keep promotional products because they’re useful. For sales swag, ask yourself one question: would one of your reps still use it on a random Tuesday in April? That’s a better test than whether the swag items look good in a kickoff mockup. The best gifts for salespeople fit naturally into how your reps already work, travel, and meet with customers.
It fits how your reps work
Think about what your sales team actually carries, wears, and uses during the week. Is it a backpack? Do they wear polos more often? What drinkware do they already own? Backpacks, tumblers, polos, quarter-zips, and travel accessories tend to make sense because your reps can take them on work trips or use them between meetings. Basically, if you’re choosing sales kickoff swag, prioritize the things your reps already need.
How many items should go in a sales kickoff swag kit?
Two to four swag items for a swag kit are usually enough. For most teams, one recognizable hero item, plus one or two supporting swag items, gives your reps plenty without filling the bag with extras they won’t use.
There’s also a budget reason to keep the kit tighter. American Express Global Business Travel’s 2026 Global Meetings and Events Forecast found that 71% of meeting professionals expect event costs to increase in 2026, while 27% plan to reduce spending on giveaways and corporate gifts. While this may not necessarily affect your company or swag budget, it’s still something to keep in mind, so you can spend your budget on fewer, better SKO swag items instead of giving everyone a large assortment.
If your budget allows, give each rep at least two stronger items, such as apparel plus a bag or drinkware. If your budget is tighter, put more of it toward one item your team will genuinely want and skip the filler. Your reps will get more use from one good quarter-zip than five smaller items they don’t have any use for.
What are 5 sales kickoff swag kit ideas for SKO 2027?
The five kits below are built around different moments during sales kickoff week, from check-in through the awards dinner. You can also mix and match between them. A lot of teams give everyone the check-in kit, then save the premium kit for the reps they recognize on stage. That said, let’s get into it!
The check-in kit for every attendee
Your sales reps will probably carry this kit around from the moment they check in, so keep it simple. Give them a tote they can use throughout the week and two or three items they’ll want to take home.
Bulk swag items you can consider adding to your kit:
Fully Custom Mesh Tote Bag ($7.59) - With a fully custom mesh tote, you have more room to use your kickoff colors and artwork than you would with a standard canvas bag. Your reps can also fold it flat into a suitcase when they head home, which matters when everyone is already traveling with luggage.
Richardson Trucker Cap 112 ($13.50) - The Richardson 112 has the classic trucker shape a lot of people already know, so it’s an easy option for a large sales team.
30 oz Stanley Quencher H2.0 Flowstate ($45.00) - Stanley is one of the brands our sales teams request most often. Your reps can carry the 30 oz Quencher from session to session during kickoff, then use it at home, in the office, or on the road afterward. It also fits most car cup holders, which makes the 30-oz size easier to travel with than some of the larger options.
On Demand apparel option for the kit:
Adidas Basic Sport Polo ($64.99) - If you want to add apparel without guessing everyone’s size upfront, this Adidas polo gives your reps an easy option they can choose for themselves. It’s made from 100% recycled polyester piqué with a hydrophilic finish, rib-knit collar, and UPF protection, so it works well for a full day of kickoff sessions. Since it’s On Demand, the $64.99 price is all-inclusive and already covers the item, decoration, shipping, taxes, and duties.
The client-ready kit
There’s a good chance your reps will wear their sales kickoff apparel to customer meetings afterward, so choose it with that in mind. For this kit, stick with polished apparel, smaller logos, and colors your team can easily wear with the rest of their work wardrobe.
Bulk swag items you can consider adding to your kit:
Bellroy 16" Laptop Sleeve ($59.99) - Your reps pull out their laptop at the start of almost every client meeting, so the sleeve gets seen as much as their apparel does. Bellroy is a brand frequent travelers know, and the sleeve slips into a backpack without adding bulk.
Stanley 20 oz Cafe-To-Go Travel Mug ($39.00) - A travel mug is smaller and more polished than a big tumbler, which makes it easier to carry into a customer's office. Your reps can use it on the drive to a meeting, then keep it on their desk the rest of the week.
Mercer+Mettle Claremont Backpack ($55.86) - The Claremont has a clean enough look for client meetings and business travel, so your team won’t feel like they’re carrying a gym bag into a customer’s office.
On Demand apparel option for the kit:
Cotopaxi Amado Fleece Vest ($104.99) - For the client-ready kit, this gives your reps a more casual layering option they can still wear after kickoff. The Amado is made from 100% recycled polyester fleece, with a zip-through collar, hand pockets, and Cotopaxi’s colorblocked look. Your reps can choose their own size through On Demand, and since it’s On Demand, the $104.99 price already includes the item, decoration, shipping, taxes, and duties.
The carry-on kit
If most of your sales team is flying to the sales kickoff venue, then make sure to give them things they can use on the trip home and on future work trips. Everything in this kit is small enough to fit into a carry-on or personal item.
Bulk swag items you can consider adding to your kit:
mophie Power Boost 10,000 mAh Power Bank ($39.99) - Your reps may end up using this before they even leave the airport. Just include a quick note with it. The FAA requires passengers to keep power banks in their carry-on luggage rather than checking them.
Mercer+Mettle Utility Case ($13.40) - By day two of kickoff, your reps probably have charging cables and adapters scattered through their bags. A utility case gives them one place to keep everything.
Thule Subterra 2 Toiletry Bag ($59.98) - For a sales team that spends a lot of time flying, a good toiletry bag can stay in rotation for years. Your frequent travelers are also likely to recognize Thule, which makes this one feel a little more premium without moving into award-gift pricing.
On Demand apparel option for the kit:
Columbia Steens Mountain Vest ($76.99) - A fleece vest is easy for your reps to pack without taking up much space, which makes this a good apparel option for the carry-on kit. It’s made from 250g polyester fleece with zippered hand pockets and Columbia branding on the back yoke. Your reps can order their own size since it’s On Demand. Similar to the two other apparel options above, the $76.99 On Demand price already covers the item, decoration, shipping, taxes, and duties.
The resort or beach kit
If you’re taking your sales team somewhere like Cancún or Scottsdale, skip the heavier layers and plan around the destination. Remember, if you’re doing your sales kickoff at a beach, swap fleece for towels and beach hats.
Bulk swag items you can consider adding to your kit:
Slowtide Quick-Dry Towel ($39.18) - Slowtide is known for its prints, so you don’t need to cover the towel in company branding. Put your logo in one corner and let your reps use it at the pool, beach, or wherever you’ve planned the downtime. The quick-dry fabric also packs down easily when they fly home.
Nike Swoosh Bucket Hat ($28.98) - Your reps can wear this for a pool day, golf outing, or any outdoor activity you’ve added to the agenda. The Nike swoosh already gives the hat plenty of branding, so keep your own mark subtle.
YETI Rambler 12 oz Colster Slim ($28.75) - YETI’s can cooler is one of those swag items that sales reps end up loving, even though it isn’t always the first item they think of. Your reps can use it by the pool during kickoff, then bring it home without taking up much room in their luggage.
On Demand apparel option for the kit:
Nike Swoosh Sleeve Legend Tee ($60.99) - For a warm-weather kickoff, give your reps something lighter they can wear around the resort or during outdoor activities. This Nike tee is made from 100% recycled polyester jersey with Dri-FIT technology, plus a tag-free label and Nike Swoosh on the sleeve. This item is also On Demand, meaning your reps can choose their sizes. What’s more, the listed On Demand price is all-in, so there are no separate charges for decoration, shipping, taxes, or duties.
The top performer kit
Your top performers shouldn’t receive the same swag kit that everyone picked up at registration. If you’re recognizing them on stage, go up a tier and choose sales kickoff gifts that feel closer to something they might buy for themselves after a strong quarter.
Bulk swag items you can consider adding to your kit:
Sony WH-CH520 Wireless Headphones with Microphone ($69.98) - If your top reps spend a lot of time on calls or traveling, these Sony headphones give them something they can use almost every day. They offer up to 50 hours of battery life, and a three-minute quick charge gives them up to 1.5 hours of playback. Your reps can also connect two devices at once, which is useful when they’re switching between a laptop and phone during the workday.
TravisMathew Duration Duffel ($83.85) - If your top reps spend much of the year traveling, a premium duffel makes sense as an award. TravisMathew has a relaxed, golf-inspired look that fits well with the kind of apparel and accessories you often see in President’s Club programs.
YETI Rambler 20 oz Tumbler with MagSlider Lid ($38.75) - Laser engrave your logo and the award name on the side so your winner gets something specific to the recognition instead of a standard company tumbler.
On Demand apparel option for the kit:
Columbia Men's Ascender™ II Soft Shell Vest ($122.99) - If you want your top performers to choose their own apparel award, this Columbia vest gives them something polished enough for work and practical enough for travel. It has a soft-shell construction with stretch, water and wind resistance, zippered pockets, and an adjustable hem. At $122.99 all-in, you’re already accounting for the vest, decoration, shipping, taxes, and duties, while your winner gets to choose their own size.
Things to Sort Out Before You Order SKO Swag
Collect sizes during registration. Add an apparel-size question to your kickoff RSVP form so you don’t have to ask people later. If you need to place the order before registration closes, our team’s fallback size curve for a mixed group is roughly 10% S, 30% M, 35% L, 20% XL, and 5% XXL. Unisex fits can also make ordering easier. Our branded apparel guide has more information on sizing and fit that you can use.
Choose colors that are less likely to be out of stock. Black and navy are usually the safest choices, with white close behind. If you choose a seasonal color and it sells out between approval and production, your team may have to make a last-minute swap.
Check where each brand can ship. If some of your reps are in Canada or India, don’t assume the same apparel will work for every location. Some US brands, including Nike and TravisMathew, can run into customs issues in Canada. For India, you’ll need apparel that can be produced and stocked locally
Build Your SKO 2027 Kits with PerkUp
Your sales kickoff can involve a lot of different sends at once. You may need to ship hundreds of kits to the venue, send individual boxes to reps who can’t travel, prepare separate awards for top performers, and still have swag ready for new hires who join a month later.
With PerkUp, your team can manage all of that from the same swag platform. For the event itself, you can plan your event swag, build swag kits, place bulk swag orders, and keep your inventory in warehousing until the venue is ready to receive it.
You can also use PerkUp’s event management view to check your production timelines and delivery status in one place. That way, your team can see what has already reached the venue before load-in and what’s still in transit. If your sales team is global, PerkUp delivers through local distribution, so each rep’s swag goes out as a local delivery from the warehouse closest to them. PerkUp’s warehouse and supplier network covers the US, Canada, Mexico, the UK, Europe, India, China, Hong Kong, Australia, and Dubai, with shipping to more than 100 countries. If your swag is produced centrally, PerkUp bulk ships it into each region, with PerkUp or its partners acting as the importer of record. For any package that crosses a border on its own, PerkUp prepays duties wherever possible, too!
For reps who can’t attend in person, give them access to a swag store with bulk and On Demand swag. From there, your reps can choose their own item and size. Plus, since On Demand is available alongside bulk swag, you don’t have to store inventory if you don’t want to. If your award winners are spread across different countries, you can also choose from 5,000+ gift cards so each of your recipients gets something relevant to where they live.
Every PerkUp account also comes with in-house designers. Your team can bring us the kickoff theme, and our designers can turn it into an SKO 2027 design that works across apparel, bags, or drinkware. If you have a specific award in mind and can’t find it in the catalog, our custom sourcing team can help you create or source it.
You can keep using the same account after kickoff, too! PerkUp connects with your HR tools through 200+ integrations, so you can automate birthday and work anniversary gifting instead of asking someone on your team to track every date manually.
Here are a few examples of teams that used PerkUp for their events and swag kits.
Wise
Wise uses PerkUp for internal event swag, including custom apparel for milestones, team gatherings, and its early-career marketing teams. For your kickoff, you can take the same approach and choose apparel that your reps can continue wearing throughout the year instead of treating SKO as a one-time order.
Microsoft
Microsoft ordered more than 1,000 custom premium letterman jackets for its team. If you want to give your top performers something they couldn’t simply buy for themselves, a custom piece like this can make the recognition feel much more specific to your company.
Impiricus
Impiricus created a collection of premium branded apparel around the quality standards it wanted for its team. You can use the same thinking for your client-ready kit. Give your reps apparel they would choose to wear on their own, and they’re much more likely to keep using it after kickoff.
Turing
Turing sent 644 matching kits to its team, with 453 going to India and 191 to the US. Instead of shipping everything internationally from one location, PerkUp produced the same kit design for both regions and fulfilled each batch locally. If your sales team is split across countries, you can take the same approach with your kickoff swag. Your reps still receive the same kit, but you can produce and ship from the region closest to them and keep the approval process to one design.
Traka
Traka built an all-black kit around an OGIO backpack and a few everyday essentials. If you’re putting together a client-ready kit, you can use the same idea by choosing one stronger item as the main piece and keeping the rest of the kit visually consistent. Sticking to one color also makes the whole kit feel more put together without needing a complicated design, which is a good approach when it comes to SKO swag.
Bottom Line
Your sales kickoff may happen in January or February, but your team needs to start on the swag much earlier. Kickoff production overlaps with the holiday season, so lock in your kits, sizes, and colors early. Get the artwork approved while you still have room in the production calendar, and give your team enough time to get everything to the venue before registration starts.
If you already have a rough headcount and kickoff city, book a demo with PerkUp!
Sales Kickoff Swag FAQs
What’s the minimum order for sales kickoff swag?
Bulk orders typically start at 50 units per item per warehouse location, and you’ll produce swag kits in bulk. If you only need a few items for late additions or reps who join after kickoff, On Demand swag starts at one unit.
Can reps choose their own kickoff swag?
Yes! You can set up a kickoff collection in a company swag store and let your reps choose from approved items without seeing the prices. They can enter their own sizes and addresses, and you can control which products different countries or teams see. If you work at a finance or fintech company with a formal security review, PerkUp is SOC 2 Type 2 certified.
Can we put more than one brand on our kickoff swag?
Of course! If your kickoff brings together several business units or teams from an acquisition, you can manage multiple logos and brands from one PerkUp account. You can also use co-branded artwork or add a second logo placement, such as a sleeve hit or nape label, for a small additional cost per item.
Are gift cards a good award for sales kickoff winners?
Gift cards can work especially well when your winners live in different countries. A rep in Sydney and a rep in Chicago can each choose something relevant to where they live instead of receiving the same physical swag items.
