Simple Ways for Makers to Grow Wholesale This Holiday Season (And Stay Sane Too)

This post is part of our August theme at Wholesale In a Box: Holiday Wholesale. We delve into that theme in the Monthly Brief that makers get, we write about it here on the blog... and we cover it on our brand new Secret Podcast! 

In Episode #2 of the Secret Podcast -- which is just for Wholesale In a Box makers -- we talk to Jonnie Estes, owner of the uber-successful jewelry line Grey Theory Mill. Jonnie shares how she has grown to 200 stockists, her tips for staying sane during makers’ craziest season, and strategies for getting great wholesale results over the holidays.

Want access to that episode? All Wholesale In a Box makers who are with us by August 1st will get the episode. So if you’ve been waiting to sign up for Wholesale In a Box, now is a great time! 

The holidays are an intense time for makers. There is a lot of pressure to make sales while the making is good. But the outreach for those sales is best done during the summer, when many makers are juggling vacations, kids, and constant craft markets. Plus, many makers fear getting more orders than they can handle. While every maker is different, it can be helpful to get answers to burning questions that feel like obstacles. 

So today, we’re rounding up some of the most common questions and concerns makers have about wholesale around the holidays. We’re digging into how to approach holiday wholesale as a newbie, how to cultivate orders with current stockists if you’re an old pro, and some simple tips to get orders in the door without a bunch of extra work. As always, though, there is no one-size-fits-all solution. So be sure to “sense check” these answers against what you know to be right for you and your business. 

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Q. I’m brand-new to wholesale and this is my first holiday season. What should I do to get ready?

If you’re newer to wholesale, you want to focus on building your wholesale foundation for the long term. And the good news is -- the things that you will want to do to build wholesale long-term are the same things you will want to do to cultivate holiday sales now, for the most part. That means developing great outreach materials, making sure you have a system for connecting with stores, getting great photos, and (of course) creating products that you can really stand behind. 

Usually, new makers focus too much on making new things; they start outreach way too late; and they don’t give their outreach materials enough careful consideration. So be on the lookout for those tendencies and try to lean the opposite way, if you can.

One other caveat here. If you’re brand new, don’t worry too much about being overwhelmed by a million sales. For the most part, it takes time to get traction and your main challenge (to be blunt) will be getting sales in the door at all. Focus on connecting with stores as much, and as effectively, as you can, rather than trying to get just the perfect amount of sales made. 

Q. I’m getting serious about wholesale this year. What do you recommend for giving myself the best possible chance of success?

First, start early. It’s not really possible to do outreach too early because generally, a store owner will ask you to circle back if the timing is wrong but they love the line. It is possible to do outreach too late, though -- so make the summer your holiday outreach season. Second, focus on relationships. Yes, you want to make sales now. And that’s a good thing. But don’t forget that you’re in this for the long haul. And it matters more that you grow dramatically over 2-3 years, than it does that you grow by a chunk in the next 2-3 months. Next: make your outreach materials as good as they can be. They don’t need to be perfect, but small changes, that aren’t that time-consuming to make, can have a big impact on how your line is perceived. Finally: create a system to connect with stores. If you’re a Wholesale In a Box maker, you already have a great system for doing outreach to stores set up for yourself. Think about whether you need to really etch out some solid time each week to send the emails and do followups, though -- and commit to keeping that schedule every week, especially for the next few months. 

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Q. What is the exact right time to do wholesale outreach for the holidays?

Stores tend to plan their buying several months in advance, so generally, they're buying for Christmas in August. But the exact way stores break down their buying seasons varies store to store and year to year. Some stores buy for the holidays well into November, especially in terms of filling gaps on the shelves. Others completely close out their holiday buying by early September. 

Makers often ask me about the ideal time to reach out to stores for the holidays, and my answer is: earlier than you think. Different stores wrap up their ordering at different times. But no matter the store, you really can’t lose by being a little too early.  July and August is a great time to start but most people delay their holiday wholesale outreach until it’s close to too late. My observation is that it’s actually fear that causes us to delay marketing and sales until the last possible minute. Because at the last possible minute, the fear that you’ve completely missed the boat starts to outweigh the fear of sharing your work. But if you can manage your own discomfort, your “return on investment” of marketing and sales work you do early will be SO much more than marketing and sales work you do at the last minute. So start early, plan what you intend to do to grow over the holidays, and take it one step at a time.

I also really encourage you to not obsess too much about the exact right timing. Even if a store isn't able to place an immediate order (but is interested), outreach always starts the conversation and builds the relationship for when they are ready to buy. Overall, the main thing is consistently reaching out to shops that are a good fit, over the long term. 

Q. I have some special holiday items in my line. Should I add a holiday themed page to my linesheet or send retailers two documents (my linesheet AND a 1-page, holiday-themed, mini linesheet)? 

A. Either approach could work well. Generally, I lean towards having one single attachment in each email -- and probably that’s best here too. Busy store owners will often only open one document, so you want to make sure that all of the information you want to share is in one place. That said, if you think your holiday line is SUPER strong and you really want that to be the main thing folks are ordering this season, you could separate it to make it even more obvious and compelling. For most makers, though, you’ll want them in the same line sheet. 


Q. I'm considering offering an incentive to retailers to place their holiday orders before a certain date. Is this a good or bad idea, what would good incentives be, and what would be optimal timing?

While not a necessity, the idea of offering retailers an incentive like this can be a great thing to do, if you have the margins to support it easily. Plus, with holiday sales increasing the stakes, an early-order incentive can help avoid a situation where a retailer loves your line, but waits to order and then ends up ordering something else because it comes along and catches their eye. 

In terms of what to offer, and how to structure it, I’d keep it fairly simple. Free shipping could be fantastic, as could a simple percentage discount. Since so many retailers do their holiday buying on the early side, you might want to make the deadline somewhere between late August and late September (but certainly not any later than that).

Q. Should I create holiday-specific items?

It depends on the maker. Most makers probably shouldn’t create holiday-specific items because of all the time it takes to do the product development, photography, line sheet creation, etc. Instead, they should focus on doing holiday-related framing, promotion, and outreach for the line they already have. Some lines, of course, are really holiday driven -- like paper lines. If that’s the case, then you’ll of course need items for all of the major holidays. But if you’re a newer maker, and your line is something that’s not, by necessity, holiday-related (for instance, a jewelry line), I’d stay away from creating new pieces. See it as an “extra” that you can add when it feels doable, not a core component of your wholesale strategy.


Q. Should I do a mass email to all my stockists to check in and give them updates on the line?

A mass email to your stockists is certainly better than not contacting them at all -- so if those are your alternatives, yes, send that mass email. That said, your relationships with your current stockists are some of the most valuable business relationships you have. So treat them as such. Consider setting aside a morning or even a full day just to do pre-holiday personal emails to all of the stores you currently sell to -- sometime in late summer. Make these emails personal, concise, and warm. Reference something that you know the store is doing or working on (perhaps something they’ve mentioned on Instagram). And catch them up on any products that they might be particularly excited about for the store this season. Be sure to attach (or link to) your line sheet or catalog and make your ordering process clear.



Q. How much should I focus on current stockists vs. new stores?

If you’re growing wholesale, it’s tempting to focus entirely on getting new orders from stores. But one of the most important things you can do is cultivate your relationships with your current stockists. In other words: love the one(s) you’re with. How to cultivate reorders during the holidays? So many store owners tell me that they don’t have a super-precise system for deciding what to reorder. So a big part of your focus should be making your line visible to the stockist and being of service to the stockist. That way you’re top-of-mind when the store owner is making their list of items to buy. The way I’d recommend doing this is “rounding up” a list of your current stockists. In the Wholesale In a Box system, you can do this easily just by filtering for Stockists. I’d recommend reviewing one by one, reflecting on who might benefit from a check-in and what they’d be interested in hearing about (whether an update or a new product). Then, schedule a task for each store that you think would be good to check in with. Again, that’s easy to do in Wholesale In a Box by clicking Add a Task -- but you can certainly do it on your own, with just a bit more leg work. Either way, the idea here is: 1) reflect on who will benefit from a check-in and 2) plan out and schedule all the check-in tasks at once rather than getting distracted and doing them one-by-one.

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Q. I’m pretty seasoned with wholesale but would like to really supercharge my wholesale game this year. Any suggestions for me?


While every maker is different I do believe there are some DOs and DON’Ts that apply for most makers. So consider these if you’re wanting to grow wholesale for your business this holiday season:


DO start outreach earlier than you think.

DON’T worry too much about nailing the exact right timing for outreach.

DO use the summer to refine your outreach materials, add individual items to your line, and get into the groove with outreach.

DON’T focus solely on making sales to new stores. Cultivating relationships and reorders with current stockists is equally or more important.

DO reach out to current stockists individually, personally, and in a way that’s relevant to them if you can possibly find the time.

DON’T take an “all or nothing” approach with improvements to your outreach to stores. Sometimes small refinements -- like new photos, better wording in your emails, or tweaks to your packaging--  can have big results. 

DO think about the “shelf appeal” of your line, including packaging, branding, store displays, signage (and also photography, which is the proof point of all of those.) 

Finally, don’t forget that you are likely the best expert on your own business. If you have several holiday seasons under your belt already, then use that experience as your guide. Claim the knowledge you have by spending 20 minutes jotting down the answers to these questions: What went well for me last holiday season? What did I wish went better last holiday season? If I were looking at my business from the outside, what would I recommend doing? What are a few things I can do differently this year to build on what worked, do less of what didn’t, and get better results? This will let you act in very concrete ways on what you’ve already learned -- and improve substantially from whatever your results were last year. 

As a maker, it’s easy to feel “behind the 8-ball” since Christmas starts, very literally, in July. But don’t let perfect be the enemy of good. Choose a handful of strategies to try this year and trust that even small steps forward will, over time, get you where you’re trying to go. 


Want more support in growing wholesale this year? Wholesale In a Box helps makers get their handmade products into more stores. Plus, this post is part of our August theme at Wholesale In a Box: Holiday Wholesale. We delve into that theme in the Monthly Brief that makers get, we write about it here on the blog, and we cover it on our Secret Podcast. All Wholesale In a Box makers who are with us by August 1 will get Episode #2 of our Secret Podcast, with Jonnie Estes of Grey Theory Mill. Jonnie is so insightful and shares her biggest tips for growing wholesale around the holidays. So if you need some guidance, training, or a secret weapon for growing wholesale this year, we’re here for it.


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