Holiday Sales Tips from a Small Business Owner


Can we make a confession? As a small business owner, the holidays are a really tough time!

It’s no secret that the period of time between Thanksgiving and Christmas is the biggest retail sales season of the year. As a full-time small business owner that relies on holiday sales to account for a large percentage of annual income, there’s a lot of pressure to “get the holidays right.”

We’re not going to lie, we’ve had a few extra glasses of wine thinking about competing with retail giants for your hard earned holiday spending cash. And while we’re thankful that more and more consumers are subscribing to the Small Business movement to support little shops like ours, it’s a constant struggle to prepare for, and execute, the “perfect” holiday sales season.

We’re experts by no means, but we have learned a few things (the hard way;)) about how to boost your holiday sales. See below for a roundup of our tried and true holiday sales tips that have helped us through this wonderfully chaotic time.

Holiday Sales Tips for Small Business Owners

  • Plan Ahead. Here’s the scenario: You’re sailing along doing your thing. You look at the calendar. It’s November 25th. You realize Thanksgiving is impending. You freak out – S.O.S.! You make a 10 page to do list and vow not to sleep until every last agenda item is checked off. Sound familiar? You’re not alone. The single best tip we can give you for staying afloat during the holidays is to NOT wait until the holidays to start preparing for the holidays. Make inventory lists ahead of time, and have products in stock well before you’ll need them. Update your social media pages, prepare graphics, plan shop sales, photograph new products, etc. weeks (if not months) in advance of November, so you can charge full steam ahead into the holidays, without worrying about how many life vests you have on the ship. Youknowwhatwemean? Be prepared, and life will be so much easier!
  • Narrow Your Focus. With so much going on during the holiday season, it’s really, really easy to lose track of the task at hand. One moment you’re packaging up 50 holiday Etsy orders, then the phone rings and you chat with your mom for 30 minutes, hop online and answer a few dozen emails, research some new merch, and return to your packing task 2.5 hours later only to realize you have no idea which items are in each of your identical packages. We definitely relate to this one! During the holidays, it’s crucial to tackle your to do list one task at a time, with no distractions in between (even if they’re productive distractions). Try this now, and thank us later!
  • Surprise and Delight. One way you can amp your holiday sales is by surprising and delighting your customers. It’s one of the ways a small business can stand out from its national chain competitors, and allows you to reinforce the reason you love being a small business owner so much! Whether it’s something simple (like including a hand written thank you note with each order placed) or something more elaborate, it’s important to thank your customers for helping support your dream. (Bonus: One way we’ve helped directly boost sales is by surprising our social media followers with exclusive sneak peaks of new products! It provides valuable user feedback on what people like, lets the anticipation for new products build, and is all around fun!)
  • Communicate with Your Customers. This one is crucial to surviving the holiday sales season. Establishing clear and direct communication between your prospective customers, current customers and your business is one of the most important things you can do. One easy way to start is by creating a shop FAQ page to anticipate customer questions. This will save you loads of time answering emails during times when you are stretched thin. Payment and shop policies, ordering process instructions, shipping timetables, holiday ordering deadlines, promotional coupon codes, etc. are some of the most common questions that we receive, and make a great place to start!
  • Don’t forget to celebrate. It’s the holidays for you too, y’know! Taking some time off (even just a weekend) to spend with your loved ones will help you be refreshed and ready to tackle the new year. Planning a trip (as opposed to just taking a weekend for yourself) gives you the added benefit of something to look forward to on those long nights of work, but at the very least you deserve a bit of R&R at home.
  • Digest & Document. A really important piece of a small business holiday sales strategy comes after the holidays are over. When the rush settles down, take time to document processes and measure successes and failures. Each year, you’ll get closer and closer to building yourself a roadmap that works for you, and each passing holiday season will be less of a guessing game and more of a “you got this!” game.
  • Forgive yourself. As well intentioned as we can be, sometimes things don’t always go as planned. While having goals and focus is important, it’s equally as important to give yourself a break if you didn’t get as much done as you wanted to this year. Owning a small business is a labor of love, and the hard parts make the wins that much sweeter!

We hope you found these holiday tips helpful. If you have any helpful tips we left off the list, we’d love to hear from you! Give us a holler at or add them to the comments below.

#SmallBizLife: A Peek Into the TDCo Team!

Tomahawk Design Company is made of a small group of fierce ladies, who happen to be best friends. We thought it’d be fun to introduce ourselves here and share a little bit about what life is like mixing business with besties.


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  1. Jill Dombroskie  |  Owner & Designer
  2. Tara Wagner  |  Communications
  3. Raquel Ciappi  |  Finance
  4. Allison Anthony  |  Design Support / Events


In 5 words or less, explain what you do for Tomahawk Design Co.?

R: Pricing / Finance

J: Owner and Creative Lead

T: Communicator and Chief Snack Organizer

A: Creative Design Support & Workerbee


What led you to get involved with Tomahawk?

R: For years, late-night wine sessions with my roommate (Jill) always turned into her saying she wanted to quit her job and start her own design company.  Next thing I know our late-night conversations were turning into a reality and I saw my best friend establish Tomahawk Design Co.  I was so interested in everything she was doing (and wanted to hang out with my bffs) that I decided to crash a brainstorming session she had set-up with Tara and Allison.  Since then I’ve been hooked and started to help out with the finances of the company as the resident math nerd.

J: I started Tomahawk as a way to ensure that both mine and my clients’ creative visions are always fulfilled—little did I know my love of Maryland would make an appearance and become such a huge part of what we do!

T: I was forced into it! Just kidding, when Jill started her new business I was excited to lend my skills to help her succeed! Coming from a background where I worked with small businesses, I knew that my experience communicating and planning for their businesses would be a valuable asset—plus, I knew it would be fun! I’m so proud of what she (and we) have accomplished over the past year and a half, and can’t wait to see where we will go over the next few years.

A: My unwavering support and sense of pride for one of my best friends starting her own business and on a personal level, reaching my ultimate life goal of turning a creative passion into a career. (Not mentioned: I also live and breathe all things MD.)


What’s your favorite quality about the teammate to your left?

R: (About Tara) Besides being the BEST snack manager in the world, she’s great at generating excitement at our meetings by bringing up new opportunities/ partnerships for us (craft shows, Baltimore in a Box, etc.). She’s always thinking ahead and making sure that we continue to plan for bigger/better (Martha Stewart Living spread here we come!)

J: (About Allison) Allison’s mind is always on the same creative brainwave as mine—we are able to bounce ideas back and forth and piggyback off each others’ to come up with the best possible solutions. We make an excellent creative team! Not to mention, she’s very punny 😉

T: (About Jill) It sounds cliche, but it’s gotta be her ambition! I’m so proud of Jill and her awesome business that she has created from scratch. She had a dream, and she made it happen! #girlboss

A: (About Raquel) Raquel brings an honesty and directness that makes her such a valuable part of any team, but especially Tomahawk. A pitfall in a lot of companies are leaders who surround themselves with “yes” people. During our (occasionally rambunctious) product brainstorming sessions, when ideas get lofty and our excitement and creativity is overflowing, Raquel level-sets us and provides her unique, creative and technical perspective without sugar-coating it — Finding someone who does that tactfully and respectfully is hard to find!


Any advice for others looking to mix friendship with business?

R: Make sure you all agree on the vision/ product of the company, and understand that it’s ok to agree to disagree.

J: Just don’t take anything too personally. Keeping your business personas and your friendship personas on two different levels is what makes it work. Otherwise, I say go for it! I love these ladies and everything they’ve helped Tomahawk achieve thus far and I would never be where I am now without them!

T: Do it, and don’t look back! Mixing business with friendship has been so fun for us – we have definitely made it work well. As long as you’re not afraid to give your opinion and speak your mind among friends, it’s a great reason to hang out, brainstorm over meals on a Tuesday night, and rally around something you are all so proud of.

A:  Having all been best friends for over 12 years, I feel like if you can make it through the drama of grade school and college, you can make it through anything! Seriously though, whoever said ‘Mixing business with friendship is a bad idea’ must have had some lackluster friends. (Note: I may be slightly impartial here…or I just know how lucky we are.) We recognize, understand and accept each other’s strengths and weaknesses which has not only solidified our close friendship over the years but also helped provide the foundation for the success of our business team. Just like our friendship circle, we can be so similar, so different and each bring a multitude of expertise and experience to this business. If I could give any advice, I’ll give a few “nevers”:

•  Never forget why you wanted to be in business together.
•  Never sweat the small stuff.
•  Never lose sight of your purpose in the business and what you bring personally and professionally to the team.


Who in the group is the most likely to keep the team meeting on track?

R: Guilty!

J: Raquel, meetings would never end without her agendas

T: Raquel sets our agenda – and reminds us when we get on a tangent about all of our exciting new product and festival plans!

A: Raquel – our official agenda generator since ’14! This girl needs a gavel.


… the most fun to work a festival with?

R: Everyone! It’s great to be able to spend a large quantity of time together.

J: Any of us. But Tara brings snacks, sooo…

T: It’s most fun when we are all working together!

A: Me (ha – am I allowed say myself?) Talking to people and engaging customers is pure fun, not work.


… the biggest brainstormer?

R: Jill

J: Me—it’s my job, after all 🙂

T: Jill always comes prepared!

A: Jill – she’s always surprising us with something new! Her design talents makes my eyes happy.


… the designated clever pun generator?

R: Allison!

J: Tara or Allison

T: I definitely bring the best (worst) puns.

A: Raquel – come on, Chesapeake Bay-by?!  That’s just gold!


… the most likely to bring wine to the strategy session?

R: I’d say all of us

J: All of us!

T: We are all equally as likely (it’s inevitable).

A: Jill – our resident wine connoisseur


… the best salesperson / sweet-talker?

R: Allison

J: Allison could sell ice cream to an eskimo—it’s fabulous

T: Allison – she knows what people want, even if they don’t know it yet! And who could resist?

A: Tara – she’s swiped more credit cards in the last year than you could shake a stick at!


Have any burning questions we didn’t answer here? Send us a note at and we’ll spill—maybe 😉


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