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  1. Home
  2. Bosses Day

Boss’s Day Cookie Gifts

Boss’s Day is October 16, 2025

This Boss’s Day, treat your bosses or supervisors to gifts like our unique cookies and treats. Our Bosses Day cookies are sure to bring a smile to your supervisor or manager!

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Thank You Treats Gift Pail
Passport Eligible

Thank You Treats Gift Pail

available to ship now

Buttercream-Frosted Thank You Sugar Cookies
Passport Eligible

Buttercream-Frosted Thank You Sugar Cookies

available to ship now

Thank You Traditions Gift Tower
Passport Eligible

Thank You Traditions Gift Tower

available to ship now

Great Big Thank You Party in a Box
Passport Eligible

Great Big Thank You Party in a Box

available to ship now

Thank You Kiss® Cardsnipe
FREE SHIPPING

Thank You Kiss® Card

available to ship now

Monster Chocolate Chip Cookiesnipe
Passport Eligible

Monster Chocolate Chip Cookie

available to ship now

Thank You Bow Gift Box
SAME-DAY DELIVERY IN SELECT AREAS
Passport Eligible

Thank You Bow Gift Box

available to ship now

Premier Buttercream-Frosted Thank You Sugar Cookiessnipe
Passport Eligible

Premier Buttercream-Frosted Thank You Sugar Cookies

available to ship now

Enjoy Cookie Gift Box - 12 cookies
Passport Eligible

Enjoy Cookie Gift Box - 12 cookies

available to ship now

Buttercream-Frosted Assorted Cupcakes - 12 cupcakessnipe
Passport Eligible

Buttercream-Frosted Assorted Cupcakes - 12 cupcakes

available to ship now

Classic Gift Bundle with Message Tag - Enjoy
Passport Eligible

Classic Gift Bundle with Message Tag - Enjoy

available to ship now

You’re Incredible Party in a Box
Passport Eligible

You’re Incredible Party in a Box

available to ship now

Thank You Cookie Gift Box
Passport Eligible

Thank You Cookie Gift Box

available to ship now

Buttercream-Frosted Celebrate Cupcakes & Cookiessnipe
Passport Eligible

Buttercream-Frosted Celebrate Cupcakes & Cookies

available to ship now

Thank You Cookie Card
FREE SHIPPING

Thank You Cookie Card

available to ship now

Thank You Treats Gift Box
Passport Eligible

Thank You Treats Gift Box

available to ship now

Thank You Bakery Assortment - Medium
Passport Eligible

Thank You Bakery Assortment - Medium

available to ship now

Thank You VIP Gift Tower
Passport Eligible

Thank You VIP Gift Tower

available to ship now

Thank You 2-Pack Cookie Card
FREE SHIPPING

Thank You 2-Pack Cookie Card

available to ship now

Best of Buttercream Cookie Box
SAME-DAY DELIVERY IN SELECT AREAS
Passport Eligible

Best of Buttercream Cookie Box

available to ship now

Cheryl’s Dessert Tray Gift Box - Grand - Thank You
Passport Eligible

Cheryl’s Dessert Tray Gift Box - Grand - Thank You

available to ship now

Classic Bakery Gift Tower with Message Tag - Thank You
Passport Eligible

Classic Bakery Gift Tower with Message Tag - Thank You

available to ship now

Thank You Cookie Gift Tin - Assorted Cookies
Passport Eligible

Thank You Cookie Gift Tin - Assorted Cookies

available to ship now

Buttercream Frosted Cut-out Cookie of the Month - Pay-as-you-go Subscription – 12 cookies
SAVE UP TO 42%
Passport Eligible

Buttercream Frosted Cut-out Cookie of the Month - Pay-as-you-go Subscription – 12 cookies

available to ship now

Cheryl’s Signature Bakery Sampler
Passport Eligible

Cheryl’s Signature Bakery Sampler

available to ship now

Thank You Gift Bundle
Passport Eligible

Thank You Gift Bundle

available to ship now

Thank You Gift Tower
Passport Eligible

Thank You Gift Tower

available to ship now

Thanks For all You Do Cookie Card
FREE SHIPPING

Thanks For all You Do Cookie Card

available to ship now

Thanks For All You Do Healthcare Party in a Box
Passport Eligible

Thanks For All You Do Healthcare Party in a Box

available to ship now

Classic Gift Bundle with Message Tag - Thank You
Passport Eligible

Classic Gift Bundle with Message Tag - Thank You

available to ship now

Buttercream Frosted Cut-out Cookie of the Month - Pay-as-you-go Subscription - 24 cookies
SAVE UP TO 40%
Passport Eligible

Buttercream Frosted Cut-out Cookie of the Month - Pay-as-you-go Subscription - 24 cookies

available to ship now

Flavor of the Month Cookie Club – Pre-pay
SAVE 33%
Passport Eligible

Flavor of the Month Cookie Club – Pre-pay

available to ship now

Buttercream Frosted Cut-out Cookie of the Month Club - Pre-pay
SAVE OVER 50%
Passport Eligible

Buttercream Frosted Cut-out Cookie of the Month Club - Pre-pay

available to ship now

Sugar-Free Thank You Cookie Gift Boxsnipe
Passport Eligible

Sugar-Free Thank You Cookie Gift Box

available to ship now

Gluten-Free Thank You Cookie Gift Boxsnipe
Passport Eligible

Gluten-Free Thank You Cookie Gift Box

available to ship now

Vegan Thank You Cookie Gift Boxsnipe
Passport Eligible

Vegan Thank You Cookie Gift Box

available to ship now

Enjoy Cookie Gift Box - 24 cookies
Passport Eligible

Enjoy Cookie Gift Box - 24 cookies

available to ship now

Classic Assorted Cookies
FREE SHIPPING WITH CODE FRSHIP
Passport Eligible

Classic Assorted Cookies

available to ship now

Our Best of Buttercream Cookies
Passport Eligible

Our Best of Buttercream Cookies

available to ship now

Cheryl’s Dessert Tray Gift Box - Large - Enjoy
Passport Eligible

Cheryl’s Dessert Tray Gift Box - Large - Enjoy

available to ship now

Classic Cookie Assortment
FREE SHIPPING WITH CODE FRSHIP
Passport Eligible

Classic Cookie Assortment

available to ship now

Best of Cheryl’s Dessert Tray - Large
Passport Eligible

Best of Cheryl’s Dessert Tray - Large

available to ship now

Thanks a Latte Cookie Card
FREE SHIPPING

Thanks a Latte Cookie Card

available to ship now

Cheryl’s Dessert Tray Gift Box - Large - Thank You
Passport Eligible

Cheryl’s Dessert Tray Gift Box - Large - Thank You

available to ship now

Cheryl's Dessert Tray Gift Box - Medium - Thank You
Passport Eligible

Cheryl’s Dessert Tray Gift Box - Medium - Thank You

available to ship now

Best of Cheryl’s Dessert Tray - Premier
Passport Eligible

Best of Cheryl’s Dessert Tray - Premier

available to ship now

Thank You Cookie Gift Box - 12 cookies
Passport Eligible

Thank You Cookie Gift Box - 12 cookies

available to ship now

Thank You Cookie Gift Box - 24 cookies
Passport Eligible

Thank You Cookie Gift Box - 24 cookies

available to ship now

Classic Buttercream Frosted Cookies and Pretzels
Passport Eligible

Classic Buttercream Frosted Cookies and Pretzels

available to ship now

Vanilla Buttercream-Frosted Sugar Cookie Flavor Box
Passport Eligible

Vanilla Buttercream-Frosted Sugar Cookie Flavor Box

available to ship now

Best of Cheryl’s Dessert Tray - Medium
Passport Eligible

Best of Cheryl’s Dessert Tray - Medium

available to ship now

Cheryl’s Sugar-Free Gift Tower with Message Tag - Enjoy
Passport Eligible

Cheryl’s Sugar-Free Gift Tower with Message Tag - Enjoy

available to ship january 05 2026

Gluten-Free Cookie & Brownie Gift Boxsnipe
Passport Eligible

Gluten-Free Cookie & Brownie Gift Box

available to ship now

Vegan Enjoy Cookie Gift Boxsnipe
Passport Eligible

Vegan Enjoy Cookie Gift Box

available to ship now

Cheryl’s Dessert Tray Gift Box - Grand - Enjoy
Passport Eligible

Cheryl’s Dessert Tray Gift Box - Grand - Enjoy

available to ship now

Tins With Pop® Best Boss Ever
Passport Eligible

Tins With Pop® Best Boss Ever

The Popcorn Factory

available to ship now

Tins With Pop® Happy Boss's Day
Passport Eligible

Tins With Pop® Happy Boss’s Day

The Popcorn Factory

available to ship now

Packed With Pop® Happy Boss's Day
Passport Eligible

Packed With Pop® Happy Boss’s Day

The Popcorn Factory

available to ship now

Cards With Pop® Happy Boss's Day
Passport Eligible

Cards With Pop® Happy Boss’s Day

The Popcorn Factory

available to ship now

Packed With Pop® Best Boss Ever
Passport Eligible

Packed With Pop® Best Boss Ever

The Popcorn Factory

available to ship now

Cards With Pop® Best Boss Ever
Passport Eligible

Cards With Pop® Best Boss Ever

The Popcorn Factory

available to ship now

Make You Smile 2 Gallon 3 Flavor Popcorn Tin
Passport Eligible

Make You Smile 2 Gallon 3 Flavor Popcorn Tin

The Popcorn Factory

available to ship now

TPF Retro 3 Flavor Popcorn Tins
Passport Eligible

TPF Retro 3 Flavor Popcorn Tins

The Popcorn Factory

available to ship now

Sweet Popcorn Sampler Box
Passport Eligible

Sweet Popcorn Sampler Box

The Popcorn Factory

available to ship now

18 Count Popcorn Variety Pack
Passport Eligible

18 Count Popcorn Variety Pack

The Popcorn Factory

available to ship now

Snack Box
Passport Eligible

Snack Box

The Popcorn Factory

available to ship now

Habanero Seasoned Popcorn Canister
Passport Eligible

Habanero Seasoned Popcorn Canister

The Popcorn Factory

available to ship now

Strawberry Sparkling Wine Flavored Popcorn Canister
Passport Eligible

Strawberry Sparkling Wine Flavored Popcorn Canister

The Popcorn Factory

available to ship now

Cookies and Crème Popcorn Canister
Passport Eligible

Cookies and Crème Popcorn Canister

The Popcorn Factory

available to ship now

Caramel Popcorn Canister
Passport Eligible

Caramel Popcorn Canister

The Popcorn Factory

available to ship now

Teatime For One with Teapot Gift Basket
Passport Eligible

Teatime For One with Teapot Gift Basket

1-800-Baskets

available to ship now

Classic Gourmet Gift Basket
Passport Eligible

Classic Gourmet Gift Basket

1-800-Baskets

available to ship now

Majestic Grandeur Gourmet Basket
Passport Eligible

Majestic Grandeur Gourmet Basket

1-800-Baskets

available to ship now

Premier Favorites Sweets & Treats Gift Basket
Passport Eligible

Premier Favorites Sweets & Treats Gift Basket

1-800-Baskets

available to ship now

Distinctive Fruit Basket & Sweets Gift
Passport Eligible

Distinctive Fruit Basket & Sweets Gift

1-800-Baskets

available to ship now

3 Count Oscar Mayer Bacon Cheddar Popcorn Bags
Passport Eligible

3 Count Oscar Mayer Bacon Cheddar Popcorn Bags

The Popcorn Factory

available to ship now

3 Count Kraft Mac & Cheese Popcorn Bags
Passport Eligible

3 Count Kraft Mac & Cheese Popcorn Bags

The Popcorn Factory

available to ship now

Godiva® Birthday Truffles Gift Box 12pc
Passport Eligible

Godiva® Birthday Truffles Gift Box 12pc

Simply Chocolate

available to ship now

Godiva® Gold Ballotin Chocolates Box - 18 piece
Passport Eligible

Godiva® Gold Ballotin Chocolates Box - 18 piece

Simply Chocolate

available to ship now

Godiva® Gold Ballotin Chocolates Box - 72 piece
Passport Eligible

Godiva® Gold Ballotin Chocolates Box - 72 piece

Simply Chocolate

available to ship now

Godiva® Signature Truffles Box - 12 Piece
Passport Eligible

Godiva® Signature Truffles Box - 12 Piece

Simply Chocolate

available to ship now

Godiva® Signature Truffles Box - 24 Piece
Passport Eligible

Godiva® Signature Truffles Box - 24 Piece

Simply Chocolate

available to ship now

Thank You Gift Box
Passport Eligible

Thank You Gift Box

Wolferman's

available to ship now

Deluxe Thank You Gift Box
Passport Eligible

Deluxe Thank You Gift Box

Wolferman's

available to ship now

Bakery Favorites Tray
Passport Eligible

Bakery Favorites Tray

Wolferman's

available to ship now

Grand Berry Breakfast Box
Passport Eligible

Grand Berry Breakfast Box

Wolferman's

available to ship now

Delicious Mornings Gift Basket
Passport Eligible

Delicious Mornings Gift Basket

Wolferman's

available to ship now

Mix & Match Thank You Bakery Gift - Pick 4
Passport Eligible

Mix & Match Thank You Bakery Gift - Pick 4

Wolferman's

available to ship now

Mix & Match Thank You Bakery Gift - Pick 6
Passport Eligible

Mix & Match Thank You Bakery Gift - Pick 6

Wolferman's

available to ship now

Mix & Match Thank You Bakery Gift - Pick 12
Passport Eligible

Mix & Match Thank You Bakery Gift - Pick 12

Wolferman's

available to ship now

Deluxe "You Rock" Gift Basket
Passport Eligible

Deluxe “You Rock” Gift Basket

Harry & David

available to ship now

You Rock Tower of Sweet Treats
Passport Eligible

You Rock Tower of Sweet Treats

Harry & David

available to ship now

"Thank You" Meat and Cheese Gift Box
Passport Eligible

“Thank You” Meat and Cheese Gift Box

Harry & David

available to ship now

Thank You White Wine Gift Box
Passport Eligible

Thank You White Wine Gift Box

Harry & David

available to ship october 13 2025

Deluxe Tower of Chocolates® Gift
Passport Eligible

Deluxe Tower of Chocolates® Gift

Harry & David

available to ship now

Gourmet Brownie Assortment
Passport Eligible

Gourmet Brownie Assortment

Harry & David

available to ship now

Deluxe Gourmet Gift Basket
Passport Eligible

Deluxe Gourmet Gift Basket

Harry & David

available to ship october 13 2025

"You Rock" Fruit and Sweets Gift Basket
Passport Eligible

“You Rock” Fruit and Sweets Gift Basket

Harry & David

available to ship now

Thank You Cookie Gift Basket
Passport Eligible

Thank You Cookie Gift Basket

Harry & David

available to ship now

"So Very Thankful" Succulents
Passport Eligible

“So Very Thankful” Succulents

Harry & David

available to ship now

Thank You Moose Munch® Premium Popcorn Tin
Passport Eligible

Thank You Moose Munch® Premium Popcorn Tin

Harry & David

available to ship now

Thank You Truffle Gift Box
Passport Eligible

Thank You Truffle Gift Box

Harry & David

available to ship now

Floral Embrace™
Passport Eligible

Floral Embrace™

1-800-Flowers

Fields of Europe® for Fall
Passport Eligible

Fields of Europe® for Fall

1-800-Flowers

Harvest Glow™ Bouquet
Passport Eligible

Harvest Glow™ Bouquet

1-800-Flowers

Wonderful Wishes Bouquet™
Passport Eligible

Wonderful Wishes Bouquet™

1-800-Flowers

November Sun Lily Bouquet™
Passport Eligible

November Sun Lily Bouquet™

1-800-Flowers

Our Favorite Fall Tulips™
Passport Eligible

Our Favorite Fall Tulips™

1-800-Flowers

Happy Gerbera Daisies, 12-24 Stems
Passport Eligible

Happy Gerbera Daisies, 12-24 Stems

1-800-Flowers

Elegant Orchid
Passport Eligible

Elegant Orchid

1-800-Flowers

Money Tree
Passport Eligible

Money Tree

1-800-Flowers

Sweet Succulent Garden
Passport Eligible

Sweet Succulent Garden

1-800-Flowers

Personalized Message in a Bottle® Just Because
Passport Eligible

Personalized Message in a Bottle® Just Because

1-800-Flowers

Butterfly Snow Globe by CoolSnowGlobes
Passport Eligible

Butterfly Snow Globe by CoolSnowGlobes

1-800-Flowers

Happiness Blooms Shadow Box and Candle Gift Set
Passport Eligible

Happiness Blooms Shadow Box and Candle Gift Set

1-800-Flowers

Sweet & Delicious™
Passport Eligible

Sweet & Delicious™

Fruit Bouquets

Delightful Daisy Treat™
Passport Eligible

Delightful Daisy Treat™

Fruit Bouquets

Your Best Smile Bouquet®
Passport Eligible

Your Best Smile Bouquet®

Fruit Bouquets

Rainbow Delight ™ Bouquet
Passport Eligible

Rainbow Delight ™ Bouquet

Fruit Bouquets

Gourmet Drizzled Strawberries™
Passport Eligible

Gourmet Drizzled Strawberries™

Shari's Berries

Gourmet Dipped Fancy Strawberries
Passport Eligible

Gourmet Dipped Fancy Strawberries

Shari's Berries

Lavender Garden & Drizzled Strawberries
Passport Eligible

Lavender Garden & Drizzled Strawberries

Shari's Berries

Cherished Blooms & Drizzled Strawberries
Passport Eligible

Cherished Blooms & Drizzled Strawberries

Shari's Berries

Caramel Sea Salt Artisan Belgian Chocolate Strawberries
Passport Eligible

Caramel Sea Salt Artisan Belgian Chocolate Strawberries

Shari's Berries

Artisan Belgian Milk & Dark Chocolate Strawberries
Passport Eligible

Artisan Belgian Milk & Dark Chocolate Strawberries

Shari's Berries

Signature Bundt Cake Assortment™ with Gourmet Drizzled Strawberries
Passport Eligible

Signature Bundt Cake Assortment™ with Gourmet Drizzled Strawberries

Shari's Berries

The Office World's Best Boss Flower Bouquet

The Office World’s Best Boss Flower Bouquet

Created By: PrimeParty

The Office Golf Balls 12 Pack
Passport Eligible

The Office Golf Balls 12 Pack

Created By: GBM GOLF

Gift Box Fox Thank You

Gift Box Fox Thank You

Created By: Love and Luck Greetings

Inspiring Message Engraved Navigator Compass
Passport Eligible

Inspiring Message Engraved Navigator Compass

Personalization Mall

Executive Tan Leather Personalized Portfolio
Passport Eligible

Executive Tan Leather Personalized Portfolio

Personalization Mall

Initially Yours Personalized Fleece Blanket
Passport Eligible

Initially Yours Personalized Fleece Blanket

Personalization Mall

Signature Style Personalized Coffee Mug
Passport Eligible

Signature Style Personalized Coffee Mug

Personalization Mall

Black Stylus Personalized Ball-Point Pen
Passport Eligible

Black Stylus Personalized Ball-Point Pen

Personalization Mall

Signature Series Personalized Full Pad Portfolio
Passport Eligible

Signature Series Personalized Full Pad Portfolio

Personalization Mall

Thankful For Personalized Farmhouse Candle Jar
Passport Eligible

Thankful For Personalized Farmhouse Candle Jar

Personalization Mall

Professional Laurels Personalized LED Nameplate
Passport Eligible

Professional Laurels Personalized LED Nameplate

Personalization Mall

Professional Monogram Personalized Marble Desk Clock
Passport Eligible

Professional Monogram Personalized Marble Desk Clock

Personalization Mall

Personalized Sand-Filled Hourglass
Passport Eligible

Personalized Sand-Filled Hourglass

Personalization Mall

The Boss Engraved Marble Keepsake
Passport Eligible

The Boss Engraved Marble Keepsake

Personalization Mall

Best Boss Ever Personalized Printed Star Award
Passport Eligible

Best Boss Ever Personalized Printed Star Award

Personalization Mall

Lavish Last Name Engraved Bamboo Charging Valet Tray
Passport Eligible

Lavish Last Name Engraved Bamboo Charging Valet Tray

Personalization Mall

Namely Yours Personalized Men's Leatherette Writing Journal
Passport Eligible

Namely Yours Personalized Men’s Leatherette Writing Journal

Personalization Mall

Modern Initials Engraved Marble Name Plate
Passport Eligible

Modern Initials Engraved Marble Name Plate

Personalization Mall

Executive Personalized Alderwood Pen Set
Passport Eligible

Executive Personalized Alderwood Pen Set

Personalization Mall

Lucca & Sons™ Sausage & Cheese Gift Box
Passport Eligible

Lucca & Sons™ Sausage & Cheese Gift Box

1-800-Baskets

available to ship now

Deluxe Thank You Occasion Gift Basket
Passport Eligible

Deluxe Thank You Occasion Gift Basket

Harry & David

available to ship october 13 2025

Grand Thank You Occasion Gift Basket
Passport Eligible

Grand Thank You Occasion Gift Basket

Harry & David

available to ship now

Supreme Thank You Occasion Gift Basket
Passport Eligible

Supreme Thank You Occasion Gift Basket

Harry & David

available to ship now

Engraved Black Small Book Clock and Keepsake
Passport Eligible

Engraved Black Small Book Clock and Keepsake

Things Remembered

Engraved Black Vegan Leather Padfolio and Pen Set
Passport Eligible

Engraved Black Vegan Leather Padfolio and Pen Set

Things Remembered

Engraved Bulova Ebony Crystal Recognition Clock
Passport Eligible

Engraved Bulova Ebony Crystal Recognition Clock

Things Remembered

Etched Corkcicle Square Cigar Glass
Passport Eligible

Etched Corkcicle Square Cigar Glass

Things Remembered

Engraved Waterford Lismore Essence Highball Pair
Passport Eligible

Engraved Waterford Lismore Essence Highball Pair

Things Remembered

Engraved Spinning Clock and Pen Stand
Passport Eligible

Engraved Spinning Clock and Pen Stand

Things Remembered

Engraved White Marble Card Holder
Passport Eligible

Engraved White Marble Card Holder

Things Remembered

Engraved Gloss Mahogany-Finish Gold Business Card Holder
Passport Eligible

Engraved Gloss Mahogany-Finish Gold Business Card Holder

Things Remembered

Engraved Professional Tan Leather Portfolio
Passport Eligible

Engraved Professional Tan Leather Portfolio

Things Remembered

Engraved Lenox Gold Monogram Bar Set
Passport Eligible

Engraved Lenox Gold Monogram Bar Set

Things Remembered

Etched Message Duet 8.5 oz. Stacking Decanter Set for Professionals
Passport Eligible

Etched Message Duet 8.5 oz. Stacking Decanter Set for Professionals

Things Remembered

Engraved Lenox "Tuscany" Monogram Cocktail Shaker Set
Passport Eligible

Engraved Lenox “Tuscany” Monogram Cocktail Shaker Set

Things Remembered

Engraved Black Hourglass Timer
Passport Eligible

Engraved Black Hourglass Timer

Things Remembered

Explore Wild Sampler - Thank You Gift
Passport Eligible

Explore Wild Sampler - Thank You Gift

Vital Choice

available to ship now

Wild Salmon Sampler - Thank You Gift
Passport Eligible

Wild Salmon Sampler - Thank You Gift

Vital Choice

available to ship now

MSC Wild Alaskan Sockeye Salmon - Thank You Gift
Passport Eligible

MSC Wild Alaskan Sockeye Salmon - Thank You Gift

Vital Choice

available to ship now

MSC Wild Alaskan Sockeye & Halibut Duo
Passport Eligible

MSC Wild Alaskan Sockeye & Halibut Duo

Vital Choice

available to ship now

MSC Wild Alaskan Halibut and Rainbow Carrots with Lemon Butter Sauce
Passport Eligible

MSC Wild Alaskan Halibut and Rainbow Carrots with Lemon Butter Sauce

Vital Choice

available to ship now

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Boss's Day Gifts: The Perfect Way to Say Thank You

Looking for the perfect Boss's Day gift? You can't go wrong with a thoughtful gift from Cheryl's. Our specially curated selection of Boss's Day cookies and gifts is designed to show your gratitude and appreciation. From delicious cookie gift baskets to festive thank you cookies, we have the perfect gift to make your boss feel valued.

Celebrate Your Boss This October 16

This October 16, 2025, celebrate your supervisor with a gift they'll truly enjoy. Send a gift basket filled with sweet treats, and show them how much you appreciate their leadership and guidance. Choose from a variety of flavors, including our famous buttercream-frosted cut-out cookies, rich chocolate cookies, and more. Each gift is carefully packaged and ready to deliver a smile right to their office.