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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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Buttercream-Frosted Thank You Sugar Cookies
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Buttercream-Frosted Thank You Sugar Cookies

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48 Reviews

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Buttercream-Frosted Assorted Cupcakes - 12 cupcakessnipe
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Buttercream-Frosted Assorted Cupcakes - 12 cupcakes

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Buttercream-Frosted Celebrate Cupcakes & Cookiessnipe
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Buttercream-Frosted Celebrate Cupcakes & Cookies

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You’re Incredible Party in a Box
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You’re Incredible Party in a Box

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Thank You Traditions Gift Tower
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Thank You Traditions Gift Tower

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Classic Gift Bundle with Message Tag - Enjoy
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Classic Gift Bundle with Message Tag - Enjoy

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Thank You Treats Gift Pail
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Thank You Treats Gift Pail

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Great Big Thank You Party in a Box
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Great Big Thank You Party in a Box

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Thank You Cookie Gift Box
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Thank You Cookie Gift Box

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Thank You Treats Gift Box
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Thank You Treats Gift Box

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Thank You Cookie Card
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Thank You Cookie Card

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Thank You Bakery Assortment - Medium
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Thank You Bakery Assortment - Medium

available to ship september 15 2025

Thank You VIP Gift Tower
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Thank You VIP Gift Tower

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Thank You 2-Pack Cookie Card
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Thank You 2-Pack Cookie Card

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

Full StarFull StarFull StarFull StarEmpty Star9 Reviews

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

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

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Thank You Cookie Gift Tin - Assorted Cookies
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Thank You Cookie Gift Tin - Assorted Cookies

Full StarFull StarFull StarFull StarFull Star1 Review

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

Full StarFull StarFull StarFull StarFull Star4 Reviews

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You’re Incredible Cookie Card
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You’re Incredible Cookie Card

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Cheryl’s Signature Bakery Sampler
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Cheryl’s Signature Bakery Sampler

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Thank You Gift Bundle
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Thank You Gift Bundle

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Thank You Gift Tower
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Thank You Gift Tower

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Thanks For all You Do Cookie Card
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Thanks For all You Do Cookie Card

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

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Classic Gift Bundle with Message Tag - Thank You
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Classic Gift Bundle with Message Tag - Thank You

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

Full StarFull StarFull StarEmpty StarEmpty Star2 Reviews

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

available to ship august 26 2025

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

Full StarFull StarFull StarFull StarFull Star2 Reviews

available to ship august 26 2025

Sugar-Free Thank You Cookie Gift Boxsnipe
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Sugar-Free Thank You Cookie Gift Box

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Gluten-Free Thank You Cookie Gift Boxsnipe
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Gluten-Free Thank You Cookie Gift Box

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Vegan Thank You Cookie Gift Boxsnipe
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Vegan Thank You Cookie Gift Box

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Enjoy Cookie Gift Box - 24 cookies
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Enjoy Cookie Gift Box - 24 cookies

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Classic Assorted Cookies
FREE SHIPPING WITH CODE FRSHIP
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Classic Assorted Cookies

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391 Reviews

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Our Best of Buttercream Cookies
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Our Best of Buttercream Cookies

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10 Reviews

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

Full StarFull StarFull StarFull StarFull Star1 Review

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Classic Cookie Assortment
FREE SHIPPING WITH CODE FRSHIP
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Classic Cookie Assortment

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Empty Star14 Reviews

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Best of Cheryl’s Dessert Tray - Large
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Best of Cheryl’s Dessert Tray - Large

Full StarFull StarFull StarFull StarFull Star1 Review

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Thanks a Latte Cookie Card
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Thanks a Latte Cookie Card

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

Full StarFull StarFull StarFull StarFull Star1 Review

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

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Best of Cheryl’s Dessert Tray - Premier
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Best of Cheryl’s Dessert Tray - Premier

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Thank You Cookie Gift Box - 12 cookies
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Thank You Cookie Gift Box - 12 cookies

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Thank You Cookie Gift Box - 24 cookies
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Thank You Cookie Gift Box - 24 cookies

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Classic Buttercream Frosted Cookies and Pretzels
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Classic Buttercream Frosted Cookies and Pretzels

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Vanilla Buttercream-Frosted Sugar Cookie Flavor Box
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Vanilla Buttercream-Frosted Sugar Cookie Flavor Box

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7 Reviews

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Best of Cheryl’s Dessert Tray - Medium
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Best of Cheryl’s Dessert Tray - Medium

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Empty Star3 Reviews

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

Full StarFull StarFull StarFull StarFull Star2 Reviews

available to ship january 05 2026

Enjoy Cookie Gift Box - 12 cookies
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Enjoy Cookie Gift Box - 12 cookies

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Gluten-Free Cookie & Brownie Gift Boxsnipe
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Gluten-Free Cookie & Brownie Gift Box

Full StarFull StarFull StarFull StarFull Star3 Reviews

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Vegan Enjoy Cookie Gift Boxsnipe
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Vegan Enjoy Cookie Gift Box

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

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Tins With Pop® Best Boss Ever
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Tins With Pop® Best Boss Ever

The Popcorn Factory

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Packed With Pop® Best Boss Ever
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Packed With Pop® Best Boss Ever

The Popcorn Factory

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Cards With Pop® Best Boss Ever
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Cards With Pop® Best Boss Ever

The Popcorn Factory

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Make You Smile 2 Gallon 3 Flavor Popcorn Tin
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Make You Smile 2 Gallon 3 Flavor Popcorn Tin

The Popcorn Factory

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39 Reviews

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TPF Retro 3 Flavor Popcorn Tins
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TPF Retro 3 Flavor Popcorn Tins

The Popcorn Factory

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Sweet Popcorn Sampler Box
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Sweet Popcorn Sampler Box

The Popcorn Factory

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26 Reviews

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Make You Smile Gift Box
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Make You Smile Gift Box

The Popcorn Factory

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19 Reviews

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18 Count Popcorn Variety Pack
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18 Count Popcorn Variety Pack

The Popcorn Factory

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43 Reviews

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Snack Box
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Snack Box

The Popcorn Factory

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16 Reviews

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Habanero Seasoned Popcorn Canister
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Habanero Seasoned Popcorn Canister

The Popcorn Factory

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Strawberry Sparkling Wine Flavored Popcorn Canister
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Strawberry Sparkling Wine Flavored Popcorn Canister

The Popcorn Factory

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Caramel Popcorn Canister
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Caramel Popcorn Canister

The Popcorn Factory

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Teatime For One with Teapot Gift Basket
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Teatime For One with Teapot Gift Basket

1-800-Baskets

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Classic Gourmet Gift Basket
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Classic Gourmet Gift Basket

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Majestic Grandeur Gourmet Basket
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Majestic Grandeur Gourmet Basket

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Premier Favorites Sweets & Treats Gift Basket
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Premier Favorites Sweets & Treats Gift Basket

1-800-Baskets

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Distinctive Fruit Basket & Sweets Gift
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Distinctive Fruit Basket & Sweets Gift

1-800-Baskets

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3 Count Oscar Mayer Bacon Cheddar Popcorn Bags
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3 Count Oscar Mayer Bacon Cheddar Popcorn Bags

The Popcorn Factory

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3 Count Kraft Mac & Cheese Popcorn Bags
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3 Count Kraft Mac & Cheese Popcorn Bags

The Popcorn Factory

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Full Star
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6 Reviews

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Godiva® Birthday Truffles Gift Box 12pc
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Godiva® Birthday Truffles Gift Box 12pc

Simply Chocolate

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3 Reviews

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Godiva® Gold Ballotin Chocolates Box - 18 piece
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Godiva® Gold Ballotin Chocolates Box - 18 piece

Simply Chocolate

Full StarFull StarFull StarFull StarFull Star5 Reviews

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Godiva® Gold Ballotin Chocolates Box - 72 piece
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Godiva® Gold Ballotin Chocolates Box - 72 piece

Simply Chocolate

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Godiva® Signature Truffles Box - 12 Piece
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Godiva® Signature Truffles Box - 12 Piece

Simply Chocolate

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Godiva® Signature Truffles Box - 24 Piece
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Godiva® Signature Truffles Box - 24 Piece

Simply Chocolate

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Thank You Gift Box
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Thank You Gift Box

Wolferman's

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Deluxe Thank You Gift Box
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Deluxe Thank You Gift Box

Wolferman's

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Bakery Favorites Tray
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Bakery Favorites Tray

Wolferman's

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172 Reviews

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Grand Berry Breakfast Box
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Grand Berry Breakfast Box

Wolferman's

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274 Reviews

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Delicious Mornings Gift Basket
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Delicious Mornings Gift Basket

Wolferman's

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

Wolferman's

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17 Reviews

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

Wolferman's

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23 Reviews

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

Wolferman's

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Deluxe "You Rock" Gift Basket
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Deluxe “You Rock” Gift Basket

Harry & David

Full StarFull StarFull StarFull StarFull Star42 Reviews

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You Rock Tower of Sweet Treats
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You Rock Tower of Sweet Treats

Harry & David

Full StarFull StarFull StarFull StarEmpty Star9 Reviews

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"Thank You" Meat and Cheese Gift Box
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“Thank You” Meat and Cheese Gift Box

Harry & David

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Thank You White Wine Gift Box
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Thank You White Wine Gift Box

Harry & David

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67 Reviews

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Deluxe Tower of Chocolates® Gift
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Deluxe Tower of Chocolates® Gift

Harry & David

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309 Reviews

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Gourmet Brownie Assortment
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Gourmet Brownie Assortment

Harry & David

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360 Reviews

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Deluxe Gourmet Gift Basket
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Deluxe Gourmet Gift Basket

Harry & David

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242 Reviews

available to ship september 01 2025

"You Rock" Fruit and Sweets Gift Basket
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“You Rock” Fruit and Sweets Gift Basket

Harry & David

Full StarFull StarFull StarFull StarFull Star1 Review

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Thank You Cookie Gift Basket
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Thank You Cookie Gift Basket

Harry & David

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70 Reviews

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"So Very Thankful" Succulents
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“So Very Thankful” Succulents

Harry & David

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Thank You Moose Munch® Premium Popcorn Tin
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Thank You Moose Munch® Premium Popcorn Tin

Harry & David

Full StarFull StarFull StarFull StarFull Star19 Reviews

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Thank You Truffle Gift Box
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Thank You Truffle Gift Box

Harry & David

Full StarFull StarFull StarFull StarFull Star24 Reviews

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Floral Embrace™
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Floral Embrace™

1-800-Flowers

Fields of Europe® for Fall
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Fields of Europe® for Fall

1-800-Flowers

Harvest Glow™ Bouquet
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Harvest Glow™ Bouquet

1-800-Flowers

Wonderful Wishes Bouquet™
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Wonderful Wishes Bouquet™

1-800-Flowers

November Sun Lily Bouquet™
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November Sun Lily Bouquet™

1-800-Flowers

Our Favorite Fall Tulips™
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Our Favorite Fall Tulips™

1-800-Flowers

Happy Gerbera Daisies, 12-24 Stems
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Happy Gerbera Daisies, 12-24 Stems

1-800-Flowers

Elegant Orchid
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Elegant Orchid

1-800-Flowers

Money Tree
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Money Tree

1-800-Flowers

Sweet Succulent Garden
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Sweet Succulent Garden

1-800-Flowers

Personalized Message in a Bottle® Just Because
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Personalized Message in a Bottle® Just Because

1-800-Flowers

Butterfly Snow Globe by CoolSnowGlobes
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Butterfly Snow Globe by CoolSnowGlobes

1-800-Flowers

Happiness Blooms Shadow Box and Candle Gift Set
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Happiness Blooms Shadow Box and Candle Gift Set

1-800-Flowers

Sweet & Delicious™
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Sweet & Delicious™

Fruit Bouquets

Delightful Daisy Treat™
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Delightful Daisy Treat™

Fruit Bouquets

Your Best Smile Bouquet®
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Your Best Smile Bouquet®

Fruit Bouquets

Rainbow Delight ™ Bouquet
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Rainbow Delight ™ Bouquet

Fruit Bouquets

Gourmet Drizzled Strawberries™
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Gourmet Drizzled Strawberries™

Shari's Berries

Gourmet Dipped Fancy Strawberries
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Gourmet Dipped Fancy Strawberries

Shari's Berries

Lavender Garden & Drizzled Strawberries
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Lavender Garden & Drizzled Strawberries

Shari's Berries

Cherished Blooms & Drizzled Strawberries
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Cherished Blooms & Drizzled Strawberries

Shari's Berries

Caramel Sea Salt Artisan Belgian Chocolate Berries
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Caramel Sea Salt Artisan Belgian Chocolate Berries

Shari's Berries

Artisan Belgian Milk & Dark Chocolate Strawberries
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Artisan Belgian Milk & Dark Chocolate Strawberries

Shari's Berries

Signature Bundt Cake Assortment™ with Gourmet Drizzled Strawberries
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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
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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
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Inspiring Message Engraved Navigator Compass

Personalization Mall

Executive Tan Leather Personalized Portfolio
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Executive Tan Leather Personalized Portfolio

Personalization Mall

Initially Yours Personalized Fleece Blanket
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Initially Yours Personalized Fleece Blanket

Personalization Mall

Signature Style Personalized Coffee Mug
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Signature Style Personalized Coffee Mug

Personalization Mall

Black Stylus Personalized Ball-Point Pen
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Black Stylus Personalized Ball-Point Pen

Personalization Mall

Signature Series Personalized Full Pad Portfolio
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Signature Series Personalized Full Pad Portfolio

Personalization Mall

Thankful For Personalized Farmhouse Candle Jar
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Thankful For Personalized Farmhouse Candle Jar

Personalization Mall

Professional Laurels Personalized LED Nameplate
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Professional Laurels Personalized LED Nameplate

Personalization Mall

Professional Monogram Personalized Marble Desk Clock
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Professional Monogram Personalized Marble Desk Clock

Personalization Mall

Personalized Sand-Filled Hourglass
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Personalized Sand-Filled Hourglass

Personalization Mall

The Boss Engraved Marble Keepsake
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The Boss Engraved Marble Keepsake

Personalization Mall

Best Boss Ever Personalized Printed Star Award
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Best Boss Ever Personalized Printed Star Award

Personalization Mall

Lavish Last Name Engraved Bamboo Charging Valet Tray
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Lavish Last Name Engraved Bamboo Charging Valet Tray

Personalization Mall

Namely Yours Personalized Men's Leatherette Writing Journal
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Namely Yours Personalized Men’s Leatherette Writing Journal

Personalization Mall

Modern Initials Engraved Marble Name Plate
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Modern Initials Engraved Marble Name Plate

Personalization Mall

Executive Personalized Alderwood Pen Set
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Executive Personalized Alderwood Pen Set

Personalization Mall

Lucca & Sons™ Sausage & Cheese Gift Box
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Lucca & Sons™ Sausage & Cheese Gift Box

1-800-Baskets

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Deluxe Thank You Occasion Gift Basket
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Deluxe Thank You Occasion Gift Basket

Harry & David

Full StarFull StarFull StarFull StarFull Star2 Reviews

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Grand Thank You Occasion Gift Basket
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Grand Thank You Occasion Gift Basket

Harry & David

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Supreme Thank You Occasion Gift Basket
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Supreme Thank You Occasion Gift Basket

Harry & David

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Engraved Black Small Book Clock and Keepsake
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Engraved Black Small Book Clock and Keepsake

Things Remembered

Engraved Black Vegan Leather Padfolio and Pen Set
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Engraved Black Vegan Leather Padfolio and Pen Set

Things Remembered

Engraved Bulova Ebony Crystal Recognition Clock
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Engraved Bulova Ebony Crystal Recognition Clock

Things Remembered

Etched Corkcicle Square Cigar Glass
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Etched Corkcicle Square Cigar Glass

Things Remembered

Engraved Waterford Lismore Essence Highball Pair
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Engraved Waterford Lismore Essence Highball Pair

Things Remembered

Engraved Spinning Clock and Pen Stand
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Engraved Spinning Clock and Pen Stand

Things Remembered

Engraved White Marble Card Holder
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Engraved White Marble Card Holder

Things Remembered

Engraved Gloss Mahogany-Finish Gold Business Card Holder
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Engraved Gloss Mahogany-Finish Gold Business Card Holder

Things Remembered

Engraved Professional Tan Leather Portfolio
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Engraved Professional Tan Leather Portfolio

Things Remembered

Engraved Lenox Gold Monogram Bar Set
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Engraved Lenox Gold Monogram Bar Set

Things Remembered

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

Things Remembered

Engraved Lenox "Tuscany" Monogram Cocktail Shaker Set
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Engraved Lenox “Tuscany” Monogram Cocktail Shaker Set

Things Remembered

Engraved Black Hourglass Timer
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Engraved Black Hourglass Timer

Things Remembered

Explore Wild Sampler - Thank You Gift
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Explore Wild Sampler - Thank You Gift

Vital Choice

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Wild Salmon Sampler - Thank You Gift
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Wild Salmon Sampler - Thank You Gift

Vital Choice

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MSC Wild Alaskan Sockeye Salmon - Thank You Gift
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MSC Wild Alaskan Sockeye Salmon - Thank You Gift

Vital Choice

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MSC Wild Alaskan Sockeye & Halibut Duo
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MSC Wild Alaskan Sockeye & Halibut Duo

Vital Choice

Full StarFull StarFull StarFull StarFull Star397 Reviews

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

Vital Choice

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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.