The Hillbrook Benefit

Each year, The Hillbrook Benefit is a memorable and fun evening celebration that supports Hillbrook's Flexible Tuition Program.
Organized by the Hillbrook School Parent Council (HSPC) and the Office of Advancement, the annual Benefit is one of the school's largest community-building events and a critical fundraiser for the Flexible Tuition Program at Hillbrook.  

Thank you in advance for your valuable support of our school!

Key Dates

The Hillbrook Benefit is a community wide celebration and event that supports our Flexible Tuition Program at Hillbrook.

Upcoming Key Dates for the Benefit:
Dates will be posted later this year - please reach out to get involved or ask questions of the Benefit co-chairs Kev Brock, Ellen Dempsey, and Alisa Lewis or Cathy Carlson and Felicity Jimenez-Howard in the office at


All are encouraged to watch the Benefit, participate in the Silent Auction, sign up for Benefit parties, and donate. If you would like to be seated at a table with friend and receive helpful reminders and Auction announcements, please register on the GiveSmart microsite.

This year, we're hosting our virtual Benefit on Stay'In, an interactive platform that will help you enjoy the evening however you'd like: you can sit back, relax, and enjoy on your own; you can also join a table or lounge with friends or your grade level (if you requested a table when you registered on GiveSmart, stay tuned for information about your table grouping on Friday!)

Check out our short FAQ video for a quick walk-through of the Stay'In platform - you'll be all ready to go by Benefit night!
Let's get the party started!


7:15 - 8:00 pm - Benefit Social Hour

Enjoy social time at your virtual table with dinner or something sweet from one of our Hillbrook family businesses! You can also visit our virtual Premium Wine Bar to hear from wine maker and Hillbrook parent Dan Lokteff. Meet him in Lounge 11 at 7:30 pm! Other lounges will also be open for virtual mingling beyond your assigned table group.

8:00 pm - Hillbrook Benefit begins!
Our Live Benefit program is hosted by emcees and Hillbrook parents Mary Hammers and Chris Janssen, along with our Head of School Mark Silver. Program highlights include special performances by our 8th grade students and Lower School music teacher Jamie Piazza, as well as our All-School and 8th-Grade videos.

9:00 pm - on — Benefit Conclusion and Virtual After-Party
Relax and enjoy the evening!


8:00 pm
Silent Auction Closes and Winners Announced

Be sure to check out the Benefit page - has a helpful FAQ section with important links which is helpful reading for new and returning families. There is no cost to attend this year!



Make sure to check out the full list of amazing gifts and experiences in our Silent Auction on the Benefit Microsite by Givesmart. 100% of the net proceeds from the Benefit go towards our Flexible Tuition Program

Silent Auction bidding is open now; bidding closes at 8 pm on Sunday, May 2.

Contact Cathy Carlson or Felicity Jimenez-Howard We look forward to connecting with you!

List of 14 frequently asked questions.

  • Q. What is the Benefit?

    The Benefit is our community celebration benefiting Flexible Tuition at Hillbrook.
    • All net proceeds support the Flexible Tuition Program at Hillbrook; over 28% of our students benefit directly from Flexible Tuition. We know that this is one way to strengthen our school and community.
    • Last year, the Benefit raised over $550,000!
    • The Benefit is attended by current and former Hillbrook parents, grandparents, faculty, staff and their guests. It is an all-school, community-building event.
    • The event includes a Live and Silent Auction, Benefit Parties and activities, and much more!
    • The Benefit is sponsored by the Hillbrook School Parent Council (HSPC).
    • This year’s virtual event is on Saturday, May 1, 2021.
  • Q. How do I make a reservation for this year?  Is there a cost to attend this year?

    • You can make a reservation for this year’s virtual Benefit on the Hillbrook Benefit Microsite by Givesmart, Reservations and virtual table requests will open February 21.
    • There is no cost to attend the event. Given there is no cost to attend we are hoping that everyone will find a way to support this important fundraiser for Flexible Tuition. There are so many ways to give!
  • Q. I can't attend the Benefit but would love to support Hillbrook's Flexible Tuition Program. What can I do?

    We will miss you at the event and thank you for thinking of ways to show your support. There are many ways you can participate including:
    • Volunteer your time before the event (solicitations and more)
    • Donate experiences and items - vacation homes, event tickets, gift certificates, wine, and goods
    • Host or Buy into a Benefit Party - Get creative and host a virtual party - have fun while creating community
    • Purchase items off the Wishlist for class baskets
    • Sponsor the event or give to Stand Up for Students with a 100% tax-deductible donation
    • Bid on Silent Auction items. You do not need to be present to bid; simply Register on the Hillbrook Benefit Microsite by Givesmart, and use your smartphone to donate, bid on Silent Auction items and buy Benefit Parties. The Silent Auction will open in April before the event.
  • Q. What can I donate?

    Top-selling Silent Auction items include:
    • Offer a stay in a vacation home (e.g. beach, ski, golf, adventure, international - all are awesome!)
    • Donate sports, concert, and event tickets
    • Share a tour or experience related to your area of expertise, profession, or hobby
    • Organize a unique experience like a scavenger hunt, cooking/dining with a chef, or behind-the-scenes tour
    • Access to private golf courses, planes, and workspaces
    • Contribute wine, top shelf liquor, restaurant gift certificates, or popular products
    • Airline miles to round out a getaway package
    • We are hoping that any experiences have long expiration dates!
    Host an Auction Party or Experience: The Hillbrook community loves a party. Get creative and have fun. Tickets to these events are popular and sell out quickly. Download last year's Benefit Catalog here for more ideas. 

    To contribute, please fill out the
    Benefit Donation Form , Benefit Party Sponsor Form, or reach out to Benefit co-chairs.
  • Q. What is Stand Up For Students?

    • All guests can raise their paddles to benefit our Flexible Tuition Program at Hillbrook.
    • This opportunity welcomes participants to raise their paddles at various levels, ranging from $100 to over $38,900 - 100% raised goes directly to benefit the Flexible Tuition Program.
    • You can also give to “Stand Up For Students” in the Silent Auction on the Hillbrook Benefit Microsite by GiveSmart or by contacting Cathy Carlson or Felicity Jimenez-Howard.
    • We invite our entire community to join together for this effort in attempting to reach our goal of $300,000.
    • All Stand Up for Students donations are 100% tax-deductible.
    • All Stand Up for Students donations can be corporate matched!
    • All Stand Up for Students donations will be recognized in the Annual Report, unless you prefer to be anonymous.
  • Q. What will the Benefit proceeds be used for?

    Proceeds raised from the Hillbrook Benefit directly support the Flexible Tuition Program. Over 28% of our students directly benefit from the Flexible Tuition Program (Hillbrook allocates over $2.2 million this year), so this event is both meaningful and essential to Hillbrook’s commitment to keeping an economically diverse student body.
  • Q. What is a Benefit Party?

    This year these experiences or parties will be virtual and are imagined and sponsored by our own parents and teachers.
    • Benefit parties are extremely popular with limited spots, so be sure to purchase early!
    • These will be virtual events anytime between May and into the Fall.
    • Parties are available for purchase on the Hillbrook Benefit Microsite by Givesmart (You can view Benefit Parties starting in April 2021.)
  • Q. What are class baskets?

    • Themed baskets are created by the HSPC with contributions from the Hillbrook parent community.
    • View our class basket wish lists by grade, buy direct from Amazon starting in mid-March, and your purchases go directly to Hillbrook School. Read Hillbrook Happenings for details!
    • You are also welcome to purchase items from any grade level’s list or donate any other item that relates to a theme.
    • Drop off donations at the Front Office anytime through Monday April 12th.
  • Q. How can I volunteer?

    We are seeking help with the following:
    • Silent Auction and Benefit Party solicitation volunteers
    • Grade Level Benefit Buddies
    • Develop Amazon wishlists for the class baskets
    • Assemble baskets
    • Write thank you notes at the Thank-a-thon (attend virtually or bring home)
    Reach out to Cathy Carlson, Felicity Jimenez-Howard, or the Benefit co-chairs to volunteer.
  • Q. How do I sponsor the Benefit?

    • Sponsorships are vital to the success of the Benefit.
    • Each year families and businesses sponsor at various levels from $10,000 to $500. 
    • Sponsors will be recognized during the event and in the Benefit Catalog. 
    • Various giving levels include Benefit tickets, recognition on the Benefit Microsite, advertising in our Auction Catalog, and social media highlights.
    • Sponsorship donations may be tax-deductible over the amount of the cost of advertising, food, wine, etc…
    • Sponsors get awesome benefits outlined here - Family and Business Sponsorship Benefits.

    Use the Family Sponsorship and Student Advertising Form and email to or use sponsor when you buy your tickets on the Hillbrook Benefit Microsite by GiveSmart.
  • Q. How do I advertise in the Benefit Catalog?

    • Your business or an associated business can purchase an advertisement in our Auction Catalog.
    • Families (and particularly those in 8th grade) have the opportunity to purchase a student advertisement in our Auction Catalog. Download the Family Sponsorship and Student Advertising Form from this page.
    • Here are some examples of Business and Student Advertisements
    • Our Auction Catalog gains visibility with over 500 families in our community.
  • Q. What can I expect on the night of the virtual Benefit?

    • Table seating - Our new platform will give us the opportunity to have a virtual ballroom where if you want to be assigned to a table or group of tables with friends and others in your grade level you can. We will help facilitate these table groups. 
    •  Silent Auction - Bidding on Silent Auction starts on Sunday, April 25 on the Hillbrook Microsite by GiveSmart and ends at 8pm on Sunday, May 2nd the day after the Benefit. There is a huge variety of items and price points - something for everyone, so be sure to take time to review the catalog.
    • Live Auction - We will have premier items this year available through the Silent Auction. Some may be highlighted during the live event.  Bidding will take place on the Hillbrook Microsite by GiveSmart.
    • Our virtual tables will be generally organized by grade. If you have a table request, fill in the seating request field when making a reservation; we do our best to accommodate.
    • Premium Wine Bar - A beloved Hillbrook tradition, these wines are donated from the private collections of Hillbrook families. Premium wine will be available for purchase on the Hillbrook Microsite by GiveSmart up to Monday, April 26. You can pick up the wine at school or it will be delivered to your home. 
    • We will also celebrate the graduating 8th grade class. Hillbrook’s 8th grade class will be part of the Benefit before heading off to their own virtual celebration!

    Schedule - We have not finalized the schedule yet. However, the tentative schedule is, as follows: 6:30pm socializing and fun table activities; 7:00pm the Benefit Show begins, including the All-school video, Keynote Speaker to be announced, and Stand Up for Students; 8:00pm Benefit After Party
  • Q. What do I need to know about the Hillbrook Benefit Microsite by GiveSmart?

    • To enable mobile bidding, respond to the welcome text you receive from “52182” with your first and last name.
    • Once you register with GiveSmart, you can sponsor the event and bid on Silent Auction items (after Sunday, April 25 at 6PM and before Sunday, May 2 at 8PM), and sign up for Benefit Parties (after Sunday, April 25 at 6PM). After registering, you will be sent a unique URL via text message and email.
    • This URL is unique to you and will provide you with the following features:
      • View detailed item information, current bid status, and what you’ve won
      • Bid anytime, anywhere during the Silent Auction (includes setting max bids)
      • Receive alerts when you’ve been outbid
      • Personalize an item ‘watch list’ for you favorite listing
  • Q. I still have questions. What can I do?

    Please reach out to Cathy Carlson or Felicity Jimenez-Howard. You can also email and reach the entire Benefit team, including Benefit Co-chairs Kev Brock, Ellen Dempsey, and Alisa Lewis. Looking forward to seeing you all on Benefit night!
An independent Junior Kindergarten -8th grade school in Los Gatos since 1935

300 Marchmont Drive
Los Gatos, CA 95032
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