2026 Spring Conference and Retreat

WBSA's exciting 2026 Spring Conference and Retreat will be held from Tuesday, April 28th to Friday, May 1st. This year's theme, Brewing Connections: Pouring into People, Purpose, and Practice is perfectly suited for our iconic host city of Portland, Oregon. Spend some time refilling your cup in Portland while honing your enrollment management skills, building connections with other admission professionals, and enjoy new and exciting perspectives on our profession.

Registration is open now. Click HERE to join us!

Conference Schedule

Tuesday, April 28

Wednesday, April 29

8:00 AM - 9:00 AM
Kimpton RiverPlace Hotel - Hawthorne Room
Breakfast

9:00 AM - 9:15 AM
Kimpton RiverPlace Hotel - Hawthorne Room
WBSA Board Opening Remarks

9:15 AM - 10:15 AM
Kimpton RiverPlace Hotel - Hawthorne Room
Workshop 1: "Yes, And" Admissions: Improv Skills for Enrollment Professionals
Miranda Anapol and Willow McCormick

Admissions work is an unscripted art. This interactive session uses improv games to help enrollment professionals strengthen listening, presence, and connection. Participants will engage in fast-paced exercises designed to help you think on your feet and build the authentic communication skills needed to make students and families feel seen, welcomed and included. This session will stock your "back pocket" with the tools to navigate important conversations, and build a more empathetic, connected school community.

10:15 AM - 10:30 AM
Kimpton RiverPlace Hotel - Hawthorne Room
Break

10:30 AM - 11:30 AM
Kimpton RiverPlace Hotel - Hawthorne Room
Workshop 2: The Enrollment Puzzle: Market or Marketing?
Dana Nelson Isaacs

In today's competitive landscape, schools often face challenges in enrollment and retention, but determining whether the issue lies in the market itself or in your marketing strategy can be tricky. This is especially true in boarding schools, where the "market" is the entire world. In this session, you'll learn how to identify the root cause of your problem by leveraging a variety of research tools, including market analysis, competitor benchmarking, and internal surveys. Once you've diagnosed the issue, we’ll explore actionable solutions tailored to your specific situation. Whether you need to adjust your marketing message or pivot to a new market strategy, you'll leave with practical insights and strategies to move your school forward. This will be an interactive session!

11:30 AM - 1:00 PM
Kimpton RiverPlace Hotel - Hawthorne Room
Lunch, Raffles, and Giveaways

1:00 PM - 2:00 PM
Kimpton RiverPlace Hotel - Hawthorne Room
Workshop 3: Before You Pour for Yourself: Brewing Balance in Admission
Sarah Garcia

Admission work often pulls professionals in multiple directions at once: travel, evening events, family needs, and peak season demands, creating stress when everything feels like a priority. This session reframes work life balance as a "work work" challenge, asking participants to look beyond individual boundaries and instead examine how the structure of the work itself supports or undermines balance.

Through admission specific examples such as redesigned summer hours, flexible interview schedules, clear expectations while on the road, and intentional workload sharing, participants will explore how thoughtful structures allow teams to be successful without burning out. The session emphasizes that sustainable balance is not a one-time fix, but an ongoing practice shaped by leadership choices, team norms, and shared responsibility.

Participants will reflect on moments when grace was extended to them, consider how to pay that forward to colleagues and early career professionals, and leave with one actionable change they can implement or advocate for to rebalance work in a way that supports both people and purpose.

2:15 PM - 3:15 PM
Kimpton RiverPlace Hotel - Hawthorne Room
Workshop 4: The Perfect Blend: When Boarding Schools and Access Programs Work Together
Andy Hoge

This session explores the power of partnerships between education access organizations and private boarding schools in expanding opportunities for talented students from low-income communities. Drawing on years of experience working with students and families navigating independent school admissions, the presentation will highlight the why, how, and purpose behind these partnerships. Attendees will gain insight into the student journey, from discovery and application to transition and persistence on campus, while also examining the challenges access programs face, including funding constraints, family trust, and campus readiness. The session will include opportunities for discussion and interaction, and attendees will leave with concrete ideas for building stronger, more effective partnerships that expand access and belonging.

3:15 PM - 4:00 PM
Kimpton RiverPlace Hotel - Hawthorne Room
Roundtable Discussion: AI, Travel, Visas, Early Decision

4:00 PM - 4:30 PM
Kimpton RiverPlace Hotel - Hawthorne Room
Presentation: WBSA Present and Future

The WBSA Steering Committee will discuss the present and exciting future of the Western Boarding Schools Association.

5:00 PM
Join us to relax and unwind at Pine Street Market!

Thursday, April 30

8:00 AM - 9:00 AM
Breakfast On Your Own

9:00 AM
Kimpton RiverPlace Hotel
Depart for member school Oregon Episcopal School. Transportation will be provided.

9:30 AM - 10:45 AM
Oregon Episcopal School
Welcome and campus tour of OES.

10:45 AM - 12:00PM
OES Faculty
Workshop 5: Sustainable Approaches to Strategic Enrollment Management
Tom Shepperd

In today’s climate of economic uncertainty, shifting global dynamics, and increasingly skeptical millennial parents, boarding schools cannot rely on tradition or reputation alone to sustain enrollment. Families are no longer simply choosing schools. They are making high-stakes investments, searching for value, and asking sharper questions about return, outcomes, and long-term value. For many boarding schools, the challenge is especially acute. Limited scale requires greater clarity. In uncertain times, enrollment growth does not come from doing more marketing. It comes from brewing stronger connections between mission, program design, student outcomes, and strategic decision-making. This session will explore how enrollment professionals can lead their schools toward a more integrated and sustainable approach to Strategic Enrollment Management (SEM), one that positions them not just as recruiters, but as institutional strategists. Grounded in real-world examples from small and mid-sized boarding schools, this session will be both aspirational and actionable, offering language, frameworks, and strategies that participants can immediately apply in their schools.

In the spirit of the conference theme, “Brewing Connections,” we will explore how the schools that will thrive are those that intentionally connect:

● Mission to market demand
● Program design to measurable outcomes
● Financial strategy to enrollment decisions
● And enrollment professionals to institutional leadership

12:00 PM - 1:00 PM
OES
Lunch (provided by Oregon Episcopal School)

1:15 PM - 2:15 PM
OES
Workshop 6: Breaking the Gatekeeper: Moving from "Fit" to Alignment

When we say a candidate isn't a "good fit," what are we actually protecting? This interactive session deconstructs the unspoken shorthand that often acts as a barrier to equity. We will move beyond "social comfort" to build a practical toolkit for mission-aligned decision-making. Through real-time polling and case studies, you will learn to conduct a "fit" audit to identify cultural bias, identify replacement phrases for more inclusive advocacy, and gain the strategies needed to reset committee conversations in real-time. Join us to move past gatekeeping language and return to campus with a concrete action plan for your next selection cycle.

2:30 PM - 3:45 PM
OES
Workshop 7: Help! I Make Too Much Money! Exploring the Middle Class Squeeze and Financial Aid Strategy
Drew Cocco

It's no secret that tuition cost is one of the biggest factors families consider when deciding whether to enroll their children in your school. Tuition rates continue to rise and with it, the average income of families who are applying (and qualifying!) for financial aid. In response, schools have needed to stretch their financial aid dollars over a wider spectrum of financial landscapes is leading to a barbell effect in which the middle of the socioeconomic spectrum begins to thin out. In this session, we'll examine data trends around income and financial aid to dig below the surface and uncover the various factors leading to the "Middle Class Squeeze" and strategies for your financial aid practice that can help alleviate the accompanying challenges.

4:00 PM
OES
Depart for Reception

4:30 PM - 6:30 PM
Amaterra Winery
Reception

Friday, May 1

8:00 AM
Kimpton RiverPlace Hotel
Breakfast, Departures

9:00 AM
Kimpton RiverPlace Hotel
Optional visit to member school Delphian

For those interested in extending their time in Portland, we are pleased to offer an optional campus visit to Delphian School on Friday, May 1.

The day will include a morning departure from Portland, a visit to campus with a welcome from school leadership, student-led tour, and lunch in the dining hall. Following the visit, there will be an optional stop in nearby McMinnville for a casual wine tasting at a location owned by a family whose son attends Delphian, and time to explore the historic downtown (recognized as one of the nation's best downtowns by USA Today, Sunset Magazine, and Parade Magazine) before returning toward Portland. Please use the following form to RSVP:

https://tinyurl.com/mse22xtw

Speakers

Miranda Anapol

Miranda Anapol is the Admissions Assistant and Marketing Coordinator at Oregon Episcopal School and a veteran of the Portland improv scene. With over 12 years of experience, she has trained and performed at CSZ Portland and Curious Comedy Theater, where she currently performs and facilitates workshops. Miranda is passionate about bringing improv techniques into professional spaces to help teams build confidence, deepen active listening, and collaborate more creatively.

Willow McCormick

Willow McCormick is the Assistant Director for Equity & Inclusion at Oregon Episcopal School and a longtime ensemble member at Curious Comedy Theater. A frequent performer at Kickstand Comedy, Willow is an improviser, sketch comic, actor, and clown. She is dedicated to using performance and the "yes, and" ethos to build empathetic, inclusive communities both on and off the stage.

Dana Nelson Issacs

Dana Nelson-Isaacs brings more than 25 years of experience helping schools thrive, partnering with admission teams, heads, boards, and faculty to strengthen enrollment strategy, communications, and community engagement. Known for her thoughtful insight and candid, collaborative style, she works across all levels of school leadership to solve complex challenges with clarity and heart.

Dana’s professional journey spans a wide range of institutions, including grades K-12, boarding and day, single-gender and all-gender, and she held key roles in enrollment and marketing before launching her consulting practice in 2013. Today, she is a trusted expert in market research, enrollment feasibility, and strategic enrollment management.

A dynamic speaker and facilitator, Dana leads workshops and speaks regularly at regional and national conferences. She facilitates The Assembly, a small group mastermind for school leaders, and offers one-on-one and team-based executive coaching.

Dana recently concluded a decade-long role as coordinator of the Bay Area Directors of Admission consortium, leading professional development and strategic collaboration for over 100 schools. She serves on the advisory board of the MarCom Society, judges the annual Brilliance Awards, and is a trustee at a K–8 independent school.
Dana holds a BA in Psychology and an MS in Counseling Psychology. She lives in Northern California with her husband, a high school Physics teacher, and their teenage daughter who literally and figuratively dances through life.

Drew Cocco

Drew is the Vice President of Client Experience at Clarity, and focuses on ensuring that school users have the training, resources, and support they need to make the most of Clarity's Financial Aid, Contracts, and Billing software products. Before joining Clarity, Drew spent the first 14 years of his career in independent schools as a Teacher, Coach, and Director of Enrollment/Financial Aid. A spreadsheet nerd at heart, he regularly publishes and presents on how to use data to optimize enrollment and financial aid strategies. Based outside of Philadelphia with his wife and three children, he enjoys fishing, carpentry, and playing music in his spare time.

Andy Hoge

Andy Hoge is an education consultant and former nonprofit leader with more than 30 years of experience in education. For 25 years, he worked in the education access nonprofit sector, partnering with independent schools, colleges, and community organizations to expand opportunities for talented students from low-income communities. Throughout his career, Andy has guided thousands of students and families through the independent school and college admissions processes while building partnerships with schools committed to increasing access and opportunity. His work has focused on helping institutions better understand and support students from nontraditional backgrounds as they transition into new academic environments. Andy continues to work with families and schools as an education consultant, helping students identify and pursue educational pathways that align with their goals, strengths, and potential.

Sarah Garcia

Sarah has worked in boarding school admission at Webb for the past ten years. Earlier in her career, she worked in college admissions recruiting international and out-of-state students, beginning that work when her twins were just one year old. She first attended a boarding school in England at age 12, inspired by a beloved boarding school book series and the promise of sneaking out of bed for midnight feasts. There she learned that the best communities balance high expectations with just enough room for a well-timed prank, a spirit she carries into her adult life in boarding school. During the pandemic admission cycle, while working from home with two seven-year-olds, she developed a more intentional workflow that kept her in control, balanced the team’s increased demands, and better supported families navigating the admissions process. Outside of work, she can be found running with her dog Joy, roughhousing with her kids, or refereeing soccer on the local fields.

Tom Sheppard

Tom Sheppard is the founder of 20 More Students, an enrollment strategy firm that partners with independent schools to strengthen enrollment through clear strategy, aligned leadership, operational excellence, and mission-driven storytelling. Over a 34-year career in independent schools, Tom served as a Head of School, a senior enrollment leader, and most meaningfully, a teacher, giving him a rare perspective on how enrollment strategy connects to institutional leadership. In 2025, Tom founded 20 More Students to pursue his passion for private school enrollment full time.

Tom previously led enrollment at Trinity-Pawling School (NY), Stevenson School (CA), and The Lawrenceville School (NJ), where he built teams, reimagined recruitment strategies, and improved yield, diversity, and revenue outcomes. He later served as Head of School or Interim Head at St. Andrew’s Episcopal School (MS), Chadwick School (CA), and University Liggett School (MA), leading strategic planning, innovation initiatives, and major institutional change.

Dyan Watson

Dr. Dyan Watson is the Director of Equity and Inclusion at Oregon Episcopal School. A Harvard Graduate School of Education alumna and leading scholar on race and teaching, Dyan’s focus has remained constant: deconstructing the barriers that prevent students from being seen and heard. She is the co-editor of Teaching for Black Lives, Rhythm and Resistance, and Rethinking Elementary Education, and the author of “Norming Suburban: How Teachers Talk About Race Without Using Race Words” and “A Letter From a Black Mom to Her Son,” among other works exploring the intersection of race and education.

Venue

This year's conference and retreat will be held at the RiverPlace Hotel in Portland. With gorgeous views of the Willamette River, this cozy classic venue is the perfect place to hone your enrollment management skills and meet other dedicated admissions professionals.

When not in workshops and panels, you'll be able to enjoy the extraordinary culture of the city of Portland!

The hotel also hosts a happy hour from 4:00PM - 5:00PM at its Portland Waterfront Restaurant. Enjoy a free drink to unwind.

We are grateful to Oregon Episcopal School for being our host school this year!

Welcome to the City of Roses: Your Portland Field Guide

OES thrilled to host the WBSA Spring Conference at the Kimpton Riverplace, nestled right on the banks of the Willamette River (Willamette... rhymes with "damn-it"). Portland in late April is a special kind of magic: the city is in "peak bloom," the food carts are buzzing, and the coffee is, quite literally, the best in the world.

Whether you have twenty minutes or an entire afternoon to explore, we've curated a list of very "Portland" experiences to help you find your new favorite book, the perfect vintage jacket, or the best bowl of noodles you've ever had. No umbrellas required (real Oregonians just use hoods), but a sense of curiosity is mandatory. Oh, and did I forget to mention shopping? No sales tax in Oregon...

Right Outside Your Door (0–5 Minute Walk)

The Waterfront Walk: You are directly on the Tom McCall Waterfront Park. Turn left (North) for a scenic stroll toward the city's famous bridges, or right (South) to watch the boats in the marina.
Dough Zone Dumpling House: Right next to the hotel. Their Xiao Long Bao (soup dumplings) and Q-bao are legendary and surprisingly affordable.
Little River Café: Your immediate go-to for a quick morning coffee and a massive breakfast burrito.
Il Terrazzo: Perfect for a quiet, upscale Italian dinner without leaving the property block.
Luc Lac Vietnamese Kitchen: Fast, vibrant, and serves the best Pho and crispy rolls in the city. Great for a high-energy group dinner.

Within Walking Distance (10-15 Minute Walk)

These are easily reachable on foot through the scenic South Park Blocks or along the river.

Powell’s City of Books: A slightly longer 15-minute walk (or a 5-minute Uber). It’s an entire city block of books. Pro-Tip: Head to the Gold Room on the top floor to see the Rare Book Room.
Fried Egg I’m In Love (Pioneer Courthouse Square): You cannot leave Portland without trying a "Yolko Ono" or an "Egg Zeppelin." Their yellow food cart is located in Pioneer Courthouse Square (often called "Portland’s Living Room"). It’s an iconic 15-minute walk from the hotel and the ultimate "people-watching" breakfast spot. The owner may be one of Chris Anderson's friends from college. If you have time, their restaurants on the East Side are wonderful and serve delightful morning beverages.
The PSU Food Cart Pod (SW 4th & Hall): About a 10-minute walk. This is where the locals eat. Look for "The Whole Bowl" and ask for the "Tali Sauce"—it is the unofficial healthy lunch of Portland.
Portland Saturday Market (May 2): A 15-minute walk north along the riverfront trail. It’s the nation's largest open-air arts and crafts market—perfect for finding a unique PNW gift before you head home.

A Short Ride Away (10–15 Minute Uber/Lyft)

These are "must-sees" that require a quick hop across town or up the hill.

Portland Japanese Garden & International Rose Test Garden: Located at the top of Washington Park. While the roses are just starting, the Japanese Garden is world-class. The view of Mt. Hood from the Pavilion is the best in the city.
Crystal Springs Rhododendron Garden: Late April is peak bloom. This 9-acre floral oasis is a 10-minute ride across the river and feels like stepping into a fairy tale.
Thrifting in the Hawthorne District: Cross the bridge to House of Vintage for a massive collective of 60+ vendors. No sales tax makes this a dangerous (but fun) place for your wallet.

The "Day Tripper" (30–60 Minutes)

Multnomah Falls: The spring snowmelt means the falls are at their most powerful. It’s a 30-minute drive into the stunning Columbia River Gorge.
Willamette Valley Wine Country: 45 minutes south for world-class Pinot Noir, and some surprising (and wonderful) whites. Many wineries hold "Spring Release" events during the final days of the conference (May 1-2). Chris Anderson will gladly volunteer suggestions.

Your Trip to Portland

Attendees taking air travel should expect to fly into Portland International Airport (PDX). The hotel is roughly a 20-minute trip by rideshare service. Portland also has a robust public transportation system.