Our Team
Decades of
Community-Building
Expertise

At Heyday, Josh leads the company’s identification and adoption of new construction technology and spearheads its construction efficiency efforts. He evaluates emerging tools, methods, and delivery systems, then implements them across the portfolio to make each build more efficient and more predictable. Applied at scale, these practices protect schedule and cost while raising the quality of the homes Heyday delivers.  Josh is the last set of eyes on most major decisions at Heyday. His attention runs to both ends of the scale, from a capital decision to a detail on a unit finish, and the standard he applies does not move depending on which one it is.

Prior to founding Heyday, Josh spent 14 years overseeing development projects for Stoneleigh Companies and Orchard Development. Throughout those critical years, which included the downturn in 2008, he participated in all aspects of real estate development: site identification, zoning and entitlement, full-time onsite construction management, and overseeing property management for a diverse national multifamily and retail portfolio. Holding leadership roles in each critical discipline has informed his vision on how a development company can create communities and homes that best serve residents, and thus create value for the company and its investors.

Josh’s unique real estate skillset also includes six years underwriting commercial real estate deals for LaSalle Bank before transitioning into development. His portfolio included construction and acquisition loan facilities primarily for multifamily and for-sale residential properties, as well as for retail and office. The knowledge and relationships gained at LaSalle Bank have been the foundation for everything that has followed.

Josh holds a Bachelor of Business Administration in Real Estate from the University of Wisconsin-Madison.

At Heyday, Ryan has standardized and streamlined how the company evaluates opportunities, building the framework that governs deal review and due diligence on every site. He has also developed strategies for unlocking complex or challenging opportunities. Ryan’s approach is data driven throughout, grounding site selection, underwriting, and diligence in measurable evidence and repeatable process.

Prior to founding Heyday, Ryan spent his career developing a comprehensive skillset in the field of real estate development, overseeing the delivery of Class A multifamily communities throughout the US: conceptualization, market analysis, acquisition, site planning, design, approvals, financing, construction, and asset management.

Over more than two decades Ryan has developed multifamily communities on behalf of Heyday, Stoneleigh Companies, and Albany Partners. His real estate experience spans just over $1B in transaction volume. His development portfolio represents best-in-class assets and significant long-term value for not only his investors, but the communities in which the properties reside. That value has been built by working collaboratively with all stakeholders throughout the development process.

Applying lessons learned from the multidisciplinary nature of the industry, Ryan created Heyday with a precise purpose: to provide innovative multifamily housing options targeting specific renter demographics forecasted to grow over the coming decades.

Ryan holds a Bachelor of Science in Architecture from Georgia Tech, where he also spent a year of graduate study in the City & Regional Planning MS program, and a Master of Business Administration from Rensselaer Polytechnic Institute.

At Heyday, Jennifer owns finance, accounting, tax, treasury, investor reporting, insurance, and contract review, and increasingly the operational infrastructure and organizational design that support a growing portfolio.

A CPA, Jennifer spent 12 years in public accounting at Lipschultz, Levin & Gray across tax, audit, and consulting, the last four as a partner. She then spent eight years as CFO of a real estate developer and general contractor, where she built the accounting team, the processes, and the internal controls from the ground up. Across her career she has closed over $1B in financing and negotiated $600M in joint venture agreements.

Jennifer works through relationships. She stays close to lenders, capital partners, consultants, and her own team, and that proximity is how she sees a need coming and has an answer ready before anyone asks for one.

Jennifer holds a Bachelor of Science in Accounting from Bradley University and completed graduate coursework at Northern Illinois University.

At Heyday, Anthony owns the development period from site identification through groundbreaking. He leads entitlements, diligence, and underwriting, including loan closings. Execution is where he is strongest, keeping municipalities, consultants, lenders, and internal teams moving on the same schedule so sites reach shovels in the ground on time.

Prior to joining Heyday, Anthony spent 11 years at Stoneleigh Companies, where he began his career as a Financial Analyst in 2014 and quickly took on roles as Development Manager, VP of Development, and Senior Vice President. During that time he assisted in the development of Class A multifamily properties, including leading the development of three build-to-rent communities in the Midwest. His experience includes comprehensive due diligence, from site selection through land entitlements, project underwriting, financing, construction management, and disposition.

In addition to his development experience, Anthony managed all facets of the operating company at Stoneleigh Companies and collaborated with partners including investors and managers. His real estate experience includes over $800M of transaction volume.

Anthony holds a Bachelor of Science in Finance from Northern Illinois University.

At Heyday, Dan oversees accounting, financial reporting, and the audit process, along with the close discipline and controls that keep reporting reliable as the portfolio grows.

Dan spent 11 years at Walton Street Capital, a Chicago real estate private equity firm, rising from financial analyst to Controller and then Director of Financial Reporting. In that time he owned fund-level accounting and reporting across a large real estate portfolio, working closely with investors, auditors, and fund administrators. He later served as Senior Vice President at Pearlmark.

Dan began his career at Deloitte, where he spent three years in audit. He holds a Bachelor of Science in Accountancy and a Master of Accounting Science from the University of Illinois at Urbana-Champaign.

At Heyday, Stefanie leads strategic growth and the development of the company’s internal software, bringing a data-first approach to how Heyday finds and evaluates opportunities. The platform she is building is designed to differentiate how the company sources, underwrites, and operates.

Stefanie’s background spans business development, mergers and acquisitions advisory, and growth strategy across technology, legal services, private equity, and sports. She has built and led sales and technology teams backed by venture capital and private equity – with a decade of work inside growth-stage startups and small businesses. Her career has been defined by strategy, innovation and measurable growth. Stefanie’s focus at Heyday has been the same as it’s always been: build the system, then let it run.

Stefanie does her best work at pivotal moments, when the question is not whether to grow but which direction actually pays off. She serves on the board of iCopy.

Stefanie holds a Bachelor of Arts in Psychology and Non-Profit Administration from Grand Valley State University.

At Heyday, Kristina owns the property management relationship, oversees leasing strategy, and ensures every unit meets the Heyday standard. She has been closely involved in the punch list process and in standardizing how units are turned.

Kristina came to asset management from the operating side. She led Heyday Sun Prairie from its lease-up in 2023, then took on senior property management and regional operations roles before joining Heyday directly as Asset Manager in 2026. Earlier in her career she held property and account management positions with Greystar at Hub Madison, TDS Telecommunications, Orosz-Fagen Properties, and Fiduciary Real Estate Development.

Fifteen years of running properties shaped how she approaches asset management, and she knows what each line of an operating statement looks like on the ground. Kristina also invests in the people on both sides of that operation, residents and vendor partners alike, and builds those relationships so both sides come out ahead.

Kristina holds a Bachelor of Business Administration in Marketing from the University of Wisconsin-Milwaukee.

At Heyday, Zach owns the front end of the acquisition pipeline. He sources and screens land across Illinois and Wisconsin, leads pre-entitlement diligence including zoning verification, entitlement feasibility, and impact fee analysis, and builds the deal-level pro formas and investment memos the principals use to make go or no-go decisions.

Zach also builds the internal tooling behind that work, automating parcel discovery, underwriting, and diligence memos so the team can evaluate more sites in less time. He manages outreach to planning directors, community development officials, and brokers, which is how many off-market opportunities reach the pipeline.

Real estate started as a personal interest for Zach and turned into a career. He came to Heyday from Cream City Cyber, where he spent a year and a half in technology and business analysis, leading assessments, implementing systems, and advising leadership on aligning technology with operational goals. That work is where his tooling ability came from.

Zach holds an Associate Degree in Cloud DevOps from Madison Area Technical College.

At Heyday, Zach builds the platform tools each team uses to work efficiently and to standardize its processes. The goal is a development and operating platform that repeats reliably as the portfolio grows.

Before Heyday, Zach spent a decade building and operating companies. He founded Novoselsky Media, which grew from a content shop into a sales automation and lead generation practice. He served as a partner at Alternative Acquisitions, working on ownership transitions for small businesses in overlooked industries, and led sales and growth at a manufacturer in that portfolio with 65 years of history. He also founded BuzzU, an intelligence platform for the college athlete market.

A former Western Michigan University football player, Zach holds a Master of Business Administration from WMU’s Haworth College of Business.

At Heyday, Paige manages administrative functions, accounting support, payables, and insurance coordination, keeping the day-to-day running across a growing set of entities and projects.

Paige came to the role from commercial banking. She served as Assistant Vice President in Commercial Lending at People’s Bank in Connecticut, managing a middle-market loan portfolio and underwriting credit on cash flow, collateral, and guarantor strength, following earlier work as a credit analyst. More recently she spent five years as a financial analyst, building P&L forecasting models, preparing board and investor reporting, and handling monthly close.

Paige holds a Master of Business Administration from the University of Connecticut.