Who Is Eryn-Ashlei Bailey?
Eryn-Ashlei Bailey is the Founder and CEO of Petcha Can!, a boutique in-home pet, plant, and house-sitting service designed for executives and globally mobile families. With a career spanning financial services, institutional investing, and executive leadership, Bailey brings strategic rigor and relationship-driven insight to every venture she builds. A Wharton MBA and former Chief of Staff, she is known for anticipating needs before they are voiced and for designing trust as a core business principle, leaving people, systems, and communities stronger than she found them.
There are careers built on momentum, and then there are careers built on intention. Eryn-Ashlei Bailey belongs firmly in the latter category. Her professional journey is not defined by abrupt reinvention, but by disciplined evolution, an arc shaped by strategic rigor, relational intelligence, and a deeply held belief that trust, when thoughtfully designed, becomes a competitive advantage.
From institutional finance and executive leadership to founding a high-touch service company for globally mobile professionals, Bailey’s career reflects a consistent throughline: an ability to anticipate needs before they are articulated, and to build systems that allow people to operate with confidence and peace of mind.
Learning How Systems and People Work
Bailey’s professional instincts were shaped early by her interest in human behavior and communication. She earned a Bachelor of Arts in Psychology from St. John’s University, developing a lens that would later distinguish her in high-stakes, people-driven environments. Understanding how individuals process information, manage uncertainty, and build trust became a quiet but enduring advantage.
Her career began in financial services at Vanguard, where precision, accountability, and fiduciary responsibility are foundational. Starting in entry-level roles, Bailey immersed herself in the inner workings of the organization, learning not only investment concepts, but how strong operations, clear communication, and inclusive leadership drive results. She progressed rapidly, earning recognition for exceeding performance benchmarks, mentoring peers, and creating space for collaborative dialogue across teams.
These early years reinforced a pattern that would define her career: Bailey was often among the first to spot opportunities for improvement and to build bridges across functions to close gaps others overlooked.
From Institutional Capital to Executive Leadership
Bailey’s next chapter brought her into institutional investing, where she joined the City of Philadelphia’s Board of Pensions and Retirement. There, she worked on infrastructure and private equity investments, contributing to the oversight and advancement of a multibillion-dollar public portfolio. Her responsibilities included streamlining investment analysis, restructuring co-investment vehicles for improved risk-adjusted returns, and presenting allocation recommendations, often $25 million or more, to Board subcommittees.
It was during this period, while immersed in institutional capital and long-term value creation, that Bailey launched The Azusa Alliance, an independent consulting practice founded during her MBA program. Azusa Alliance focused on projects at the intersection of strategy, governance, and innovation, including increasing the representation of women of color on corporate boards, assessing institutional loan fund growth projections, and exploring the implications of artificial intelligence and machine learning in emerging industries.
Built with discipline and intention, Azusa Alliance operated with an extraordinary ~98% profit margin, demonstrating Bailey’s ability to design lean, high-impact ventures alongside demanding institutional roles.
Bailey earned her MBA from The Wharton School, where she further refined her strategic toolkit and deepened her understanding of organizational leadership. She later completed a Corporate Communication Certificate at Cornell University, formalizing a skill she had long practiced, translating complexity into clarity for diverse stakeholders.
Following business school, Bailey moved into senior strategic roles, serving as Chief of Staff and in communications and operations leadership positions. Working closely with executive teams, she helped align strategy with execution, monitored performance metrics, and ensured that priorities translated into measurable outcomes. These roles placed her at the center of decision-making, reinforcing her belief that the most effective leaders are those who combine vision with operational fluency.
Her commitment to leadership development extended beyond her own roles through her involvement with Chief, a private network designed to support senior women leaders and foster cross-industry exchange at the highest levels.
Designing Trust as a Service Model
Despite professional success across finance and strategy, Bailey identified a gap that felt both personal and systemic. High-performing executives, she observed, often struggled to secure consistent, high-quality care for the most personal parts of their lives, pets, homes, and routines, especially amid unpredictable travel schedules.
In 2024, Bailey founded Petcha Can!, a boutique in-home pet, plant, farm, and house-sitting service designed specifically for executives, internationally mobile families, and clients with complex lives. The company was not a departure from her prior work, but a synthesis of it.
The moment Bailey recognized the venture as a strategic pivot came when clients began requesting her availability before booking travel. She had become an integral part of their planning processes.
“Executives can’t always anticipate or fully articulate what they’ll need,” she explains. “The ground shifts beneath them. My role is to anticipate, communicate clearly, and execute in a way that allows them to focus on everything else.”
Petcha Can! is fully insured, cat and dog first-aid certified, and built around repeatable, high-touch service, not scale at the expense of quality. While still in a growth phase, the company reflects Bailey’s core philosophy: trust is earned through consistency, boundaries, and respect. She does not rush relationships or manufacture familiarity. Instead, she shows up, delivers, and allows trust to compound over time.
Her guiding principle remains central: “I leave people and places better than I found them.” This ethos shapes how she supports contractors, communicates with clients, and extends impact beyond her immediate business through community redistribution and relationship-driven giving.
Her perspective on this evolution, and on redefining entrepreneurship as a strategic extension of executive leadership, was recently explored in a featured podcast conversation on Your Move with Lori & Jett., where Bailey discussed career pivots, anticipation as a leadership skill, and building service-based businesses rooted in credibility and care.
A Legacy of Care, Strategy, and Community
Today, Bailey defines success not by titles or industries, but by alignment.
“I wake up excited to go to work every day,” she says. “I’m working directly with clients and pets, while also setting strategy and monitoring performance. I’m intellectually challenged daily.”
Looking ahead, she is focused on building a legacy grounded in trust, compassion, and community, where clients are not transactions, but long-term partners and advisors. In Bailey’s view, a service company succeeds when relationships endure and systems are designed to absorb uncertainty with grace.
Editorial Note
Eryn-Ashlei Bailey’s journey reminds us that the most durable careers are not defined by industry labels, but by values carried forward with discipline and purpose. Her story invites leaders to ask a deeper question: Where can trust be designed more thoughtfully in your own work—and what becomes possible when it is?
