Shayna Guigliano is an accomplished sales executive, go-to-market strategist, and technology leader with more than two decades of professional experience helping organizations accelerate growth, build exceptional teams, and navigate transformational change. Throughout her career, she has consistently demonstrated an ability to scale revenue organizations, develop future leaders, and translate emerging technologies into practical business solutions. With deep expertise in SaaS, artificial intelligence, property technology, and customer-centric sales strategy, Shayna has earned a reputation as a trusted executive who combines operational excellence with an unwavering commitment to people development.
Currently serving as Head of Sales at Vendoroo, Shayna leads the company’s go-to-market strategy for an innovative agentic AI platform revolutionizing property maintenance operations. Joining the organization during an exciting period of growth, she was tasked with building the sales organization from the ground up while establishing scalable systems capable of supporting long-term expansion. Under her leadership, Vendoroo achieved approximately three times annual recurring revenue growth during its first year, successfully launched high-performing sales and SDR teams, and developed a scalable outbound sales engine that now drives the majority of the company’s new business pipeline.
One of Shayna’s greatest strengths lies in her ability to introduce emerging technologies into traditional industries by focusing on customer outcomes rather than product features. As artificial intelligence continues reshaping business operations, she has successfully repositioned sales conversations around operational efficiency, workflow optimization, and customer trust. Her leadership has helped Vendoroo establish itself as a credible AI partner within the property management industry while developing strategic relationships with leading property management software providers and influential organizations such as NARPM, RPM, and other respected industry networks.
In addition to her executive leadership responsibilities, Shayna is the Founder and Principal of SEG Consulting, where she advises early-stage SaaS and AI companies on go-to-market strategy, sales organization design, customer acquisition, and leadership development. Working directly with founders and CEOs, she helps organizations establish scalable revenue operations, refine customer segmentation, hire high-performing sales teams, and create disciplined growth strategies that position companies for long-term success. Her advisory work reflects both her entrepreneurial mindset and her passion for helping innovative businesses navigate the complexities of rapid growth.
Prior to Vendoroo, Shayna spent more than eleven years with AppFolio, one of the property technology industry’s most successful software companies. Joining the organization before its IPO, she played an instrumental role in helping the company grow from approximately $26.5 million in annual revenue to more than $800 million. Throughout her tenure, she steadily advanced through increasingly senior leadership positions, culminating as Vice President of Sales where she led the company’s largest sales segment across multiple offices and was responsible for delivering approximately half of all new residential annual recurring revenue. Her teams consistently achieved industry-leading win rates, expanded outbound revenue generation, strengthened competitive positioning, and maintained exceptional employee engagement scores.
Earlier in her career, Shayna built a strong foundation in enterprise technology sales while serving in multiple leadership positions at Citrix. As both an individual contributor and sales manager, she consistently exceeded performance expectations, earned multiple President’s Club recognitions, and developed future sales leaders through coaching, mentoring, and professional development. Her leadership philosophy emphasizes accountability, collaboration, continuous learning, and empowering individuals to reach their highest potential. Across multiple organizations, she has helped promote more than one hundred employees into advanced leadership and sales positions, reflecting her long-standing commitment to developing people alongside business performance.
Shayna’s leadership extends well beyond revenue generation. She is recognized for creating highly engaged workplace cultures where employees thrive, innovation flourishes, and customer success remains the central focus. Her teams have consistently produced outstanding employee engagement scores while maintaining strong retention and internal promotion rates. She believes sustainable business growth begins with investing in people, fostering transparent communication, and creating an environment where accountability and support exist in equal measure. This philosophy has become one of the defining characteristics of her executive leadership style.
Outside of her executive responsibilities, Shayna remains deeply engaged in her professional community through her involvement with the Chamber of Commerce and industry organizations including PropTech associations, NARPM, and PMI. She regularly participates in local industry speaking engagements where she shares practical insights on technology adoption, sales leadership, customer engagement, and business growth. Beyond her professional achievements, she enjoys volleyball, coaching, and mentoring emerging professionals, reflecting her genuine passion for helping others achieve success both personally and professionally.
Shayna is actively pursuing board service because she believes her experience building organizations, partnering with executive leadership, and scaling high-growth technology companies can provide meaningful strategic value to organizations facing growth, transformation, or innovation initiatives. Having worked alongside CEOs throughout much of her career, she understands the importance of balancing operational execution with long-term strategic vision. Her expertise spans revenue growth, artificial intelligence adoption, sales operations, financial oversight, talent development, customer experience, and organizational leadership, making her a valuable contributor to boards seeking practical executive insight and forward-thinking leadership.
Throughout every stage of her career, Shayna has remained guided by a simple yet powerful philosophy: show up, work hard, and be fully present for her team. Whether building high-performing sales organizations, mentoring future leaders, advising startup founders, or helping companies embrace emerging technologies, she consistently demonstrates integrity, resilience, and an unwavering commitment to delivering results. Her ability to blend strategic thinking with authentic leadership continues to make her a respected executive and a trusted advisor across the technology and artificial intelligence landscape.
Character:
Shayna leads with integrity, humility, and an authentic commitment to helping others succeed. She consistently creates environments where accountability, trust, and professional growth become the foundation for long-term organizational success.
Knowledge:
Her extensive expertise in SaaS, artificial intelligence, go-to-market strategy, sales leadership, and property technology enables her to solve complex business challenges with confidence. She combines decades of practical executive experience with a deep understanding of emerging technologies and evolving customer expectations.
Strategic:
Shayna possesses a proven ability to build scalable organizations, establish sustainable revenue strategies, and guide companies through periods of rapid growth and transformation. She approaches every opportunity with a long-term perspective that balances operational execution with strategic innovation and measurable business outcomes.
Communication:
A collaborative communicator who builds strong relationships with executives, customers, partners, and employees alike. Her ability to simplify complex concepts, inspire teams, and foster alignment enables organizations to execute effectively while maintaining a strong customer-first culture.
