Matthew Gillespie

Dedicated operations and community engagement professional with 12+ years of experience managing high-touch client relationships, conflict resolution, crisis response, and collaborative team environments. Strong background in communication, emotional intelligence, organizational leadership, and supporting diverse communities through complex and fast-paced situations. Graduate of Carroll School with a personal connection to supporting students with language-based learning differences, including dyslexia.

Passionate about helping students build confidence, self-advocacy, positive peer relationships, and emotional resilience within structured and supportive educational environments.

Client Relationship Management: Capable of building trust with clients to deliver portfolio growth and retention; able to identify lucrative market opportunities, using negotiation, persuasion, and collaboration skills.

Delivering Quantifiable Results: Able to define and execute strategies that achieve sales, relationship management, and business development goals, including the accomplishment of monthly, quarterly, and annual quotas.

Creativity & Agility: Demonstrated track record of adapting to a continuously evolving business environment in several sectors and overcoming obstacles by designing innovative solutions to complex problems.

Project Management: Adept at planning and executing multi-million dollar projects from concept to completion in collaboration with cross-functional teams; strong budgeting, scheduling, time management, and prioritization skills.

Property Manager - First Realty Management, Inc. - Boston, MA

(2023-01 - 2025-11)

• Lead daily operations of a 256-unit condominium community as primary liaison for trustees, owners, and contractors.
• Manage financials, budgets, and vendor contracts, securing cost savings and aligning service quality with KPIs.
• Direct multi-million-dollar capital projects from planning through execution, while leading risk management, compliance inspections, and emergency response initiatives.

Property Manager - Mediate Management Company - Boston, MA

(2014-01 - 2023-01)

• Managed a portfolio of 20+ residential clients, building long-term relationships surpassing client expectations.
• Oversaw financial planning, budgeting, cost control, vendor negotiations, and regulatory compliance processes.
• Led large capital projects and advised boards on investment strategies, operational improvements, and risk mitigation.

Real Estate Agent - Coldwell Banker Residential - Winchester, MA

(2007-01 - 2014-01)

• Worked with clients to facilitate sales, marketing, and acquisition activities in the Real Estate sector.
• Developed client relationships, built a valuable network, and negotiated purchase and sales contracts.
• Handled interactions between counterparties to a deal, navigating disputes and resolving conflicts.
• Acted as a focal point for all stakeholders, enabling open and clear communication of issues and contractual terms.

Sales Executive - TD Garden - Boston, MA

(2004-01 - 2006-01)

• Executed sales strategies, acquired new accounts, and maintained client relationships to achieve revenue goals.
• Provided exceptional client service, developing new business through lead generation, networking, and cold calling.
• Managed sales contracts, delivered compelling client presentations, and handled product placement during events.
• Maintained an in-depth understanding of market trends and the competitive landscape to source new opportunities.

Bachelor of Arts - Political Science - Washington College