Massimo Di ioia

Senior commercial executive with 15+ years of experience driving enterprise SaaS growth, strategic account development, customer retention, and market expansion across North America. Proven track record of delivering measurable business results, including 120% market-share growth, managing relationships across 700+ customer organizations, sustaining 90%+ customer retention, and leading commercial teams contributing to more than 100 new customer acquisitions. Experienced in developing executive-level relationships, negotiating complex commercial agreements, expanding recurring revenue, and leading cross-functional initiatives that strengthen customer lifetime value and long-term business performance.

Combines the strategic perspective of an executive leader with the commercial discipline of a revenue owner, bringing a strong understanding of enterprise customer engagement, go-to-market execution, account expansion, and organizational growth.

Key Account Executive - 360Player - North America

• Lead strategic commercial development across North America, engaging executive stakeholders to identify business challenges, technology transformation opportunities, and long-term revenue potential.
• Develop and execute account growth strategies, including multiyear commercial agreements, subscription expansion, pricing negotiations, and recurring revenue development.
• Build relationships with senior executives and organizational decision-makers, positioning SaaS technology as a strategic solution to operational and commercial challenges.
• Structure and negotiate commercial agreements, including subscription packages, strategic pricing, and multi-year partnerships to support customer acquisition and recurring revenue growth.

Director Key Accounts, North America - Playermaker - North America

• Directed strategic account relationships across North America, serving as a primary commercial partner to senior customer stakeholders and executive leadership.
• Developed customer growth and retention strategies, achieving an 82% first-year renewal rate while identifying opportunities to expand long-term customer value.
• Led strategic account planning, customer performance reviews, renewal forecasting, and commercial risk assessments to strengthen portfolio performance.
• Identified opportunities for account expansion through deeper technology adoption, executive engagement, and alignment with evolving customer priorities.
• Provided executive leadership with actionable insights into portfolio health, revenue opportunities, customer risk, and strategic growth initiatives.

Vice President Business Development North America - Coachbetter - North America

• Led North American business development, including commercial strategy, new-market entry, strategic partnerships, and customer acquisition.
• Recruited, mentored, and coached a remote sales team whose efforts contributed to 100 new customer wins.
• Built repeatable prospecting, pipeline management, performance review, and go-to-market processes to support scalable growth.

Customer Success Manager / North American Key Accounts Project Manager - Spiideo - North America

• Managed strategic customer relationships across a North American portfolio of 700+ organizations, maintaining customer retention above 90%.
• Led customer engagement, business reviews, and account performance analysis to strengthen executive relationships and long-term customer success.
• Identified opportunities to increase recurring revenue through account expansion, cross-selling, upselling, and deeper platform adoption.
• Collaborated across Sales, Product, Engineering, and Customer Success to resolve complex customer challenges and improve delivery outcomes.
• Provided leadership with forecasting, customer-health analysis and business intelligence to support strategic decisions

Strategic Partnerships (Soccer)– North America - Hudl - North America

• Led Canadian market expansion strategy within Hudl's North American soccer business, delivering 120% market-share growth over three years.
• Developed strategic partnerships with senior executives, governing organizations, and key institutional stakeholders to accelerate technology adoption and commercial growth.
• Identified new market opportunities, strengthened enterprise relationships, and supported the execution of long-term commercial growth initiatives.

Sporting Director - FC LORO

• Partner with board leadership on organizational strategy, operational planning and growth for a youth sports organization.
• Provide leadership across technical operations, program development, staff coordination, and organizational performance, aligning day-to-day execution with long-term strategic objectives.
• Founded and lead La Grinta Tournament, a flagship annual fundraising event that has grown into a premier regional competition, generating new revenue streams, strengthening community partnerships, and enhancing the club's brand and social impact.
• Drive organizational transformation through the development of player pathways, coach education programs, operational processes, and long-term growth initiatives.
• Build strategic partnerships with municipalities, governing bodies, sponsors, and community stakeholders to expand the club's reach, resources, and competitive positioning.
• Lead cross-functional teams, volunteers, and technical staff while fostering a high-performance culture centered on accountability, collaboration, and continuous improvement.
• Champion innovation across club operations by implementing scalable systems, enhancing member experience, and supporting sustainable organizational growth.

Technical Director - Brampton SC

• Provided senior technical and operational leadership for a major Canadian youth soccer organization serving approximately 5,300 members.
• Oversaw club-wide player development, coaching operations, technical programming, and organizational performance standards.
• Contributed to strategic business planning, organizational development, and long-term operational initiatives.

Men’s Senior Team – CONCACAF Nations League Lead Scout - Canadian Soccer Association

• CONCACAF Nations League scout for Canada MENS Program.
• Provide in depth opposition analysis for future & upcoming Nations League opponents to John Herdman’s men’s team staff.

Head of High Performance - CF Montreal (Major League Soccer)

• Overlook the entire scouting network & NCAA Superdraft process.
• Assist MLS Head Coach in current player and opposition scouting.
• Prepare, analyze, and breakdown opposition through video and data analytics.
• Represent CF Montreal on the MLS Sub-Committee.

Physical Education - McGill University

Business Management - LaSalle College