Jason MacLellan

Dynamic and results-driven VP of Sales with a proven track record of leading high-performing teams and driving double-digit revenue growth. Expert in strategic planning, compensation design, and operational execution across subscription and transaction-based sales models. Adept at aligning cross-functional teams, optimizing cost of sale, and scaling revenue through data-driven decision-making and incentive programs.

Leadership & Revenue Growth

FY26 (FY: Feb. 1st, 2025 to Jan 31st, 2026)

• Spearheaded the AAA Sales Team to $4.912M as of September 2025 in total bookings, achieving 18.4% YoY growth.
• FY26 Pace: $7.858M 18% Growth YoY
• Delivered 15% growth in transaction revenue, exceeding FY26 targets.
• Increased total team quota attainment and expanded market share across M&A and Industry verticals.

Team Management & Compensation Strategy

• Managed a team that consisted of a Sr Director of Sales, Revenue Enablement, Customer Onboarding Manager, BDR Manager, and 8 Sales Executives, and 10 BDRs implementing performance-based compensation plans.
• Designed and executed OTE increases and variable incentive structures, improving retention and motivation.

Strategic Planning & Forecasting

• Built and executed multi-tiered quota and compensation plans across M&A, Industry, and BDR teams.
• Introduced accelerator and SPIFF programs that drove overachievement and increased pipeline velocity.
• Developed forecasting models for subscription conversions, renewals, and overages, enabling precise planning.

Operational Excellence

• Led President’s Club planning and execution, recognizing top performers and reinforcing a high-performance culture.
• Oversaw headcount planning and hiring for new roles in Quebec and Industry teams, ensuring coverage and scalability.

FY25 Results (FY: Feb. 1st, 2024 to Jan. 31st 2025)

• Led the AAA Sales Team to $6.661M in total bookings
• Delivered 8.1% growth in subscription revenue, reaching $1.49M, and 7.5% growth in transaction revenue, totaling $5.161M.

FY24 Results (FY: Feb. 1st, 2023 to Jan 31st 2024)

• Led AAA Sales Team to $6.614M in total bookings
• Delivered 10.4% growth in subscription revenue, reaching $1.385M, and 6.5% growth in transaction revenue, totaling $5.57M.

FY23 Results (FY Feb1st, 2022 to Jan 31st, 2023)

• Led AAA Sales Team to $7.160M in total bookings, achieving 4.8% YoY growth from FY22.
• Delivered 4.3% growth in subscription revenue, reaching $1.417M, and 4.9% growth in transaction revenue, totaling $5.57M.

FY22 Results (FY Feb. 1st, 2021 to Jan 31st, 2022)

(Note: Firmex acquired by Datasite July 2021)

• Led AAA Sales Team to $6.835M in total bookings, achieving 30% YoY growth from FY21.
• Delivered 63.4% growth in subscription revenue, reaching $1.359M, and 23.7% growth in transaction revenue, totaling $5.476M.

• Developed and implemented strategic sales initiatives to enhance revenue growth.
• Analyzed market trends to identify opportunities for expansion and product positioning.
• Led cross-functional teams to execute sales campaigns, ensuring alignment with corporate objectives.
• Cultivated relationships with key clients, enhancing customer satisfaction and loyalty.
• Monitored sales performance metrics, providing insights for continuous improvement strategies.
• Trained and mentored junior sales staff, fostering professional development and team collaboration.
• Streamlined reporting processes using CRM tools to improve data accuracy and accessibility.
• Collaborated with marketing teams to create targeted promotional materials that drive engagement.
• Enhanced customer satisfaction levels by addressing concerns promptly and providing tailored solutions.
• Achieved regional sales targets through effective territory management and relationship building with key clients.
• Increased sales revenue by developing and implementing strategic plans and setting performance goals for the sales team.
• Managed team of sales representatives, providing guidance, coaching and support.
• Analyzed market trends to identify opportunities for product expansion, leading to increased revenue streams.
• Managed complex negotiations with key accounts resulting in long-term contracts that bolstered annual revenue figures significantly.
• Established ambitious sales targets, managed deployment strategies, and developed go-to-market plans to capitalize on every revenue opportunity.

• Developed and executed sales strategies to drive revenue growth and market share.
• Mentored and trained sales team members to enhance product knowledge and customer engagement.
• Analyzed market trends to identify opportunities for new product launches and promotional campaigns.
• Implemented CRM systems to streamline sales processes and improve client relationship management.

• Developed and executed strategic sales plans to achieve revenue growth targets.
• Cultivated relationships with key clients to enhance customer satisfaction and loyalty.
• Analyzed market trends to identify new business opportunities and adjust sales strategies accordingly.
• Led cross-functional teams to streamline sales processes and improve operational efficiency.
• FY19: $1.305M
• FY18: $1.102M
• FY17: $905K
• FY16: $655K

• Developed strategic sales plans to penetrate new markets and increase customer base.
• Cultivated relationships with key clients, enhancing customer satisfaction and loyalty.
• Analyzed market trends and competitor activities to inform pricing strategies and product offerings.
• Conducted presentations and product demonstrations to showcase benefits and features effectively.