Jonathan Paulo
Toronto
Summary
Dynamic sales professional and strategic leader with over a decade of experience, including eight years in the IT sector and nearly seven years at Softchoice across diverse territories and roles. Proven track record of driving impactful outcomes for internal stakeholders while empowering teams to excel in delivering exceptional customer service. Recent focus on individual contributions complemented by a strong leadership presence, particularly in the last 2.5 years within a Microsoft role, fostering collaboration and innovation. Committed to leveraging expertise to enhance organizational success and customer satisfaction.
Overview
10
10
years of professional experience
1
1
Certification
Work History
Senior Microsoft Technology Specialist
Softchoice
07.2025 - Current
- Promoted to Senior MTS of TSD Canada with an increased focus on providing strategic guidance and GTM for sellers
- Focused on creating systems for sellers to handle renewals and lesser strategic accounts by self serving material for their QBRs/SLS'
- Increased participation of reps in cross collaboration with CSLs, JAs - hosting weekly meetings to drive deals forward and penetrate most strategic accounts in territory
- Provided guidance to TSD Canada through the Microsoft FAQ chat, enablement sessions alongside Kierra Schweitz, and knowledge sharing of impactful wins
- Improved presence in TSD Canada's MTS team by helping other members of the team with GTM, strategy and how to work with other internal teams
- Worked with other MSMs on strategy for 3 year CSPs and moving EA customers to CSP through delivery strategies like "re-bundling teams" and loading SKUs prior to price changes
- Took on increased responsibility in providing guidance to the TSD Canada market, Microsoft teams, and driving improvements in GTM strategy
- Hosted multiple office hours for many sellers in TSD Canada to attend and have questions answered & advise on deals
Microsoft Solutions Specialist
Softchoice
10.2023 - 07.2025
- Analyzed client needs to provide tailored M365, Azure product and managed services solutions
- Collaborated with cross-functional teams to enhance customer experience and satisfaction
- Developed enablement material that was presented to teams and to the whole organization through win wires and town halls
- Streamlined collaboration between sellers, customer solutions leads, journey architects and migration teams to ensure efficiencies in sales
- Worked on various internal projects that included: CSP case path improvement, sales messaging for Microsoft licensing assessments, and improvement of forecast and pipeline reports
- Net CSP Award winner (+42)
- +12 Microsoft BAs and +17 Net Microsoft BAs
- 108.3% Plan attainment, $3,039,761/$2,808,138, 26% growth
Senior Account Executive L3/L4 - Ontario
Softchoice
01.2023 - 09.2023
- Promoted to L3 July 2023, after achieving ~110% to plan, 37% growth, +5 NBAs, NBA leader Q2
- Prospecting focused, targeting various roles and senior leaders in IT, Operations, Finance
- Competed for and won Lennox & Addington County General Hospital's sizeable M365 contract, against 5 other VARs, by right sizing and presenting SKUs to IT Management that provided better security, functionality and $18,000 in annual savings without compromising FM.
- Won a competitive Azure Partner bid for Amphenol Canada, a prospect, by working closely with SSE, Microsoft Direct AE, and Partner funding
- Helped test and provided feedback for internal Microsoft ChatBot(Wanda), by cross referencing questions and case paths
Senior Account Executive - CAN R&D
Softchoice
05.2022 - 01.2023
- Oversaw the retention and diversification of net new categories for 10-12 BAs at a time
- Continuously achieved high NPS Promoter Scores
- Worked within various MS agreements: Open Value, Open Value Charity, MPSA, EA, CSP
EB Account Executive - US East
Softchoice
05.2021 - 05.2022
- Worked closely with distribution, partners and their AEs to quickly serve inbound leads and customer requests
- Responsible for leading the majority of the EB team's Microsoft engagements, mentored by both Alanna Bobinski and Helena Fraga da Silva, and designated "MSS lite" to help onboard new Microsoft clients
- Worked on and completed 80+ Microsoft Partner portal engagements, onboarding 8+ CSPs
- Mentored and helped others with their Microsoft opportunities
- Trained and mentored new AEs in between sales academy and team placement
Territory Account Representative
Softchoice
03.2019 - 05.2021
- Responsible for 10 buying accounts and 40 prospects in Western Canada
- First exposure and completion of Microsoft licensing training
Business Development Manager
Costek Inc.
07.2017 - 03.2019
- Sourced leads and developed strategy to bring in new logos. In this role I focused on cold calling and setting meetings with CFOs, IT Directors/Managers.
- Brought in 50 net new clients and sourced over $5,000,000 in revenue, managing the full sales cycle
- Mentored by and reported directly to CEO
Sales & Service
Scotiabank
02.2016 - 07.2017
- Responsible for generating new sales by matching financial products and services to individuals and organizations
- Mentored and trained new hires on systems, processes and how to match product/services to unique customer personas
Education
Bachelors of Business Management -
Toronto Metropolitan University
Toronto06.2016
Skills
- Leadership
- Strategic Thinking
- Problem Solving
- Business Acumen
- Collaboration
- Risk Management
- Analytical
- Time Management
- Decision Making
- Adaptability
Accomplishments
- Most NBAs in TSD YTD in 2023
- ~$7M in FM won as an MTS/Sr. MTS since October 2023
- 2024 Net CSP Award Winner - +42
- Overachievement in 2024 managing 3 TSD Ontario teams- 24% growth in MS Product and 60%+ growth in Professional Services with $3M in FM
- Overachievement in 2025 managing 2 TSD Ontario Teams- 32% growth and over $3.1M FM
- Consistent double digit Workplace and Azure CSP contract growth YoY
Languages
English
Native or Bilingual
Portuguese
Native or Bilingual
Certification
- Challenger Sales Program- July 2022
- Microsoft 365 Fundamentals, Exit Certified - November 2022
- Microsoft 365 Fundamentals Certified, PearsonVue- November 2025
- Azure Fundamentals Certified, PearsonVue - November 2025
Timeline
Senior Microsoft Technology Specialist
Softchoice
07.2025 - Current
Microsoft Solutions Specialist
Softchoice
10.2023 - 07.2025
Senior Account Executive L3/L4 - Ontario
Softchoice
01.2023 - 09.2023
Senior Account Executive - CAN R&D
Softchoice
05.2022 - 01.2023
EB Account Executive - US East
Softchoice
05.2021 - 05.2022
Territory Account Representative
Softchoice
03.2019 - 05.2021
Business Development Manager
Costek Inc.
07.2017 - 03.2019
Sales & Service
Scotiabank
02.2016 - 07.2017
Bachelors of Business Management -
Toronto Metropolitan University