Stefan Santilli
Sales Professional
Toronto,ON
Summary
I'm Stefan - a strategic and results-driven Leader, Sales and Sales Enablement Professional with 7+ years of experience delivering exceptional revenue growth, team leadership, and client satisfaction in fast-paced SaaS and IT environments. Proven track record of driving revenue growth, improving client retention, and boosting team productivity through data-driven solutions, consultative selling, and collaborative cross-functional partnerships. Adept at leading sales teams, developing high-impact training programs, and building long-lasting relationships with C-suite stakeholders across various industries. Passionate about coaching and mentoring sales professionals, and colleagues to exceed performance targets, foster professional development, and create a culture of positivity and continuous learning.
Overview
8
8
years of professional experience
Work History
Senior Account Executive
TAB FusionRMS
Toronto, Ontario
12.2023 - 09.2024
- Revenue Generation: Spearheaded sales initiatives that resulted in increased annual recurring revenue and on-prem maintenance revenue by 8%, by aligning tailored SaaS and on-premises records management solutions with client needs.
- Client Relationships: Developed strong, trust-based relationships with C-suite executives across multiple industries, leading to 23% improved customer satisfaction and 28% reduction in churn through personalized solutions.
- SaaS Sales & Strategy: Led the SaaS transformation for key accounts, negotiating contracts that ensured a 30% increase in deal size compared to legacy on-premises systems. Skilled at positioning cloud-based solutions and driving full software transitions, including API integration.
- Thought Leadership: Actively represented TAB at industry conferences (AIIM, ARMA Canada, NAGARA), generating over 100+ leads and expanding TAB’s presence in the B2B SaaS market.
- Cross-functional Collaboration: Partnered with internal teams, including IT, operations, and product development, to ensure seamless software deployments, driving 100% successful SaaS transition rate.
- Mentorship: Trained and mentored junior sales team member, resulting in improved sales performance by 17%.
Sales Enablement Manager
Otter
09.2022 - 10.2023
- Sales Enablement Strategy: Designed and implemented comprehensive sales enablement programs that reduced onboarding time by 33%. Built curriculum, training sessions, and onboarding processes for SDRs, AEs, and Sales Managers.
- Internal Collaboration: Collaborated with senior leadership to support the development of sales teams, offering targeted coaching that resulted in increased tool adoption and improved forecast accuracy by 18%.
- Sales Assessments & KPIs: Created detailed assessments, tracking performance metrics and KPIs to improve individual and team outcomes. Enhanced rep productivity by analyzing Gong and SalesLoft data to offer actionable insights during 1:1 sessions.
- Cross-Functional Collaboration: Worked closely with sales, marketing, IT, and operations to align go-to-market strategies, ensure consistency in messaging, and drive the adoption of effective sales collateral and enablement tools.
- Sales Technology Expertise: Improved sales productivity through instructing use of deep tech stack (Salesforce, Gong, Google Suite, Zoominfo) and innovative sales practices, leading to 14% increase in day-to-day productivity.
- Sales Playbooks & Collateral: Developed and maintained sales playbooks, decks, and other collateral, providing reps with the tools needed to execute deals effectively. Increased deal win rates by 21% through structured sales guidance.
Sales Manager
Otter
Toronto, Ontario
09.2022 - 01.2023
- Team Leadership: Managed a team of 9 high-performing SDRs and AEs responsible for generating new business, conducting demos, and closing sales for Otter’s SaaS products. Implemented coaching strategies that resulted in 120% revenue achievement and 80% quota attainment across the team.
- Sales Coaching: Delivered 1:1 and group coaching sessions, focusing on consultative selling techniques, objection handling, and pipeline management, leading to an average increase of 1.8 CW deals per team member, per month.
- Sales Strategy Execution: Created and implemented sales strategies to expand market share, driving 10% MRR growth through targeted outreach and the development of strategic partnerships with key accounts.
- Performance Tracking & Forecasting: Utilized Salesforce and Gong to accurately forecast pipeline and provide weekly reports on progress, leading to 30% improved accuracy in sales predictions.
- Team Collaboration: Conducted daily team huddles to foster alignment and teamwork, resulting in 0 team turnover and improvement in rep engagement and collaboration across the team.
Sales Instructor
CDW Canada
10.2021 - 09.2022
- Developed and delivered comprehensive sales training program for awide array of technologies (SaaS, Data Center, Compute) to equip sales teams with essential skills and techniques to enhance their performance and drive revenue growth.
- Conducted in-depth assessments of sales team members' strengths and areas for improvement, and customized training plans to address individual skill gaps and maximize their potential, with proven increase of employee retention.
- Implemented structured sales training curriculum that covered prospecting, qualifying leads, effective communication, objection handling, negotiation strategies, and closing techniques.
- Provided ongoing coaching and mentorship to sales professionals, offering guidance on individual sales challenges, refining their techniques, and fostering culture of continuous improvement.
Corporate/Mid Market Account Manager
CDW Canada
01.2017 - 10.2021
- Managed complex sales cycles/projects for book of business consisting of 100+ corporate and enterprise clients. Assess > Design > Deploy strategy.
- Negotiated profitable proposals with major companies securing long-term accounts worth over $2,000,000 annually.
- Working through use of CRM systems on daily basis. Maintain relationships and analyze customer needs through use of data reports
- Prospect, maintain and manage high-importance customer relationships.
- Help customers achieve positive ROI on IT investments; including but not limited to improving employee productivity through efficient systems solution design and implementation.
- Developed tangible personal and business relationships with network of IT, Finance, and Procurement professionals.
- Enhanced profitability by developing pipelines utilizing marketing, sales strategies, and organizational skills.
- Secured competitor business via strategic marketing, service programs and interpersonal skills.
- Established partnerships in various sectors to grow account base.
- Multi-tasking: Effectively orchestrated management of multiple mission-critical client projects and engagements with parallel timelines.
- Resolved problems with high-profile customers to maintain relationships and increase return customer base
- Achieved sales goals and service targets by cultivating and securing new customer relationships
- Managed accounts to retain existing relationships and grow share of business
Education
Bachelor of Commerce - Business Management
2017
Skills
- Cross-Functional Collaboration: I'm an expert collaborator that understands the value and importance of working alongside Primary and Secondary internal and external stakeholders to achieve a common goal
- Sales Expertise: I bring 5 Years of experience selling SaaS, and other IT products and services to SMB, Corporate, Mid Market, and Enterprise clientele
- Relationship Management: People are my passion I have a natural and practiced ability to nurture and grow internal and external relationships This includes business relationships with a variety of clientele in different segments and verticals
- Verbal & Written Communication: Whether through a formal written proposal, or crafted executive presentation I have experience presenting solutions and providing industry insights/suggestions to new and existing customers, including C-Suite contacts
- Exceptional Interpersonal Skills: I've connected, and communicated with a diverse group of internal and external teams in adaptable and effective manner to make tangible impact
- B2B Sales: My track record of cultivating and maintaining strong client relationships, driving revenue growth through strategic prospecting and negotiation has led me to consistently achieve, and exceed quotas Adept at identifying client needs and providing tailored solutions to meet and exceed sales targets
- Sales Process: I'm Proficient in optimizing the sales process to enhance efficiency, from prospecting and lead qualification to closing deals and post-sale support Adept at implementing best practices and utilizing sales technology for streamlined operations and improved results
- Leadership: I've led teams with a strong record of revenue growth My experience with coaching as a Sales Instructor and Sales Enablement Manager has led me to value the importance of ongoing team development I'm skilled in strategy, relationship-building, negotiation, and data-driven decision-making, as well as utilizing CRM systems and datasets to track performance
- Training, Coaching & Ongoing Development: I have experience at Otter and CDW as a Sales individual contributor, curriculum developer, and team leader I'm able to effectively empowering others and effectively communicate learnings due to my understanding of all aspects of a sales organization
Accomplishments
- Awarded "Residency Champion" at CDW Canada for achieving top sales, gross profit, and efforts within the residency class (under 2 years of service at CDW)
Additional Information
https://www.linkedin.com/in/stefan-santilli
Timeline
Senior Account Executive - TAB FusionRMS
12.2023 - 09.2024
Sales Enablement Manager - Otter
09.2022 - 10.2023
Sales Manager - Otter
09.2022 - 01.2023
Sales Instructor - CDW Canada
10.2021 - 09.2022
Corporate/Mid Market Account Manager - CDW Canada
01.2017 - 10.2021
Ryerson University - Ted Rogers School of Management - Bachelor of Commerce, Business Management
Similar Profiles
George Abdul HakGeorge Abdul Hak
Head of Strategy & Operations at OtterHead of Strategy & Operations at Otter
Luis Daniel Rosas FriasLuis Daniel Rosas Frias
Custpmer Success Asociate at OtterCustpmer Success Asociate at Otter
Feben AberaFeben Abera
Account Executive at OtterAccount Executive at Otter