JAKOB BENDER
Toronto
Summary
Award-winning Sales Leader with 8+ years of experience driving B2B SaaS growth. Expert in strategic planning, pipeline generation, and customer acquisition/retention. Skilled in executing go-to-market strategies, exceeding targets, and leveraging Salesforce for data analysis and forecasting. Known for a customer-centric approach, building long-term relationships, and growing existing accounts through up/cross-selling. Effective leader who empowers teams to drive performance and scale in competitive markets. Recipient of President's Club and Sales Leader of the Year Awards.
Overview
9
9
years of professional experience
Work History
Sales Director, Outbound
ButterflyMX
01.2025 - Current
- Generated $7.5K ARR in Q0 by executing highly targeted outreach; conducted in-depth research prior to each call, anticipated objections , and tailored messaging to engage developers, property managers, and installers.
- Achieved Q1 quota on Day 1 by closing $35K in ARR, becoming the first new hire to do so — setting a company record for fastest ramp to revenue. Success driven by strategic, personalized outreach and deal execution.
- Contributed to Market Expansion as part of the inaugural team; collaborated directly with the VP to analyze market gaps, uncover trends, and define a go-to-market strategy tailored to Canadian buyers.
- Built a reputable outbound workflow by refining call scripts, objection handling tactics, and follow-up cadences, helping inform best practices for future BDR teams and scaling efforts.
Manager, Inside Sales
TouchBistro
01.2022 - 01.2024
- Oversaw revenue targets of $65K ACV/per rep, for a team of 10 quota-carrying Account Executives, ensuring team alignment with sales goals.
- Delivered comprehensive training for new hires, covering sales process and consultative selling sales methodology, operating procedures, and competitive industry intelligence.
- Leveraged Salesforce data to monitor team progress, identifying and addressing reasons for gaps in KPI achievement.
- Achieved 122% annual sales attainment in FY-2022, earning prestigious Sales Leader of the Year and Presidents Club awards for outstanding performance.
- Led highest-achieving Inbound Sales Team in FY-2023, finishing first amongst Inbound Sales Leaders with 101% annual attainment.
- Entrusted by Chief Sales Officer in FY-2023 to identify and analyze revenue gaps in the business, subsequently presenting findings and recommendations to Senior Leadership Team.
Senior Account Executive, Inbound
TouchBistro
01.2021 - 01.2022
- Partnered with management and enablement teams to refine/enhance inbound sales process, developing a comprehensive sales playbook and organizational structure, boosting inbound attainment by 105% in FY-2021 and 2022.
- Led training initiative as team lead, coaching Account Executives on deep discovery techniques leveraging BANT and conscious selling; enhanced ability to align solutions with customer challenges and accelerating ramp to revenue by 10%.
- Consistently met and/or exceeded monthly sales quotas, achieving first place overall out of 25 account executives and earning the prestigious Presidents Club Award in 2021.
- Achieved impressive quota attainment of 128% in FY-2021, showcasing exceptional sales ability and commitment.
Account Executive, Inbound
TouchBistro
01.2019 - 01.2021
- Established and managed pipeline of 70+ prospects, guiding each from initial discovery to successful deal closure, driving consistent results, exceeding $60K in annual contract value per month for 9 consecutive months.
- Collaborated with restauranteur clients to support increased efficiency, service speed, and enhanced transparency of numbers/business through restaurant technology; closed ~6 deals per month with an average size of $9K.
- Surpassed quota attainment for 9 consecutive months in FY-2020, despite challenges from the pandemic, demonstrating tenacity and persistence.
- Achieved notable quota attainment numbers, with 102% in FY-2019 and 115% in FY-2020, showcasing consistent sales performance and growth.
Account Executive & Business Development Representative
ContactMonkey
01.2017 - 01.2019
- Drove end-to-end outbound sales strategy, conducting targed cold calls and personalized email outreach to close 13-high value deals worth over $750K, contributing to significant revenue growth.
- Conducted market research to identify key decision makers using ZoomInfo and Salesforce; executed targeted outreach to build a qualified pipeline, contributing to a 5% increase in lead-to-opportunity conversion.
- Maintained healthy pipeline of 60-80 clients, selling to C-suites, senior leadership teams, and marketing/HR VPs.
- Surpassed sales quotas by 173% in FY-2018, demonstrating business acumen, relationship skills, and consultative sales proficiency.
Customer Service Representative
TD Canada Trust
01.2016 - 01.2017
- Formulated strategic action plans to significantly drive sales, consistently exceed customer expectations, and contribute to overall revenue growth for the branch.
- Consulted with customers on financial products such as mortgages, credit lines, and mutual funds.
- Recognized as an exemplary employee by management and selected to represent branch at 'The Legendary Experience Workshop', highlighting outstanding performance and dedication.
Education
Bachelor of Arts degree - Political Science
Dalhousie University
Skills
- B2B Sales
- Sales Team Training
- Coaching & Development
- Forecasting
- Data Analysis
- Contract Negotiation
- Competitor Analysis
- Customer Relationship Management
- Pipeline Management
- Lead Generation
- Sales Process Optimization
- Executive Presentations
- Highly Self-Motivated
- Cross-Functional Collaboration
- Proficient in Salesforce, HubSpot, ZoomInfo, Gong
Websites
Education And Professional Development
- Bachelor of Arts, Political Science, Dalhousie University, NS, Dean's List
- Principal Sales Methodology Training, Conscious Selling, Inc.
- Leading Others Program, Crestcom, Toronto, ON
Timeline
Sales Director, Outbound
ButterflyMX
01.2025 - Current
Manager, Inside Sales
TouchBistro
01.2022 - 01.2024
Senior Account Executive, Inbound
TouchBistro
01.2021 - 01.2022
Account Executive, Inbound
TouchBistro
01.2019 - 01.2021
Account Executive & Business Development Representative
ContactMonkey
01.2017 - 01.2019
Customer Service Representative
TD Canada Trust
01.2016 - 01.2017
Bachelor of Arts degree - Political Science
Dalhousie University
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