Ben Oldale
Toronto,ON
Summary
Competitive and empathetic sales professional with 8+ years of experience in digital media and software sales. Proven track record of consistently exceeding team and individual revenue targets by efficiently managing each stage of the sales pipeline, from lead generation to customer acquisition. A clear communicator of technical services and products to clients who may not be familiar with the terminology or complexity. Strong ability to quickly build relationships throughout the customer journey, ensuring effective and long-lasting bonds with high-value prospects and clients across industries.
Overview
8
8
years of professional experience
1
1
Certification
Work History
Senior Account Executive
OnDeck Marketing
06.2024 - Current
- Company Overview: Launched in June 2024, OnDeck Marketing operates Canada's largest high school Digital Out-of-Home (DOOH) network, helping higher customers effectively advertise to today's youth through a blend of digital media strategies
- Lead a sales team of 5, driving $2.3M in revenue in the first six months, surpassing the revenue target by 30%
- Personally onboarded 40+ new customers generating over $800,000 in revenue, exceeding target by over 35%
- Created and tracked sales team activity KPIs, resulting in 130% of the revenue target year-to-date
- Implemented company-wide sales and marketing processes designed to provide value and creative insights to prospects throughout the buying cycle
- Oversaw, created, and tested new outreach strategies enabling the partnerships team to acquire 250 display locations (high school partners) in 6 months
- Deliver presentations at industry conferences, enhancing brand visibility and building new relationships
- Conduct thorough discovery calls with prospects to understand their unique needs and provide comprehensive advertising solutions
- Manage the creation and development of internal sales and marketing standard operating procedures (SOPs)
- Launched in June 2024, OnDeck Marketing operates Canada's largest high school Digital Out-of-Home (DOOH) network, helping higher customers effectively advertise to today's youth through a blend of digital media strategies
Director of Sales
Goodkind Software Corporation
01.2024 - 05.2024
- Company Overview: Goodkind is a Canadian EdTech company offering higher education institutions integrated video messaging, texting, and chatbot services
- Exceeded 120% of sales quota during first 3 months and secured the largest new client of the fiscal year, generating 100% of monthly quota
- Oversaw a team of six BDRs, bolstering sales team productivity by over 20% through the implementation and optimization of HubSpot
- Managed opportunities, activities, and reporting via Salesforce prior to the mandated transition to HubSpot mentioned above
- Originated and acquired new customers through both existing relationships and tailored outbound sales strategies
- Conducted in-depth discovery calls to identify client pain points and provide consultative solutions
- Represented Goodkind at conferences across North America, strengthening brand presence and building relationships with senior leadership
- Collaborated with cross-functional teams and leadership to develop webinars, white papers, case studies and tailored marketing email campaigns with the purpose of providing consistent value to prospects and customers
- Goodkind is a Canadian EdTech company offering higher education institutions integrated video messaging, texting, and chatbot services
Senior Account Executive
Glacier Communications
12.2016 - 01.2024
- Company Overview: Glacier is a digital advertising agency specializing in youth engagement, offering both in-house digital media strategy and a self-serve Demand-Side Platform (DSP)
- Acquired in March 2023, the company continues to empower higher education clients with innovative digital marketing solutions
- Surpassed revenue targets four consecutive years, consistently achieving 125% of the annual quota and generating up to $2M in new business annually
- Secured high-value accounts worth up to $600,000, utilizing solution-selling techniques to address specific client needs
- Increased the average new customer deal value by 100%, from $20,000 - $40,000, and acquired up to 50 clients annually
- Developed and executed paid media campaigns exceeding $500,000 in ad spend
- Presented at and attended 12+ industry conferences annually, expanding the customer network and enhancing client education
- Prepared and delivered custom proposals, negotiated terms, and facilitated smooth onboarding of new customers
- Collaborated with marketing to optimize MQL and SQL processes, increasing conversion rates by 100% over 6 years
- Led internal deal-strategy sessions ensuring product and service alignment with client needs
- Worked with Client Success Team to ensure continuity of care and seamless customer experience post-sale
- Utilized HubSpot for prospect follow-up and account management to maintain a robust pipeline of opportunities generated over the course of multiple years
- Executed and improved daily outbound sales strategies, including cold calling, email sequences, and LinkedIn Sales Navigator
- Glacier is a digital advertising agency specializing in youth engagement, offering both in-house digital media strategy and a self-serve Demand-Side Platform (DSP)
- Acquired in March 2023, the company continues to empower higher education clients with innovative digital marketing solutions
Education
BSc - Earth Sciences - Geology
University of Victoria
01.2014
Skills
- B2B Sales Strategy
- Relationship Building
- Consultative Selling
- Client Presentations
- Active Listening
- Customer Care
- Contract Negotiations
- Self-Starter
- Results-Driven
Certification
- Inbound Sales Certification, HubSpot
- Sales Software Certification, HubSpot
- Advanced Negotiations and Discovery Masterclass, pclub.io (new coursework in progress)
- Multi-Media & Marketing Sales Course, Perrco Consulting Inc.
Timeline
Senior Account Executive
OnDeck Marketing
06.2024 - Current
Director of Sales
Goodkind Software Corporation
01.2024 - 05.2024
Senior Account Executive
Glacier Communications
12.2016 - 01.2024
BSc - Earth Sciences - Geology
University of Victoria
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