Job Title: Head of Sales, Enterprise
Location:
Preferred in Office- Saskatoon | Open to US/Canada Remote
The mission of the Head of Sales, Enterprise Direct is to lead the overall strategy, execution, and performance of Vendasta’s enterprise sales division. This role exists to scale high-impact revenue growth by building a predictable and repeatable sales engine focused on acquiring and expanding relationships with large, multi-location businesses across North America.
About the Job
As a senior leader within the revenue organization, you will define the long-term enterprise sales vision, lead the development of go-to-market strategies, and oversee the success of multiple solution lines within the enterprise portfolio. You will play a critical role in shaping the future of Vendasta’s enterprise market presence, driving innovation in AI-enabled sales execution, and ensuring best-in-class performance across the team. Key responsibilities include defining and evolving long-term sales strategy, building scalable AI-assisted go-to-market motions, and leading a high-performing enterprise sales leadership team. You will own the enterprise revenue target, drive strategic account expansion, and serve as the strategic voice of enterprise sales at the executive level.
Your Impact
- Enterprise Revenue Attainment: Achievement of quarterly and annual revenue targets across all enterprise segments, including new business and expansion.
- Enterprise Pipeline Health: Maintain qualified pipeline coverage, opportunity creation, average deal size, and sales velocity across target enterprise segments.
- Forecast Accuracy: Maintain forecast accuracy within an acceptable variance to actual bookings.
- Strategic Growth Contribution: Drive growth of key solution lines (e.g., Broadly and core Vendasta platform) to enterprise revenue portfolio and overall company performance.
- Team Performance: Drive enterprise team quota attainment, improve deal win rates on strategic opportunities, and ensure team retention and leadership pipeline health.
What You Bring to the Table
- Minimum 10+ years in enterprise sales leadership roles, with proven experience managing $10M+ revenue portfolios.
- Bachelor’s degree preferred (Marketing, Advertising, Business, or a related field preferred).
- Proven success building large-scale enterprise sales organizations with strong AI integration in a SaaS or tech environment.
- Ability to architect sales organizations that can scale efficiently, with consistent quota attainment and operational discipline.
- Deep understanding of enterprise segmentation, account targeting, territory design, and sales process optimization.
- Demonstrated ability to manage complex solution portfolios and drive adoption across multiple product lines.
- Strong command of pipeline management, sales KPIs, forecast hygiene, and operational best practices.
- Deep experience in leading large, distributed sales teams and building high-trust environments.
- Executive presence and the ability to engage internal and external stakeholders at the highest levels.
- A track record of navigating complex change and leading through ambiguity in scaling companies.
- Ability to communicate clearly and effectively in written and verbal formats.
About Vendasta
We help businesses get more customers. And keep them. Vendasta is an AI-powered customer acquisition and engagement platform built for SMBs and the partners who support them, providing the tools needed to attract, engage, and retain customers, increasing lifetime value and building loyalty. From creating awareness to nurturing lasting customer relationships, Vendasta offers a suite of solutions with AI assistants that streamline every stage of the customer journey. By combining a business's unique data with AI and automation, Vendasta simplifies marketing, sales, and operations, eliminating the need for multiple disjointed systems.
Perks
Join the Vendasta team, where your happiness and health are our top priorities! Dive into a world where competitive health benefits meet flexibility with flex time and an annual work-from-anywhere policy. Embrace the opportunity to grow with us through our Employee Options Program and savour every bite in our cafeteria, delighting in daily snacks, and unwinding with catered Friday lunches at our offices. Fuel your ambition with education reimbursement, in-house learning, and an array of leadership development programs, all nestled within a culture brimming with Drive, Innovation, Respect, and Agility. Engage your heart in community events and volunteer opportunities. At Vendasta, we're not just offering a job; we're inviting you to build a thriving career in an environment that champions your growth and well-being. Let's soar together!
Discover your potential. Build something that matters.
Help us lead the AI revolution from right here in Saskatoon Chennai Boca Raton.
