Location: North America (Toronto or Boston – Hybrid)
Reports to: Chief Growth Officer
Level: VP / Senior Director+

About Flybits

Flybits is the Contextual Engagement Company. We transform data into contextual intelligence that guides when, how, and whether to engage a customer. Flybits layers into existing systems enabling interactions that reflect timing, intent, and circumstance, and feel like service, not interruption.

We help data-rich enterprises bridge the gap between data and engagement, identifying what matters so they can meet their customers with the right experience, in the right channel, at the right moment.

The Role

Flybits is seeking a VP Enterprise Sales & Business Development to lead enterprise revenue growth and help define how we go to market globally. This is a senior, hands-on leadership role for a proven enterprise seller who can set strategy and personally close business.

You will own new business execution, source and advance complex enterprise opportunities, and shape Flybits’ enterprise sales motion as we scale. Working closely with Growth, Product, Marketing, and Customer teams, you’ll translate Flybits’ contextual intelligence platform into clear, differentiated value for financial institutions navigating digital transformation, AI adoption, and responsible data use.

This role is ideal for a builder—someone comfortable with ambiguity, long sales cycles, regulated buyers, and selling transformation, not point solutions.

What You’ll Do

Enterprise Revenue Leadership

• Own enterprise new-business revenue targets and pipeline health
• Personally source, qualify, and close high-value enterprise opportunities within Flybits’ ICP
• Manage complex, multi-stakeholder sales cycles from first engagement through contract execution
• Build and maintain a disciplined, high-quality enterprise pipeline
• Maintain accurate forecasting, pipeline visibility, and sales rigor using Salesforce
• Recruit, coach, and lead enterprise sellers as the team scales
• Establish sales standards, operating cadence, and performance culture

Executive Selling & Market Presence

• Lead executive discovery sessions, presentations, and strategic product demonstrations
• Clearly articulate Flybits’ value across contextual intelligence, AI, data, and measurable growth outcomes
• Engage senior leaders across digital, data, AI, marketing, cards, and line-of-business teams
• Navigate enterprise buying committees and regulated decision environments with confidence
• Represent Flybits at strategic industry events, partner forums, and executive customer meetings
• Build long-term credibility and trusted relationships across banks, credit unions, card issuers, and ecosystem partners

Go-To-Market Leadership

• Shape and evolve Flybits’ enterprise sales narrative, positioning, and demo strategy
• Identify gaps in messaging, proof points, and enablement—and drive continuous improvement
• Develop creative, signal-driven prospecting approaches that cut through enterprise noise
• Improve sales process, deal qualification, and execution effectiveness as Flybits scales
• Contribute to pricing, packaging, and commercial model discussions for enterprise customers

Cross-Functional Leadership

• Partner closely with Marketing to align outbound motion, ICPs, and account-based strategies
• Collaborate with Product and Solutions teams to ensure relevance, clarity, and value realization
• Support the evolution of sales operations, tooling, and scalable GTM execution
• Work with the CGO to define segment focus, pipeline investment, and growth priorities
• Help build a durable, customer-centered growth engine rooted in trust and long-term value

Who You Are

• 10+ years of enterprise B2B sales experience, including senior AE roles
• Proven success selling complex, data-driven, AI-enabled, or platform solutions
• Direct experience selling into regulated industries, especially financial services, fintech, payments, or martech
• Comfortable operating as both strategist and hands-on closer
• Strong executive presence and credibility with C-suite and EVP-level buyers
• Disciplined in execution, thoughtful in engagement, and resilient through long sales cycles
• Motivated by building, not inheriting high-impact sales motions

The base salary range for this role is $150,000 - $180,000. This role is eligible for on target earnings. 

Non-Automated Screening: Please note that we do not use artificial intelligence or automated ranking systems to evaluate candidates. All applications are reviewed manually by our hiring team to ensure a comprehensive and equitable assessment of your professional experience.

Flybits is an Equal Employment Opportunity Employer. Employment, recognition and advancement at Flybits are based solely on individual merit and qualifications directly related to professional competence. We provide equal opportunity regardless of race (though currently we hire only humans), color, gender, ethnicity, ancestry, national origin, age, religious affiliation (or lack thereof), sexual preference or orientation (or lack thereof), pregnancy status, medical condition, marital status, or any other characteristic protected by law.

We will also make all reasonable accommodations to comply with the Americans with Disabilities Act (ADA) and similar Canadian, State, and Provincial disability laws.