Location: North America (Toronto or Boston – Hybrid)
Reports to: VP of Enterprise Sales & Business Development
Experience: 5+ years enterprise sales

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 looking for an Enterprise Account Executive to drive new enterprise customer acquisition across financial services, fintech, and adjacent regulated industries.

This role sits directly under the Head of Enterprise Sales and is designed for a seller who thrives in complex, consultative sales environments—someone who can manage long sales cycles, multiple stakeholders, and value-based conversations at the executive level.

You’ll own a set of named accounts or target segments and work closely with leadership, solutions, and marketing to land and expand enterprise customers.

What You’ll Do

• Own the full enterprise sales cycle from prospecting through close
• Build and manage a pipeline of complex, multi-stakeholder enterprise opportunities
• Engage senior buyers across digital, data, AI, marketing, cards, and innovation teams
• Run structured discovery to uncover customer needs, constraints, and success metrics
• Position Flybits’ contextual intelligence platform as a strategic growth enabler
• Partner with Solutions and Product teams to shape proposals and enterprise use cases
• Maintain accurate forecasting, deal tracking, and pipeline hygiene in Salesforce
• Expand existing accounts through upsell, cross-sell, and long-term relationship building

What You Bring

• 5+ years of enterprise B2B sales experience
• Required experience selling into financial services, fintech, payments, or martech
• Proven ability to navigate long, complex sales cycles with enterprise buyers
• Experience selling platforms or data-driven solutions (not just point tools)
• Strong communication skills and executive-level presence
• High ownership mindset with strong internal collaboration skills
• Comfort operating in a fast-growing, evolving environment

The base salary range for this role is $110,000 - $140,000. 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.