Location:North America (Toronto or Boston – Hybrid)Reports to:VP of Enterprise Sales & Business DevelopmentExperience:5+ years enterprise salesAbout FlybitsFlybits 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 RoleFlybits is looking for anEnterprise Account Executiveto 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 incomplex, 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 DoOwn the full enterprise sales cycle from prospecting through closeBuild and manage a pipeline of complex, multi-stakeholder enterprise opportunitiesEngage senior buyers across digital, data, AI, marketing, cards, and innovation teamsRun structured discovery to uncover customer needs, constraints,



and success metricsPosition Flybits’ contextual intelligence platform as a strategic growth enablerPartner with Solutions and Product teams to shape proposals and enterprise use casesMaintain accurate forecasting, deal tracking, and pipeline hygiene in SalesforceExpand existing accounts through upsell, cross-sell, and long-term relationship buildingWhat You Bring5+ years of enterprise B2B sales experienceRequired experience selling into financial services, fintech, payments, or martechProven ability to navigate long, complex sales cycles with enterprise buyersExperience selling platforms or data-driven solutions (not just point tools)Strong communication skills and executive-level presenceHigh ownership mindset with robust internal collaboration skillsComfort operating in a fast-growing, evolving environmentThe 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.#J-18808-Ljbffr

📌 Enterprise Account Executive - $110,000 - $140,000 A Year (Winnipeg)
🏢 Flybits
📍 Winnipeg