Note: The job is a remote job and is open to candidates in USA. CheekyFit is an AI-powered fashion-technology company that helps fashion brands integrate artificial intelligence into their platforms and scale globally. The B2B SaaS Sales Executive will drive new business by prospecting, conducting discovery calls, delivering technical product demonstrations, and managing the full sales cycle through contract execution. The role also collaborates with marketing, product, and leadership teams to refine messaging, share market feedback, and support customer onboarding.
Responsibilities
- Driving new business and closing deals with fashion brands that can benefit from CheekyFit’s AI integrations
- Prospecting and qualifying leads
- Conducting discovery calls
- Delivering technical product demos
- Managing the full sales cycle from initial contact to contract execution
- Collaborating closely with marketing, product, and leadership teams to refine messaging
- Passing along valuable market feedback from client interactions
- Ensuring seamless customer onboarding
- Managing aggressive pipeline growth
- Executing consultative outreach
- Driving global brand adoption
Skills
- Strong B2B SaaS or technology sales experience, including cold outreach, pipeline management, and closing consultative enterprise deals
- Familiarity with fashion tech, e-commerce platforms, or AI-driven digital transformation solutions
- Proficiency in using CRM tools, sales engagement software, and pipeline tracking metrics to manage prospects effectively
- Excellent communication, presentation, and negotiation skills, with the ability to explain technical AI concepts to fashion brand decision-makers
- Proven ability to work autonomously in a fully remote environment, manage personal priorities, and achieve sales targets
- Comfortable working under an uncapped, high-reward commission-only compensation structure with strong self-discipline
- Pre-existing network of fashion brand founders, retail executives, or e-commerce directors is highly advantageous
- Commitment to transparent, ethical sales practices and building long-term customer relationships
Benefits
- Remote role
- Uncapped, high-reward commission-only compensation structure
Company Overview