Senior Sales Executive; AMER

Location

The Americas, Canada

Full time

Remote

Go To Market

The best jobs are often restricted to a few wealthy cities, but talent exists everywhere. Oyster set out to change this by launching a global employment platform that enables companies to hire, pay, and support talent anywhere.

We’re proof that a strong, engaged culture doesn't require an office. Since January 2020, Oyster has:

• 🌏 Built a distributed team of 400+ across 60+ countries
• 👩💻 Featured in Forbes as #9 in Flex Jobs Top 30 Companies for remote jobs
• 🌈 Formed a diverse leadership team and a workforce that’s 60% female
• 🏆 Earned top employee engagement scores
• 🦄 Raised $286 million; valued at $1.2 billion
• 💚 Achieved B Corp status in 2023

Our momentum shows the power of global employment, and we’re just getting started! If you want to help us drive change and work remotely, we’d love for you to apply!

Location: While this position is posted in a specific location, all of Oyster’s positions are fully remote and you can work from home. Forever. To create the best experience for this employee and to meet the business needs, this role requires you to be located within the Americas region with right-to-work status for the country you reside in.

We’re looking for a Senior Sales Executive (AMER) to drive growth by focusing on nurturing our largest customer accounts and turning high-potential prospects into long-term customers. This is a hands‑on role where you’ll lead high‑value, strategic deals and have a real impact on revenue, while helping shape how we work with our key accounts.

In this role, you’ll:

• Expand and build high-value customer relationships through land-and-expand strategies
• Deliver substantial net new revenue by managing and growing a portfolio of strategic accounts while converting new business leads
• Drive sophisticated commercial negotiations and customer acquisition with a consultative approach
• Build and maintain an exceptional sales pipeline using advanced methodologies like MEDDIC

As a senior individual contributor, you’ll work closely with Sales, Business Development, Customer Success, and Rev Ops to deliver results that matter for both customers and Oyster.

• Strategically convert high‑potential qualified leads into key business logos
• Collaborate with cross‑functional teams to identify and deliver high‑impact value for larger accounts.
• Leverage Salesforce and Gong for forecasting and insights
• Maintain exemplary account documentation and system hygiene
• Continuously develop skills to align with evolving product and market dynamics
• Role model the performance of core metrics aligned to effective opportunity growth and healthy book management
• Provide guidance and mentorship to junior sales team members, sharing best practices and sales techniques
• Support company‑wide projects and OKRs when required, in line with driving wider revenue team performance

• Commercial Performance
  • 4+ years of experience in both new business sales and account management
  • Proven track record of consistently meeting and exceeding quota, including success across complex, high-value accounts
  • Demonstrated success managing multi‑stakeholder sales cycles
  • Experience contributing to commercial initiatives, such as cross‑sell opportunities and partner‑led referrals
  • End-to-end sales experience, with a strong ability to close high-complexity opportunities
• Sales Methodology
  • Advanced proficiency in MEDDICC and 3 Why’s frameworks
  • Expertise in predictive pipeline management and strategic forecasting
  • Proven ability to design and implement complex lead qualification strategies
• Professional Capabilities
  • Demonstrated success in navigating complex organizational landscapes
  • Proven track record of building and maintaining executive-level relationships
  • Track record of leading cross‑functional initiatives
  • Expert in managing global, distributed sales environments
  • Ability to drive strategic change and mentor junior sales professionals
  • Coachability and demonstrated peer mentorship and coaching
• Communication
  • Exceptional strategic communication skills
  • Proven ability to articulate complex business value…