Senior Sales Executive (AMER)

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 FlexJobs 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

• Prospect for new business opportunities, which may include limited amounts of travel to events or prospect offices

As a senior individual contributor, you’ll work closely with Sales, Business Development, Customer Success, and RevOps 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.

• Generating pipeline through prospecting activities, including cold calls, emails, LinkedIn, and some travel to events

• 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 sales experience with a strong preference for Sales Executives with 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 propositions

  • Track record of transforming customer challenges into strategic solutions

• Motivational Drivers

  • Demonstrated leadership in driving systemic change

  • Proven passion for scaling global business impact

  • Customer-centric mindset focused on sustainable, healthy growth and relationship strategies

Bonus Qualifications:

• Experience in the EOR industry or working with HR buyers would be a plus

• Experience in consultative sales transformation

• Strong, existing industry relationships

You'll also need

• A reliable home internet connection (or be able to get one).

• Fluent English language skills.

Our values guide the work we do, the decisions we make, and the culture that makes us special. We make it happen. We drive change. We build and give trust, and we are a united team.

Our mission is to create a more equal world, one global hire at a time. Everything we do ladders up to our mission, and that doesn’t just mean building software. We develop programs, participate in workshops, and create dedicated teams to ensure we successfully support companies and knowledge workers in this new world of work. 

We embrace asynchronous communication and collaborative work and share our practices in the Oyster Public HQ to help other global teams learn from our experiences.

With diverse locations, cultures, and needs, we created How YOU Work; a program supporting your whole human experience at Oyster:

• Work from anywhere: Oyster has no borders or HQ. As long as work is timely, your team is supported, and you're authorized to work where you live, you can work from anywhere.

• Paid time off: Enjoy 40 days off per year (including holidays and vacation), or more if required by your country.

• Mental health support: Access Plumm, our mental well-being service.

• Wellbeing allowance: Each month, receive a wellbeing allowance in your ThanksBen wallet. Spend it on a wide range of options; see the benefits catalogue for ideas.

• Flexible parental leave: All new parents are eligible for at least three months’ paid leave, with job protection for up to 12 months or as required locally.

• WFH stipend: Receive a stipend for your laptop and home office equipment to get you set up quickly.

We embrace diverse perspectives and intentionally build our product and company with an inclusive, global mindset. We encourage you to apply, even if you don’t meet every criterion, and are committed to a trust-based, thriving environment.

Oyster is committed to ensuring equal opportunity of employment for qualified persons with disabilities and actively fosters an inclusive work environment. If you require reasonable accommodations throughout the recruiting process, please email [email protected] with the subject line: Interview Accommodations.

Our available positions are on our careers page. Our team will only contact you from an @oysterhr.com email, and we will never ask for money as part of an interview process or job offer. If you receive a suspicious email about Oyster jobs or are directed to a site other than www.oysterhr.com/careers, please report it via our Compliance and Ethics Helpline.