✨ One platform, a whole world of opportunity

Right now, the best jobs are limited to people in a handful of the world’s wealthiest cities, yet brilliant people are everywhere. Driven to overturn the status quo and distribute opportunities equally around the world, Oyster launched its global employment platform to help companies hire, pay, and care for talent anywhere.

When it comes to global employment, we walk the walk. We’re proof that companies don't need an office to create a highly-engaged culture. Since the company’s inception in January 2020, Oyster has:

🌏 Created a fully-distributed, vibrant team of 500+ employees across 60+ countries

👩‍💻Featured in Forbes having ranked #9 in Flexjobs Top 30 Companies for remote jobs

🌈 Established a diverse leadership team and an employee base that’s 60% female

🏆 Achieved one of the highest employee engagement scores in its class

🦄 Raised $286 million to date, with a current valuation of $1.2 billion!

💚 B Corp status achieved in 2023

Our momentum speaks to the power of global employment—and we’re just getting started! If you want to change the world with Oyster and be empowered to work remotely while doing so, 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 our new hire this role does require that you be based within -8 / -5 UTC.

Role Overview

Oyster is hiring a seasoned and strategic Sales Director to lead our Americas sales organization through the next phase of growth. This role is critical to scaling Oyster’s presence in a less mature but high-potential market, and will own both new business and expansion revenue across the region. You’ll lead a hybrid team of managers and ICs, act as a key member of the global revenue leadership team, and partner cross-functionally to build a high-performing, values-led, and data-informed sales engine.

We’re looking for a commercial leader with a proven ability to lead through change, collaborate across global functions, and bring clarity and momentum to complex go-to-market environments. If you're energized by building in white space, influencing at the executive level, and developing high-performing sales cultures—this role is for you.

Key Responsibilities

As Sales Director, AMER, you’ll be responsible for defining and executing the regional strategy to achieve Oyster’s ambitious growth and retention goals. Reporting to the Chief Revenue Officer, you’ll lead a distributed team of sales managers and senior sellers across the Americas region, and drive close alignment with cross-functional partners across Product, Finance, Marketing, Sales Ops, and Customer Success.

Strategy

• Own and evolve the AMER go-to-market strategy, adapting structure, tactics, and resourcing to regional market maturity and opportunity

• Identify whitespace and develop tailored plays to expand reach within our ICP, across both new business and expansion

• Deliver repeatable pipeline generation strategies and rigor across all stages of the funnel

• Leverage data to continuously iterate on strategy and improve sales effectiveness and efficiency

• Translate company priorities into regional sales plans with clear objectives, forecasting discipline, and aligned incentives

Performance & Operational Leadership

• Drive quota attainment, Net Dollar Retention, and win rates through strong sales process and leadership discipline

• Oversee accurate, insight-driven forecasting and reporting through Salesforce and associated tooling

• Use performance data to coach managers and sellers, improve funnel conversion, and inform enablement

• Set the tone for a proactive, accountable, and feedback-rich performance culture

People Leadership & Culture

• Lead, coach, and develop a team of high-performing managers and ICs, with a focus on execution, engagement, and growth

• Build a resilient and inclusive culture that reflects Oyster’s values and helps people do the best work of their lives

• Be a visible, empathetic leader through change—modeling agility, humility, and courage

• Champion a coaching-led approach that emphasizes development and autonomy

Cross-functional Partnership

• Collaborate with Sales Ops, Revenue Acceleration, Product, Marketing, Finance, Legal, and Customer Success to remove friction and accelerate deals

• Act as the voice of the AMER field in company-wide planning and GTM decisions

• Establish strong feedback loops to share market intel, product insights, and customer needs with internal teams

• Influence senior stakeholders across time zones with clarity and credibility

Minimum Requirements

• 10+ years of SaaS sales leadership, including experience leading managers and managing managers

• Experience scaling sales in a remote-first, globally distributed organization

• Demonstrated success leading teams selling to SMB and Mid-Market customers in a competitive, fast-moving environment

• Direct experience with HR Tech, with strong commercial understanding of the buyer landscape

• Proven success building and executing pipeline generation strategies and consistently delivering against revenue targets

• Deep experience managing performance through Salesforce and building scalable processes with related GTM tooling

• Strong analytical and decision-making skills, with the ability to synthesize complex data into clear strategies

• Track record of leading teams through change and navigating ambiguity with calm and confidence

• Demonstrated ability to collaborate cross-functionally to improve internal processes and unlock customer value

• Exceptional communication, coaching, and storytelling skills—able to motivate, align, and influence globally

• A passion for inclusion and belonging, and a leadership style grounded in trust and humility

• Team-first mentality, strong bias for action, and the ability to bounce back from failure with insight and energy

• [BONUS] Experience in a high-growth scale-up environment, especially during go-to-market transitions

You'll also need...

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

• Fluent English language skills

🦪 How we work together at Oyster

Our values guide the work we do, the decisions we make, and the culture that makes us special. We elevate talent. 🙌 We build trust. 🤝 We thrive together. 🌍

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 we share how we work in the Oyster Public HQ —to help other global teams learn from our experiences.

💌 How YOU work

Different countries have different statutory benefits, different cultures have different norms, and different people have different needs! In order to best support and encourage our diverse team, we’ve created How YOU Work; a program of policies, practices, and perks to support your whole human experience as an employee at Oyster.

• Work from anywhere: Oyster is a borderless, HQ-less company. As long as your work gets done on time, your team has the support they need, and you're authorized to work where you live, the world is truly your Oyster.

• Paid time off: We’re all about taking breaks—we all need it. Oyster provides employees with 40 days off each year, which includes public/bank holidays and vacation/holiday leave (unless your country mandates more).

• Mental health support: We consider your mental health a top priority. We offer access to Plumm, a mental well-being service, to support your mental health.

• Wellbeing allowance: Each month, Oyster will top up your ThanksBen wallet with a wellbeing allowance. You can get pretty much anything that your heart desires! ThanksBen offers a wide array of options for spending your wellbeing allowance. Check out their benefits catalogue here for inspiration.

• Flexible parental leave: Families are created in lots of different ways. Our parental leave policy applies to all employees who are becoming parents, regardless of how they become a parent. Oysters are eligible for a minimum of three months of paid parental leave and your job will be held for 12 months (or longer if required by local jurisdiction).

• WFH stipend: Stipend to spend on your laptop and any other equipment you need for your home office; we'll get you up and running in no time!

✨ The best jobs should be available to everyone

At Oyster, we celebrate a variety of perspectives and experiences and we’ve intentionally built our product and our company with an inclusive, global mindset. We know from experience that people from underrepresented groups often don’t apply for roles they don’t feel they meet all the criteria for. We’re committed to elevating talent by creating a trust-based environment where we can all thrive together. So if you think you have what it takes, but don’t necessarily check every single box, please consider applying. We’d love to hear how you might contribute to our mission and our team.

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 jobs@oysterhr.com with the subject line: Interview Accommodations.

Our available positions are published on our careers page and should you be invited to interview with us, our recruitment team will only ever contact you directly from an @oysterhr.com email address. We will never ask you to send us money as part of a job offer. If you receive a suspicious email relating to opportunities at Oyster from any other email domain where someone is claiming to be a part of our recruitment team, or are directed to anywhere other than www.oysterhr.com/careers to view our available jobs we encourage you to submit a report through our Compliance and Ethics Helpline.