Sales Director, Americas

Oyster; Toronto; Remote; CAD 130,000 - 180,000; Full time

Job summary

Oyster is seeking a strategic Sales Director for the Americas to drive growth and enhance operational effectiveness in a fully remote environment. The ideal candidate will possess extensive SaaS sales leadership experience and excel in creating data-informed strategies while fostering a collaborative and inclusive work culture.

Benefits

40 days paid time off

Mental health support

Flexible parental leave

Work-from-home stipend

Wellbeing allowance

Qualifications

• 10 years of SaaS sales leadership experience required.
• Experience in a remote-first organization is a plus.
• Demonstrated success in pipeline generation and revenue targets.

Responsibilities

• Define and execute regional strategy for growth.
• Drive forecast accuracy and reporting through Salesforce.
• Lead a hybrid team and develop a high-performing sales culture.

Skills

SaaS sales leadership

Pipeline generation strategies

Data analysis

Coaching and development

Collaboration

Tools

Salesforce

Job description

One platform a whole world of opportunity

Right now the best jobs are limited to people in a handful of the worlds 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. Were proof that companies dont need an office to create a highlyengaged culture. Since the companys inception in January 2020 Oyster has :

Created a fullydistributed 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 thats 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 employmentand were just getting started! If you want to change the world with Oyster and be empowered to work remotely while doing so wed love for you to apply!

Location : While this position is posted in a specific location all of Oysters 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 Oysters presence in a less mature but highpotential market and will own both new business and expansion revenue across the region. Youll lead a hybrid team of managers and ICs act as a key member of the global revenue leadership team and partner crossfunctionally to build a highperforming valuesled and datainformed sales engine.

Were looking for a commercial leader with a proven ability to lead through change collaborate across global functions and bring clarity and momentum to complex gotomarket environments. If youre energized by building in white space influencing at the executive level and developing highperforming sales culturesthis role is for you.

Key Responsibilities

As Sales Director AMER youll be responsible for defining and executing the regional strategy to achieve Oysters ambitious growth and retention goals. Reporting to the Chief Revenue Officer youll lead a distributed team of sales managers and senior sellers across the Americas region and drive close alignment with crossfunctional partners across Product Finance Marketing Sales Ops and Customer Success.

Own and evolve the AMER gotomarket 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 insightdriven 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 feedbackrich performance culture

Lead coach and develop a team of highperforming managers and ICs with a focus on execution engagement and growth

Build a resilient and inclusive culture that reflects Oysters values and helps people do the best work of their lives

Be a visible empathetic leader through changemodeling agility humility and courage

Champion a coachingled approach that emphasizes development and autonomy

Crossfunctional 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 companywide 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

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

Experience scaling sales in a remotefirst globally distributed organization

Demonstrated success leading teams selling to SMB and MidMarket customers in a competitive fastmoving 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 decisionmaking 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 crossfunctionally to improve internal processes and unlock customer value

Exceptional communication coaching and storytelling skillsable to motivate align and influence globally

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

Teamfirst mentality strong bias for action and the ability to bounce back from failure with insight and energy

BONUS Experience in a highgrowth scaleup environment especially during gotomarket transitions

Youll also need...

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

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 worldone global hire at a time. Everything we do ladders up to our missionand that doesnt 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 workand 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 weve 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 HQless company. As long as your work gets done on time your team has the support they need and youre authorized to work where you live the world is truly your Oyster.

Paid time off : Were all about taking breakswe 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 wellbeing 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; well 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 weve intentionally built our product and our company with an inclusive global mindset. We know from experience that people from underrepresented groups often dont apply for roles they dont feel they meet all the criteria for. Were committed to elevating talent by creating a trustbased environment where we can all thrive together. So if you think you have what it takes but dont necessarily check every single box please consider applying. Wed 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 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 @ 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 domainwhere someone is claiming to be a part of our recruitment team or are directed to anywhere other than to view our available jobswe encourage you to submit a report through our Compliance and Ethics Helpline.

Required Experience :

Director

Key Skills

Employment Type : Full-Time

Experience : years

Vacancy : 1

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