Senior Deal Strategy & Operations Specialist

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 our new hire, this role requires you to be based within +2 / -6 UTC.

Role Summary

Deal Strategy is the commercial engine of Oyster's sales motion. We prioritise and progress the deals that grow revenue while protecting our margins and managing legal and financial risk.

Our goal is to scale the function: moving routine support to automated, guardrail-driven, self-serve processes and reserving high-touch attention for our largest, most complex deals. As our Senior Deal Strategist, you'll run the day-to-day engine - reviewing pricing and discount requests against tiered guardrails with FP&A, triaging T&C and commercial-agreement redlines with Legal, and handling deposit-waiver, payment-term, payment-method and credit-check exceptions with Treasury. You'll be the single intake point that keeps deals moving fast and consistently.

As Oyster moves to a global support model, coverage should follow the deals.

Key Responsibilities

• Own the Deal Strategy intake board: review, approve, reject, or route requests against guardrails or triage where net new

  • Triage and process T&C and commercial-agreement redlines with Legal support including inserting pre-agreed custom clauses into order forms.

  • Handle deposit-waiver, payment-term, payment-method other Treasury exceptions with Treasury, weighing ROI and credit risk.

• Review order forms for pricing, currency and billing accuracy before close.

• Prioritise deals by $ impact (MRR), close date and risk exposure (credit, legal, compliance).

• Maintain the clause library and pre-approved pricing/terms playbooks so reps can self-serve standard cases.

• Run XFN taskforces for our largest deals and keep XFN blockers moving.

• Track and report Deal Approval metrics (time-to-decision, % self-serve vs high-touch, rework/reroute rate); use the data to propose guardrail tweaks.

• Design and evolve guardrail frameworks and exception-handling processes; drive adoption cross-functionally

• Design enablement programs for large deals and competitive positioning topics

Core Requirements

• Can independently own day-to-day deal exceptions in a B2B environment — e.g. 2+ years Deal Desk, RevOps, commercial finance, sales ops, or commercial-contracts work.

• Strong grounding in the legal and finance mechanics of deals — confident evaluating T&C/commercial-agreement redlines, deposit waivers, payment-term/method exceptions, and credit risk, and partnering closely with Legal, Treasury and FP&A.

• Hands-on ownership of pricing/discount approvals or commercial exception handling.

• Sound commercial judgment — weighs growth, margin, credit, legal and competitive risk and makes a defensible call.

• Excellent async, documentation-first communication across global, XFN stakeholders.

• [BONUS] Using data/AI to surface deal insights and automate approval flows

• [BONUS] EOR / global-employment knowledge is a plus but fully trainable here — we're prioritising legal/finance deal expertise.

• [BONUS] Background in management consulting, investment banking, or corporate finance

You'll also need

• A reliable home internet connection and fluency in both written and spoken English

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.