You’ll join Sales Executives on calls with prospects evaluating Oyster and existing customers expanding rapidly. You’ll guide the technical conversation — walking through cost breakdowns across 10+ countries, explaining how employment works in different jurisdictions, comparing benefits packages, and preparing implementation readiness plans that validate what needs to happen for a successful transition.
You’ll create templates, automations, and AI-powered tools that help the broader sales team self-serve on technical validation for smaller deals (e.g. automated benefits comparisons, country assets, risk calculators, value and champion decks).
For larger deals, you’ll build business case materials, test whether the right stakeholders are engaged through implementation readiness plans, and help the sales team navigate competitive situations with well-prepared positioning.
Product feedback loops, enablement for the sales team, and surfacing patterns from large deals.
Use data to inform improvements, enable the rest of the team on changes, and work to influence at the XFN level on projects from the SC roadmap.
Requirements
Customer facing/Consultative: Can influence a customer conversation about complex topics (compliance, payroll, tax, employment law) and make them feel clear and simple for the audience
Strong project management: Can scope and plan a multi-country project — validating requirements across stakeholders, surfacing risks, and preparing a clear brief for the team that executes the implementation
Comfortable with Automation & AI: Are comfortable using AI tools and automation to scale your own output, and can explain how you’ve done this before
Remote skills: Can work independently in a remote-first, async-heavy environment across multiple time zones
Are curious about global employment, HR, and payroll — even if you’re still building that knowledge
BONUS
Familiarity with HR and Payroll concepts (probation periods, termination types, time off, taxes, contributions)
BONUS
Experience with a structured sales methodology like MEDDICC
A reliable home internet connection (or be able to get one)
Fluent English language skills.
Benefits
Enjoy 40 days off per year (including holidays and vacation), or more if required by your country.
Access Plumm, our mental well-being service.
Each month, receive a wellbeing allowance in your ThanksBen wallet. Spend it on a wide range of options; see the benefits catalogue for ideas.
All new parents are eligible for at least three months’ paid leave, with job protection for up to 12 months or as required locally.
Receive a stipend for your laptop and home office equipment to get you set up quickly.