Deal Commercial Strategy & Operations Lead

Role Description

Remote is solving modern organizations’ biggest challenge – navigating global employment compliantly with ease. We make it possible for businesses of all sizes to recruit, pay, and manage international teams. With our core values at heart and future-focused work culture, our team works tirelessly on ambitious problems, asynchronously, around the world.

What this job can offer you:

• A senior IC role with real strategic influence — you'll work directly with the Senior Manager to shape how the Deal Desk operates and evolves.
• The opportunity to lead cross-functional initiatives and drive meaningful process improvements across the Sales organization.
• A clear path towards people management as the team matures.
• A truly async, flexible work environment where ownership and proactivity are valued over process for its own sake.

Qualifications

• 5+ years of experience in Deal Desk, Sales Operations, Revenue Operations, or a related function in an Enterprise SaaS/B2B company required; previous Lead or Supervisor experience is a plus.
• A proven deal desk operator with a track record of handling complex, high-stakes situations across deal structure, pricing, and contract exceptions.
• Strong understanding of Quote-to-Cash processes, revenue recognition principles, and order management.
• Deep hands-on knowledge of Salesforce (SFDC) and CPQ systems, including troubleshooting and workflow optimization.
• Natural relationship builder with the ability to engage, influence, and collaborate effectively with senior stakeholders across Go-to-Market, Legal, and Finance.
• Data-driven and analytically sharp — you turn deal trends and operational signals into clear recommendations, not just observations.
• Excellent communicator with outstanding written and spoken English.
• Calm under pressure with strong prioritization instincts, able to keep the team unblocked during high-volume periods without dropping quality.
• Self-starter who thrives in a fast-paced, fully remote, and globally distributed environment.
• Demonstrates strong automation and AI capabilities.
• It's not required to have experience working remotely, but considered a plus.

Requirements

• Act as the team's operational leader and the Senior Manager's closest extension — the go-to for escalations, the standard-setter for quality, and the primary mentor for Associates and Specialists.
• Represent the Senior Manager in cross-functional forums with Sales VPs and Sales Leadership — aligning on Deal Desk priorities and surfacing team needs and blockers.
• Serve as a senior point of contact and escalation for complex deals, non-standard pricing requests, and contract exceptions.
• Oversee deal approval processes and pricing compliance, stepping in on escalations and exceptions that require senior judgment.
• Ensure the team maintains SLA standards, stepping in to unblock or resolve complex or time-sensitive cases as needed.
• Act as the eyes and ears of the Sales team — proactively identifying deal friction, recurring blockers, and emerging risks before they escalate.
• Own the working relationship with Legal and Finance on behalf of the Senior Manager — aligning on policy, setting expectations, and ensuring the team has the guidance needed to handle non-standard situations independently.
• Develop and maintain deal playbooks and sales enablement resources, ensuring the Sales team has the guidance they need before they need to ask.
• Build and scale automated workflows that reduce manual effort and allow the team to focus on higher-value work.
• Track Deal Desk performance metrics and deal trends, translating data into actionable recommendations and feeding directly into the Senior Manager's planning and prioritization.
• Act as the Senior Manager's operational extension — driving the Deal Desk improvement roadmap across processes, tooling, automation, and policy, and leading initiatives through to execution.
• Support month-end and quarter-end close operations to ensure smooth and accurate deal execution.

Benefits

• Work from anywhere.
• Flexible paid time off.
• Flexible working hours (we are async).
• 16 weeks paid parental leave.
• Mental health support services.
• Stock options.
• Learning budget.
• Home office budget & IT equipment.
• Budget for local in-person social events or co-working spaces.