Senior Director of Sales

Senior Director of Sales

Rain is hiring a Senior Director of Sales to lead our global sales organization. This role is responsible for driving new revenue across all segments and regions. You will set the commercial direction of the organization and ensure consistent execution against company targets.

You will oversee sales planning, forecasting accuracy, resource allocation, and performance management across the team. This includes determining where we invest, how we structure coverage, and how opportunities move from initial engagement through close and expansion. You will partner closely with executive leadership to ensure revenue plans are grounded in product readiness, regulatory realities, and market demand.

As Senior Director of Sales, you will elevate the quality and consistency of execution across complex sales cycles. You will strengthen how we navigate multi-stakeholder negotiations, structure long-term commercial relationships, and expand strategic accounts over time.

This is a global leadership role with direct accountability for revenue outcomes and requires comfort operating at both strategic and operational levels within complex infrastructure sales environments.

The Impact You Will Have

• Help take a successful team to the next level by defining and executing on an 12 - 24 month vision that unlocks further global expansion and continues to improve on core business metrics
• Raise the performance ceiling of the sales organization by improving win rates, shortening sales cycles, and increasing average deal size
• Expand and deepen executive-level relationships across fintechs, platforms, and financial institutions
• Increase consistency in how complex, multi-stakeholder deals are navigated and closed
• Strengthen commercial leverage in negotiations, pricing strategy, and long-term partnership structures
• Improve talent density across the team through strong hiring, coaching, and performance management
• Create greater visibility and confidence in revenue trajectory at the executive and board level
• Create organizational clarity around targets, coverage, and performance expectations while ensuring tight coordination with Product, Marketing, RevOps, Compliance, Legal, and Operations
• Shape the renewal and expansion motion to drive stronger customer LTV beyond the initial contract, including influencing how success metrics, pricing structures, and executive relationships are managed post-close
• Help position Rain as the long-term infrastructure partner within its most strategic accounts

What We're Looking For

• 10+ years of enterprise sales experience, with substantial leadership experience in fintech, payments, or financial infrastructure
• Deep familiarity with stablecoins, cross-border payments infrastructure, and card issuing ecosystems
• A demonstrated track record of owning significant annual revenue targets and delivering consistent growth across multiple years
• Experience leading high-performing sales organizations through different stages of scale, including building structure, accountability, and performance management systems
• Experience in senior roles at both large enterprises and startup or scale-up companies. Demonstrated ability to identify process improvements, build scalable solutions, and thrive in fast-moving, iterative environments.
• Existing network of crypto, payments, and fintech relationships to accelerate outbound pipeline generation and provide warm entry points into high-priority accounts
• Deep experience closing complex platform or infrastructure agreements involving executive, product, legal, technical, and compliance stakeholders
• Strong commercial judgment across pricing, negotiation strategy, and long-term partnership structuring
• Proven ability to operate effectively in regulated environments and navigate sophisticated procurement processes
• Operational strength across forecasting, performance management, hiring, and organizational planning
• Executive presence and credibility with C-level buyers and strategic partners
• Clear, disciplined communicator who can translate technical capabilities into compelling business value

Things that enable a fulfilling, healthy and happy experience at Rain:

Unlimited time off: Unlimited vacation can be daunting, so we require Rainmakers to take 10 days minimum for themselves.

Flexible working: We support a flexible workplace – work from home, come into an office, or both. We want everyone to work in an environment where they're their most confident and productive selves. New Rainmakers receive a stipend to set up a comfortable home workspace.

Easy to access benefits: For US Rainmakers, we cover 95% of your health, dental, and vision plan costs and 90% for your dependents, plus a 100% company-subsidized life insurance plan.

Retirement goals: Plan for the future with confidence. We offer a 401(k) with a 4% company match.

Equity plan: Every Rainmaker gets an equity option plan so we all benefit from our success.

Health and Wellness: High performance begins from within. Rainmakers receive a monthly stipend to be used for eligible health and wellness spending like gym memberships/fitness classes, massages, acupuncture - whatever recharges you!

In-office meals: Rainmakers working from the office enjoy lunch and dinner on us, covered with a DoorDash credit.

Team summits: Summits play an important role at Rain. Time together helps us build relationships and a common destiny. Expect team and company offsites, both domestic and international.