Account Executive (Strategic)

Rain Technologies Inc.

About The Position

Rain is the world's first AI Financial Health Platform, serving 3.5 million employees at leading organizations like McDonald's, Marriott, and T-Mobile. Rain works in the background to optimize every employee's financial life to prevent shortfalls and build long-term stability. Backed by top investors including QED and Prosus, Rain has raised $150M in venture funding to fuel our next stage of hyper growth. As a Strategic Account Executive, you will be working in Rain's most ambitious market segment, targeting organizations with over 50,000 employees. This is a high-visibility, high-impact role where you will move beyond a transactional product sale to become a Trusted Advisor to the C-suite of the world’s largest employers. Your mission is to reposition Rain from a point solution for Earned Wage Access into a comprehensive financial health partner, navigating the most complex procurement environments in the HR tech space. You will work in lockstep with our senior executive team to architect and close landmark deals that define the future of our company.

Requirements

10+ years of experience in enterprise SaaS sales, with a proven track record of closing seven-figure deals within the Strategic or Global account segments
Mastery of complex sales methodologies (e.g., MEDDPICC, Challenger, or Value-Based Selling) and experience navigating procurement, security, and legal hurdles at 50,000+ employee organizations
Extensive background in HR tech, fintech, or employee benefits, allowing you to speak fluently to the pain points of human capital management leaders
Exceptional C-suite presence and communication skills, with the ability to distill complex financial products into compelling strategic narratives for executive audiences
Highly collaborative leader who knows how to marshal internal resources, including Product, RevOps, and Executive leadership, to move a deal across the finish line
Consistent history of meeting or exceeding $1M+ annual recurring revenue (ARR) quotas in a fast-paced, high-growth environment
Deep intellectual curiosity regarding financial health and motivated by the mission of improving the financial lives of millions of workers
Comfortable with ambiguity and possess the entrepreneurial spirit required to build a "Strategic" playbook while simultaneously executing on it
Bachelor’s degree in Business, Marketing, or a related field

Nice To Haves

MBA or advanced degree is preferred but not required

Responsibilities

Own the end-to-end sales strategy for a select portfolio of "Strategic" accounts with 50,000+ employees, managing long-term, high-stakes sales cycles
Lead complex, multi-stakeholder discovery sessions to align Rain’s financial health mission with the broader HCM and ESG objectives of Fortune 500 companies
Act as the primary architect for bespoke deal structures, collaborating with Legal, Finance, and RevOps to ensure solutions meet the rigorous demands of large-scale enterprises
Partner directly with Rain’s CEO and executive leadership team to leverage senior-level relationships and bring maximum resources to bear on top-tier opportunities
Develop and execute account-based marketing and sales plans in coordination with the Marketing and BDR teams to penetrate massive, global organizational structures
Build deep, lasting relationships with CHROs, CFOs, and VPs of Benefits, positioning Rain as an essential pillar of their employee value proposition
Coordinate with Channel Sales and Partnership teams to leverage existing HCM, payroll, and timekeeping ecosystems (e.g., Workday, SAP, ADP) within target accounts
Provide consistent, data-driven forecasting and pipeline updates to the executive team, offering insights into market trends and competitive dynamics at the top of the market
Champion the transition of Rain's market positioning from a tactical EWA tool to a holistic financial wellness platform through thought leadership and strategic storytelling