Account Executive (Strategic)

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.

What you’ll do

• 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

Who you are

• 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

• You are a master of complex sales methodologies (e.g., MEDDPICC, Challenger, or Value-Based Selling) and have experience navigating procurement, security, and legal hurdles at 50,000+ employee organizations

• You have an extensive background in HR tech, fintech, or employee benefits, allowing you to speak fluently to the pain points of human capital management leaders

• You demonstrate exceptional C-suite presence and communication skills, with the ability to distill complex financial products into compelling strategic narratives for executive audiences

• You are a highly collaborative leader who knows how to marshal internal resources, including Product, RevOps, and Executive leadership, to move a deal across the finish line

• You have a consistent history of meeting or exceeding $1M+ annual recurring revenue (ARR) quotas in a fast-paced, high-growth environment

• You possess deep intellectual curiosity regarding financial health and are motivated by the mission of improving the financial lives of millions of workers

• You are comfortable with ambiguity and have the entrepreneurial spirit required to build a "Strategic" playbook while simultaneously executing on it

• You hold a Bachelor’s degree in Business, Marketing, or a related field; an MBA or advanced degree is preferred but not required

Compensation

$185,000 Base | $435,000-$450,000 OTE. Note this is a range and we take in a variety of factors when determining total compensation for the position.

How we care for our team:

• Flexible PTO

• Medical, Dental, Vision, Life, Disability coverage

• Maternal/Parental leave

• Monthly stipend

• Equity options

Diversity, Equity and Inclusion Commitments

As part of our dedication to the diversity of our workforce, Rain is committed to Equal Employment Opportunity and does not discriminate based on race, religion, color, national origin, ethnicity, gender, sex (including pregnancy), protected veteran status, age, disability, sexual orientation, gender identity, gender expression, or any unlawful criterion existing under applicable federal, state, or local laws. If you need assistance or accommodation due to a disability, you may contact us at [email protected].

What’s Next

Ensuring a smooth and enjoyable candidate experience is critical for us. Our interview process tends to take about 4 weeks to complete, but may fluctuate depending on the role. Learn more about our hiring process here. Don’t be afraid to let us know if you need more flexibility.