Head of Sales

About

Jeeves is a groundbreaking financial operating system built for global businesses that provides corporate cards, cross-border payments, and spend management software within one unified platform. The company operates across 20+ countries including Brazil, Canada, Colombia, Mexico, the United Kingdom, across Europe, and the United States, and serves over 5,000 clients ranging from venture-backed startups to SMBs around the world. Jeeves combines cutting-edge financial technology with exceptional team expertise to transform the business financial landscape. Recognized as one of The Information's 50 Most Promising Startups in 2023, a Y Combinator Top Company 2021-2023, and winner of “Fintech of the Year" at the European Fintech Awards.

Since graduating from Y Combinator in 2020, Jeeves has raised over $380 million and is backed by top investors including Andreessen Horowitz, Y Combinator, CRV, Tencent, Stanford University, Clocktower Ventures, and founders of more than 15 unicorns.

Why this role, why now

Brazil is Jeeves' clearest path to category leadership in LatAm. The AE team is performing but under-covering the opportunity. The role is to scale from a position of strength with a rigorous, metrics-driven, methodology-focused, and AI-native sales organization.

What you'll do

• Own the numbers with ambitious targets and data-driven cadence.
• Run and embed MEDDPICC, SPIN, and Challenger sales methodologies.
• Shorten sales cycles and improve win rates through discipline.
• Hire and develop accountable, fast-learning, winning AEs.
• Build an AI-native sales org using tools like Claude, Gong, Clay, and CRM copilots.
• Sell alongside your team engaging strategic prospects and customers.
• Coach AEs to land and expand with CFOs, founders, and finance leaders.
• Shape go-to-market strategy with Product, Marketing, Pricing, and RevOps.
• Build scalable operating systems including playbooks, onboarding, scorecards, and ramp plans.

What success looks like in year one

• Meaningful AE team scaling with improved productivity.
• Full embedding of MEDDPICC, SPIN, and Challenger methodologies.
• Qualification is non-negotiable.
• Forecast accuracy within 10% of plan and pipeline coverage at 3–4x quota.
• AI-augmented team with faster prospecting, sharper calls, and better multithreading.
• Personally closed 3–5 strategic logos and built executive relationships.

Minimum Qualifications

• 8+ years in B2B SaaS sales or business development with 3+ years leading AE teams.
• Fluent in Portuguese and English; Spanish proficiency a plus.
• Proven track record of AE teams meeting or exceeding quota in SaaS.
• Deep expertise in MEDDPICC, SPIN, Challenger or similar methodologies.
• Strong analytical and forecasting skills; proficient with HubSpot, Salesforce, BI tools.
• Hands-on experience with AI sales productivity tools.
• Success negotiating and closing complex deals with C-level executives.
• Strong executive communication and presentation skills.

Nice to have

• Background in high-growth fintech, payments, or financial services.
• Multi-market or cross-border commercial experience in LatAm.
• Operating experience in fast-scaling or early-stage companies.
• Network of B2B relationships with mid-market and enterprise companies in Brazil.
• Experience building sales playbooks, onboarding programs, and scalable processes.

Why Jeeves

We're building the financial OS that LatAm companies have been waiting for, at the speed and ambition of a company that plans to win. If you want to own how a category-defining fintech wins Brazil with modern tools, serious methodology, and a team that expects excellence, we'd love to talk.