Head of Sales, Brazil
Full-timeJob Overview
About the role
Jeeves is building the financial operating system for companies across Latin America — and Brazil is our fastest-growing, and most strategic market. We're looking for a Head of Sales to own how we win it.
This is not a seat-warmer role. You'll inherit a team that's already producing, a product that's already winning, and a market where we have more demand than we can currently cover. Your job is to turn that momentum into a dominant commercial machine — one that is unapologetically metrics-driven, methodology-rigorous, and AI-native.
You'll report directly to the Country Manager, Brazil, and partner with global leaders across Marketing, RevOps, Customer Success, and Product to shape how Jeeves goes to market in the region.
Why this role, why now
Brazil is Jeeves' clearest path to category leadership in LatAm. The AE team is performing, but we're under-covering the opportunity in front of us — you'll get to scale it from a position of strength, not from scratch. We have a strong point of view on how a modern sales org should run: rigorous methodology, clean pipeline data, disciplined forecasting, and AI as a true force multiplier. Your job is to execute that point of view in Brazil and set the bar for the rest of the region.
What success looks like in year one
- You've scaled the AE team meaningfully while improving — not sacrificing — productivity per rep.
- MEDDPICC (alongside the best of SPIN and Challenger) is embedded end-to-end: every deal, every forecast call, every QBR. Qualification is non-negotiable.
- Forecast accuracy is consistently within 10% of plan, and pipeline coverage sits at 3–4x of quota.
- The team is demonstrably AI-augmented: reps are faster at prospecting, sharper on calls, and better at multithreading complex deals.
- You've personally closed 3–5 strategic logos and built executive relationships Jeeves will leverage for years.
About the role
Jeeves is building the financial operating system for companies across Latin America — and Brazil is our fastest-growing, and most strategic market. We're looking for a Head of Sales to own how we win it.
This is not a seat-warmer role. You'll inherit a team that's already producing, a product that's already winning, and a market where we have more demand than we can currently cover. Your job is to turn that momentum into a dominant commercial machine — one that is unapologetically metrics-driven, methodology-rigorous, and AI-native.
You'll report directly to the Country Manager, Brazil, and partner with global leaders across Marketing, RevOps, Customer Success, and Product to shape how Jeeves goes to market in the region.
Why this role, why now
Brazil is Jeeves' clearest path to category leadership in LatAm. The AE team is performing, but we're under-covering the opportunity in front of us — you'll get to scale it from a position of strength, not from scratch. We have a strong point of view on how a modern sales org should run: rigorous methodology, clean pipeline data, disciplined forecasting, and AI as a true force multiplier. Your job is to execute that point of view in Brazil and set the bar for the rest of the region.
What success looks like in year one
- You've scaled the AE team meaningfully while improving — not sacrificing — productivity per rep.
- MEDDPICC (alongside the best of SPIN and Challenger) is embedded end-to-end: every deal, every forecast call, every QBR. Qualification is non-negotiable.
- Forecast accuracy is consistently within 10% of plan, and pipeline coverage sits at 3–4x of quota.
- The team is demonstrably AI-augmented: reps are faster at prospecting, sharper on calls, and better at multithreading complex deals.
- You've personally closed 3–5 strategic logos and built executive relationships Jeeves will leverage for years.
What you'll do:
- Own the numbers. Set ambitious but credible targets, manage to them relentlessly, and run a data-driven operating cadence — weekly pipeline reviews, forecast calls, QBRs, and performance dashboards that tell the truth.
- Run the methodology. Embed MEDDPICC, SPIN, and Challenger into how the team qualifies, sells, and forecasts. Shorten cycles and lift win rates through discipline, not hustle.
- Hire and develop world-class AEs. Build a team that operates with accountability, learns fast, and wins consistently. Raise the bar with every hire.
- Build an AI-native sales org. We expect every rep to be AI-augmented — using Claude, Gong, Clay, and modern CRM copilots as daily tools, not novelties. You'll set the standard and raise it every quarter.
- Sell alongside your team. Engage directly with strategic prospects and customers. Land and expand with CFOs, founders, and finance leaders — and coach your AEs to do the same.
- Shape GTM. Feed market signal back into Product, Marketing, Pricing, and RevOps. Help decide what we build, how we price it, and how we position it in Brazil.
- Build the operating system. Playbooks, onboarding, scorecards, ramp plans — own the infrastructure that lets the team scale without breaking.
Minimum Qualifications:
- 8+ years in B2B SaaS sales or business development, with 3+ years leading Account Executive teams.
- Fluent in Portuguese and English (written and verbal), Spanish language proficiency a plus.
- Proven track record of building and leading AE teams that consistently meet or exceed quota in a SaaS or subscription-based business.
- Deep expertise in structured sales methodologies — MEDDPICC, SPIN, Challenger, or similar — and demonstrated ability to embed them into how a team operates day-to-day. You have a point of view on qualification and you enforce it.
- Strong analytical and forecasting muscle. Comfortable in HubSpot, Salesforce, and BI tools; you live in dashboards, not gut feel.
- Hands-on experience using AI tools to drive sales productivity — prospecting, call intelligence, outreach personalization, CRM copilots. You can point to specific tools you've deployed and results you've gotten.
- Demonstrated success negotiating and closing complex, high-impact deals with C-level executives (CFOs, founders, partners).
- Strong executive communication and presentation skills, with the ability to articulate value to financial decision-makers.
- Fluent in Portuguese and English, written and verbal.
Nice to have:
- Background in high-growth fintech, payments, or financial services.
- Multi-market or cross-border commercial experience within LatAm.
- Operating experience in fast-scaling or early-stage companies.
- A network of transferable B2B relationships with mid-market and enterprise companies in Brazil (helpful, not required).
- Track record of building sales playbooks, onboarding programs, and scalable processes from the ground up.