Web3 Startup Jobs in Canada

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. With a mission to empower businesses with more efficient and cost-effective financial solutions worldwide, Jeeves combines cutting-edge financial technology with exceptional team expertise to transform the business financial landscape. Jeeves has been recognized as one of The Information's 50 Most Promising Startups in 2023, as well as a Y Combinator Top Company 2021-2023 and won “Fintech of the Year" at the European Fintech Awards.Since graduating from Y Combinator in 2020, Jeeves has successfully raised over $380 million and is backed by top world-class investors including Andreessen Horowitz, Y Combinator, CRV, Tencent, Stanford University, Clocktower Ventures, and founders of more than 15 unicorns including David Velez (Nubank), Carlos Garcia (Kavak) and Sebastián Mejía (Rappi).

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.

Location: This role is based out of São Paulo, Brazil, and is a full-time position where it is required to come into our office at complexo JK Iguatemi (3 days/week). #LI-Hybrid

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 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.

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.

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.

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.

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, a serious methodology, and a team that expects excellence — we'd love to talk.We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses and identifying potential inconsistencies or verification signals in application materials based on available information. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.