CSO

Job Title

Chief Sales Officer (CSO) — GTM Leader (WealthTech / Capital Markets) | Hybrid (New York or Toronto)

Overview

DealMaker is building the infrastructure that makes online capital raising mainstream. We’re looking for a Chief Sales Officer to design and lead the next go-to-market engine—defining where the market is heading, translating that vision into a practical commercial strategy, and staying close to execution to ensure results. You’ll unify Sales, Marketing, Partnerships, and RevOps, drive new-issuer growth, and help establish retail capital as a mainstream financing category.

Required Skills

• Senior sales leadership (CSO/EVP/SVP-level) with ownership of new-business growth
• Proven GTM engine-building (not just inheriting an existing machine)
• Account-based selling and executive-level origination (CEO/CFO/board)
• Strong pricing/packaging, funnel economics, forecasting, and sales operations discipline
• Ability to build warm ecosystems (advisors, law firms, bankers, investors, founders, customers)

Nice to Have Skills

• Experience scaling revenue roughly $40M → $150M
• Partnerships-led distribution strategy and category education/demand creation
• Background selling in regulated, trust-dependent environments

Preferred Education and Experience

• 10+ years in commercial leadership with a track record hiring/developing high-performance teams
• Experience in fintech, capital markets, or adjacent B2B platforms preferred

Other Requirements

• Hybrid working model; location New York or Toronto
• Hands-on, low-ego operator comfortable working directly on accounts and critical deals

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