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
If you’re ready to build a category-defining commercial engine and lead from strategy through execution, apply now and let’s start the conversation.