Probook is building in a greenfield, unsaturated space, defining how GenAI is applied in a massive legacy industry. Every outbound conversation is market discovery, every experiment shapes how we win. As our first SDR, you won’t just be booking meetings - you’ll help write the playbook for how an entire industry modernizes.
We’re assembling one of the most talent-dense teams in NYC and If you want to build your career as an operator - not just a salesperson - this is your chance to sit at the center of it.
What you’ll do
Own outbound from scratch: research, prospect, and break into high-value accounts.
Rapidly test channels, sequences, and messaging to figure out what works.
Feed insights from the market directly into product and strategy.
Work hand-in-hand with founders to define how sales at Probook scales.
Move fast, wear multiple hats, and help us figure out the unknowns of 0 → 1.
What we’re looking for
0 - 3 years of experience
Hungry to learn and build — you care about company-building, not just closing deals.
Gritty, scrappy, and energized by rejection and iteration.
Strong communicator who can balance execution with strategic thinking.
Comfortable with intensity: 100% in-office, 6 days/week — you want to be in the room.
Why join us
Build from the ground up in a category-defining company applying GenAI to a legacy industry.
Founding-level seat at a Sequoia-backed startup, working directly with leadership.
Exposure to every part of the business: sales, product, recruiting, strategy.
Learn how a zero-to-one startup scales — and build the foundation to move into operator or strategy roles as we grow.
Comp
90 - 110K + Equity + Bonuses
1K monthly food and wellness stipend
Full Benefits (dental, health, vision)
Unlimited PTO
Office Perks: Hang board (for climbers), Office dog, snacks, coffee, espresso, team lunches and dinners.
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