Caddie AI
Job Description
Caddie is hiring on behalf of a fast-growing, AI-powered workforce management company based in New York.
Location:
New York, NY (Hybrid, 2–3 days/week in office near Bryant Park)
Base Salary:
$130,000 – $150,000 USD
On-Target Earnings (OTE):
Competitive (base + commission)
Overview Our client is redefining how companies manage and understand their people using AI. Recognized as one of the fastest-growing software companies in the US, they are building a modern platform that helps organizations unify processes, gain deep workforce insights, and operate more efficiently.
Role You’ll be responsible for running full-cycle sales motions across mid-market accounts, from outbound prospecting through close. You’ll work closely with senior leadership to refine deal strategy, pricing, and sales processes as the company continues to scale.
This is a hands‑on role for someone who wants to build, not just maintain, a sales motion.
What You’ll Do
Own and execute the full sales cycle for mid‑market accounts
Prospect through outbound outreach, discovery, and qualification
Lead product demos, negotiations, and contract close
Navigate increasingly complex buying committees as deal sizes grow
Develop deal strategy, pricing, and negotiation plans
Build and maintain strong relationships with prospects, customers, and internal stakeholders
Consistently meet or exceed quarterly and annual revenue targets
Accurately track pipeline, activity, and forecasts in Salesforce
Collaborate closely with leadership to mature the mid‑market sales motion
What We’re Looking For
Required Experience
5–10 years of experience as an Account Executive selling B2B SaaS
Proven success in Series A, B, or C startup environments
Experience closing mid-market deals end to end
Track record of consistent quota attainment or overperformance
Experience closing $20K+ ACV deals (typical range $15K–$60K)
Strong negotiation, deal structuring, and pricing experience
Ideal Profile
Experience selling full-UI SaaS platforms (e.g., CRMs, project management tools, ERPs)
Comfort adapting sales motions as segments and buyer complexity evolve
Strong executive presence and communication skills
High emotional intelligence with the ability to build trust across stakeholders
Hands‑on, roll‑up-your-sleeves mindset
High energy, disciplined, and self‑motivated
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Location:
New York, NY (Hybrid, 2–3 days/week in office near Bryant Park)
Base Salary:
$130,000 – $150,000 USD
On-Target Earnings (OTE):
Competitive (base + commission)
Overview Our client is redefining how companies manage and understand their people using AI. Recognized as one of the fastest-growing software companies in the US, they are building a modern platform that helps organizations unify processes, gain deep workforce insights, and operate more efficiently.
Role You’ll be responsible for running full-cycle sales motions across mid-market accounts, from outbound prospecting through close. You’ll work closely with senior leadership to refine deal strategy, pricing, and sales processes as the company continues to scale.
This is a hands‑on role for someone who wants to build, not just maintain, a sales motion.
What You’ll Do
Own and execute the full sales cycle for mid‑market accounts
Prospect through outbound outreach, discovery, and qualification
Lead product demos, negotiations, and contract close
Navigate increasingly complex buying committees as deal sizes grow
Develop deal strategy, pricing, and negotiation plans
Build and maintain strong relationships with prospects, customers, and internal stakeholders
Consistently meet or exceed quarterly and annual revenue targets
Accurately track pipeline, activity, and forecasts in Salesforce
Collaborate closely with leadership to mature the mid‑market sales motion
What We’re Looking For
Required Experience
5–10 years of experience as an Account Executive selling B2B SaaS
Proven success in Series A, B, or C startup environments
Experience closing mid-market deals end to end
Track record of consistent quota attainment or overperformance
Experience closing $20K+ ACV deals (typical range $15K–$60K)
Strong negotiation, deal structuring, and pricing experience
Ideal Profile
Experience selling full-UI SaaS platforms (e.g., CRMs, project management tools, ERPs)
Comfort adapting sales motions as segments and buyer complexity evolve
Strong executive presence and communication skills
High emotional intelligence with the ability to build trust across stakeholders
Hands‑on, roll‑up-your-sleeves mindset
High energy, disciplined, and self‑motivated
#J-18808-Ljbffr