SkyLink · 2 weeks ago
Revenue Lead / Senior Sales IC for Complex Enterprise Sales
New York, NY, US
Full-time
Onsite
Senior Level, Lead/Staff
11+ years expSkyLink is building a corporate travel chatbot that enhances enterprise travel management. They are seeking a Revenue Lead / Senior Sales Individual Contributor to manage complex enterprise sales deals and convert early traction into sustainable revenue.
Artificial Intelligence (AI)SaaSTravel
Responsibilities
Own enterprise deals end-to-end, from first executive conversation through close
Build and maintain strong relationships with senior decision-makers across finance, operations, and technology
Partner with founders on early deals and progressively lead transactions independently
Navigate long, multi-stakeholder sales cycles with high deal complexity
Provide clear signal on deal dynamics, buyer motivations, and competitive positioning
Help define and refine:
Ideal customer profile
Deal qualification standards
Realistic sales cycles and ACVs
Represent the company in executive meetings, customer visits, and industry events
Travel as needed to support relationship-driven enterprise sales
Qualification
Required
Prior experience closing complex enterprise SaaS deals as a senior individual contributor
Demonstrated success at one or more of the following stages: $0 → $1M ARR, $1M → $10M ARR with similar deal sizes (i.e., $100K- $xxM) and sales motion
Comfort operating in founder-led sales environments with ambiguity and limited process
Strong executive presence, charisma, and rapport-building ability
A relationship-driven approach to enterprise sales, with an understanding that trust and credibility matter more than volume
Ability to clearly articulate: Typical deal sizes, Sales cycles, Buyer personas and signing authority
Willingness and ability to introduce former customers you have personally sold to
Positive backchannel references from former colleagues and customers
Active engagement in the enterprise ecosystem, including conferences and in-person relationship building
Preferred
Exposure to adjacent industries or problem spaces relevant to our customers
Benefits
Senior IC compensation with meaningful upside
Performance-aligned incentives tied to outcomes, not activity
Equity participation aligned with long-term value creation
Structure designed for individuals who are comfortable betting on themselves
Company
SkyLink
SkyLink is a unified travel management and collaboration platform that uses AI to automate trip management via email and chat.
51-200 employees
Funding
Current Stage
Growth StageTotal Funding
unknown2022-03-22Seed
Recent News
Business Travel News
2025-12-28
PhocusWire
2025-11-10
2025-11-10
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