Revenue Lead / Senior Sales IC for Complex Enterprise Sales

Skylink • New York, NY

4d

About The Position

We are hiring a Revenue Lead / Senior Sales Individual Contributor to own complex enterprise deals and help convert early traction into repeatable revenue. This role sits between founder-led sales and a future scaled go-to-market function. You will work closely with the founders, engage directly with senior enterprise stakeholders, and play a critical role in shaping how revenue is generated at this stage of the company. This is a senior, high-judgment IC role with material ownership, autonomy, and visibility.

Requirements

• 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

Nice To Haves

• Exposure to adjacent industries or problem spaces relevant to our customers

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

Benefits

• Senior IC compensation with meaningful upside
• Performance-aligned incentives tied to outcomes, not activity
• Equity participation aligned with long-term value creation

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed