Sybill
Head of Sales
Building the revenue machine to scale Sybill from $1M to $10M ARR — systematizing founder-led sales into a repeatable outbound motion and establishing Sybill as the default Gong alternative for growth-stage B2B companies.
Sybill has proven the product. What it does not have is a revenue machine. The gap between $1M and $10M ARR is not a product gap — it is the absence of a structured outbound motion, a defined ICP, a sales methodology, a competitive positioning framework against Gong, and AEs who know how to replicate the founder's instinctive sales process. The 140% NRR is an asset that can fund an aggressive expansion motion — every retained dollar offsets CAC on new logos. The company needs a first sales leader who has built outbound infrastructure before, who understands how AI-native products are sold differently from traditional SaaS, and who can simultaneously hire, coach, and close while architecting the systems that will scale beyond them.
$6M ARR (outbound motion slower to convert; 2 AE hires take 60 days to ramp)
$8M ARR (outbound producing 50% of pipeline by Q3; partner channel contributing 15%)
$10M ARR (Gong displacement campaign outperforms; 1 enterprise deal >$200K ACV closes in Q4)
Core Opportunity
Sybill has proven product-market fit with 140% NRR and 10x ARR growth — but growth is structurally dependent on word-of-mouth with zero systematic pipeline generation. The gap between $1M and $10M ARR is not a product gap; it is the absence of a revenue machine.
Execution Thesis
Deploy systematized founder sales documentation, AI-powered outbound infrastructure, Gong displacement campaigns, and partner channel activation to deliver $6M–$10M ARR — building the repeatable revenue engine that funds the Series B narrative.
Production systems, not theory. Revenue captured, not demos given.