Director of CDN Sales (Fully Remote)

CacheFly•Chicago, IL

43d•Remote

About The Position

CacheFly powers fast, secure content delivery across the globe. We are a performance-driven, remote-first technology company that values ownership, accountability, and speed. You will lead CacheFly’s revenue organization across new business acquisition, onboarding, retention, and expansion. Manage Account Executives (AE), Account Managers (AM), and Customer Success (CS) to deliver predictable, profitable Annual Recurring Revenue growth through disciplined execution, coaching, and cross-functional alignment.

Requirements

5+ years of sales leadership experience overseeing AEs and/or AMs in B2B technology.
Background in CDN, cloud, networking, or technical infrastructure required.
Proven ability to build and scale a structured sales operating cadence.
Demonstrated success improving deal quality, win rates, and pipeline discipline.
Strong commercial acumen (pricing, negotiation, forecasting).
Excellent coaching, communication, and cross-functional collaboration skills.
Comfortable working directly with Engineering and Operations on technical deals.
Highly organized, data-driven, and effective in a remote-first environment.
Up to 25% travel for industry events, key customer and team meetings.

Responsibilities

Team Leadership: Build a high-performance environment grounded in preparation, ownership, accountability and continuous improvement. Manage and develop AEs, AMs, and CS. Establish clear expectations, coaching rhythms, and performance standards.
Recurring Revenue Growth: Drive consistent outbound, inbound qualification, discovery, pricing, and POC execution. Ensure AEs generate high-quality pipeline aligned to Ideal Customer Profiles (Media & Entertainment, Gaming, Ad Tech).
Deal Execution: Improve deal quality, deal size, and win rates by enforcing structured discovery, technical scoping, documented success criteria, and disciplined follow-up. Ensure trial accounts have defined timelines, technical requirements, and success metrics. Partner with Engineering and Operations to remove blockers and accelerate adoption.
Customer Lifecycle: Oversee the AE to AM transition process to ensure smooth onboarding, early usage ramp, and customer alignment during the first six months. Partner with AMs to identify risk, monitor usage trends, and support expansion opportunities. Ensure renewal forecasting and expansion pipelines are accurate and well-documented.
Forecasting & Reporting: Own pipeline accuracy, forecasting discipline, and weekly sales meetings. Provide clear, data-driven visibility to executive leadership.
Process Excellence: Implement standardized sales processes for out bounding, lead routing, discovery, pricing, POC execution, onboarding, and renewals. Enforce CRM hygiene and documentation standards.
Market & Competitive Insight: Stay current on CDN, cloud, networking, and performance infrastructure trends. Equip the team with competitive positioning and deal guidance.