SDR Manager

Letter AI•Chicago, IL

3d•Onsite

About The Position

Letter AI is the world's first unified revenue acceleration platform powered natively by generative AI. Our platform empowers sales teams at customers like Adobe, Lenovo, and Figma to ramp up faster with AI-powered training and coaching, instantly find and personalize collateral for customers, and engage their buyers with the industry's first AI Sales Room. We recently raised a $40M Series B led by Battery Ventures, with participation from existing investors including Y Combinator, Lightbank, Northwestern Mutual Future Ventures, Stage 2 Capital, and Formus. The round comes just four months after announcing our Series A, indicating a shift we're seeing in real time: revenue teams aren’t asking for more content or tools. They’re asking for better outcomes, and Letter AI is bringing those outcomes to life! We 10Xed our revenue last year and are looking for the best of the best in Chicago to join us on the adventure 📈. As our first SDR Manager at Letter AI, you will play a pivotal role in building, scaling, and leading our Sales Development function from the ground up. You will directly manage and grow a team of high-performing SDRs, establishing the outbound strategies, playbooks, and metrics that fuel our top-of-funnel pipeline. Working closely with leadership and marketing, you’ll have complete autonomy to shape our outbound engine in a rapidly growing market, significantly impacting the company's revenue trajectory and your own career growth.

Requirements

3+ years of total experience in SaaS sales/sales development, with at least 1–2+ years of direct experience managing, leading, or mentoring SDRs/BDRs.
Proven track record of exceeding outbound pipeline quotas as both an individual contributor and team leader.
Deep understanding of modern outbound sales tech stacks, sequence orchestration, multi-channel prospecting, and data-driven pipeline management.
Strong coaching and mentoring abilities, with a passion for helping early-career tech sales professionals grow and advance.
High adaptability, grit, and comfort operating in a fast-paced, ambiguous startup environment.
Strong communication, analytical, and problem-solving skills with a proactive, "figure it out" mentality.

Responsibilities

Recruit, hire, onboard, and coach our founding team of SDRs, establishing a culture of high performance, accountability, and continuous learning.
Design, test, and iterate on outbound prospecting playbooks, multi-channel sequences, messaging, and account prioritization strategies.
Drive consistent qualified lead flow and meeting creation to meet or exceed monthly and quarterly sales pipeline goals.
Collaborate closely with Account Executives, Marketing, and Revenue Operations to refine lead handoffs, target account lists, and messaging resonance.
Track and analyze key SDR performance metrics (activity levels, conversion rates, pipeline quality), using data to optimize performance and report on pipeline health to leadership.