Build and lead Letter AI’s first SDR team, recruiting and coaching representatives while creating outbound prospecting strategies, playbooks, sequences, and account prioritization. Drive qualified pipeline and meeting generation, establish performance metrics, analyze conversion and activity data, and collaborate with Account Executives, Marketing, and Revenue Operations on lead handoffs, messaging, and target accounts.
About Letter AI
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 📈.
The RoleAs 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.
Why Join?- Exponential Growth Potential: Be part of an early-stage startup in a transformational space, where you get to build a core team from scratch and directly drive company expansion.
- Autonomy & Impact: Enjoy the freedom to make key decisions, design outbound playbooks, test cutting-edge prospecting tech, and truly own the SDR function.
- AI-Powered Platform: Work at the forefront of AI technology, leveraging our own unified revenue acceleration platform to give your team an unfair advantage.
- Build from the Ground Up: This is a rare opportunity to lay the foundations of our SDR organization, shaping GTM strategy for a fast-growing startup (we're being recognized as the fastest-growing AI startup in Chicago!).
- Team Building & Leadership: Recruit, hire, onboard, and coach our founding team of SDRs, establishing a culture of high performance, accountability, and continuous learning.
- Outbound Strategy & Execution: Design, test, and iterate on outbound prospecting playbooks, multi-channel sequences, messaging, and account prioritization strategies.
- Pipeline Generation: Drive consistent qualified lead flow and meeting creation to meet or exceed monthly and quarterly sales pipeline goals.
- Cross-Functional Alignment: Collaborate closely with Account Executives, Marketing, and Revenue Operations to refine lead handoffs, target account lists, and messaging resonance.
- Data & Performance Management: 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.
- 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.
At Letter AI, we operate by a set of core principles:
- Customer-obsessed: Make your customers unreasonably happy and everything else will fall into place
- Ambitious yet practical: Set big goals, but stay grounded with disciplined execution and ruthless prioritization
- Direct yet kind: Never hold back from speaking your mind, but do so in a way that is kind to your colleagues
- Driven yet humble: Push for excellence and deliver fast, but keep your humility
- Ownership: Every full-time teammate receives Letter stock options, so you can share in the value you help create
- Benefits that have you covered: Comprehensive medical, dental, and vision coverage, plus a 401(k) with company match
- Benefits for the everyday: Company-supported commuter, connectivity, and wellness benefits, plus daily lunch in our Chicago and San Francisco offices
- Team events: Happy hours, dinners, events, and offsites with a team that genuinely enjoys spending time together
- Build with us: Join a fast-growing startup where you’ll have meaningful ownership and impact, working closely with top-notch teammates to help build and scale Letter
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