Mid-Market Account Executive

LettrLabs is looking for a Mid-Market Account Executive to own the full sales cycle with mid-market prospects, from first conversation through close. This is not a "sit and wait for inbound" role. You will be phone-first, integrating email, video, and in-person touchpoints, and you will find a way to break into accounts and multi-thread deals.

You will sell an automation layer across a prospect's omnichannel marketing ecosystem, and you will win by selling funnel economics and ROI rather than features. Deals typically carry a $30K - $50K ACV and a roughly 30-day sales cycle, so you will manage a high volume of deals with strong organization and "backwards planning" discipline.

• High-ownership role: you own your territory, your pipeline, and your number.

• Sell a differentiated product where you can quantify the impact on a prospect's bottom line.

• Work directly with the Sales Lead and an experienced sales team that shares best practices and helps each other win.

• Merit-driven culture where contribution, hard work, and results matter more than titles.

• Fully remote, with in-person events (6-8+ per year) to build pipeline and connect with the team.

• Competitive compensation with equity upside in a fast-growing company.

Key Objectives

• Hit monthly and quarterly quota through a high-velocity, well-forecasted pipeline.

• Source net-new opportunities through multi-channel prospecting, including phone, email, video, and in-person.

• Run advanced discovery that uncovers pain, success criteria, decision-makers, and the cost of inaction.

• Quantify the ROI of LettrLabs for mid-market companies and tie it directly to financial outcomes.

Pipeline & Forecasting

• Manage a high volume of deals while maintaining intense organizational rigor.

• Forecast based on critical events and qualification signals, not hope.

• Qualify ruthlessly, including walking away from deals that do not fit to focus on high-probability wins.

Deal Strategy & Execution

• Navigate mid-market deal dynamics: identify and develop champions, multi-thread, and handle multi-stakeholder objections.

• Defend pricing with ROI-anchored responses rather than defaulting to discounts.

• Turn "No" into a discovery opportunity rather than a dead end.

• Run tailored demos that map product capabilities directly to the prospect's discovered pain.

Events & Team

• Execute at 6-8+ events and trade shows per year, moving from booth conversations to high-level networking and sourcing net-new opportunities.

• Contribute as a force multiplier: share best practices, help teammates, and put the company's success alongside your own.

• Prior quota-carrying Account Executive experience selling to mid-market or larger customers.

• Average deal sizes of $30K or more, with a track record of ROI- or value-based selling.

• Phone-based selling experience and a "find a way" approach to prospecting.

• Strong discovery skills and the ability to maintain call control while digging into a prospect's marketing attribution gaps.

• Demonstrated forecasting accuracy and qualification discipline.

• An extreme ownership mindset: you take full responsibility for your results and do not blame lead quality or the economy.

• Comfort working remotely and traveling to events.

• Medical, dental, and vision coverage

• Equity in a fast-growing company

• 401(k) plan

• Flexible PTO and paid holidays