Enterprise Account Executive

Lob

34d•$102,500 - $250,000•Remote

About The Position

As an Enterprise Account Executive at Lob, you'll join a sales team that's on a strong growth trajectory—and help shape our plans for 2027 and beyond. You'll drive growth by building relationships with companies across industries that rely on direct mail. Lob's platform and Print Delivery Network (PDN) replace traditional print vendors, letting organizations send direct mail at scale through a modern API. You'll compete with legacy solutions, making the case for a more innovative, efficient, and scalable approach—guiding prospects toward a modern, programmatic way of operating. You'll own your book of business, prioritizing the accounts and activities with the greatest impact, and running your territory like it's your own business. You'll also work closely with Product and Solutions to shape tailored solutions, advocating for customers and helping steer Lob's roadmap based on real-world needs.

Requirements

5+ years of B2B SaaS selling experience, including 3+ years hunting and closing Enterprise accounts ($100k deal sizes).
Demonstrated success navigating Enterprise-level contract negotiations, including six-figure deal sizes.
Ability to research, develop, and execute account strategies across both Mid-Market and Enterprise segments, ideally leveraging the MEDDICC sales methodology.
Deep experience with a consultative and value-based selling approach, focused on solving business challenges and driving ROI—rather than leading with features.
Skilled at delivering compelling presentations and facilitating executive-level conversations in both remote and in-person settings.
Experience working effectively with Solutions Engineering, Account Management, Partnerships, and other go-to-market teams to drive customer success.
Willingness to travel periodically (10–15%) for customer meetings, conferences, and internal team events.

Responsibilities

Own the Full Sales Cycle: Actively identify and pursue target accounts sending direct mail across the Mid-Market/Enterprise segment.
Drive Pipeline Growth: Craft compelling outbound messaging to build a strong, sustainable pipeline
Engage Executive Stakeholders: Develop and nurture relationships with executive decision-makers and key stakeholders within your accounts.
Respond to Opportunities: Lead or support responses to RFPs and RFIs when applicable.
Cross-Functional Collaboration: Partner closely with teams across Marketing, Account Management, Sales Enablement, Sales Engineering, Product, and Engineering to ensure alignment and execution.
Become a Trusted Advisor: Build deep expertise in Lob’s value proposition, product capabilities, and the broader direct mail ecosystem—establishing yourself as a thought leader for customers and prospects.
Lead Technical Discovery: In partnership with a Solutions Engineer, deliver tailored, value-based product demonstrations aligned with each customer’s specific needs and use cases.
Work in a POD Structure: Collaborate within a dedicated POD (Account Executive, Account Manager, Pre/Post-Sales Solutions Engineer) to ensure a seamless customer experience from onboarding to expansion and renewal.
Problem-Solve Creatively: Approach customer challenges with curiosity and creativity—meeting them where they are today while guiding them toward scalable, future-forward direct mail strategies.