Enterprise Account Executive

Lob was founded in 2013 by technical co-founders with a vision to connect the world one mailbox at a time. Today, we're transforming the way businesses use direct mail and bringing the power of technology to a traditionally manual channel. Our modern logistics and fulfillment engine helps businesses to build and scale high-quality, personalized direct mail programs without the operational burden. As we grow to meet the evolving needs of our customers and expand our product offerings, we’re building a team to shape the future of direct mail. Enterprise Account Executive 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. As the Enterprise Account Executive, you’ll… 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. What will you bring to this role… Proven Sales Success: 5+ years of B2B SaaS selling experience, including 3+ years hunting and closing Enterprise accounts ($100k deal sizes). Contract Negotiation Experience: Demonstrated success navigating Enterprise-level contract negotiations, including six-figure deal sizes. Strategic Account Planning : Ability to research, develop, and execute account strategies across both Mid-Market and Enterprise segments, ideally leveraging the MEDDICC sales methodology. Consultative, Value-Based Selling: Deep experience with a consultative and value-based selling approach, focused on solving business challenges and driving ROI—rather than leading with features. Strong Communication & Presentation Skills: Skilled at delivering compelling presentations and facilitating executive-level conversations in both remote and in-person settings. Cross-Functional Collaboration: Experience working effectively with Solutions Engineering, Account Management, Partnerships, and other go-to-market tea…