Note: The job is a remote job and is open to candidates in USA. Lob provides a technology platform and Print Delivery Network for scalable direct mail programs. The Enterprise Account Executive owns the sales cycle and enterprise accounts, builds pipeline and executive relationships, and partners with cross-functional teams to develop tailored solutions and grow customer business.

Responsibilities

• Actively identify and pursue target accounts sending direct mail across the Mid-Market/Enterprise segment
• Craft compelling outbound messaging to build a strong, sustainable pipeline
• Develop and nurture relationships with executive decision-makers and key stakeholders within your accounts
• Lead or support responses to RFPs and RFIs when applicable
• Partner closely with teams across Marketing, Account Management, Sales Enablement, Sales Engineering, Product, and Engineering to ensure alignment and execution
• 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
• In partnership with a Solutions Engineer, deliver tailored, value-based product demonstrations aligned with each customer’s specific needs and use cases
• 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
• Approach customer challenges with curiosity and creativity—meeting them where they are today while guiding them toward scalable, future-forward direct mail strategies

Skills

• 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
• Ideally leveraging the MEDDICC sales methodology

Benefits

• Variable compensation
• RSUs
• Remote working opportunities in AZ, CA, CO, DC, FL, GA, IA, IL, MA, MD, MI, MN, MT, NE, NC, NH, NJ, NV, NY, OH, OR, PA, RI, TN, TX, UT, and WA

Company Overview

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