Senior 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.

Senior Enterprise Account Executive

As a Senior Enterprise Account Executive at Lob, you’ll play a critical role in driving growth by building and managing relationships with companies across various industries and use cases that rely on direct mail. Lob’s technology platform and Print Delivery Network (PDN) replaces traditional print-vendor relationships, empowering organizations to send direct mail at scale through a modern API.

In this role, you’ll often find yourself competing with legacy solutions. Your challenge—and opportunity—will be to demonstrate how Lob offers a more innovative, efficient, and scalable approach. You'll articulate the unique value of our solution and guide prospects through the shift toward a more automated and programmatic way of operating.

You’ll take full ownership of your book of business, often spanning both Mid-Market and Enterprise segments. This means prioritizing activities and engagements that deliver the greatest impact—treating your accounts with the same care and strategy as if you were running your own company.

Success in this role requires a solution-oriented mindset. You’ll collaborate closely with our Product and Solutions teams to co-develop tailored solutions, acting as a strong advocate for your customers and helping shape the future of Lob’s offerings based on real-world needs.

As a Senior Enterprise AE, you will also:

• Own the Full Sales Cycle: Actively identify and pursue target accounts sending direct mail across both Mid-Market and Enterprise segments.
• 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: A consistent track record of exceeding quota, with 4+ years of experience in a closing role leading customers through complex B2B sales cycles.
• Contract Negotiation Experience: Demonstrated success navigating Mid-Market and 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 teams to drive customer success.
• Travel Readiness: