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 teams to drive customer success.
• Travel Readiness: Willingness to travel periodically (10–15%) for customer meetings, conferences, and internal team events.
• A current and accurate LinkedIn profile 

Why this role is different:

• Because direct mail is a physical good, there’s a lot more stability in this opportunity as opposed to other standard SaaS opportunities. (uniquely positioned with a physical product)
• Lob is profitable! Tremendous total addressable market and strong product-market fit.

Compensation Information:
The compensation for this role is comprised of an annual base salary, variable compensation, and RSUs

Annual Base Salary: $125,000 - $145,000
Variable Salary: $125,00 - $145,000

<#LI-REMOTE #LI-RW1

“Lob’s salary ranges are based on market data, relative to our size, industry and stage of growth. Salary is one part of total compensation, which also includes equity, perks and competitive benefits. Salary decisions are based on many factors including geographic location, qualifications for the role, skillset, proficiency and experience level. Lob reasonably expects to pay candidates who are offered roles within the provided salary ranges.”

We offer 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, unless specified otherwise in the job description above. 

If you are looking for a progressive, fun-spirited, and mentally stimulating environment, come join us at Lob!

Our Commitment to Diversity

Lob is an equal opportunity employer and values diversity of backgrounds and perspectives to cultivate an environment of understanding to have greater impact on our business and customers. We encourage under-represented groups to apply and do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, disability status, or criminal history in accordance with local, state, and/or federal laws, including the San Francisco’s Fair Chance Ordinance.

Recent awards

#88 on BuiltIn's Best Remote Midsize Companies to Work For in 2025
BuiltIn Best Remote Midsize Companies to Work For in 2024
BuiltIn Best Midsize Companies to Work For 2022