Job description
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: Willingness to travel periodically (10–15%) for customer meetings, conferences, and internal team events.
Compensation Information
This role will include a combination of base salary + variable, and RSUs
Annual Salary: $125,000
Annual Variable: $125,000
<#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, 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
