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Model this offer in the calculatorJob 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.
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.
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: $102500 - $125000
Variable Salary: $102500 - $125000
<#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
Skills Required
- 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 strategic account plans across Mid-Market and Enterprise segments.
- Familiarity with MEDDICC sales methodology.
- Consultative value-based selling experience focused on driving ROI.
- Strong communication and presentation skills for executive-level conversations (remote and in-person).
- Experience working cross-functionally with Solutions Engineering Account Management Partnerships and go-to-market teams.
- Ability to lead technical discovery and deliver tailored product demonstrations with a Solutions Engineer.
- Willingness to travel periodically (10-15%) for customer meetings conferences and internal events.
- Experience responding to RFPs and RFIs when applicable.
- Comfort operating within a POD structure (AE Account Manager Pre/Post-Sales Solutions Engineer).
What the Team is Saying
Lob Compensation & Benefits Highlights
- Healthcare Strength—Coverage includes multiple medical plan options plus dental vision HSA support and mental‑health services. Feedback suggests the employer contributes substantially and coverage begins on day one.
- Parental & Family Support—Programs include paid parental leave for all parents and comprehensive family‑forming support via a specialized partner including adoption assistance and hormonal health support. Feedback suggests these offerings are inclusive and comparatively robust.
- Leave & Time Off Breadth—A remote‑first approach is paired with flexible or unlimited PTO volunteer time and periodic company‑wide days off. Feedback suggests time away is actively supported alongside distributed work norms.
Lob Insights
What We Do
Lob was founded in 2013 by technical co-founders with a vision to connect the world one mailbox at a time. 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.
Why Work With Us
We believe automation is a catalyst for business success and we’re looking for unique people like you to bring to life our vision of increasing the connectivity between the offline and online worlds. We are proud to be a carbon neutral business!
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Lob Offices
Remote Workspace
Employees work remotely.
We are a remote first company! We celebrate flexibility in our working environment by being a remote first company and sponsoring co-working space use.
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