Enterprise Account Executive

Lob.com, Inc.; United States; Remote; USD 120,000 - 180,000; Full time

Job summary

Lob is seeking an Enterprise Account Executive to own the full sales cycle, drive pipeline growth, and engage executive stakeholders across Mid-Market and Enterprise accounts. You will collaborate with cross-functional teams, lead tailored product demonstrations, and become a trusted advisor on direct mail solutions.

Remote-friendly role with travel 10–15% for select meetings and events. Candidates should have 5+ years of B2B SaaS sales, 3+ years closing Enterprise deals ($100k+), and strong

Qualifications

• 5+ years of B2B SaaS selling experience, including 3+ years hunting and closing Enterprise accounts ($100k deal sizes).
• Experience navigating Enterprise-level contract negotiations, including six-figure deal sizes.
• Ability to research, develop, and execute account strategies across Mid-Market and Enterprise segments (MEDDICC a plus).
• Deep experience with a consultative and value-based selling approach.

Responsibilities

• Own the full sales cycle from prospecting to close for Mid-Market and Enterprise accounts.
• Drive pipeline growth by crafting outbound messaging and building a strong, sustainable pipeline.
• Engage executive stakeholders and lead executive-level conversations in remote and in-person settings.
• Respond to opportunities by leading or supporting responses to RFPs and RFIs when applicable.
• Collaborate with Marketing, Account Management, Sales Enablement, Sales Engineering, Product, and Engineering to ensure alignment.
• Become a trusted advisor with deep knowledge of Lob’s value proposition and product capabilities.
• Lead technical discovery with a Solutions Engineer, delivering tailored product demonstrations.
• Work within a POD structure to ensure a seamless customer experience from onboarding to expansion and renewal.
• Approach challenges with curiosity and creativity to guide customers toward scalable direct mail strategies.

Skills

Proven Sales Success

Contract Negotiation

Strategic Account Planning

Consultative Selling

Strong Communication

Cross-Functional Collaboration

Travel Readiness

Job description

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

<#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.