Whatnot

Sales Director, North America

Whatnot • $120K — $180K *
Enterprise Technology
8 - 10 years of experience
Job Overview by Ladders

Qualifications

  • 8-12+ years of enterprise technology sales experience
  • 5+ years selling complex infrastructure, security, or platform software
  • Proven track record of closing large, complex enterprise deals ($500K-$5M+)
  • Experience in regulated or security-sensitive environments
  • Strong knowledge of cryptography, encryption, and key management concepts
  • Comfortable leading architecture-level discussions with technical buyers
  • Executive-level communication skills, both written and verbal

Responsibilities

  • Own and grow a multi-million-dollar enterprise pipeline across North America
  • Drive new customer acquisition and strategic expansion within existing accounts
  • Lead complex sales cycles involving multiple stakeholders
  • Position cryptographic solutions in various environments including on-premises and cloud
  • Translate technical requirements into business value for clients
  • Build relationships with executives in security and infrastructure roles
  • Collaborate with channel partners and technology allies to enhance market presence

Benefits

  • Health, dental, vision, life, and short/long-term disability insurance
  • Paid vacation, holidays, and sick leave
  • Competitive compensation and opportunities for advancement
  • Retirement plan with employer contribution match
  • Welcoming, family-style corporate culture
  • Recognized as one of San Antonio's 'Best Places to Work' for nine consecutive years
Full Job Description
Overview -

We are seeking a Sales Director, North America to lead enterprise growth across the region for our cryptographic security portfolio, including Hardware Security Modules (HSMs), Key Management Systems (KMS), Public Key Infrastructure (PKI), and data protection services-delivered on-premises, hybrid, and cloud-native.

This role is designed for a high-caliber enterprise sales leader with strong technical fluency, proven success selling mission-critical infrastructure into large organizations, and the ability to operate credibly with C-suite, security architects, and platform engineering teams alike.

You will own strategic accounts, drive complex deal cycles, influence technical buying decisions, and help shape go-to-market strategy as we scale.

Key Responsibilities -

Enterprise Revenue Ownership
  • Own and grow a multi-million-dollar enterprise pipeline across North America
  • Drive net-new logo acquisition and strategic expansion within existing enterprise accounts
  • Lead complex, multi-stakeholder sales cycles involving security, infrastructure, cloud, legal, compliance, and procurement teams


Technical & Solution-Led Selling
  • Position HSMs, key management, PKI, and data protection solutions across:
    • On-premises data centers
    • Public cloud (AWS, Azure, GCP)
    • Hybrid and regulated environments
  • Translate cryptographic, security, and compliance requirements into business value for enterprise buyers
  • Partner closely with Sales Engineering, Product, and Architecture teams to deliver technically sound solutions


Executive & Security Buyer Engagement
  • Build trusted relationships with:
    • CISOs, CIOs, CTOs
    • Heads of Security, Infrastructure, and Cloud Platforms
    • Risk, Compliance, and Payments teams
  • Confidently engage in discussions around:
    • Encryption and key custody models
    • Cloud security architectures
    • Compliance frameworks (PCI DSS, FIPS, ISO, SOC, regional regulatory requirements)


Channel & Ecosystem Collaboration
  • Work effectively with:
    • Cloud providers
    • Technology partners
    • System integrators and resellers (where applicable)
  • Influence joint go-to-market motions and enterprise solution positioning


Forecasting & Operational Rigor
  • Maintain accurate forecasting and pipeline hygiene
  • Provide leadership with market feedback, competitive insights, and customer-driven product input
  • Operate with discipline in CRM, deal reviews, and executive reporting

Requirements

Required Experience & Qualifications -

Sales Leadership & Enterprise Expertise
  • 8-12+ years of enterprise technology sales experience, with at least:
    • 5+ years selling complex infrastructure, security, or platform software
  • Proven track record of closing large, complex enterprise deals ($500K-$5M+)
  • Experience selling into regulated or security-sensitive environments (financial services, payments, cloud, SaaS, government, or critical infrastructure)


Technical Aptitude
  • Strong working knowledge of:
    • Cryptography, encryption, and key management concepts
    • Cloud and hybrid architectures
    • APIs, integration patterns, and platform services
  • Ability to earn credibility with technical buyers without being a hands-on engineer
  • Comfortable leading whiteboard discussions and architecture-level conversations


Communication & Presence
  • Executive-level communication skills-clear, confident, and technically grounded
  • Ability to articulate complex security topics in business terms
  • Strong written and verbal presentation skills


Preferred Background -
  • Experience selling:
    • HSMs, KMS, PKI, or data protection platforms
    • Cloud security, identity, or infrastructure software
  • Prior roles at high-growth technology companies or established enterprise vendors
  • Familiarity with payments, fintech, SaaS, cloud platforms, or regulated industries


What Success Looks Like -
  • Consistently exceeds revenue targets across enterprise accounts
  • Becomes a trusted advisor to customers and internal stakeholders
  • Helps shape enterprise go-to-market strategy and product positioning
  • Builds long-term customer relationships that drive expansion and renewals


Why Join Us -
  • Mission-critical technology at the core of modern security and cloud infrastructure
  • Opportunity to sell deep, differentiated cryptographic platforms-not commodity software
  • Direct impact on enterprise adoption, market strategy, and company growth
  • Collaborative, technically sophisticated culture with executive visibility

Benefits
  • Health, dental, vision, life, and short/long-term disability insurance
  • Paid vacation, holidays, and sick leave
  • Competitive compensation and opportunities for advancement
  • Retirement plan with employer contribution match
  • Welcoming, family-style corporate culture uniquely suited to fast-paced, entrepreneurial, and motivated individuals
  • One of San Antonio's "Best Places to Work" for nine consecutive years

About Whatnot

Whatnot is a Los Angeles-based startup that creates a place where avid collectors could come together over shared interests. Whatnot is a marketplace to buy and sell authentic collectible items. Whatnot was founded in 2019, in California.

Whatnot Careers

Joining Whatnot presents an unparalleled opportunity to become part of a leading team in the marketplace, where innovation meets diversity and professional growth. Whatnot is renowned for its unique culture that fosters leadership and promotes career advancement through continuous learning and development.

Explore Job Opportunities

Whatnot is actively seeking talented individuals who are eager to drive innovation and lead in a dynamic environment. The company offers a variety of job opportunities that cater to professionals looking to make a significant impact in their fields. With positions ranging from technology to marketing, Whatnot ensures that every team member’s skills are harnessed effectively.

Experience Professional Growth

At Whatnot, growth is not just a possibility—it is an expectation. The company is committed to the professional development of its employees through robust training programs, including leadership development and diversity training. These initiatives are designed to enhance skills and prepare individuals for future challenges and opportunities.

Engage in Meaningful Work

Every position at Whatnot is designed to challenge team members while contributing to the company’s overarching goals of innovation and service excellence. Employees are encouraged to take ownership of their projects and drive results that influence the company’s trajectory and success.

Internship Programs

For those starting their career journey, Whatnot offers internship programs that provide a comprehensive learning experience. Interns at Whatnot gain hands-on experience, working alongside seasoned professionals and participating in projects that offer real-world applications of their studies.

Benefits and Culture

Whatnot is dedicated to supporting its team members not only in their professional lives but also in their personal growth and well-being. The company offers competitive benefits packages that address health, financial security, and work-life balance. Whatnot’s culture is built on a foundation of respect and inclusion, where diversity is celebrated and every voice is heard.

Join the Team

Whatnot is hiring! Explore open positions that match your skills and interests. The company values curious, creative, and solution-driven team players. Prepare your resume and ready yourself for an interview where you can showcase your abilities and fit for the team.

Networking and Career Advancement

Whatnot believes in the power of networking to unlock new opportunities and insights. Employees are encouraged to engage with industry leaders and peers through various professional networking events sponsored by the company. These connections can lead to innovative ideas and collaborations that propel both personal and company growth.

Stay Connected

Keep up to date with the latest from Whatnot by following the company’s career blog. Gain insider perspectives, career tips, and industry-leading insights that you can apply to your professional life. Personalize your subscription to receive job alerts and the latest news tailored to your preferences.

Discover Whatnot

Whatnot invites you to explore the exciting and rewarding opportunities that await. Join a team where your career aspirations can be realized through dedication, hard work, and a commitment to excellence.
Learn more about Whatnot
Size
251 employees
Industry

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