Anagram's mission is to build a future where security awareness is engaging, personalized, and powerful—turning human behavior from a liability into an organization’s greatest defense.

We're replacing outdated, one-size-fits-all training with interactive, role-specific exercises that reflect how people actually learn. We believe that thoughtful, engaging tools help people make better decisions. When you trust and invest in people, they don’t become your biggest risk—they become your greatest defense.

We partner with leading enterprise organizations, including Fortune 500 companies, to deliver solutions that make a tangible impact on their cybersecurity resilience. We're backed by some of top Silicon Valley's investors including Madrona, General Catalyst, and Bloomberg Beta.

As an early sales hire, you’ll help drive Anagram’s enterprise growth. You'll own the full sales cycle with Fortune 500 companies, from initial discovery through closed-won. Working directly with our CEO and founding team, you'll sell to CISOs, CTOs, and security leaders at the world's largest organizations. These buyers need someone who can speak their language, understand their complex environments, and actually solve their problems.

You'll jump in fast—shadowing the CEO on active deals to learn our approach while starting to build your own pipeline within the first few weeks. You'll navigate procurement processes, coordinate contract negotiations, and manage multi-threaded deals with multiple stakeholders. When deals stall, you'll figure out why and get them unstuck.

We’re looking for a consultative seller. A challenger who can uncover the pain of legacy programs, help prospects envision new outcomes, and build compelling business cases.

This isn't a "follow the script" AE role. You’ll work closely with leadership, learning the art and science of winning in our market. You’ll also have the autonomy to experiment and help shape our positioning, messaging, and sales process as we scale.

This is a contract-to-hire position. You'll start on a month-to-month contract with a path to full-time employment after 3-months.

You will

Own the full sales cycle: discovery, demos, champion development, pilots/POCs, stakeholder alignment, technical and legal reviews, and closing.
Build strong, multi-threaded relationships with champions, coaches, and executives to drive urgency and consensus.
Collaborate with product and executive teams to channel customer insights into our messaging and roadmap.
Proactively overcome deal blockers and reframe value to address core customer challenges.
Advocate for customers internally to ensure Anagram delivers transformative results—not just compliance checkboxes.
Become an expert in modern security challenges, using behavioral science, content, and data to influence decisions.

You have

sold enterprise software or security solutions to large organizations, consistently winning through a consultative, problem-solving approach.
curiosity and are genuinely interested in learning about prospects, their businesses, and their challenges. You ask thoughtful, probing questions and love mastering the details of your product and how it solves customer problems.
insane amounts of drive, bringing high energy and motivation to exceed goals. You pair this with a constant desire to find smarter, more effective ways to work.
the ability to thrive in high-volume environments, skillfully managing many priorities while maintaining quality and attention to detail.
an openness to feedback, and eagerness to grow. You have a strong growth mindset and apply learnings to improve.
the desire to build high-quality, lasting relationships—seeing customers as partners and contributing to a positive, human-first sales culture.

Working at Anagram

We're a fully remote startup that values deep work and flexible collaboration.

Values

Move fast, adapt: Jump in, make decisions, break things, fix them, and learn. If something doesn’t work, toss it and move on. Progress over perfection — we're always growing.

Ego-free zone: No jerks, no drama. Every voice on the team matters. We deliver results, embrace failures, celebrate wins, and make magic happen together.

Own it: See a problem? Fix it. Idea? Pitch it. Question? Ask it. Everyone has the power and responsibility to make us better. This isn’t a place for passengers.

How We Work

No timesheets: Results matter, schedules don't. Work when it's right for you.

Real-time feedback: Immediate, clear, and constructive. Growth shouldn't wait.

With kindness: Respect others, communicate with care, assume good intent.

Fully remote: Work where you work best. Twice a year, we meet in person.

Benefits

Flexible PTO: Take time when you need it, federal holidays and Dec 24–Jan 1.

Optional Fridays: No internal meetings. Work or recharge as needed.

Healthcare: Medical, dental, and vision provided.

Parental leave: Time off for life’s biggest moments.

Equity: Own a piece of what we’re building.

401(k) matching: Save for the future with company matching.

Stipends: Office setup, remote work, and learning support.

We are an affirmative action and equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, disability, age, sexual orientation, gender identity, national origin, veteran status, or genetic information. We're committed to providing access, equal opportunity and reasonable accommodation for individuals with disabilities in employment, its services, programs, and activities.

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