Anagram builds lasting awareness by teaching people to see, think, and act differently in an always-changing security landscape. Instead of boring videos and pointless quizzes, we have puzzles, simulations, and an AI companion that coaches people in real time. We do more than check boxes. We change behavior by making ongoing security second nature. Fortune 500 companies like Disney, Kraft, and Pfizer use us because their employees actually absorb our training.

As one of our first sales hires, 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, while also building your own pipeline alongside leads from our BDR. Working directly with our CEO and founding team, you'll sell to CISOs, CTOs, and security leaders at the world's largest organizations.

We’re looking for someone with 5+ years of experience who can hit the ground running with minimal ramp time.

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. 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 while having the autonomy to experiment and help shape our positioning, messaging, and sales process as we scale.

We're looking for someone who can turn complex enterprise challenges into closed deals:

You own the entire sales cycle with Fortune 500 accounts. From first discovery call to signed contract, you navigate procurement processes, coordinate legal reviews, and manage multi-threaded deals with 8+ stakeholders who all have different priorities.
You're a consultative challenger who uncovers real pain. When a CISO says "our current training is fine," you ask the right questions to reveal why their employees still click phishing emails and help them envision better outcomes.
You build relationships that drive deals forward. You develop champions, coaches, and executive sponsors who fight for you internally when you're not in the room, creating urgency and consensus across complex organizations.
You get stalled deals unstuck. When a $500K deal goes quiet for three weeks, you figure out what's really happening behind the scenes and find the path to close, whether that's addressing new technical requirements or reframing value for a skeptical stakeholder.
You become the customer's advocate internally. You channel insights from customer conversations back to our product and executive teams, ensuring Anagram delivers transformative results, not just compliance checkboxes.
You master the details that matter. You understand modern security challenges, behavioral science, and how our platform actually works so you can speak credibly with technical buyers and build compelling business cases.
You experiment and improve constantly. You try new messaging approaches, test different demo flows, and share what's working with the team, helping shape our sales process as we scale.
You build your own pipeline. You'll get qualified leads from our BDR and inbound, but you also identify and work your own prospects through networking, referrals, and strategic outreach to hit your numbers.

People thrive in different environments. You'll probably be happier elsewhere if you prefer:

Transactional sales over long relationship building. Our deals take 6-12 months and require deep partnerships with multiple stakeholders across the organization.
Following established playbooks over building new approaches. You'll be creating our sales process while executing it, with lots of autonomy to experiment and iterate.
Simple deals over complex enterprise sales. You'll navigate procurement, legal reviews, technical evaluations, and executive approval processes, often all happening simultaneously.
Working solo over collaborating constantly. You'll work daily with our CEO, product team, and technical specialists to win deals and improve our approach.
Staying in your sales lane. Some weeks you might help with marketing messaging, review competitive positioning, or join customer success calls, we need someone who thrives wearing multiple hats.

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 equal opportunity employer. All qualified applicants will receive consideration without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, veteran status, or genetic information. We provide reasonable accommodations for individuals with disabilities.

300000 - 360000 USD a year

Base: $150K - $180K

OTE Commission: $150K - $180K

We also have a generous equity pool available for our founding team.

Apply now

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