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We're replacing outdated, one-size-fits-all training with interactive, role-specific exercises that reflect how people actually learn.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.

Working directly with our founding sales team and CEO, you'll build the systems and processes that drive our growth. You'll be prospecting enterprise CISOs, CTOs, and other security decision-makers who've seen it all. These executives value expertise and authenticity above slick pitches. Your job is to break through the noise, spark their interest, and book qualified meetings.

We expect you to jump in and start booking meetings within your first few weeks. There's no formal onboarding or training program, you'll learn by doing while helping us build the playbook as you go. You'll share what's working (and what's not), brainstorm new approaches with the team, and help everyone level up.

This role requires serious autonomy and initiative. You'll manage your own schedule, double down on what's working, and run 2-3 new experiments weekly. Expect experiments to fail—we need someone comfortable testing lots of ideas quickly to discover the few that really work. You'll own the execution from initial outreach to qualified handoff.

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

You will

Make cold calls your bread and butter (600+ per week)
Build targeted prospect lists and book qualified meetings for our AEs
Write and refine messaging for calls, emails, and LinkedIn that sparks real conversations
Test 2-3 new outreach experiments weekly, while scaling what works
Attend key conferences and local events to build face-to-face credibility
Stay current on security trends and build your industry reputation through social media engagement
Be a resource for the security community, make introductions, solve problems, add value beyond selling
Share insights with the team to shape our product and strategy
Update HubSpot daily, it's our source of truth and we document everything
Track your metrics to make data-driven decisions

You have

Communication skills that make busy stakeholders actually listen
Strong organizational skills to juggle multiple outreach campaigns and follow-ups
Natural curiosity about how things work and how to make them better
The ability to research, adapt, and figure things out without a playbook

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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