Senior Recruiter, GTM & Customer Success

About the Company

America is under sustained cyber attack. Our adversaries infiltrate our networks, steal our IP, and degrade the digital infrastructure that modern life runs on. They’ve learned—correctly—that those attacks rarely produce consequences.

Twenty was founded to change that, by making our adversaries think twice before they attack us. Our vision is American and allied primacy in cyberspace—a future where they cannot contest us, deterrence is assured, and the free world remains secure.

Founded in 2024, Twenty Technologies (www.twenty.io) industrializes offensive cyber operations for the U.S. and its allies. Headquartered in Arlington, Virginia, Twenty has raised $168M from Khosla Ventures, Accel, Caffeinated Capital, Friends & Family Capital, Point72 Ventures, General Catalyst, and In-Q-Tel.

Role Summary

Twenty builds AI-native offensive cyber and mission software for the U.S. government and its allies. As Senior Recruiter, GTM & Customer Success, you’ll build the teams that bring those capabilities to customers and missions: the people who open new opportunities, build trusted partnerships, and turn customer needs into lasting mission impact.

You’ll own sourcing-heavy recruiting across Sales, Growth, business development, government relations, partnerships, and customer/mission-facing leadership. Working directly with business and mission leaders, you’ll help define what each hire needs to accomplish, shape candidate profiles and assessment plans, and advise on scope, level, and market realities. From the first outreach through the close, you’ll turn those priorities into exceptional hires.

This is a chance to shape both who joins Twenty and how we build relationships in the markets we serve. You’ll develop trusted networks across cyber, defense, national security, and cleared talent communities, where credibility, discretion, and sustained engagement matter. We’re looking for someone with recruiting experience in defense technology, cyber, or companies serving government and national security customers—someone who brings curiosity, sound judgment, and urgency, and can turn a specialized search into a clear plan, a strong pipeline, and a successful hire.

Who You Are

• You have a sourcing-first mindset and turn cold outreach into real pipelines and hires.

• You bring strong GTM judgment and assess what candidates have actually owned and delivered—not just their titles or past employers.

• You communicate crisply and move with urgency—candidates and stakeholders always know what’s next.

• You thrive in startup ambiguity, turning loose inputs into clear profiles, assessment plans, and repeatable processes.

• You pair operational rigor with high standards, thoughtful stakeholder management, and a fast, high-touch candidate experience.

• You build trust beyond an immediate opening, earning introductions and referrals in close-knit talent communities.

• You exercise discretion with sensitive information and use AI thoughtfully to reduce repetitive work.

What You’ll Do

• Own full-cycle recruiting across Sales, Growth, business development, government relations, partnerships, and customer/mission-facing leadership, based on business priorities.

• Partner with hiring managers on role outcomes, candidate profiles, interview plans, scorecards, and calibration.

• Build lasting relationships in cyber, national security, and cleared talent communities through industry events, referrals, and engagement beyond open searches.

• Tailor structured screens to each role’s proof points, distinguishing commercial results, partnership development, customer trust, and mission credibility.

• Partner with technical recruiters and subject-matter experts on specialized mission-facing searches, with clear ownership and domain assessment.

• Lead high-touch closing efforts around Twenty’s mission, the role’s impact, and candidate motivations; surface concerns early.

• Use market intelligence to advise leaders on role scope, leveling, candidate availability, and realistic search timelines; maintain fast feedback and accurate ATS records.

• Partner with TAOps on logistics; improve outreach, candidate preparation, and workflows using AI within company guidelines.

Must Have

• You have 5+ years of recruiting experience, including full-cycle GTM or business hiring in competitive markets.

• You have recruiting experience in defense technology, cyber, or companies serving government and national security customers.

• You’ve recruited Sales, business development, partnerships, or customer-facing leaders, with depth in at least one area and range to learn adjacent functions.

• You’ve built qualified outbound pipelines and closed passive candidates, including senior individual contributors or leaders.

• You calibrate effectively with hiring managers and learn complex customer and mission contexts quickly.

• You turn ambiguous hiring needs into executable plans and advise leaders candidly on scope, market realities, and closing.

• You use funnel data to improve outcomes, with strong ATS hygiene, follow-through, and process discipline.

• You are comfortable working in-office in Arlington, VA (Washington, DC area) or New York, NY.

Nice To Have

• Familiarity with government-facing business development, government relations, complex sales cycles, or mission-facing talent.

• Direct experience recruiting for roles with clearance requirements, including navigating their impact on talent pools, recruiting timelines, and closing.

• An established network in cyber, defense, national security, or cleared talent communities.

• Experience building GTM teams at startups or growth-stage companies.

• Familiarity with Ashby, structured interviewing, and AI-assisted recruiting workflows.

Recruiting Tools (You Might Work With)

• Ashby (ATS, workflows, reporting)

• LinkedIn Recruiter and Juicebox

• AI-assisted research, sourcing, and workflow tools within company guidelines

Benefits
What's on the table:

• Health. Medical, dental, and vision plan options. Life / AD&D, disability coverage options.

• Family. Paid parental leave for eligible full-time employees. 12 weeks for birthing parents, 4 for non-birthing parents, 6 weeks for adoptive, foster, or intended parents through surrogacy.

• Vacation. Paid holidays and flexible PTO. Take what you need.

• Retirement. 401(k) with pre-tax and Roth options. HSA/FSA options, dependent care FSA.

Benefits vary by location, role, and eligibility. Full plan details provided during the interview and offer process.

If this role sounds like you, apply and share with us your interest

Due to U.S. government contract and security requirements, this role is limited to U.S. citizens. Some positions may also require eligibility to obtain and maintain a U.S. Government security clearance. Any active clearance requirement will be listed in the role description.

Twenty is an equal opportunity employer. We consider all qualified applicants without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, veteran status, disability, or any other protected status, consistent with applicable law.

If you need a reasonable accommodation during the hiring process, let us know and we will work with you.