Head of Sales Development

Truffle Security Co.

Head of Sales Development managing SDR team and driving sales strategy for cybersecurity solutions. Leading automation-driven outbound strategy with a focus on AI and metrics.

Posted 4/22/2026full-timeRemote • 🇺🇸 United StatesLead💰 $135,000 - $150,000 per yearWebsite

About the role

Key responsibilities & impact

Lead the hiring and onboarding of a new cohort of SDRs to support our aggressive AE growth targets
Define what "good" looks like across cold calling, email, and LinkedIn, and build the playbooks to help your team get there
Foster a "builder" mentality within the SDR team, encouraging experimentation and professional growth
Deep dive into current processes to identify bottlenecks and manual friction points
Build and manage sophisticated data enrichment workflows in Clay (or similar tools) to drive signal-based outbound efforts
Use metrics to diagnose performance, track pipeline contribution, and tie SDR activity directly to revenue outcomes
Work closely with RevOps to ensure our tech stack is integrated and our data models are actionable

Requirements

What you’ll need

Proven track record of managing and scaling an SDR/BDR team in a high-growth environment
You think in terms of systems and data, not just activity while using metrics to drive every decision
Strong understanding of prospecting, sequencing, messaging and having built playbooks from scratch
You are proficient with Clay (or equivalent enrichment tools) and have hands-on experience implementing AI-driven workflows
You have led sales development teams selling into Security, DevOps, or IT sectors

Benefits

Comp & perks

Fully remote within the U.S. – We believe opportunity shouldn’t be limited by geography. Our remote-first approach lets us hire the best people across the United States and empowers them to do their best work from wherever they are.
A culture of mentorship, equity, and psychological safety – We’re committed to fostering an environment where you can thrive, learn, and feel valued.
Competitive salary & meaningful equity – Be rewarded for your contributions with a strong compensation package and a stake in our shared success.
Flexible paid time off – We operate with a high level of autonomy and trust, giving you the flexibility to take time off as needed—no strict limits, just the expectation that you’re meeting your commitments and getting your work done.
14 paid holidays – Including Thanksgiving, Winter Break, and "Truffle Holidays" when the entire company takes a well-deserved day off together.
Comprehensive health benefits – Medical, dental, and vision coverage with 80% of premiums covered for you and your dependents.
Remote work stipend – Get set up for success with an $800 new hire stipend and $100/month to keep your workspace comfortable.
Health & wellness stipend – $1,200/year to support your physical, mental, and emotional well-being— we believe that feeling good helps you do great work.
Learning & development stipend – $2,000/year to invest in your growth, whether it’s courses, certifications, or industry conferences.
401(k) match – We match 100% of the first 6% of your contributions on every paycheck, helping you build financial security for the future.
100% remote + company off-sites – Twice a year, we come together in amazing locations like Hawaii, Cabo, and the Rocky Mountains to collaborate and connect.

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

data enrichment workflowsmetrics analysisplaybook developmentprospectingsequencingmessagingAI-driven workflows

Soft Skills

leadershipteam buildingexperimentationprofessional growthproblem solvinganalytical thinking