Federal AE - Security Sales

This is a high-ceiling, high-accountability enterprise sales role at a Series C/D-stage cybersecurity startup with Tier-1 VC backing (Sequoia, Kleiner Perkins, IVP). The $350K OTE (50/50 split = ~$175K base + $175K commission) is at or above market for federal AE roles in the security space, where typical OTE ranges from $280K–$350K for senior reps.

• Federal healthcare (HHS, VA, DHA) is a highly specialized and in-demand vertical — expertise here is transferable to Palantir, AWS Gov Cloud, Leidos, and other defense-adjacent tech companies
• MEDDPICC mastery at a fast-growing startup builds elite enterprise sales discipline valued industry-wide
• Supply chain security and open-source hardening are regulatory tailwinds (SBOM mandates, EO 14028) — Chainguard is well-positioned for multi-year growth

Green flags: Remote-first culture, 10-year option exercise window (rare and very founder/employee-friendly), 100% premium-covered health insurance, and strong investor backing signal financial stability and employee-centric values.

Watch for: The 50/50 OTE split means half your compensation is variable — federal procurement cycles are notoriously long (12–24 months), so deal timing risk is real. Ramp periods and quota relief terms should be clarified before signing. Startup processes are still evolving, which suits ambitious self-starters but may frustrate those who prefer structured environments.

Chainguard is the trusted source for open source. By delivering hardened, secure, and production-ready builds of all the open source software engineers and AI agents rely on, Chainguard helps organizations build faster, stay compliant, and eliminate risk.

Our customers include Fortune 500 enterprises and global industry leaders, including Anduril, Canva, Fortinet, Hewlett Packard Enterprise, OpenAI, Snap Inc., and Snowflake.

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Chainguard is venture-backed by leading investors, including Amplify, IVP, Kleiner Perkins, Lightspeed Venture Partners, Mantis VC, Redpoint Ventures, Sequoia Capital, and Spark Capital.

The Role, in a Nutshell:

Chainguard is looking for a Federal Health Account Executive to help expand our presence within large organizations. In this role, you'll own the full sales cycle with federal customers—from building pipeline through closing complex deals.

Train Managers

Successful candidates are disciplined in their sales process, strong at developing pipeline, and comfortable navigating complex federal buying environments. You'll work closely with sales leadership, sales engineering, marketing, and customer success to help organizations adopt Chainguard's solutions and improve how they build and secure software.

What You'll Do

• Own the full sales cycle from prospecting through close
• Build and manage pipeline within a defined set of federal accounts
• Lead discovery, qualification, and deal strategy using frameworks such as MEDDPICC
• Communicate Chainguard's value to technical stakeholders, security leaders, and executive buyers
• Partner with Sales Engineering, Public Sector Partner Team, and Customer Engineering to support evaluations and technical validation
• Manage complex Federal sales cycles including procurement, security reviews, and negotiations
• Maintain accurate pipeline visibility and forecasting
• Consistently meet or exceed revenue and pipeline targets

What We're Looking For

• 8–10+ years of experience selling complex technical products into federal organizations
• 5+ years of closing experience in the SaaS/Security/Dev Ops industry required
• 5+ years' experience covering Federal Healthcare, HHS, VA, and DHA
• A track record of building pipeline and consistently closing revenue
• Comfortable running disciplined sales…