Federal AE at Chainguard - $350K OTE Security Sales

Chainguard; Chicago (IL); Remote; USD 315,000 - 385,000; Full time

Benefits offered by this job

Remote-first culture

100% Covered Health Insurance

Stock options with 10-year exercise

Unlimited PTO

18 weeks paid parental leave

Monthly coworking stipend

Job summary

Chainguard is seeking a Federal Health Account Executive to expand our presence within large federal organizations. You will own the full sales cycle—from prospecting to closing—within a remote-first environment across the United States.

We value MEDDPICC discipline, strong stakeholder management, and a proven ability to close complex deals in the SaaS/security space, with a focus on Federal Healthcare accounts (HHS/VA/DHA).

Qualifications

• 8–10+ years of experience selling complex technical products into federal organizations.
• 5+ years of closing experience in SaaS/Security/DevOps.

Responsibilities

• 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 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.

Skills

MEDDPICC

Pipeline development

Complex sales

Federal healthcare

Job description

Federal AE at Chainguard - $350K OTE Security Sales — Remote

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 GovCloud, 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/DevOps 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 processes (MEDDPICC or similar)
• Ability to identify customer pain and sell based on measurable business value
• Experience navigating multi-stakeholder buying cycles from technical teams to executives
• Strong deal management and forecast discipline across complex opportunities
• Excellent communication, relationship-building, and negotiation skills
• Comfortable operating in fast-growing environments with evolving processes

Desired Qualifications:

• Domain experience with one or more of the following strongly recommended: Compute platforms (Kubernetes, Docker, AWS, Azure, Google Cloud), DevOps Tooling, CI/CD platforms (GitHub, GitLab, Jenkins), and overall SDLC
• Startup experience
• A strong sales aptitude and fundamental understanding of the sales process
• A sound, tech-savvy business acumen and the ability to articulate a compelling value proposition in a complex and evolving business environment
• Ability to thrive in an agile environment with an ever-evolving set of solutions

Compensation: $350,000 OTE (50/50)

About Us

We live and breathe our company values:

• We are customer obsessed — We focus on delivering solutions to our customers that create value and make their lives better.
• We have a bias for intentional action — We prioritize, plan, try things, and fail fast.
• We don't take ourselves too seriously (but we do serious work) — We are solving an important problem which takes focus, but we also like to enjoy the journey.
• We trust each other and assume good intentions — We're transparent with decisions to empower team members to make well-informed decisions.

A few of the benefits we offer:

• Flexible & Remote-First Culture: Work remotely with team meetup opportunities, bi-annual destination summits, and a monthly stipend for coworking spaces, phone and internet costs.
• Our Approach to Equity: Receive stock options upon hire and promotion. Plus, you can participate in secondary offerings and have 10 years to exercise your options.
• 100% Covered Health Insurance: We cover 100% of your health, vision, and dental insurance premiums for you and your dependents. Nothing comes out of your paycheck.
• Unlimited Flexible Time Off: Take the time you need — to do our best work, we need to recharge and reset.
• 18 Weeks Paid Parental Leave: We offer 18 weeks for birthing parents and 12 weeks for non-birthing parents, with the option to use it all at once or throughout your child's first year.

If your experience is close but doesn't fulfill all requirements, please apply. We're building the best team in technology and are focused on hiring "Chainguardians" with unique backgrounds, perspectives, and experiences.

Chainguard is an equal opportunity employer. We do not discriminate based upon race, religion, color, national origin, sex (including pregnancy, childbirth, reproductive health decisions, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, political views or activity, or other applicable legally protected characteristics. We also consider qualified applicants with criminal histories, consistent with applicable federal, state and local law.

Is this role fully remote or does it require being in a specific location? This role is remote-first within the United States. While there is no required office location, candidates covering federal healthcare accounts (HHS, VA, DHA) may benefit from proximity to federal facilities in areas like Washington DC or San Antonio. What is the compensation structure for this Federal Health Account Executive role? The total on-target earnings (OTE) are $350,000 with a 50/50 split, meaning approximately $175,000 base salary and $175,000 in target commission. What federal agencies will I be selling into? The role focuses on Federal Healthcare accounts, specifically including the Department of Health and Human Services (HHS), the Department of Veterans Affairs (VA), and the Defense Health Agency (DHA). What sales methodology does Chainguard use? Chainguard uses MEDDPICC (or similar structured frameworks) for discovery, qualification, and deal strategy across complex federal sales cycles. What benefits does Chainguard offer beyond salary? Chainguard offers 100% covered health, vision, and dental insurance for employees and dependents, unlimited PTO, 18 weeks paid parental leave, stock options with a 10-year exercise window, and a monthly stipend for coworking spaces, phone, and internet.

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