• Own end-to-end sales motions: prospecting, qualification, scoping, proposal development, negotiation, and close. • Build and execute a territory plan that expands new logo acquisition and grows revenue across existing enterprise accounts. • Position the full suite of offensive security services—pen testing, red teaming, cloud security testing, and managed offensive capabilities. • Maintain a strong pipeline with 3x+ quota coverage and predictable forecasting. • Lead consultative discussions with CISOs, engineering leaders, AppSec teams, and procurement stakeholders. • Partner with technical SMEs and consulting leads to shape solutions aligned to client risk, maturity, and regulatory requirements. • Establish multi-threaded relationships within accounts to improve deal velocity and renewal rates. • Deliver compelling client presentations, statements of work, and value-based proposals. • Work closely with the consulting delivery team to scope engagements accurately and ensure high customer satisfaction. • Align with marketing on targeted campaigns, regional events, and ABM programs. • Achieve or exceed quarterly and annual bookings targets. • Maintain accuracy of CRM data, forecasting, and pipeline metrics. • Drive healthy mix of services revenue: net-new logos, expansion, and multi-project programs.

• Lead and mentor a multi-disciplinary engineering team focused on building scalable security products. • Drive the technical roadmap and execution for security features, including threat detection, identity management, and data protection. • Manage delivery timelines, inter-team dependencies, and proactive risk mitigation to ensure successful execution of product milestones. • Establish and lead sustaining engineering practices prioritizing technical debt reduction. • Collaborate with Product Management and Security Architects to define product requirements. • Ensure high standards of code quality and operational excellence.

• Perform scoped and open-ended assessments on internal and external facing systems • Perform threat and vulnerability research to identify new ways of achieving the program’s mission and act as a source for innovation within the cybersecurity industry • Assisting in the sales process with potential or existing clients, and acting as a client’s primary program contact for projects delivered by Cyber Advisors’ Offensive Security team • Develop and implement tools that assist with execution of security assessments, including custom tools and automation • Work with the customer Blue Team to identify gaps, address findings, and improve breach response

1 in 4 people in the US have a treatable mental health condition, but most providers don't accept insurance, making therapy too expensive for most people. Headway’s mission is to fix this by building a new mental healthcare system everyone can access. We started by solving the biggest barrier to care: insurance. The admin work - credentialing, claims, payment reconciliation - is a nightmare. We've automated that. But we're going further. Over 75,000 providers across all 50 states run their practice on our software, serving over 1 million patients. We are building the best tools for therapists to run their entire practice, reimagining the experience of finding a therapist, and investing in the platform foundations to enable this at scale. We aren't just a billing layer; we are becoming the platform where care actually happens. We're a Series D company with $325M+ in funding (a16z, Accel, Spark Capital, etc.), looking for exceptional people to help us achieve this mission. We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better. Building a new mental healthcare system at Headway is only possible because of the scale and leverage that software can provide. The IT team at Headway is an essential function at Headway that builds operational efficiency into everything we do, giving our organization the tools needed to achieve our goals of reshaping mental healthcare. In this role, you’ll have the unique opportunity to be the builder and driver of our dedicated, in-house IT Engineering efforts. You will execute projects, both technically and organizationally, to tackle challenges as the company continues to rapidly scale. You’ll love this role if you want to: - Design, develop, and standardize the IAM lifecycle and associated workflows for Headway employee accounts. - Drive automation and integration excellence by configuring and managing workflows to automate provisioning, de-provisioning, and access changes, eliminating manual effort and ensuring speed and accuracy. - Strengthen the security foundation by completing and maintaining key IdP integrations of varying levels of complexity with business applications. - Lead the transition to least-privilege. Actively drive and support the organization-wide Role-Based Access Control (RBAC) initiative, ensuring access is governed by job function and need. - Maintain documentation for all core applications and processes. - Address and resolve identity related incidents and escalated service requests. - Work collaboratively with major stakeholders to establish IAM policies and governance that foster a culture of least-privilege. You may be a good fit if you: - An experienced SaaS environment expert with at least 5 years in a fast paced, supporting a distributed workforce, specifically focused on Identity & Access Management (Okta experience is strongly preferred). - Possess subject matter expertise in IAM technologies; you’ve led large scale projects to completion centered on IdP implementation, JML automation, and integrating SaaS applications using APIs, SCIM, and OIDC/SAML protocols. - You’ve driven organization change by leading or playing a significant role in large scale company access controls deployments that require cross functional collaboration and user impact management. - You excel at partnering with stakeholders across the business to synthesize and present technical solutions that drive business efficiency. - You practice methodical project ownership and management with autonomy by consistently planning and executing work with visibility. - Are a team player who actively seeks and provides feedback with a growth mindset. - Stay up-to-date on the latest technology and privacy best practices and requirements. Tools we use: - Identity and Access Management: Okta, Lumos - Email and Messaging: Gmail and Slack - Document Creation and Collaboration: Google Workspace, Confluence - Credential Management: 1Password - Ticketing: Jira Service Desk, ZenDesk, Jira Projects - Project Planning: Jira - Endpoint Management: JAMF, InTune, ChromeOS, Kolide We believe a team's strength is in its people, and we cannot achieve this mission without a team that reflects the diversity of this problem – across race, ethnicity, gender, sexuality, age, national origin, religion, family status, disability, military status, and experience. Headway is committed to the full inclusion of all qualified individuals. As part of this commitment, Headway will ensure that persons with disabilities are provided with reasonable accommodations. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or receive other benefits and privileges of employment, please inform the recruiter when they contact you to schedule your interview. Headway participates in E-Verify. To learn more, click here. A notice to Headway applicants: To protect yourself against phishing and recruitment fraud, please note that Headway only accepts applications through our official careers page at https://headway.co/careers. Headway will never refer you to external websites, ask for payment or personal information, or conduct interviews via messaging apps. All official communication will come from a @findheadway.com email address. If you are contacted by someone claiming to be from Headway via an unofficial channel, please do not share any information and report it as spam.