Location: Remote, with a preference for candidates within ~2 hours' drive of Williamsburg, VA (nice-to-have, for periodic on-site audit and consensus work).

We are seeking a highly skilled Lead Information Security & Compliance Specialist to spearhead our security initiatives and governance frameworks. In this role, you will bridge the gap between high-level compliance and hands-on technical security engineering. You will manage our compliance pipelines, protect our fintech workflows, and champion a security-first culture across our entire organization.

If you are a proactive security professional who thrives in SaaS environments and loves securing cutting-edge tech ecosystems (including cloud, mobile, and AI), we want to hear from you.

Key Responsibilities

• Compliance Leadership: Lead and manage the end-to-end process of achieving and maintaining our SOC 2 compliance.
• Policy & Governance: Create, enforce, and govern comprehensive IT and Information Security policies across the entire organization.
• Client Security Liaison: Serve as the primary security liaison for enterprise clients, confidently answering complex security questionnaires and navigating financial audits.
• Vendor Management: Interface directly with client security teams, respond to vendor security questionnaires, and optimize our IT Managed Service Provider (MSP) relationships to dictate how we best leverage them.
• Security Engineering: Act as a hands-on security engineer to review and improve secure coding practices across our React and Node.js codebase, ensuring the safety of our fintech workflows.
• Vulnerability & DevSecOps Management: Manage and monitor DevSecOps tools like Snyk to catch vulnerabilities early in the CI/CD pipeline.
• Testing & Infrastructure Security: Conduct internal penetration tests, review Firebase/Firestore security rules, and rigorously develop disaster recovery plans.
• AI Security Implementation: Design and execute vulnerability testing specifically for our AI features, running prompt injection tests against our LLMs and chat-bots to ensure data integrity.
• Security Culture: Take full ownership of company-wide security awareness training, actively building an internal culture of vigilance and security awareness.

Job Requirements & Skills

Core Requirements (Must Have)

• SOC 2 Expertise: Experience managing/leading the end-to-end process of achieving and maintaining SOC 2 compliance, OR comparable/translatable audit and compliance frameworks (e.g., ISO 27001, HIPAA, PCI-DSS). — Recent experience preferred; minimum 5 years; multiple audits/renewals preferred.
• SaaS & Industry Background: A proven background working within SaaS environments, with a strong preference for candidates experienced in logistics, supply chain, or short-haul trucking platforms (specifically dealing with truck routing and fleet dispatch).
• Enterprise Experience: Proven experience serving as a primary security contact for medium to large enterprises.
• Ecosystem Exposure: Strong exposure to secure processes for diverse, interconnected ecosystems across web, mobile, cloud infrastructure, and APIs.

These are valued pluses, not core requirements. This role is process- and compliance-led; deep hands-on software-security engineering is a bonus and not expected day one.

Technical & Next-Level Requirements

• Codebase Security: Ability to work hands-on with React and Node.js codebases to implement secure coding practices.
• Tooling & Testing: Direct experience with DevSecOps tools (e.g., Snyk), CI/CD pipelines, internal penetration testing, and Firestore/Firebase security rule governance.
• AI Vulnerability Testing: Experience or strong capability in running prompt injection tests and securing LLM-powered chatbots.

Nice to Have (Bonus Points)

• Familiarity with cloud security, preferably within the Google Cloud Platform (GCP) and Firebase ecosystem.
• Familiarity with modern AI security frameworks, including protecting custom AI models and securing Model Context Protocol (MCP) servers.

Success in this role means that security is seamlessly integrated into our engineering and business operations, culminating in a state where the entire company becomes thoroughly aware of the importance of security throughout everything we do.

Why Iron Sheepdog?

• Transform a Legacy Industry: Be part of a team that is revolutionizing the massive, essential short-haul trucking industry. We’re creating an tech enabled future that addresses the entire construction materials supply chain.
• The Iron Sheepdog Standard: Experience a unique business model where industry-leading software is backed by a relentless commitment to personal service and operational excellence.
• High-Growth Environment: Experience the thrill of a scaling startup where your contributions are essential to our collective success.
• Innovation at the Core: Join a company that values "what’s next," where we use technology to solve real-world problems for hard-working people.

Total Rewards Package

Iron Sheepdog is committed to offer a competitive compensation and benefits package to include salary, bonus, 401k, healthcare, dental, and PTO.

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Equal Opportunity Employer

Iron Sheepdog is an equal opportunity employer and prohibits discrimination against all candidates.

We are seeking an autonomous and driven Product Manager to take full ownership of our product lifecycle. In this role, you will act as the definitive voice of the customer, bridging the gap between user needs, executive leadership, and engineering execution. You must be completely comfortable operating as the sole member of the product team to start, taking full responsibility for all duties in a lean, fast-paced startup shipping culture.

If you are a data-driven professional who loves conducting deep-dive customer discovery, managing dynamic backlogs, and designing intuitive user experiences within a fast-evolving ecosystem, we want you on our team.

Key Responsibilities

• Customer Discovery: Conduct deep-dive interviews and research with brokers, haulers, and contractors to uncover core pain points and truly understand their "WHY".
• Backlog Management: Own the product backlog entirely, writing clear, actionable epics and requirements so the engineering team can focus strictly on execution.
• Leadership Relief: Act as the definitive voice of the customer, successfully relieving the CTO, COO, VP of Engineering, and Head of Software Operations from daily tactical requirements gathering.
• UI/UX & Prototyping: Leverage your strong UI/UX sensibilities and hands-on experience with design tools to create wireframes and mockups that guide engineering discussions and validate concepts with users before development.
• Data Analytics: Maintain a data-driven approach to product development, utilizing feature analytics to analyze user behavior, measure success, and make strategic prioritization decisions.
• Stack Collaboration: Collaborate closely with engineers to ensure proposed solutions are highly feasible within our Node.js and Firebase stack while aligning with our lean engineering philosophy.
• Fintech Workflows: Define and optimize critical fintech workflows—specifically involving payment gateways, escrow logic, or complex financial workflows—to ensure seamless payment experiences for our users.
• Market Strategy: Continuously analyze the market and our competitors to ensure Iron Sheepdog’s feature set remains two steps ahead while executing our 5-year growth strategy.
• AI-Powered Product Workflows: Leverage generative AI tools to accelerate daily product responsibilities, including generating feature suggestions, streamlining customer research synthesis, and utilizing AI-assisted design/wireframing platforms.

Job Requirements & Skills

Core Requirements (Must Have)

• Product Management Experience: 4+ years of professional product management experience, ideally with a proven track record in a fast-paced environment or startup culture.
• Targeted Environments: Background or strong preference for experience within B2B SaaS or construction logistics.
• Extreme Autonomy: Ability to take initiative and thrive independently as the sole product team member handling all initial responsibilities.
• Design Tool Competency: Practical, hands-on experience using design tools (such as Figma, Balsamiq, Sketch, or modern AI design tools) to build wireframes and mockups; the general experience with design tools is valued over a specific platform.
• Analytical Skills: Strong analytical capabilities with a deeply data-driven approach to product development.

Nice to Have (Bonus Points)

• Industry Expertise: Direct experience in the construction, short-haul trucking, or logistics industries, with an emphasis on platforms dealing with truck routing and fleet dispatch.
• Preferred Analytics Tools: Experience utilizing Amplitude for feature analytics, as well as familiarity with BI data analysis tools like BigQuery, Data Studio, or similar platforms.
• Architecture Awareness: A foundational understanding of Firebase or serverless cloud architectures to better comprehend our technical constraints.
• Pragmatic AI Exposure: An active interest in or exposure to Artificial Intelligence, specifically regarding how it can be pragmatically applied to improve user experiences without over-complicating the underlying technical stack.

Why Iron Sheepdog?

Transform a Legacy Industry: Be part of a team that is revolutionizing the massive, essential short-haul trucking industry. We’re creating an tech enabled future that addresses the entire construction materials supply chain.

The Iron Sheepdog Standard: Experience a unique business model where industry-leading software is backed by a relentless commitment to personal service and operational excellence.

High-Growth Environment: Experience the thrill of a scaling startup where your contributions are essential to our collective success.

Innovation at the Core: Join a company that values "what’s next," where we use technology to solve real-world problems for hard-working people.

Total Rewards Package:

Iron Sheepdog is committed to offer a competitive compensation and benefits package to include salary, bonus, 401k, healthcare, dental, paid time off and much more.

Equal Opportunity Employer:

Iron Sheepdog is an equal opportunity employer and prohibits against the discrimination against all candidates.

Grow Our Network. Shape Our Product. Build Our Brand.

Iron Sheepdog is revolutionizing the short-haul trucking and construction materials supply chain, and we're scaling fast — from roughly 44 to 70+ people over the next 12 months. We're hiring Sales Representatives who can open doors and close broker deals, but who also want a direct hand in shaping our product and our brand while we're still early enough for one person's fieldwork to move the needle. You'll spend most of your time building the broker network market by market, while channeling what you hear in the field straight back into product decisions and representing Iron Sheepdog with real credibility everywhere you show up. If you're competitive, self-motivated, and want more ownership than a typical sales seat offers, this is built for you.

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Role Objectives

In the first 6–12 months, this person owns growth of the broker network in their assigned markets — building a healthy, well-managed pipeline and closing new business consistently. Alongside that, "winning" means becoming a trusted field channel for product feedback (surfacing real broker and contractor pain points to the product team) and a visible, credible face of the Iron Sheepdog brand at every market touchpoint. Strong performance in this seat is the primary path toward promotion into Area Sales Manager.

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Ramp-Up: Customer Success Immersion

Before taking full ownership of a new-business pipeline, every Sales Representative spends an initial period embedded with the Customer Success team — supporting broker onboarding, implementation, and day-to-day platform support. This grounding builds real fluency in the platform, our implementation process, and how brokers actually operate day to day, so that by the time this person is prospecting and closing, they're speaking from firsthand experience rather than a script.

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Responsibilities

• Identify and pursue new broker opportunities across assigned markets and submarkets, building a healthy pipeline through outreach, networking, referrals, events, and market research.
• Own opportunities end-to-end — first conversation through qualification, pursue plan, close, and implementation handoff — keeping the CRM organized and current.
• Build trust with broker owners, dispatchers, and market decision-makers, positioning Iron Sheepdog as a long-term partner.
• Drive market growth by expanding density in existing markets and supporting strategic entry into new submarkets.
• Capture recurring broker, dispatcher, and contractor pain points and translate them into clear, actionable feedback for the product team.
• Participate in early product conversations and pilot new capabilities with select brokers, gathering structured feedback on usability and adoption.
• Train brokers and their customers on the Iron Sheepdog platform, driving adoption and safeguarding data integrity within the system — a critical operational focus heading into 2027.
• Serve as a visible, credible representative of the Iron Sheepdog brand at industry events, association activity, and day-to-day market interactions.
• Contribute ideas on market positioning, local partnerships, and regional brand-building initiatives.
• Collaborate cross-functionally with the Area Sales Manager, product, customer success, credit, and operations to ensure the right opportunities are pursued and new brokers are set up for success.

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Skills and Qualifications

• Experience in sales, business development, account management, or another customer-facing role.
• Strong relationship-building and prospecting skills, with the ability to manage opportunities in a CRM.
• Ability to work independently and manage a territory or group of submarkets with minimal direction.
• Comfortable working across Google Workspace, Slack, CRM platforms, and other modern business tools.
• Willingness and ability to travel within assigned markets as needed.

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Additional Skills are a Bonus

• Experience running a P&L or managing a small business — many of our brokers are business owners themselves, and firsthand experience on that side of the table builds natural credibility and faster trust in the field.
• Experience contributing field feedback into a product roadmap, or working closely with a product team at a fast-growing company.
• Experience acting as a brand ambassador or field representative for an early- or high-growth-stage company.
• Experience in construction, trucking, logistics, heavy civil, aggregates, asphalt, or related industries.
• Experience selling operational, financial, or technology solutions in a B2B environment.
• Familiarity with HighLevel, Command Alkon, HCSS, Procore, or similar construction/dispatch/production platforms.

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Why Join Us?

• Direct ownership of a market — your pipeline, your relationships, your results.
• A real seat at the table shaping our product roadmap, not just selling what already exists.
• The chance to define what the Iron Sheepdog brand looks and feels like in markets we're just entering.
• A clear, visible path to Area Sales Manager for strong performers.

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Why Iron Sheepdog?  

• Transform a Legacy Industry: Be part of a team that is revolutionizing the massive, essential short-haul trucking industry. We're creating a tech-enabled future that addresses the entire construction materials supply chain.
• The Iron Sheepdog Standard: Experience a unique business model where industry-leading software is backed by a relentless commitment to personal service and operational excellence.
• High-Growth Environment: Experience the thrill of a scaling startup where your contributions are essential to our collective success.
• Innovation at the Core: Join a company that values "what's next," where we use technology to solve real-world problems for hard-working people.

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Total Rewards Package  

Iron Sheepdog is committed to offering a competitive compensation and benefits package to include salary, bonus, 401(k), healthcare, dental, paid time off, and much more. The posted pay range for this role is listed above under and reflects a good-faith estimate; final offers are based on experience, location, and internal equity.

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Equal Opportunity Employer  

Iron Sheepdog is an equal opportunity employer. We prohibit discrimination and harassment of any kind on the basis of race, color, religion, sex, sexual orientation, gender identity or expression, national origin, age, disability, genetic information, marital status, pregnancy or pregnancy-related conditions, veteran or military status, citizenship status, or any other characteristic protected by applicable federal, state, or local law in the jurisdictions where we operate.

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The physical demands and work environment described above are representative of those an employee encounters while performing the essential functions of this role. Reasonable accommodations may be made to enable individuals with disabilities to perform these essential functions. Iron Sheepdog is committed to providing reasonable accommodation to qualified individuals with disabilities in accordance with the Americans with Disabilities Act (ADA) and applicable state and local law. To request an accommodation, contact the Director of People.

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