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.

The Sales Representative role is built for someone who knows how to open doors, build trust, and move opportunities forward. You’ll be responsible for identifying and developing new broker relationships, growing activity in assigned markets, and helping qualified prospects understand how Iron Sheepdog can support their business through technology, operations, and financial solutions.

If you’re competitive, self-motivated, and energized by building something in the field, this is an opportunity to join a fast-growing company and play a direct role in scaling the ISD Broker Network.

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Position Summary

The Sales Representative will be responsible for developing new business opportunities, managing a pipeline of broker prospects, and helping expand Iron Sheepdog’s footprint across targeted submarkets. This person will work closely with sales leadership, customer success, marketing, and operations to identify the right prospects, move deals through the pipeline, and support successful onboarding into the network.

This is a high-accountability role for someone who can prospect, qualify, pursue, and close while representing the brand with professionalism and energy, while also helping existing brokers grow their business within the Iron Sheepdog Broker network through stronger contractor relationships, increased truck activity, and expansion into new opportunities and markets.

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What You’ll Do

Prospect & Build Pipeline
Identify and pursue new broker opportunities in assigned markets and submarkets. Build and maintain a healthy pipeline of qualified prospects through outreach, networking, referrals, events, and market research.

Develop Relationships
Build trust with broker owners, dispatchers, and market decision-makers. Understand their business, challenges, and growth goals, and position Iron Sheepdog as a valuable long-term partner.

Manage the Sales Process
Own opportunities from first conversation through qualification, pursue plan, close, and implementation handoff. Keep pipeline activity organized and up to date in the CRM.

Drive Market Growth
Help expand density within existing markets while supporting strategic entry into new submarkets. Stay close to market activity, contractor opportunities, broker movement, and competitive dynamics.

Collaborate Cross-Functionally
Work with leadership, customer success, credit, and operations to ensure the right opportunities are being pursued and new brokers are positioned for success.

Represent the Brand
Serve as a strong field representative for Iron Sheepdog in meetings, events, association activity, and day-to-day interactions. Communicate with confidence, professionalism, and consistency.

Support Expansion Goals
Contribute ideas around market development, broker recruiting strategies, local partnerships, and regional growth initiatives that support broader company goals.

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Who You Are

Relationship-Driven: You are well connected across the construction ecosystem — including contractors, producers, materials suppliers, and service partners — and know how to build credibility, earn trust, and create lasting business relationships.

Competitive and Self-Motivated: You like to win, take ownership of your market, and don’t need constant direction to stay moving.

Organized and Accountable: You manage your pipeline, follow through on next steps, and understand that disciplined CRM activity matters.

Strong Communicator: You can clearly explain value, ask good questions, and adapt your message to different audiences.

Growth-Minded: You want to improve, develop your craft, and grow within a company that is scaling.

Field-Oriented: You’re comfortable being in the market, traveling as needed, and staying close to the people and activities that drive results.

Tech-Savvy: You are comfortable working across modern business and marketing tools, including Google Workspace, Slack, CRM platforms, Adobe, video tools, and AI-based tools. Experience with HighLevel, Command Alkon, HCSS, Procore, or other construction, project, dispatch, or production-related platforms is a plus.

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Preferred Qualifications

• Experience in sales, business development, account management, or a related customer-facing role
• Strong relationship-building and prospecting skills
• Experience managing opportunities in a CRM
• Ability to work independently and manage a territory or group of submarkets
• Bonus if you have experience in construction, trucking, logistics, heavy civil, aggregates, asphalt, or related industries
• Bonus if you have experience selling operational, financial, or technology solutions in a B2B environment

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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 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.

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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. 

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