Company Description

OBRYN GUARD™ supports hospitality ownership groups, hotel operators, and leadership teams in managing cyber risk, strengthening compliance readiness, and improving audit preparedness. Built specifically for hotel environments, OBRYN GUARD™ provides cyber risk assessments, vendor risk analysis, policy documentation, operational security guidance, and support aligned with frameworks such as PCI DSS, SOC 2, ISO 27001, NIST, and related cyber insurance expectations. The company is focused on helping hotels move beyond basic compliance by creating clearer visibility into operational cyber exposure, reducing preventable risk, and providing leadership teams with defensible, actionable insights. OBRYN GUARD™ is building a premium, enterprise-level client experience for the hospitality industry, with a strong focus on professionalism, accuracy, confidentiality, and measurable risk reduction.

Role Description

This is a remote, performance-based leadership role for a Head of Sales. The Head of Sales will support OBRYN GUARD™ by helping build, manage, and improve the company’s sales function across outbound prospecting, SDR performance, Account Executive support, pipeline quality, sales process execution, team communication, and revenue growth. This role is responsible for helping create structure, accountability, and consistency across the sales team. The Head of Sales will help oversee Sales Development Representatives, support Account Executives, improve outreach standards, review pipeline activity, assist with recruitment, support training, and help ensure prospects receive a professional, accurate, and enterprise-level experience. This is not a passive title-based role. This is a hands-on sales leadership position requiring outbound understanding, strong communication, strong follow-through, team accountability, pipeline discipline, and the ability to lead in an early-stage company environment. Compensation may include commission, leadership override, and performance-based incentives tied to measurable sales activity, team performance, qualified pipeline contribution, and closed hotel accounts. Future compensation structure, equity consideration, or expanded leadership terms may be reviewed based on performance, company needs, and written agreement. The ideal candidate is professional, disciplined, confident, organized, and capable of leading sales activity with hotel owners, operators, executives, general managers, internal sales representatives, Account Executives, and company leadership.

Responsibilities

Help lead, organize, and improve the OBRYN GUARD™ sales function across SDRs, Account Executives, outreach, pipeline management, sales process, and team accountability. Oversee Sales Development Representatives and help ensure outreach quality, prospecting consistency, professional communication, CRM accuracy, and proper follow-up standards. Support Account Executives by improving lead handoffs, preparing prospect context, reviewing sales opportunities, and helping maintain pipeline discipline. Help train SDRs on professional outreach, first impressions, qualification standards, objection handling, follow-up, CRM usage, and proper communication with hospitality decision-makers. Help develop and improve outreach scripts, qualification guidelines, prospecting standards, meeting booking processes, and sales team operating procedures. Monitor outbound activity, booked meetings, follow-ups, prospect status, lead quality, and sales team performance. Review pipeline activity and help identify weak points in outreach, qualification, handoff, follow-up, communication, or sales execution. Support recruitment, onboarding, training, and performance review of SDRs, Account Executives, and future sales team members. Help ensure the sales team communicates OBRYN GUARD™’s value clearly without overpromising, exaggerating, or speaking outside their role. Maintain professional standards across all prospect-facing communication, including email, phone, LinkedIn, CRM notes, meeting preparation, and internal updates. Help identify qualified hotel ownership groups, hotel operators, management companies, independent hotels, boutique hotels, and hospitality decision-makers. Support outbound strategy for reaching hotel executives, owners, operators, general managers, operational leaders, and hospitality groups. Escalate cybersecurity, compliance, PCI DSS, SOC 2, ISO 27001, insurance validation, platform, legal, or technical questions to the proper internal advisor instead of guessing. Collaborate with company leadership, client success, security advisors, technical advisors, SDRs, and Account Executives to improve sales execution and client experience. Help create a professional, accountable, and performance-driven sales culture. Represent OBRYN GUARD™ with accuracy, confidentiality, professionalism, and executive-level communication.

Qualifications:

Strong sales leadership, communication, and organizational skills. Experience in sales management, sales development leadership, business development, outbound sales, inside sales, B2B sales, SaaS, cybersecurity, compliance, hospitality, insurance-related services, or professional services. Ability to lead and support SDRs, Account Executives, or sales teams in a performance-driven environment. Strong understanding of outbound prospecting, pipeline management, qualification, meeting booking, CRM discipline, follow-up, and sales process execution. Comfortable working in a remote, early-stage, performance-based company environment. Ability to communicate clearly with hotel owners, operators, general managers, executives, internal sales representatives, and company leadership. Ability to improve team standards without micromanaging or creating unnecessary complexity. Strong attention to detail, professionalism, confidentiality, accuracy, and follow-through. Ability to hold sales team members accountable to activity, quality, communication, and performance expectations. Experience using CRM systems, sales engagement tools, prospecting platforms, lead tracking systems, email outreach tools, LinkedIn, or sales reporting tools. Ability to explain company services clearly without overcomplicating, overpromising, or speaking outside the role’s scope. Knowledge or exposure to cybersecurity, compliance frameworks, cyber insurance, risk management, SaaS, or the hospitality industry is considered an asset. Bachelor’s degree in Business, Marketing, Communications, Hospitality, Information Systems, Sales, or a related field is preferred but not required.

Preferred Experience:

Experience managing SDRs, BDRs, Account Executives, sales representatives, appointment setters, or outbound sales teams. Experience building or improving sales processes in an early-stage company, startup, B2B services company, SaaS company, cybersecurity company, compliance firm, or hospitality-focused business. Experience prospecting or selling to hotel owners, general managers, executives, operators, ownership groups, management companies, or hospitality teams. Experience supporting or managing sales pipelines, CRM reporting, prospect handoffs, meeting quality, follow-up systems, and sales activity tracking. Experience with B2B services, SaaS, cybersecurity, compliance, consulting, insurance-related services, vendor risk, or professional services. Exposure to PCI DSS, SOC 2, ISO 27001, NIST, cyber insurance, vendor risk, phishing, access control, incident response, or operational security. Experience recruiting, onboarding, training, coaching, or reviewing sales representatives. Experience working directly with founders, executives, technical advisors, security advisors, or client success teams.

Ideal Candidate:

The ideal candidate is disciplined, professional, direct, organized, and execution-focused. This person understands that a Head of Sales role requires more than motivation and meetings. It requires structure, accountability, pipeline control, team standards, accurate communication, and consistent follow-through. This person should be comfortable helping build a sales department from the ground up, supporting SDRs, guiding Account Executives, improving outbound performance, reviewing pipeline quality, and protecting the company’s reputation with serious hospitality prospects. This person should know how to create momentum without overpromising, lead a team without creating confusion, communicate with executives professionally, and escalate technical or compliance questions instead of guessing. OBRYN GUARD™ is looking for someone who can help build a serious sales function, improve team performance, protect client trust, support revenue growth, and represent the company at a high professional standard.

Thank you for your interest in OBRYN GUARD™ Sincerely, Leadership Team OBRYN GUARD™