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Sales Development Representative | July 14th, 2026

OBRYN GUARDabout 22 hours ago
Remote
Toronto, Ontario, Canada
Entry Level
Full-Time

About the role

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, commission-based role for a Sales Development Representative — SDR. The Sales Development Representative will support OBRYN GUARD™ by identifying, researching, and engaging qualified hotel ownership groups, hotel operators, executives, general managers, and hospitality decision-makers. This role is responsible for creating new business opportunities by starting professional conversations, qualifying prospects, booking meetings, and supporting the sales pipeline. This is an outbound-focused, performance-driven sales development role. Compensation is commission-based and tied to measurable sales development performance, including qualified outreach, booked meetings, pipeline contribution, and successful sales opportunities created for the company. The SDR is not responsible for closing deals. The Account Executive leads the sales process and owns the close. The SDR is responsible for prospecting, outreach, qualification, follow-up, CRM documentation, and helping create serious sales opportunities for the company. The ideal candidate will be disciplined, professional, confident, organized, and capable of communicating clearly with hotel owners, operators, general managers, executives, and internal sales leadership.

Responsibilities

Research and identify qualified hotel ownership groups, hotel operators, management companies, independent hotels, boutique hotels, and hospitality decision-makers. Conduct outbound prospecting through email, phone, LinkedIn, CRM tools, and other approved outreach channels. Start professional conversations with hotel executives, owners, operators, general managers, and operational leaders. Qualify prospects based on business fit, property type, decision-making authority, cybersecurity concerns, compliance needs, insurance-related needs, and interest level. Book qualified discovery calls or sales meetings for Account Executives or company leadership. Clearly communicate OBRYN GUARD™’s value at a high level without overpromising, exaggerating, or speaking outside the role’s scope. Follow approved messaging, outreach scripts, qualification guidelines, and internal sales processes. Maintain accurate records of outreach activity, prospect status, objections, follow-ups, meeting notes, and pipeline movement inside company tracking systems. Follow up consistently with prospects to reduce missed opportunities and improve meeting conversion. Support Account Executives by preparing basic prospect context before scheduled meetings. Escalate cybersecurity, compliance, PCI DSS, SOC 2, ISO 27001, insurance validation, platform, legal, or technical questions to the proper internal advisor. Represent OBRYN GUARD™ with professionalism, confidentiality, accuracy, and executive-level communication. Help build a consistent pipeline of qualified hospitality prospects and support company growth.

Qualifications

Strong communication and customer service skills with the ability to build trust quickly with prospects. Comfortable working in a commission-based, performance-driven sales development role. Experience in sales development, outbound sales, lead generation, appointment setting, business development, B2B services, SaaS, hospitality, cybersecurity, compliance, or professional client-facing roles. Strong organizational skills with the ability to manage multiple prospects, follow-ups, outreach sequences, deadlines, and CRM updates. Ability to explain company services clearly without overcomplicating, overpromising, or speaking outside the role’s scope. Strong research skills for identifying qualified hospitality prospects, decision-makers, ownership groups, and business opportunities. Ability to work independently in a remote environment while collaborating with Account Executives, leadership, client success, technical advisors, and security advisors. High attention to detail, professionalism, confidentiality, and accuracy. Experience using CRM systems, sales engagement tools, lead tracking platforms, email outreach tools, LinkedIn, or prospecting software. Comfortable making outbound calls, sending professional outreach messages, handling objections, and following up consistently. Knowledge or exposure to cybersecurity, compliance frameworks, cyber insurance, risk management, or the hospitality industry is considered an asset. Bachelor’s degree in Business, Marketing, Communications, Hospitality, Information Systems, or a related field is preferred but not required.

Preferred Experience

Experience prospecting hotel owners, general managers, executives, operators, ownership groups, management companies, or hospitality teams. Experience in SDR, BDR, lead generation, appointment setting, outbound sales, inside sales, or business development roles. Experience selling or supporting SaaS, cybersecurity, compliance, consulting, insurance-related services, B2B services, 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 supporting Account Executives by booking qualified sales meetings and maintaining clean pipeline records. Experience documenting prospect information, tracking outreach activity, managing follow-ups, and coordinating internal handoffs. Experience working in an early-stage company, startup, B2B services company, cybersecurity company, compliance firm, or hospitality-focused business.

Ideal Candidate

The ideal candidate is disciplined, professional, confident, and consistent. They understand that outbound sales requires structure, persistence, accurate communication, and strong follow-through. This person should be comfortable in a commission-based role where success depends on consistent prospecting, qualified conversations, booked meetings, and pipeline contribution. This person should be able to create interest without pressuring prospects, support the Account Executive without taking over the sale, explain OBRYN GUARD™ at a high level without overpromising, and escalate technical or compliance questions instead of guessing. OBRYN GUARD™ is looking for someone who can generate qualified conversations, protect trust, maintain accurate records, and help build a strong sales pipeline within the hospitality industry.

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

About OBRYN GUARD

Hotels and Motels
2-10 employees

OBRYN GUARD™ helps hospitality ownership groups and operators strengthen cyber risk, compliance, and audit readiness.

Built for hotel environments, we support leadership teams with cyber risk assessments, control gap analysis, vendor risk visibility, policy documentation, executive reporting, and readiness support for PCI DSS, SOC 2, ISO 27001, NIST CSF, HIPAA, and cyber insurance requirements.

Our focus is simple: help hospitality organizations move beyond checkbox compliance toward measurable risk reduction, stronger operational control, and defensible security maturity.

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