Sales Development Representative

Job Overview

As an Outbound Sales Representative, you are responsible for proactively identifying, engaging, and qualifying prospective vacation rental homeowners and property management opportunities to support portfolio growth across assigned markets.

This role focuses on outbound prospecting efforts including cold calling, lead follow‑up, nurture campaigns, change‑of‑ownership opportunities, and strategic outreach initiatives designed to create high‑quality sales opportunities for local market teams and franchise partners.

Daily responsibilities include managing outbound cadences, researching and prioritizing target accounts, documenting activity within CRM systems, and collaborating closely with sales, marketing, and operations teams to ensure a seamless homeowner experience.

This position reports to a manager within the Franchise Growth Dept.

Responsibilities

• Execute high-volume outbound prospecting efforts through phone calls, email, SMS, and other communication channels to generate qualified homeowner opportunities.
• Manage and maintain outbound cadences within platforms such as Salesloft, Salesforce, and other sales engagement tools.
• Identify and engage homeowners through multiple lead sources including marketing‑generated leads, nurture campaigns, site re‑engagements, referrals, and change‑of‑ownership opportunities.
• Qualify prospects based on homeowner goals, property fit, market alignment, and readiness to engage with local sales teams.
• Accurately document all outreach activity, lead status updates, call notes, and opportunity progression within CRM systems.
• Collaborate with marketing and sales leadership to provide feedback on lead quality, campaign performance, and outbound strategy effectiveness.
• Maintain SLA expectations for speed‑to‑lead and outbound follow‑up standards to maximize conversion opportunities.
• Consistently meet or exceed activity and performance metrics including outbound calls, conversations, qualified opportunities created, and appointment‑setting goals.
• Participate in ongoing sales training, call coaching, and team development initiatives to improve communication skills and sales effectiveness.
• Collaborate with cross‑functional teams and stakeholders to align departmental goals with broader organizational strategy.
• Support continuous improvement initiatives by identifying process gaps, workflow inefficiencies, and opportunities to improve outbound conversion performance.
• Contribute to a collaborative work environment that promotes open communication, innovation, and employee engagement.
• Other duties as assigned because every day is different in sales and hospitality!

Qualifications

• 1–3 years of experience in outbound sales, business development, SDR/BDR, inside sales, hospitality sales, or a related customer‑facing role preferred.
• Experience working in hotel, hospitality, vacation rental, real estate, or similar industry is highly preferred.
• Proven ability to confidently communicate with prospects through outbound phone outreach and relationship‑based conversations.
• Strong organizational skills with ability to manage multiple lead pipelines, follow‑up timelines, and competing priorities simultaneously.
• Comfortable working in a metrics‑driven environment with performance expectations tied to activity and opportunity generation.
• Experience using CRM and sales engagement platforms such as Salesforce, Salesloft, Hub Spot, Twilio, or similar technologies preferred.
• Tech‑savvy with experience using various digital systems and applications and comfortable using mobile apps, tablets, and various software platforms.
• College education is strongly preferred, though we recognize that great talent comes from many different paths.
• Strong written and verbal communication skills with ability to explain information clearly, professionally, and thoughtfully.
• Self‑motivated with ability to work independently while contributing positively within a collaborative team environment.

Compensation

• $19 – $24 / hour. Actual pay will vary based on a candidate's skill, experience, education and/or location.
• Top performers in this role have the opportunity to exceed standard earning expectations.
• Workplace Environment
• This position is 100% remote.

Ability to work from home and resides in one of the following states: AK, AL, AZ, CA, CO, DE, FL, GA, HI, ID, IL, IN, LA, MA, MD, ME, MI, MN, MO, MT, NC, NH, NJ, NM, NV, OH, OK, OR, PA, RI, SC, SD, TN, TX, UT, VA, VT, WA, WI, or WY.

Physical Demands

Ability to move freely (standing, stooping, walking, bending, pushing, pulling, and repetitive hand/finger motions) and lift up to a maximum of twenty‑five (25) pounds without assistance.

Benefits

• Health/dental/vision insurance based on hours worked
• Employer Sponsored & Voluntary Supplemental Benefits based on hours worked
• 401K retirement savings plan with immediate 100% company match on the first 4% you contribute
• Health & Dependent Care Flexible Spending Accounts based on hours worked
• Paid Vacation & Sick Time
• Employee Assistance Program (EAP)
• Employee Discounts
• Equal Opportunity Employer

Casago is an equal opportunity employer committed to fostering a diverse and inclusive workplace.

We do not discriminate against applicants based upon race, color, religion, sex (including pregnancy, gender identity, and sexual orientation), national origin, age, disability, genetic information, or other classes protected by applicable law.

Veterans are encouraged.

Casago is committed to maintaining a safe and productive work environment.

Possession, use, or being under the influence of alcohol or illegal drugs in the workplace is prohibited.

Additional Employment Details

Some positions may require that you drive a personal vehicle and/or company vehicle for work purposes.

Employees who are required to drive a personal vehicle must have reliable transportation, a valid driver’s license, and be at least 18 years of age.

Employees who are required to drive a company vehicle must have a valid driver’s license, be at least 21 years of age, and have been a licensed driver for no less than 3 years.

An offer of employment for this role will be contingent upon the successful completion of a background check and / or an OFAC screening, country dependent.

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