Sales Development Representative

Inside Real Estate is a fast-growing, independently-owned real estate software firm that serves as a trusted technology partner to over 500,000 top brokerages, agents, and teams. Their branded portfolio, BoldTrail, includes BoldTrail (Front Office), BoldTrail BackOffice and BoldTrail Recruit, solutions that create a complete tech ecosystem for clients, and deliver seamless end-to-end operations to scale success at any level. With an accomplished leadership team and its talented staff, Inside Real Estate brings the resources, scale, and vision to deliver ongoing innovation and success to their growing customer base.

As a Sales Development Representative (SDR), you will be responsible for generating qualified sales pipeline through a combination of proactive outbound prospecting and timely engagement of inbound leads. Your primary objective is to identify, engage, qualify, and schedule meetings with prospective customers that result in high-quality sales opportunities for our Sales Executives.

This is a quota-carrying sales role that requires persistence, resilience, curiosity, and a disciplined approach to multi-channel prospecting. While inbound lead engagement is an important component of the role, outbound prospecting remains a critical responsibility and a key driver of long-term pipeline growth.

Sales Development Representatives may support one or more product lines, customer segments, lead sources, or strategic initiatives, with responsibilities evolving as business needs change. Success in this role comes from consistently creating new opportunities, executing high-quality discovery, maintaining accurate CRM data, and contributing to the overall growth of the business.

Key Responsibilities:

Outbound Prospecting

• Proactively identify and engage prospective customers through cold calling, email, text messaging, LinkedIn, referrals, and other approved outreach channels.
• Research accounts and contacts to develop personalized outreach strategies that create meaningful conversations.
• Execute structured, multi-touch prospecting cadences designed to generate qualified meetings and sales opportunities.
• Build and maintain a healthy sales pipeline through disciplined daily prospecting activities.
• Prospect into assigned market segments, product lines, lead sources, and strategic account lists, adapting quickly as business priorities evolve.
• Re-engage dormant leads, closed-lost opportunities, and inactive prospects through strategic outreach campaigns.
• Consistently meet or exceed daily, weekly, and monthly activity expectations while maintaining high-quality customer interactions.

Inbound Lead Management

• Respond quickly and professionally to inbound inquiries with a strong sense of urgency.
• Engage prospects through timely, multi-channel follow-up.
• Conduct discovery conversations to understand business goals, challenges, and solution fit.
• Qualify inbound opportunities and schedule meetings with Sales Executives.
• Ensure every qualified lead receives a best-in-class customer experience.

Discovery & Qualification

• Conduct consultative discovery conversations to uncover customer challenges, business objectives, and growth opportunities.
• Identify buying signals and determine whether prospects meet qualification criteria.
• Effectively handle initial objections while creating curiosity and demonstrating value.
• Clearly communicate the value proposition of our solutions and confidently position next steps.

CRM & Sales Process

• Maintain accurate and timely records within Salesforce and other sales technology platforms.
• Document customer interactions, discovery notes, next steps, and key business insights.
• Follow established sales processes, lead management procedures, and Rules of Engagement.
• Maintain exceptional CRM hygiene to ensure accurate reporting and forecasting.

Collaboration

• Partner closely with Sales Executives to ensure seamless opportunity handoffs.
• Participate in coaching sessions, call reviews, role plays, and ongoing sales training.
• Collaborate with Marketing, Revenue Operations, and Leadership to improve lead quality and sales effectiveness.
• Share best practices and contribute to a high-performance, team-first culture.

Performance Expectations:

Success in this role will be measured through a combination of quality, productivity, and business impact, including:

• Qualified Opportunities Created
• Qualified Meetings Scheduled
• Opportunity Conversion Rate
• Speed-to-Lead
• Outbound Calls
• Meaningful Prospect Conversations
• Daily Prospecting Activity
• CRM Accuracy & Data Hygiene
• Pipeline Contribution

What Success Looks Like:

Top-performing Sales Development Representatives:

• Own their pipeline instead of waiting for opportunities.
• Prospect consistently every day, regardless of inbound lead volume.
• Create qualified opportunities through both outbound prospecting and inbound engagement.
• Adapt quickly to changing products, customer segments, lead sources, and business priorities.
• Balance persistence with thoughtful personalization in every customer interaction.
• Execute disciplined follow-up until prospects either engage or clearly opt out.
• Embrace coaching, accountability, and continuous improvement.
• Integrate & embrace AI tools into their daily motion to drive sales effectiveness
• Maintain a positive attitude, competitive mindset, and commitment to achieving team and individual goals.

Qualifications:

Required

• Bachelor's degree or equivalent professional experience preferred.
• Previous sales, customer-facing, or business development experience preferred.
• Excellent verbal and written communication skills.
• Strong organizational and time management skills.
• Comfortable making a high volume of outbound calls and engaging customers across multiple communication channels.
• Ability to thrive in a fast-paced, metrics-driven sales environment.
• Highly coachable with a strong desire to learn and improve.
• Competitive, self-motivated, and results-oriented.

Preferred

• Experience selling SaaS or technology solutions.
• Experience using Salesforce or another CRM platform.
• Experience using Sales Engagement platforms (Salesloft, Outreach, etc.).
• Experience within the real estate technology industry is a plus.
• Familiarity with consultative sales methodologies such as Challenger, SPIN, MEDDICC, or similar frameworks.

Why Join Our Team?

As a Sales Development Representative, you'll play a direct role in driving company growth while developing foundational sales skills that can accelerate your career. You'll receive structured onboarding, ongoing coaching, mentorship from experienced sales leaders, and opportunities for career advancement into closing sales, account management, leadership, or other revenue-generating roles.

You'll join a collaborative, high-performing team that values accountability, continuous learning, and celebrating success together.

We offer a competitive total rewards package including:

• Competitive salary
• 3 Medical plans to choose from - 1 PPO and 2 HDHPs
• 2 Dental plans to choose from
• Vision
• HSA - company-funded
• FSAs - healthcare, limited purpose, dependent care
• Short-Term Disability - company-paid
• Long-Term Disability - company-paid
• Basic Employee Life Insurance - company-paid
• Voluntary Dependent Life Insurance
• Voluntary Accident Insurance
• Voluntary Critical Illness
• Voluntary Hospital Indemnity
• ID Protection
• Pet Insurance
• 401(k) Retirement Savings with company match
• Paid PTO/Vacation/Sick Time
• 11 company-recognized holidays
• Company-paid Parental/Disability Leave

In addition, at IRE, we focus on driving top results providing:

• Opportunities to grow within our company;
• Potential to work in a remote setting;
• Exciting/energetic work environment and fun, creative culture.

IRE EEO Statement - We believe that the unique contributions of all Insiders are the driver of our success. To make sure that our products and culture continue to incorporate everyone's perspectives and experiences we never discriminate on the basis of race, religion, national origin, gender identity or expression, sexual orientation, age, marital, veteran, or disability status.