Sales Development Representative

At Side, we believe everyone should own their path.

Side partners with top-producing real estate professionals to help them own and operate their own boutique real estate companies, without the legal, regulatory, or operational complexity of running a traditional brokerage. As a pioneer in the Brokerage-as-a-Service model, Side provides a proprietary platform that increases efficiency, strengthens client relationships, and enables entrepreneurs to focus on what they do best — selling real estate and growing their businesses.

Headquartered in San Francisco and backed by more than $300 million from top-tier venture capital firms, Side is recognized as one of the most innovative and fastest-growing companies in real estate. At Side, you’ll work alongside experienced industry leaders and world-class engineers to help shape the future of real estate and empower exceptional professionals to thrive as business owners.

About the Role

This isn’t a generic SDR seat. You’ll be dialing directly to decision makers — top-producing real estate agents doing $20M–$100M+ in annual volume who think like business owners, not salespeople. No gatekeepers, no middle managers. Your job is to earn their attention and book high-quality intro calls for our Ambassadors (Account Executives). You’ll sit on a lean, high-impact sales team (2 SDRs, 2 Ambassadors) reporting directly to the Head of Sales, with real visibility into deal strategy and direct exposure to enterprise-level conversations.

What You’ll Own:
• Dial directly to decision makers — you’re not calling gatekeepers or office managers. You’re picking up the phone and reaching top-producing agents and team leaders ($25M+ annual volume) who own their business.
• Execute 75+ daily touches by phone to maintain a steady flow of qualified conversations with real decision makers.
• Research prospects before outreach — know their production, team size, current brokerage, and what’s likely keeping them stuck. Personalize every touchpoint so it lands.
• Book 15–20 qualified intro calls per month for our Ambassador team with agents who fit Side’s ideal partner profile.
• Qualify prospects against clear criteria: production volume, team size, brand ambition, and readiness to move. No vanity meetings.
• Own the handoff — prep Ambassadors with context on every booked call so they walk in informed.
• Drive attendance to Side-hosted events, activations, and experiences by personally reaching out to target agents and industry leaders.
• Represent Side at industry events and conferences — build your network and identify high-potential prospects in person.
• Maintain meticulous records in Salesforce — every touch, every conversation, every outcome logged in real time.
• Collaborate with Marketing and Sales leadership to align outreach with campaigns, events, and strategic priorities.

Who You Are - Must-Haves:
• 2+ years in sales development, business development, recruiting, or a high-volume customer-facing role. You’ve hit quota before and know what daily discipline looks like.
• Exceptional communication skills — written and verbal. You can write a 3-sentence cold email that gets a response from a $50M producer and hold your own on a call with a seasoned entrepreneur.
• High activity tolerance. 75+ calls/day doesn’t scare you — it’s how you build a pipeline.
• Self-starter mentality. You don’t wait to be told what to do. You find the gap, fill it, and tell your manager after.
• Strong organizational skills and CRM hygiene.
• Salesforce is your second home.
• Genuine curiosity about real estate as a business. You don’t need to have sold homes, but you should be interested in how top agents build and scale their businesses.

Who You Are - Nice-to-Haves:
• Real estate industry experience — brokerage, proptech, mortgage, title, or adjacent.
• Experience selling to entrepreneurs, business owners, or high-net-worth individuals (not just mid-market or enterprise IT buyers).
• Familiarity with Salesforce, and outbound sequencing tools.
• Track record of exceeding SDR metrics (meetings booked, pipeline generated, conversion rates).

Why This Role Is Different:
• You’re calling the decision maker directly. No gatekeepers, no procurement teams, no layers of bureaucracy. You pick up the phone and talk to the person who makes the call — top-producing agents doing $20M–$100M+ who think like CEOs.
• Small team, big impact. With 2 SDRs and 2 Ambassadors, your work directly moves the pipeline. No hiding in a 50-person BDR bullpen.
• Direct access to leadership. You report to the Head of Sales and sit in on deal strategy. You’ll learn how $65K+ ACV deals get closed, not just booked.
• Clear path forward. This role is designed to develop into an Ambassador (AE) position as you build the skills and relationships.

Side is dedicated to working with the highest skilled people from the most inclusive talent pool feasible. We maintain that diversity in all aspects leads to positive change, solutions and innovation for our customers and career fulfillment for our employees. All qualified individuals are encouraged to apply!

Side uses the E-Verify employment verification program.

Our stewardship of the data of many of our customers means that a background and DRE license check is required to join Side. We will, nonetheless, consider qualified applicants with arrest and conviction records in accord with applicable law, including the San Francisco Fair Chance Ordinance.